Dean lived in relative peace for the first four years of his life. When his parents had an argument when he was about three, Dean comforted his mother, promising her that John still loved her. Dean was soon joined by a brother, Sam. Six months later, Azazel visited the house to feed Sam demon blood. Mary tried to stop him, leading Azazel to set the nursery on fire with Mary pinned to the ceiling.
John came rushing in and took Sam from his crib and handed him to Dean. He then instructed his son to get out of the house as fast as he could. Dean ran out and watched as the flames destroyed his home, his childhood, and his mother. John left Lawrence with Dean and Sam before Dean's fifth birthday.
When Dean was 6 or 7, John took Dean out shooting for the first time, using bottles as target practice. According to Dean, he bulls-eyed every one of them. Dean has cited this story as one of his fonder memories of his father.
On an occasion when John was hunting a Shtriga in Wisconsin and left Sam and Dean alone in a hotel room, Dean got bored and went out. When he came back, he found the Shtriga feeding on Sam. John returned in time to scare the Shtriga off. For a long time Dean was haunted by his failure to defend his brother. In 1991, when Dean was in sixth grade, he made his first sawed-off shotgun.
Once when 12 year-old Dean was left to babysit Sam (8 years old) while John was on a hunt, Sam began to interrogate Dean about what it was that their dad actually did. Dean responded with "You know that. He sells stuff." When Sam moved on to ask about their mother, Dean got angry and stormed out after yelling, "Shut up! Don't you ever talk about mom! Ever!" Upon his return, Sam revealed to Dean that he had found and read their dad's journal, and demanded to know if monsters are real. Dean finally resigned himself to telling Sam the truth.
|“|| Dean: I swear, if you ever tell dad I told you any of this, I will end you.|
Dean: First thing you have to know is... we have the coolest dad in the world. He's a superhero.
Sam: He is?
Dean: Yeah. Monsters are real. Dad fights em. He's fighting them right now.
— Dean and Sam
in A Very Supernatural Christmas
Dean continually excused his father's flaws while the tension between Sam and John was clearly starting to take root. Disappointed with John's lying and absence, Sam gave Dean a Christmas present intended for his father: an amulet. Dean wears the amulet from this time on.In 1995, Dean lost all of his and Sam's food money in a poker game and was caught stealing food. As a result, he was sent to a reform school run by a man named Sonny who is an ex-con that turned his life around and eventually got the charges against Dean dropped. While living at the home, Dean flourished. He became a high school wrestling champion, made friends and was doing well in school. Dean met a girl named Robin who was Dean's first love interest. She shared Dean's desire not to go into the "family business". Dean's dreams at the time was to become a rockstar or a mechanic and he was supposed to go to a dance with Robin, but his father returned the night of the dance to pick him up and refused to delay even for one night. Sonny offered Dean the chance to stay permanently, but Dean reluctantly left because he couldn't leave Sam.
One time in New York City, Dean, Sam and John were working on a haunting in Long Island when Dean and Sam begged John to let them go out into the city and enjoy the sights. After convincing John, they all went out on the town to see the sights, ride on the subway, eat a lot of pizza, etc. Then one night at midnight, when Sam and John were tuckered out and sleeping, Dean snuck away from them and went to CBGB for the first time, despite being "way underage at the time", according to Sam.
Dean snuck in to the bar, and he describes it as "nuts." His mind was alone away and he was unsure of what to do. He saw people drinking, smoking, etc. Dean says he saw a "500-pound guy on stage with a mohawk just screamin'." Then a woman walks to Dean and asks him to join her and her friends at a table, which Dean immediately agreed to. Though they get him completely drunk for the first time, Dean says it wasn't "fun drunk." He wasn't sure what was in the drink, but after drinking, he saw that the room started spinning and he even felt like he was gonna throw-up endlessly. But at that same moment, John then shows up, and when he says "Dean Winchester", everyone around Dean is suddenly afraid of him, nobody was even looking at him. Dean himself was freaked out because John was just standing there and not saying a single word. Even a boy with a safety pin through his nose and a "Kill Everything" tattoo looks at John and said to him, "Sorry, sir". So after getting him out of there, Dean yelled at John for embarrassing him and tells John he hates him. But John stopped, turn to Dean, and responds, "Son, you don't like me? That's fine. It's not my job to be liked. It's my job to raise you right."
Sometime later in 1995, Dean goes on a hunt with his father and burns the monster they were hunting in the nearby woods. As it burns, Dean thinks to himself he's only sixteen and he's seeing things normal teenagers would never even know of. From that point, Dean chooses to forget being regular and embraces the hunting life.
|“||Sammy's waiting in the car and me and my dad take the thing into the woods, burn it to a crisp. I'm sitting there and looking into the fire and thinking to myself, "I'm sixteen-years old. Most kids my age are worried about pimples, prom dates. I'm seeing things they'll never even know. Never even dream of".||”|
— Dean on when he embraced the hunting life
During the summer of 1997 John, Dean, and Sam were hunting a werewolf. In November 1997, John "parked" the kids in a small town in Indiana where they attended Truman High School. While Sam was having trouble with a bully named Dirk, Dean got a girlfriend, Amanda. He became uncomfortable when she asked him to meet her parents. When she caught Dean cheating on her with another girl, she challenged him, charging that his "cool", persona was just a cover for his pathetically sad loneliness.
|“|| Amanda: I thought maybe ... under your whole "I could give a crap", bad boy thing that there was something more going on. Like the way you are with you brother. But I was wrong. You spent so much time trying to convince people that you're cool, but it's just an act. We both know that you're just a sad, lonely little kid and I feel sorry for you, Dean.|
Dean: You feel sorry for me, huh? Don't feel sorry for me. You don't know anything about me. I save lives. I'm a hero. A hero!
in After School Special
Dean never graduated high school, but did manage to get his GED. Around 1998, Dean and John left Sam alone to go hunt a Kitsune. At this time, Dean also gave Sam advice over the phone on how to talk to girls.
In 1998 or 1999, Dean went on a road trip that was supposed to be "5 states, 5 days" while Sam was "in Orlando with dad, wrapping up that banshee thing". However, he spent most of his time in Lisa Braeden's loft.
Sometime between 2001-2005, Sam left for Stanford. While there, he became estranged from Dean and his father and didn't speak to them for at least a couple of years. During this time, Dean met Cassie Robinson while he and John were in Athens, Ohio, for a hunt. She and Dean dated for a couple of weeks. Before Dean left, he told Cassie the 'big family secret' about hunting. It was then that Cassie promptly called him 'nuts' and dumped him. Dean hunted a Vetala by himself during this period.
On June 21, 2003 in Nyac, New York, Dean hunted Edward Trenton, a man who had become an unknown species of monster that ate livers. Dean never encountered Edward's race of monster before or since but was able to kill him by slitting Edward's throat with a silver-coated steel knife. After killing Edward, Dean was found by his 13-year-old son Cole who believed Dean had murdered his father.
|“||I think he wants us to pick up where he left off. Saving people, hunting things, the family business.||”|
When Dean was four years old, his mother Mary was killed in his younger brother Sam's bedroom. Twenty-two years later, the demon responsible for their mother's death kills Sam's girlfriend, Jessica Moore. Together, Dean and Sam go on a road trip to fend off supernatural creatures and search for their father, John, who occasionally leaves new missions for them to complete.Early in the season (Skin), Dean and Sam battle a shapeshifter responsible for a string of brutal murders in the St. Louis, MO area. During the course of the episode, the shapeshifter assumes Dean's form, causing police to believe that Dean is responsible for the murders. The shapeshifter also gains insight on Dean's inner conflict, partially revealing his secret self-loathing and resentment of his father being gone and Sam leaving them to go off to college. However, Dean kills the shape-shifter while it is still in his form, and the authorities officially declare him dead.
|“||He's sure got issues with you. You got to go to college. He had to stay home. I mean, I had to stay home. With Dad. You don't think I had dreams of my own? But Dad needed me. Where the hell where you? [...] See, deep down, I'm just jealous. You got friends. You could have a life. Me? I know I'm a freak. And sooner or later, everybody's gonna leave me.||”|
— Shapeshifter channeling Dean's hidden insecurities and frustration
In Home, Dean first becomes aware of Sam's psychic abilities when Sam has a vision of trouble at their old home in Lawrence, Kansas. In Asylum, while influenced by the spirit of Doctor Ellicott, Sam tries to shoot Dean in a spirit-induced rage over Dean's insistence in obeying John's orders rather than going to California to find their father. In the following episode, Sam actually does leave Dean, insisting he and John are both selfish because all they care about is revenge. Later, Dean tells Sam he was always proud of how he pursued what he wanted. Sam eventually goes looking for Dean when he can't reach his brother on his cell phone.
In Faith, Dean acquires a fatal heart condition when he is electrocuted during a hunt. Later, he is saved by a faith healer, Roy Le Grange, whose wife is controlling a Reaper. When Dean asks why he was saved, Roy Le Grange says he looked into Dean's heart and saw "A young man with an important purpose. A job to do. And it isn't finished."
In Shadow, as they prepare to battle Meg, Sam confesses to Dean that he will return to Stanford after they kill Azazel, the demon who killed their mother and Sam's girlfriend, Jessica Moore. Dean becomes upset with Sam and insists that they keep fighting together.
|“||Don't say just in case something happens to you, I don't want to hear that freaking speech, man. Nobody's dying tonight, not us, not that family, nobody. Except that demon. That evil son of a bitch ain't getting any older than tonight, understand me?||”|
In the last episode of Season One, Azazel possesses Dean's father in an attempt to get the Colt for his own. After Dean realizes this, The Yellow-Eyed Demon pins him and Sam to a wall and reveals that John favors Sam over Dean. The demon also tells Dean that he was responsible for sending the demon's children back to Hell. After Dean makes a sarcastic remark about the situation, the demon tortures him and Dean pleads for his father's help before losing consciousness.
The season finale concludes with Sam, Dean, and John escaping from a clash with The Yellow-Eyed Demon in Salvation, Iowa. While Sam is driving to the hospital after Dean and John were injured, a demon-possessed driver drives his truck into the Impala, causing massive damage to the car and the Winchesters inside.
|“||Back at the hospital, I made a full recovery. It was miracle. Five minutes later Dad's dead and The Colt's gone. You can't tell me there's not a connection there. I don't know how the demon was involved, I don't know how it went down exactly, but Dad's dead because of me and that much I do know.[...] You and Dad... you're the most important people in my life. And now... I never should've came back. I was dead. And I should've stayed dead.||”|
— Dean's spiraling depression
in Children Shouldn't Play With Dead Things
All three of the Winchesters survived the wreck, although Dean was more severely injured than his father or brother. In the first episode of Season 2, In My Time of Dying, Dean is in a coma and a reaper, Tessa, tries to convince him to cross over. In an effort to save Dean, John makes a deal with Azazel, trading his life for Dean's. Before John dies, he tells Dean that someday Dean may have to kill Sam.
Over the course of the second season, Dean struggles with the death of his father and the resulting guilt that he should have died instead. This, however, Dean's hides under hunting and at first brushing off every attempt Sam did to make him talk about his feelings. Dean became more reckless and harsh, particularly in hunting until Sam finally made him get more of a handle on it.
|“||You're lucky this turned out to be a real case. Because if it wasn't, you would've just found something else to kill.[...] You're on edge, you're erratic. Except when you're hunting because then you're downright scary. You're tailspinning, man. And you refuse to talk about it and you won't let me help you.||”|
— Sam describing Dean's reckless behavior
in Children Shouldn't Play With Dead Things
During an investigation in Baltimore, MD, (The Usual Suspects), Dean is arrested in connection with another series of murders. It is revealed that Dean has a rather impressive police record with charges including credit card fraud, breaking and entering, and grave desecration. Although Sam and Dean are able to prove that the murders were actually committed by one of the detectives on the case, it is unclear whether or not the charges against Dean were ever officially dropped. However, the problem still remains that the authorities have realized that Dean is not dead as they had previously believed.
Shortly afterward, while doing a case revolving around deals with the crossroads demon and trying to save a man named Evan, Dean learns from the demon John went to Hell when he exchanged his soul for Dean's life. Dean's self-loathing and guilt increases, believing John should've went out fighting against the yellow-eyed demon, not bargaining and getting tortured for his sake. While Sam believes it's enough to save people and keep up his memory, Dean remains unconvinced.
Dean becomes more and more pressured under John's final order — to kill Sam if he couldn't "save" him — after knowledge of Sam's destiny to turn evil and side with the Yellow-eyed demon in coming war. He continues to draw in on himself, tormented between obeying his father and his love for Sam. Dean begins to consider quitting hunting, chalking the "job" as nothing more than a catalyst for all the bad luck they ever had.
During this time, after hunting cases and misunderstandings in Baltimore and Milwaukee, Sam and Dean gain attention from the cops. Dean, in particular, is described as a wanted criminal and charged for "murder" and several different crimes. Both brothers are tailed by the relentless Special Agent Henriksen and forced to cover their tracks more persistently. Sam and Dean allow themselves to be arrested once while doing a case for an old friend of John's, but soon break out of prison.
Later, Dean is caught by a djinn and cast in an alternate reality where their mother never died and he and Sam never became hunters. He has a girlfriend and a normal life. John is still dead and the brothers were no longer close since they never hunted together, though in real life Dean is slowly dying from the monster. Dean is happier in this life, but suffers the guilt of realizing every one they saved died. Ultimately Dean was forced to sacrifice his happiness for his life and the lives of everyone he saved, but the experience left him more disillusioned and tired of the hunting life.
|“||All of them. Everyone you saved, every one Sammy and I saved. They're all dead. [...] It's like my old life is coming after me or something. Like it doesn't want me to be happy. [...] Why? Why is it my job to save these people? Why do I have to be some kind of hero? What about us, huh? Mom's not allowed to live her life, Sammy's not allowed to get married. Why do we have to sacrifice everything, Dad?!||”|
— Dean talking to John's gravestone in an alternate reality
in What Is And What Should Never Be
|“||Look at me, Sam. It's not even that bad. It's not even that bad, alright? Sammy? Sam! Listen to me. We're going to patch you up, okay? You'll be as good as new. I'm gonna take care of you, okay? I'm going to take care of you. I've got you, because that's my job, right? Watching after my pain in the ass little brother? (realizes Sam is already dead) Sam? Sam? Sam?! Sammy?! No. No, no, no, no. Oh no come on. Oh God. (pulls Sam's body against his and yells) SAM!||”|
— Dean while Sam dies
in All Hell Breaks Loose - Part 1
Inconsolable, Dean lapses into anger and self-loathing. He brushes off the incoming threat and outright refuses when Bobby Singer suggests they burn Sam's body, prompting Bobby to leave the cabin. After his monologue with Sam, during which he confesses his failure as an older brother, Dean storms out of the cabin in a furious rage. At his wits end, he travels to a crossroads to recklessly make a deal with a "crossroads demon" for Sam's life in exchange for his soul. In the end, Dean is allowed one year to live and Sam is resurrected.
|“||You know, when we were little, you couldn't have been more than five, you'd just started asking questions. How come we didn't have a mom; Why do we always have to move around; Where'd Dad go.. when he'd take off for days at a time. I remember I begged you, quit askin' Sammy. Man, you don't wanna know. I just wanted you to be a kid. Just for a little while longer. I always tried to protect you, keep you safe. Dad didn't even have to tell me. This was always my responsibility, you know. It's like, I had one job. I had one job. And I screwed it up. I blew it. And for that I'm sorry. I guess, that's what I do. I let down the people I love. I let Dad down, and now I guess I'm supposed to let you down too. How can I? Am I supposed to live with that? What am I supposed to do? Sammy... God.. What am I supposed to do? WHAT AM I SUPPOSED TO DO?!||”|
— Dean to Sam
in All Hell Breaks Loose - Part 2
Sam quickly comes to life, but with no memory of anything past Jake stabbing him. Dean is overjoyed to see his brother alive, but hides the fact he died and that he made a deal. Bobby is the only one to figure it out immediately and furiously yells at Dean for his impulsiveness and sending himself to Hell. Dean explains everything to him, even admitting he felt like this deal made his life mean something again, and pleads for him to not tell Sam as he knows it will upset him.
Soon after, along with Sam, Bobby, and Ellen, Dean arrives at a Devil's Gate that had been sealed off from other demons thanks a huge devil's trap made by Samuel Colt. Jake, however, manages to open it with the Colt, releasing hundreds of demons from Hell. Dean is visibly disturbed when he sees Sam brutally kill Jake without hesitation afterwards, nursed further nursed when the Yellow-eyed Demon mocks if he truly believes what he brought back was "pure Sam". John's spirit, which escaped from Hell, suddenly appeared and distracted Azazel just long enough for Dean to kill him with the Colt's last bullet, avenging his parents' death. John makes peace with both of them, then flickers out.
Sam soon figures out Dean's deal, realizing he only has one year, and is angry and hurt over his decision. Dean pleads that his job was to protect him and he couldn't let him die like that. Sam vows to find a way to get him out of the deal and the two brothers set out to exterminate the freed demons.
|“||I've got nothing to lose now, right? [...] Dad brought me back, Bobby. I'm not even supposed to be here. At least this way, something good can come of it, y'know? It's like my life can mean something. [...] I couldn't let him die, Bobby. I couldn't. He's my brother.||”|
— Dean to Bobby on his deal
in All Hell Breaks Loose - Part 2
|“||Yeah, you're right. It was selfish. But I'm okay with that. [...] After everything I've done for this family, I think I'm entitled. Truth is, I'm tired, Sam. I don't know, it's like there's a light at the end of the tunnel [...] You're alive. I feel good, for the first time in a long time. I got a year to live, Sam. I'd like to make the most of it. So what do you say we kill some evil sons of bitches and raise a little hell, huh?||”|
— Dean on going to Hell
in The Magnificent Seven
Dean decides to make the best of his final year, indulging in various acts of hedonism while Sam tries desperately to find a loophole in the crossroads demon's deal. Dean accepts his deal to Hell with unnerving calm, telling Sam there was no way out of this without Sam himself dying again and that he should give up on saving him. Dean seems to have lost will for life and just wants to save as many people as he can before he goes. Against his brother's wishes, Sam continues to look for loopholes anyway.
While doing a case, Dean drops by an old girlfriend Lisa Braeden that hasn't seen in almost nine years. She has a son named Ben that's just turned eight and bears striking resemblance to Dean. Dean believes him to be his son. After saving them from changelings, Lisa insists Ben isn't his and she did a blood test long ago just to be sure. Dean is disappointed, admitting that since he was going to Hell he was starting to wonder what he would leave behind.
After hearing the female demon Ruby's proposition to Sam, Dean is angry at his brother's lenience with her and believes Ruby to be lying about getting him out of Hell. He refuses to trust her, though Sam wants to use her. Dean learns from a surprisingly amicable demon named Casey the chaos surrounding the demon word with Sam's refusal to lead them and how many are after his brother. After Sam kills two demons — including Casey who wanted to spare Dean — with the remade Colt thanks to Ruby and Bobby, Dean is shocked at his brother's ruthlessness and starts worrying Sam truly came back "different".
Early in the season, the brothers meet up with another beautiful woman, Bela Talbot. Bela acquires magical objects and sells them for a large profit, is unscrupulous and seemingly amoral. Meanwhile, Dean continues to bar Sam's attempts to break his deal of going to Hell, not still not to wanting Sam to risk dying. Dean tries to tell him he'll be fine with him and he's sorry for the pressure he put on him, but Sam only grows angrier and insists he care more about the fact he's dying, not how he feels.
After being pitted against Gordon Walker once again, Dean is show to be increasingly more reckless in his hunting, knowing he was going to die soon anyways. Sam is furious over this and calls out Dean's cavalier behavior on going to Hell being only a front to hide how scared he truly was. Dean denies this, but nonetheless decides to hold back on his recklessness in hunting for Sam's sake. He still seems resigned to his death, teaching Sam a "thing or two" on working on his Impala and even celebrating Christmas since it's his "last year".
Dean finally comes face to face to Ruby during a witch case, who warns them to stay away considering the powerful demon they're worshipping. Dean immediately points the Colt at her, accusing her of manipulating Sam. The two argue and Dean shoots at her, only for Sam to make him miss. He is angry at his brother defending Ruby and demands they kill her before she betrays them, but Sam is adamant on using her. Dean also confronts Sam on his growing ruthless and learns Sam is trying to "change" for this war to be "more like Dean", worrying him.
After Dean is about to die from the powerful demon's spell, Ruby suddenly swoops in and saves him with witchcraft. Dean begins to soften towards her, particularly after she fought against the head demon of the witches, but realizes she lied about being able to break his deal. The brothers also learn from her that all demons used to be human but had their humanity burned away in the fires of Hell. Dean realizes this will eventually happen to him when he goes to Hell and begins to show real fear of dying for the first time.
Ruby shares with them a knife that can kill demons. Dean begins to train Sam to fight demons alone for after Dean's contract is up.
In Dream a Little Dream of Me, when Bobby falls into a coma, Sam and Dean investigate the murder of a scientist. While viewing Dean's dreams it becomes clear that Dean believes Sam was their father's favorite but only thought of Dean as a tool. It confirms that Dean is so resigned to death out of self-loathing and his belief that he is worthless. Dean also encounters a future, demonic version of himself in a nightmare, which shocks him into starting to fight for his life. After waking up, Dean admits to Sam that he doesn't want to die. Meanwhile, Bela steals the Colt, meaning they won't have it when the hellhounds come for Dean.
|“||My father was an obsessed bastard! All that crap he put on me about protecting Sam, that was his crap. He was the one who couldn't protect his family. He's the one who let Mom die! He wasn't there for Sam, I always was! He wasn't fair! I didn't deserve what he put on me! And I don't deserve to go to Hell!||”|
— Dean to himself
in Dream A Little Dream Of Me
In Mystery Spot, Sam is forced to relive the same day, a Tuesday, over and over again. On each new day, Dean dies a different way despite Sam's frantic efforts to save him. Sam later discovers that the culprit is the Trickster, a villain from Season 2. It finally becomes Wednesday, but this time, Dean dies and doesn't come back. Sam spends months trying to hunt down the Trickster, who reveals that he has been trying to get Sam to understand that he and Dean can't keep making sacrifices for each other, and that Dean is going to die no matter what Sam does. The Trickster then sends Sam back to Wednesday, despite Sam failing to learn the Trickster's lesson. Sam is warned by Ruby that Dean might not make it back from hell.
In Jus In Bello, the FBI and Agent Henriksen capture Sam and Dean, thanks to a tip from Bela. While Sam and Dean are in jail, a host of demons come to kill them. This causes Henriksen to believe their stories and ask how to defeat the threat as Ruby comes to help them, but is furious to learn that they have lost the Colt. She says that she knows of a spell that will destroy all the demons nearby, including herself, and that she is willing to die in order to help Sam. However, they will need the heart of a virgin. Sam and the virgin, Nancy, agree to the plan, but Dean refuses to let her die. Dean's plan to exorcise the demons works, but one demon manages to escape and tells Lilith who, taking the form of a little girl, blows the police station up, killing everyone inside.
Lilith, it turns out, wants to kill Sam, as she sees him as a rival. According to Azazel's plan, Sam was supposed to lead the demon army, and Ruby was ready to follow Sam. Now, Lilith has become their main enemy.
Dean and Sam do a case of people committing suicide because of phone calls from their dead loved ones'. Dean gets a call from John, who tells him the demon is holding his contract is in town and there's an exorcism that can kill it. Despite the suspicious timing, Dean obeys the phone calls unquestionably in hopes he could be saved. In actuality, the calls were a Crocotta. Lured to a house, Dean nearly kills a man until he realizes it was a human and not a demon. After killing the monster, Dean apologizes to Sam and admits he just wanted to believe there was a chance he could've been saved.
|“||I wanted to believe so badly there was a way outta this. I mean, I'm staring down the barrel at this thing. Y'know, Hell, for real, forever and I just ...[...] I'm scared Sam. I really, really scared. I guess I was willing to believe anything.[...] Hope doesn't get you jack squat. I can't expect Dad to show up with some miracle at the last minute. I can't expect anyone to, y'know? I mean, the only person that can get me out of this thing is me.||”|
— Dean to Sam
in Long-Distance Call
Dean continues to search for a means to save himself from his fate, though knows there is likely no way out of it. Shortly before Dean's contract comes due, he learns from Bela that Lilith, the demon pursuing Sam, holds his contract; Bela had also made a deal with a demon. Bela pleads with Dean that she needs help and explains everything. Dean is unsympathetic, telling they might've helped her if she told them sooner and leaves Bela to die by Hellhounds and dragged to Hell.
As the brothers search for Lilith with Bobby's help, Dean begins suffering nightmares and hallucinations of his hellish fate. When Lilith is located, the three head to New Harmony, Indiana, and Dean discovers that he now has the ability to see the faces of demons underneath their human hosts.
|“||If this is my last day on earth, I don't want it to be socially awkward.||”|
— Dean to Sam
in No Rest for the Wicked
Dean, with 30 hours left, still desperately tries to free himself. However, Dean outright refuses to summon Ruby when Sam suggests to and reiterates he still sees her as nothing more than a liar and a manipulator. Knowing Sam would summon her anyway, Dean challenges her and uses the opportunity to steal her demon-killing knife. With help from Bobby, he discovers Lilith is in Indiana. While the trio head to Indiana, Dean discovers he can see who is possessed and can see demons, such as hellhounds. After a quick struggle with Ruby, the four manage to escape a mob of demons using holy water. Now inside the house where Lilith was hiding, the three quickly manage to locate her.However, Dean discovers that Lilith has switched bodies as Sam is about to kill the little girl. As the clock strikes midnight, Dean smiles and tells Sam to be brave and to continue what he's doing. The brothers and Ruby run from the hellhounds and place a salt barrier to protect themselves. However, Dean realizes Lilith is in Ruby.
|“|| Sam: "I'm not gonna let you go to Hell, Dean!" |
Dean: "YES, YOU ARE! Yes, you are ... I'm sorry. I mean, this is all my fault. I know that. But what you're doing, it's not gonna save me. It's only gonna kill you. [...] Keep fighting. Take care of my wheels. Sam, remember what Dad taught you ... okay? And remember what I taught you."
— Dean shortly before he dies
in No Rest for the Wicked
Too late. The demon uses her powers to subdue the two, opening the door for the hellhounds. Sam watches as his brother is mauled to death by the hellhounds, pleading that Lilith stop. As Lilith leaves an unconscious Ruby, Sam holds the dying Dean in his hands, frantically yelling out to him.
Now in Hell, Dean is tortured and desperately yelled out for help, calling out to his brother Sam but receives no help.
Dean was in Hell for a total of four months, which he later states "felt like 40 years", as in Hell, time is different from the mortal world. He was tortured by a demon named Alastair every day, and was even offered the option to torture other souls instead. Dean repeatedly refused his offer for thirty years until finally giving in, triggering the first seal to Lucifer's Cage.
|“||Do you even know how far off the reservation you've gone? How far from normal? From human?[...] Slippery slope, brother. Just wait and see. Because it's gonna get darker and darker and God knows where it ends.[..] It's already gone too far, Sam. If I didn't know you ... I would want to hunt you.||”|
— Dean to Sam
The fourth-season premiere, Lazarus Rising, begins four months after the third-season finale. Dean awakes to find himself in a coffin and manages to dig himself out. He then breaks into a nearby gas station where he gets some water, food and cash. Before leaving the store, Dean finds his injuries from his fight with Lilith was healed but sees that he has a hand mark on his shoulder as the television and radio flicker on and a powerful whine that shatters the gas station's windows. Dean calls Sam but learns that Sam's number has been disconnected. He calls Bobby who hangs up on him and threatens to kill him the second time he calls. As a last resort, he hot-wires a parked car and goes to Bobby's house. A fight ensues until Dean is able to prove to Bobby that it is really him by using a silver knife and holy water on himself. Dean and Bobby then believe Sam had a hand in his resurrection and find him in a town right near where Dean was buried and the latter has the same reaction Bobby had but is soon persuaded that it's really his brother resurrected. Dean questions why Sam was in a hotel with a girl, who as it turns out, is Ruby in a new vessel, and it becomes clear that Sam lied to Dean when he told him he didn't know where Ruby was. Sam claims that he was in town searching for a demon.
The Winchesters soon attempt to track down the force that ripped Dean from Hell. Dean is functional, albeit dazed, from his experience in Hell. He claims he has no memory of it, but it's clear it's a lie as he continues to get flashes of the torture, becoming shaken up by the thought. At first, Dean believes Sam made a deal to save him and is furious, but Sam insists while he tried, it wasn't him. The brothers see a physic named Pamela Barnes who flirts with them and reveals through a séance that the being who saved Dean was named Castiel before her eyes are burned out for looking at its true form, despite its warning. By the end of the episode, Dean and Bobby go to a barn where they are approached by a mysterious being who takes their bullets and knife attacks with no problem as he knocks out Bobby. It is revealed that the being is the same person who rescued Dean, Castiel. Dean questions what he is as Castiel reveals he is an angel who pulled Dean from Hell on God's command. Dean doesn't believe it, thinking angels don't exist. He is silenced when Castiel reveals his Angel's Wings, proving his story. Though shocked to see an actual angel before him, Dean berates him for what he did to Pamela, as Castiel brings up he did warn her as his true form was overwhelming. He then tells Dean that his true voice was the same shriek Dean heard at the gas station and hotel so he took on a vessel to better communicate. Dean then asks why he was saved as Castiel tells him God has work for him.
In Are You There, God? It's Me, Dean Winchester, Dean is still unwilling to believe angels exist and is unnerved that God himself ordered him to be brought back. He becomes further disillusioned, showing contempt for God allowing all these horrible things to happen to people and not absolutely anything to stop it. However, he soon calms down after Bobby and Sam show him proof and how he's lucky to be alive again.
During this time, the brothers are haunted by the ghosts of Meg Masters, Henriksen and Ronald Reznick who want to kill them for not saving them. Bobby figures out they're witnesses and the appearance of them is meant to be the first sign of the apocalypse. Dean, with guidance from Bobby, ultimately lays their souls to rest.
That night, Dean is visited by Castiel who appears to him in a dream. Dean is informed that Lilith cast a spell that released the Witnesses. He explains that this is the first of the 66 Seals that, if all broken, will release Lucifer, who Dean didn't think was real until he learns this is why Angels have returned to Earth. When Dean protests that they didn't come to help them deal with the Witnesses, Castiel says that the armies of Heaven have bigger concerns. He also says that some of the Angels died in battle that week and that Dean should show him more respect if he doesn't want to be thrown back into Hell.
|“||See, this is why I can't get behind God. [...] If he doesn't exist, fine. Bad things happen to good people. That's how it is. There's no rhyme or reason. Just random, horrible evil. I get it, okay? I can roll with that. But if he is out there, what's wrong with him? Where the hell is he while all these decent people are getting torn to shreds? How does he live with himself? You know, why doesn't he help?||”|
— Dean's disgust with God
in Are You There, God? It's Me, Dean Winchester
He soon reveals the angels are trying to stop Lilith breaking the 66 Seals for if she does, Lucifer will be freed from his cage and walk the Earth. Dean believes that Lucifer is a fairy tale told in "Demon Sunday School," but Castiel is serious and confirms Lucifer is all too real. Castiel's warning confirm Bobby's suspicions on the Apocalypse if Lucifer is set free. The next morning, Dean asks Sam if he believes in the Devil.
In In The Beginning, it shows Dean sleeping and having nightmares about his time in Hell. He wakes up to Castiel watching him, with a touch Castiel sends him to 1973 where Dean learns about the Winchester and Campbell history. He meets his parents, John Winchester and Mary Campbell, before he is born. Although tempted to stop Azazel from killing his mother, he realizes that he and Sam will no longer be hunters and all the people they saved will die. Dean learns that his father was not always a hunter but his mother was a hunter and came from a long line of hunters. Dean also learned he and Sam were named after their grandparents.
Teaming up with his future mother and grandfather, they plan to take out Azazel with a borrowed Colt. Azazel, however, is one step ahead and possesses Samuel, Dean's grandfather. Dean fails to stop him and the possessed elder finds John about to propose to Mary. Azazel kills John and makes a deal with Mary. A heartbroken Mary confirms a deal with Azazel, allowing him "permission" in 10 years. Dean arrives shortly and watches the future being set in motion before Castiel appears and sends Dean home as he realizes he can't change destiny. Castiel then warns Dean of Sam's dark actions behind his back and he must stop it before the angels have to kill Sam. Castiel gives Dean the location, he goes there and sees Sam's actions for himself.
|“||Your brother is headed down a dangerous road, Dean. And we don't know where it leads. So stop it... or we will.||”|
— Castiel to Dean
in In The Beginning
in Metamorphosis, Dean catches Sam exorcising a demon with his mind and discovers Ruby is still working with him. He is furious with Sam for lying and using his demon-given powers, punching him twice for it. Dean reveals Castiel told him of the events and the warning, he tells Sam this means God doesn't want him doing it either. Sam explains he's using it to help people. Dean is unconvinced, knowing it was only going to get darker from here. The brothers argue, but after a case of a rugaru, Dean acknowledges he was too judgmental, though stands by his uneasiness over his psychic ability. Sam suddenly tells him he was right and that he wasn't going to use his powers anymore.
Dean continues hunting with Sam, but still suffers from flashes of his torment in Hell. It's revealed time flows differently in Hell and he was there for "forty years" rather than four months. Despite this, he still hides this from his brother. Dean also begins to feel the weight of the angels' special interest in him and feels more responsible for people's lives.
In Monster Movie, Dean admits while he recently resented the cost of hunting, ever since he came back from Hell he sees it as more as a "mission from God". After saving a woman from a shapeshifter, he presumably slept with the woman later, Dean soon realized hunting was something he knew best and accepted it.
In It's the Great Pumpkin, Sam Winchester, Dean and Sam work to stop the rise of a powerful demon called Samhain, who's presence would break one of the 66 seals. They investigated a series of deaths in town and suspect they are being done by a witch who they believe is masquerading as a teenager to fool people.
Heading to their motel room, they find two people waiting for them and Dean stopped Sam from attacking them. He introduced Sam to Castiel before they met Uriel who were prepared to wipe out an entire town to stop the demon Samhain from rising, since it was a seal. However, both brothers refuse to let that occur.
The angels back down under Dean's orders, who forces them to give them more time to stop it. Unfortunately they fail and the seal breaks, letting Samhain roam free. Sam manages to use his psychic ability to exorcise the demon, which Dean witnesses in secret.
|“||So I failed your test, huh? I get it. But y'know what? If you waved that time-travelling magic wand of yours and we had to do it all over again, I'd make the same call. 'Cause see, I don't know what's gonna happen when these seals are broken. Hell, I don't even know what's gonna happen tomorrow. But what I do know is that this, here? These kids, the swings, the trees ... all of it is still here because of my brother and me.||”|
— Dean to Castiel
in It's the Great Pumpkin, Sam Winchester
In the aftermath, Castiel visits Dean at a park and the two talk. Castiel reveals he's not as black-and-white as the other angels and their "true" orders is to follow whatever Dean says. The choice with the town had been a test. Castiel informs Dean that a seal is still broken nonetheless and he doesn't envy his importance in the upcoming battles.
Dean starts to become overwhelmed by all his memories of Hell, using alcohol and work as a crutch. Sam, who was told by Uriel that Dean actually remembers Hell, is suspicious of his excessive drinking and tries to get Dean to tell him the truth.
Eventually, Dean is confronted by Sam on this while on a case Dean at last admits he remembers Hell, but refuses to open up about it, telling Sam there's nothing he could say to make him feel better.
In I Know What You Did Last Summer, Dean and Sam hearing a young woman in a mental ward named Anna Milton who hears angels and has suspiciously accurate knowledge about the apocalypse. Sam and Dean warily protect her, knowing she didn't seem like a bad person. However, they're attacked by a powerful demon named Alastair, Hell's grand torturer who Dean has a history with "downstairs". Sam and Dean are badly wounded, but manage to get Anna to safety and escape. During this time, Dean finally learns what Sam did during the four months he was in Hell and why he suddenly trusts Ruby so much. Dean still doesn't trust Ruby fully, but is grateful she was there for Sam. Just then, Castiel and Uriel appear and Dean wanted them to help but they demand for Anna to kill her.
In Heaven and Hell, both brothers refuse to hand Anna over. Anna then activates a angel banishing sigil with her blood, though doesn't know how she knew. Sam and Dean take her to psychic Pamela Barnes to retrieve her memory and it's revealed Anna was once an angel who "fell" for becoming too human (catching human emotions). The group tracks down Anna's grace which will turn her into an angel again and grant protection, but the time they arrive at the location it's already gone. During this time, Dean develops a soft spot for Anna, intrigued that she'd rather be human than an angel and relates to her unease of taking orders from an absent father.
Sam, Dean, and Ruby continue to protect Anna, but the angels raise the stakes and demand her or they'll send Dean back to Hell. Still they refuse. Anna and Dean have a moment and soon have sex in the backseat of The Impala, but Uriel invades Dean's dreams and catches onto Dean's reasons for helping Anna. He threaten to throw Dean back in Hell but Dean is unfazed before Uriel threatens to kill Sam. Dean reluctantly gives up their location, but demons appear too and a battle between both sides take place. During the fray, Dean saves Cass from Alastair until the demon knocks him away. With everyone distracted, Anna takes her grace and becomes an angel again, disappearing in a white light.
In the aftermath Dean, finally reveals to Sam what happened to him in Hell: Time flows differently there, so four months on Earth was forty years in Hell. During that time, he was "cut, carved, and torn" until there was nothing left of him, only to be made whole again just so the demons could start over. Dean reveals that at the end of every day the demon Alastair would offer to take him "off the rack" if Dean would put other souls on and torture them. Dean resisted for thirty years (three months), but eventually gave in and spent ten years torturing people in Hell to escape being tortured himself.
In Family Remains, Dean confesses to Sam that he enjoyed torturing souls, as he finally had the chance to dish out the same pain that he'd endured for the past thirty years.
|“||It wasn't four months, you know. It was four months up here, but down there...I don't know. Time's different. It was more like 40 years. [...] They, uh... sliced and carved and tore at me in ways that you... Until there was nothing left. And then, suddenly... I would be whole again... like magic... just so they could start in all over. And Alastair...at the end of every day... every one... he would come over. And he would make me an offer to take me off the rack... if I put souls on... If I started the torturing. And every day, I told him to stick it where the sun shines. For 30 years, I told him. But then I couldn't do it anymore, Sammy. I couldn't. And I got off the rack. God help me, I got right off it, and I started ripping them apart. I lost count of how many souls. The -- the things that I did to them. [...] How I feel... this... inside me... I wish I couldn't feel anything, Sammy. I wish I couldn't feel a damn thing.||”|
— Dean on his experience in Hell
in Heaven and Hell
In Death Takes A Holiday, in a case involving ghosts and people not dying Dean meets up again with the reaper, Tessa, who greets him but he doesn't remember her until she kisses him. This awakens his memories of their previous encounter with a kiss, as Dean confesses that there has been a "hole" in his mind since that time and realizes that it is related to her. Soon after, Tessa is taken by Alastair in his quest to break another of the 66 seals; breaking the current seal involves killing reapers. The boys ask their psychic friend Pamela Barnes to help them astral project so that they may find the kidnapped reapers. Once they have, they are captured, but Sam is able to break them out and Tessa is able to continue reaping souls. However, before Dean is able to return to his body, Alastair corners him only to be captured by the angels; Castiel then appears and informs Dean that they have won this seal. As Dean awakes in his body, Pamela is dying from the injuries she obtained during a fight with a demon, while the boys were "out." Dean and Sam sit beside her as she dies, but Pamela secretly whispers to Sam she "sensed" his powers and his intentions are far from pure.
Since he was Alastair's "student" in Hell, Dean is pressed into service by Castiel and Uriel, who need him to torture Alastair for information on who is killing angels in On The Head Of A Pin. Dean refuses at first, he requests Uriel leave while he talks to Cass and Uriel is amused by his defiant attitude. Dean asked Castiel about him taking orders from Uriel as Castiel reveals he was demoted for getting too close to Dean. Though Dean tells him again, he doesn't want to stir his old self who tortured in Hell, but eventually agrees.
Dean brutally tortures him and even seems to enjoy it, but is distracted when Alastair succeeds in getting Alastair to reveal that Dean himself was the first seal to break by virtue of giving in and torturing souls in Hell. ("The first seal shall be broken when a righteous man sheds blood in Hell. As he breaks, so shall it break.") It was also revealed Dean's father John was originally meant to break it after his death, but even after a hundred years of torture, he still didn't break. As a result, Dean is plagued with further guilt and self-loathing as well as the realization he still couldn't live up to his father.
Alastair manages to free himself, the Devil's Trap set up by Castiel having been eroded by a leaking pipe. Alastair nearly kills Dean and then comes close to sending Castiel back to Heaven when Sam, having grown stronger in his demonic abilities, arrives and uses his powers to torture Alastair in to revealing he does not know who is killing the angels; Sam kills Alastair shortly thereafter. Later, as Dean recovers in the hospital, Castiel informs him about Uriel's betrayal; Uriel had been killing angels who did not join his cause to free Lucifer from Hell. Castiel also confirms Alastair's claim that Dean was the first seal, but adds that because of this, Dean is the only man capable of averting the Apocalypse. However, Dean does not believe he is able to do it and tells Castiel to find someone else as tears run down his face.
|“|| Castiel: "It's not blame that falls on you, Dean. It's fate. The righteous man who started it is the only one who can finish it. You have to stop it. [...] I know our fate rests with you."|
Dean: "Well, then you guys are screwed. I can't do it, Cass. It's too big. Alasdair was right. I'm not all here. I'm not-I'm not strong enough. Well, I guess I'm not the man either of our dads wanted me to be. Find someone else. It's not me.
— Dean rejecting carrying the fate of the world
in On The Head Of A Pin
In It's A Terrible Life, in an effort to put Dean back on the "right path," Zachariah, Castiel's superior, re-writes Dean and Sam's memories to remove their knowledge of supernatural creatures, making them believe they are average people working regular jobs, and drops them in a haunted building. Ironically, Dean, unlike Sam, is the one who most rebels against life hunting monsters, but eventually realizes he wasn't meant for his normal job. After the brothers proceed to defeat the ghost behind the hauntings, Dean quits his job before Zachariah (who posed as Dean's boss) restores Dean's memories to show him that hunting is in his blood. This only renews Dean's resolve and Dean threatens to later kill the angel.
In the episode The Monster at the End of This Book, Dean and Sam discover their lives were turned into a book series called "Supernatural" by a prophet named Chuck Shurley and that he had a vision of Lilith coming to town and about to sleep with Sam. While Sam wants to use it as a plan to kill Lilith, Dean refuses and knows they're not ready to kill her. Dean admits he doesn't trust Sam, that he knows that he killed Alastair, but not how and is afraid he'll turn evil. He enlists Castiel for help and the angel suggests he uses Chuck as bait. Dean brings Chuck to the motel room where Lilith is. Her presence near Chuck summons an archangel. Lilith is thus forced to flee. Sam tells Dean the vision was Lilith making a deal with him — the deal was they both die and she doesn't break any more seals (it's written she doesn't survive the apocalypse) — but he refused it on the grounds of not trusting her. Dean doubts his sincerity, knowing demons rarely break contracts, and fears Sam might now value revenge more than self-sacrifice.
During Jump the Shark, Dean and Sam are contacted by a young man named Adam Milligan who claims their late father is his father as well, making him their half-brother. The two go to meet him suspicious with Dean even preparing traps to expose him as a monster but nothing works. As Adam talks about John, Dean becomes frustrated and soon explodes as Adam begins to describe John's beautiful Impala, angrily insisting he's lying. "I'm sorry, but the who the hell are you to call me a liar?" Adam asks. "We're John Winchester's sons, that's who!", Dean yells. Adam stares, audibly shocked that he has brothers. Dean, adamant that they are not brothers, accuses him of being a hunter playing games. Adam angrily retorts that he's never been hunting in his life. Exasperated, Dean gets up to leave and tells Sam to follow. Adam calls out after them that he can prove it.
At the Milligan's house, Dean realizes it was all true as he and Sam stare at a picture of their father and Adam together. Trying unsuccessfully to contain his ire, after he finds out that John took Adam to a baseball game for his fourteenth birthday. "He took you to a friggin' baseball game?" He asks twice, to confirm. Adam says yes and quite innocently asks what "Dad" did for Dean's birthday. He can only manage a fake smile in response. Sam asks Adam how long his mother has been missing and he replies that a neighbor saw her three days ago. Her supervisor at the hospital called the police when she failed to show up at work. He says he drove home from school as fast as he could."She wouldn't leave without telling anybody. It was like she just dropped off the face of the earth, you know? "
Convinced, Sam and Dean help Adam figure out what happened to his mother, and it isn't until Adam demands answers that Sam reveals (despite Dean's protests) about hunters and hunting.
Adam seems cool with it and even wants to partake, but Dean refuses. He points out that John wanted to protect Adam from this life, yet Sam goes ahead and teaches him some skills.
While Sam is teaching Adam, Dean goes about the town asking for clues and only gets small details. Dean then goes back to his brothers and helps Adam save Sam from something grabbing him under the truck. Afterwards, Sam suggests they use Adam as bait (much as he dislikes the idea, Dean outright refuses) and starts to train him. Dean is still not liking the idea because he wants Adam nowhere near the hunting lifestyle.
While Dean is out, he heads to the cemetery and while searching for something he is trapped in the crypt by something. As he looks for a way out, he finds a tunnel leading to a hidden room. He crawls in and sees a severed arm on the ground with a pair of eyeglasses lying next to it, which he recognizes as Joe Barton's. Suddenly, he hears the blocks shifting at the entrance and looks up to see them being moved back over the hole. He fires his shotgun, but dirt falls down and fills up the tunnel.
Dean is searching for a way out of the crypt when he notices a fairly new looking coffin at the side. He opens it to find Kate, the bottom half of her body torn apart. He opens the other and discovers Adam's body in the crypt before returning to save Sam.
At that moment, "Adam" had captured Sam along with his "mother". It is revealed the two are ghouls who are the children of the Ghoul that John killed years ago and they wanted revenge on him, so they killed people he was close to in town and took on the forms of Adam and Kate intending to lure him back. Since John was already dead, Dean and Sam had to pay the price for his crime against their family. Adam's "mother" then taunts Sam by revealing him that the real Adam was indeed their brother.
After they've defeated and killed the ghouls, Sam and Dean give the real Adam a hunter's funeral in respect for the brother they never knew.
In The Rapture, Castiel contacts Dean in his dreams to warn him about something, but is expelled from his vessel Jimmy Novak and sent back to Heaven for his near-rebellion. Dean later witnesses Sam drink the blood of a demon in the midst of battle and then promptly exorcise a demon possessing Amelia Novak, discovering the source of his power. Meanwhile, Castiel, now restored in his true vessel, dismisses his warning to Dean and that his allegiance lies only with Heaven.
Later in the Impala, Dean tells Sam he has nothing to say about him using his powers before Sam receives a request to go to Bobby's house. Once there, it is revealed Dean and Bobby tricked Sam and lock him in Bobby's panic room to detox him from the demon blood.
While Sam is going through painful withdrawal symptoms from the demon blood, Dean asks Castiel for help. He takes an oath to serve God and the angels if it would mean that Sam wouldn't have to kill Lilith. Sam escapes the panic room after Castiel releases him, and Dean tracks him down to a hotel, despite Sam's efforts to shake him. They argue over whether or not Ruby is corrupting Sam, if Dean is supposed to stop the Apocalypse, and if Sam is turning into a monster. The argument leads to a fight that Sam wins. On the floor and in pain, Dean calls to Sam, "If you walk out that door, don't you ever come back" — the same ultimatum John gave Sam when he left for college years before — after which Sam leaves the room.
|“||She's poison, Sam! Look what she did to you. I mean, she up and vanishes weeks at a time, leaving you cracking for another hit. [...] That is French for manipulating your ass ten ways from Sunday! [...] You don't know what you're doing, Sam. [...] Because it's not something you're doing, it's what you are! It means ... it means you're a monster.||”|
— Dean'a anguish at Sam's choices
in When the Levee Breaks
Dean swears his alliance to serve Heaven and is then held captive by Zachariah. Zachariah tried to appease Dean by giving him his favorite foods and drinks but Dean did not partake and asked questions but was ignored by the latter. Dean soon realizes the angels never wanted to stop the Apocalypse and that they want to free Lucifer to destroy him. Dean does have a "destiny", but only to stop Lucifer. A paradise will exist once Lucifer is destroyed, but at the cost of thousands of lives. Zachariah says Sam as well plays a part while Dean horrified at their lack of concern for the lives of innocent people and asks where God is in this plan and is told he left. Desperate to get free, Dean tries to persuade Castiel to helping him but the latter can't since they would be hunted down and Dean tells him to leave.
Eventually, Dean nearly gives into the food before Castiel returns and banishes Zachariah with an angel banishing sigil. He admits Lilith is the final seal and tells Dean this is his chance to stop Sam. He teleports them to Chuck's house and holds off the Archangel as Dean goes after Sam, but Ruby who had been manipulating Sam all along for this moment, shuts the door on him. After Sam kills Lilith, Dean presses at her as she tells him he's too late but he ignores her and with help from Sam kills her. Sam, ashamed and broken beyond description, apologizes. The season ends with Sam and Dean watching as Lucifer rises and the Apocalypse begins.
|“||Destiny? Don't give me that destiny crap. It's all a bunch of lies, you poor, stupid, son of a bitch! It's just a way for your bosses to keep me and keep you in line. You know what's real? People. Families. That's real. And you're gonna watch them all burn? [...] You can take your peace and shove it up your lily-white ass. 'Cause I'll take the pain and the guilt. I'll even take Sam as is. It's a lot better than being some Stepford bitch in paradise!||”|
— Dean to Castiel
in Lucifer Rising
|“|| Dean: It's my job. Somebody has to save people's asses', yours included. [...] I mean, it's a damn biblical Apocalypse, and if I don't stop it and save everyone, then no one will and we all die.|
Dr.Carthwright: That's horrible. [...] I mean, apocalypse or no apocalypse, monsters or no monsters ... that's a crushing weight to have on your shoulders. To feel like six billion lives depend on you ... God. How do you get up in the morning?
Dean: ...That's a good question.
— Dean's burden
in Sam, Interrupted
The fifth season picks up right where season 4 ends when the portal to Hell opens. As Lucifer escapes, the brothers are teleported into an airplane by an unknown force (later revealed to be God). They travel to Chuck's house and learns from him that Castiel was killed by the Archangel and are dismayed to learn that. Zachariah and two other angels teleport inside Chuck's house and he tells Dean that play time is over and that he needs to come with him. Dean angrily tells him to stay away from him, causing the angel to note Dean is upset. Dean voiced that it's because the angels started the Apocalypse, Zachariah corrects him and states that they let it happen, they didn't start it. Dean is annoyed when the angel deflects the full blame on Sam and states that he had a chance to stop Sam and failed, but now they're on the same team again, since both the brothers and the angels want Lucifer dead. Dean refuses again to go with them, Zachariah angrily explains that they need to strike now before Lucifer finds his vessel and that Dean has the power to stop Lucifer, but he needs their help. Dean angrily tells them that he wants nothing from them because of their manipulations. Zachariah begins to approach Dean to tell him more, but stops when he notices that Dean's hand is bleeding. Stating that it is an insurance policy in case the angels showed up, Dean reveals an angel banishing sigil and banishes Zachariah and his men, as revenge for their manipulation. Dean states that it was a trick he learned from Castiel
At a motel, they go over how to find a way to defeat Lucifer. The brothers soon meet Becky Rosen, a fan of the books about them who tells them that Michael's sword is on earth. Afterwards, they call Bobby who tells them of the Archangel Michael. Dean watched as Bobby scolded Sam for his actions and his brother leaving the room. Dean then gets the location before he is attacked by Bobby who is possessed by a demon. Dean also meets Meg again who voices her chance to kill him since he is so important. She kisses Dean roughly, to his disgust and instructs the possessed Bobby to kill him but instead of killing Dean he kills the demon inside himself, using Ruby's knife, in turn paralyzing himself from the waist down. Dean then kills the other demons in the room as Sam returns and helps, Dean advances on Meg but she flees her vessel. The brothers rush the injured Bobby to a hospital and make their way to the lock-up.
At their father's lockup, they are confronted by Zachariah and Dean is told that he is really the "Sword of Michael", which means the Archangel Michael will use his body as a vessel to lead the forces of Heaven. Dean was shocked to learn he is the Archangel's true vessel but refuses to give up his body as Sam is tortured by Zachariah. An irritated Zachariah tells Dean of his importance, as Dean realized that Michael needs his consent and Zachariah begrudgingly confirms this by offering bribes such as healing Bobby. Dean appeared tempted but refused even stating there has to be another way to stop Lucifer. Zachariah states there is no alternative and tortures Dean, as he tells him to comply but Dean tells Zachariah to kill them before a resurrected Castiel arrives and saves them. Castiel then forces a scared Zachariah to fix the brothers and leave after hinting how he returned was connected to the brothers being placed on the plane. Castiel brands them with an Enochian Sigil, hiding them from all demons and angels, Lucifer and himself included. Dean's relationship with Sam is severely damaged by Sam starting to Apocalypse and eventually he admits to him he doesn't think he can trust him the way he did ever again.
In Good God, Y'all, Dean and Sam fight the Horseman War in a town where the people think that their neighbors are demons. In this town are Ellen, Jo, and Rufus all trying to hunt the demons, who turn out to be normal people War has altered to make look like demons. Once the brothers cut the ring finger off of War, sending the town back to normal, Dean worries that Sam cannot control his urge to drink demon blood. The brothers then agree to go their separate ways because Sam is a liability with his demon blood lust.
In Free To Be You and Me, Dean does solo hunts in the meantime. Later, Castiel finds Dean and they work to draw out the Archangel Raphael to ask the location of God. Dean also gets a glimpse of possession by an Archangel when seeing Raphael's comatose vessel. He grows closer to Castiel, admitting he had more fun with him in 24 hours than he had with Sam in years. Dean and Castiel later succeeded in drawing out Raphael, who threatened to take Dean to Michael. Dean refused to go with him, in spite of Raphael threatening torture, before Dean traps him in a Holy Fire circle. Dean watched as Raphael told them God was dead but Castiel rejected this by bringing up his resurrection, to which Raphael stated Lucifer could have did it. Though Castiel denied this and told Dean they are leaving, as Raphael demanded his release and threatened to find them, but Castiel left him where he was, telling him that "Maybe one day, but today you're my little bitch". This comment amused Dean, who agreed with Cass.
In The End, Dean is contacted by Castiel over their plan to fight Lucifer and is amused by him having problems with his cellphone. Dean sets an appointment for Castiel to retrieve him. Later that night, Sam contacts Dean to tell him that he is Lucifer's vessel, which meant the angels would fight each other in the brothers' bodies. Dean was not too surprised by this revelation as Sam tries to get back to hunting with him but Dean refuses. Subsequently, he is transported five years in the future by Zachariah to the year 2014. Zachariah revealed how he located Dean and tells him to endure three days until he is ready to consent to Michael. Dean meets his future self, a hardened and cynical leader leading a ragtag group of Croatoan Virus survivors in a post-apocalyptic world. Present Dean realizes Future Sam said "yes" to Lucifer and that Future Dean's biggest regret was never agreeing to Michael to stop all this from happening. Dean is shocked at his future self's ruthless, both in torture and willingness to sacrifice his friends to defeat the devil. Future Dean knocks his present self out and recklessly goes ahead with his plan to use the Colt on Lucifer, only to die at his hands which his arriving counterpart witnesses. Dean was horrified and enraged to see Lucifer possessing his brother as the latter tells present Dean nothing will change this outcome though Dean promises to find a way to kill him before he is brought back to present by Zachariah.
Despite Zachariah and Future Dean's protests, Dean still refuses to become Michael's vessel before Castiel rescues Dean from Zachariah. Nonetheless shaken by his grim future, Dean calls Sam and decides they should stay together to "keep each other human".
In the episode Changing Channels, the brothers are investigating a case where a person was killed in a bizarre way. They realize it was The Trickster, who Dean was eager to get payback on for killing him multiple times. After tracking him, the brothers are thrown in an alternate universe where they're in TV shows and have to "play their roles". It's revealed this had been another "lesson" by The Trickster to "accept" their roles as Michael and Lucifer.
When Castiel tries to save them, he is warped away. After going through more shows, they are warned by Castiel that trickster may be something else, before he is banished by him, to Dean's anger. After a failed attempt to kill him, they go over clues that give an answer such as the Trickster's familiarity with Cass and his reaction to a comment Dean made causes them to realize the trickster was an angel all along. After pretending to surrender, they trap him in a ring of holy fire, Dean and Sam learn that he is really the archangel Gabriel, who fled Heaven as he couldn't bear his father and brothers fighting. They then learn why they are the true vessels of the Archangels as their relationship mirrored the angels. Dean learns that as the older brother who is loyal to an absent father, his relationship was similar to that of Michael and God's relation which was only further proof there was no stopping their "destiny". Dean and Sam still refuse, though began to doubt how they'll be able to stop the "inevitable". Dean then forced Gabriel to bring Castiel back after threatening him. They start to leave while Gabriel asks if they intend to leave him trapped as Dean berates him for not standing up to his family before releasing him from the holy fire trapping him.
|“||No, we're not. 'Cause we don't screw with people the way you do. And for the record, this isn't about some prized fight between your brothers or some destiny that can't be stopped. This is about you being too afraid to stand up to your family! Don't say I never did anything for you.||”|
— Dean to Gabriel
in Changing Channels
After a time at a Supernatural convention, Dean and Sam learn from the Becky the Colt is in possession of a demon named Crowley, who gives the Winchesters the gun to kill Lucifer and end the Apocalypse. Sam and Dean spent their "last night on Earth" with Jo, Ellen, Castiel and Bobby before setting out to find and kill Lucifer the next day. While looking for Lucifer in Carthage, Missouri, Castiel sees reapers all over the town and is later captured by Lucifer while investigating. The hunters run into Meg, who sicks a pack of hellhounds on the group. Jo is severely injured by one of the hellhounds during their escape while saving Dean.
The group finds shelter in a hardware store where they make bombs out of rock salt and iron nails to kill the hellhounds. Jo plans on setting off the bomb since she is going to die anyways, but Ellen insists on staying with Jo and both die in the blast. Sam and Dean find Lucifer performing his ritual. Dean manages to shoot Lucifer point-blank with the Colt, only to find it has no affect. The Winchesters find out Lucifer is one of the five things in the world the Colt cannot kill. The brothers return home and both grieve with Bobby for Ellen and Jo. Having failed to kill Lucifer and lost two allies and friends, Dean becomes more disillusioned and hopeless.
Sam and Dean check themselves in a mental institution to hunt a monster for their old friend Martin. Dean admits he feels personally responsible for the lives of everyone, not just a few. It's indicted in the hallucinations the wraith conjures for him that this mostly driven out of his own self-loathing enhanced by Jo and Ellen's death along with his failure to kill Lucifer, believing that he can never save anyone and always fails. The brother manage to kill the wraith and break out of the institution.
While having a dream, Dean is visited by Anna who requests a visit from him and Sam but Cass goes in their place. Anna travels back in the year 1978 to kill John and Mary, resolving to prevent the Winchesters' birth to stop the Apocalypse and Lucifer, Dean and Sam follow her with help of Castiel. The brothers work with their younger parents, but Anna enlists the help of a past Uriel and soon catches up with them. Dean struggles against Uriel.
Ultimately, Anna succeeds in landing a fatal blow on Sam, but Michael at last appears (in John's body) and burns her alive before banishing Uriel. Realizing who he is, Dean demands for Michael to heal Sam but the latter says they need to have a long awaited talk. Dean discovers that his whole bloodline are possible vessels dating back to Cain and Abel (their ancestors), but he is Michael's true vessel. Michael appeals to Dean that he can relate to him for his love to his little brother, but he still has to kill Lucifer for his father. Dean doesn't like the idea but Michael counters saying everything happened due to destiny, and that free will is an illusion. Michael tells him he won't leave him a drooling mess after being done with him before he resurrects Sam and sends him back to the future and turns to Dean. Michael says he'll see him again before sending him off. In their own time, the brothers help a weaken Castiel after he touches down and begin to worry about their fate as Michael got their father to consent and everyone believes they will consent. Dean responds by stating they have choices as he labels him, Sam and Cass as Team Free Will.
Under pressure of his "destiny" combined with his responsibility for the Apocalypse and repeated losses, Dean is gradually driven into depression. After the Horseman Famine plagues a town and affects everyone with insatiable hunger (money, sex, food, etc.), Dean is the only one unaffected. It's indicated by Famine that Dean is so broken and defeated, he's too "dead inside" to want anything. Sam manages to defeat Famine with his psychic powers after feeding on demons due to his effect, Sam demands to be locked away by Dean and Castiel in Bobby's panic room again. This triggers Dean to break down and pray to God for help.
|“||That is one deep, dark nothing you got there, Dean. Can't fill it, can't you? Not with food or drink. Not even with sex. [...] I can see inside you, Dean. I can see how broken you are, how defeated. You can't win, and you know it. But you just keep fighting. Keep ... going through the motions. You're not hungry, Dean. Because inside ... you're already dead.||”|
— Famine to Dean
in My Bloody Valentine
In Dark Side of the Moon, Dean and Sam are shot by hunters and sent to Heaven. While there they are contacted and instructed by Castiel to find an angel named Joshua, who supposedly talks to God. While fleeing the angels, the brothers are able to reunite with Ash and Pamela Barnes. They discover Heaven is just a collection of the person's best memories and that they've both been there before (the angels having removed their memories). Dean is upset by Sam's "heaven" being of memories away from him while Dean's is the exact opposite. Before leaving Ash's heaven, Dean talks with Pamela about his answer to Michael and she kisses him. After being captured by Zachariah who beats them for ruining his status, Sam and Dean were saved by Joshua---an angel that 'talks' to God--- who tells them God was on Earth and he really talks to Joshua not the other way around. Joshua gives God's message which is for them to stop looking for him. He could do something to stop the apocalypse, but he won't as it wasn't his concern. Joshua told what God has done for them lately such as putting them on the plane to get them away from Lucifer and bringing back Castiel. However, Dean is deeply upset, as God had been his last hope.
Sam and Dean return to Earth in their bodies, this time with memories of their experience in Heaven. Dean, losing faith knowing God doesn't see the battle with Lucifer to be 'his' problem, throws out the amulet Sam gave him and starts to see no way out of his destiny as Michael's vessel.
During Point of No Return, Dean prepares for his possession by Michael before he's found by Sam and Castiel who return him to Bobby's house. Dean justifies he can't bear the guilt of the whole world burning if he didn't agree and later admits to Sam he doesn't trust him enough to say no to Lucifer forever. If anyone will stop him, it would have to be him. They convince Dean to allow them some more time in order to research another method of stopping Lucifer; however, the resurrection of their brother Adam (who agreed to be Michael's vessel) forces Sam, Bobby and Castiel to keep both Adam and Dean from Zachariah. Dean escapes by banishing Castiel, as Sam leaves to find him allowing Adam to be removed by angels. Dean tries to lure the angels but Castiel finds him first and proceeds to beat Dean up as he gave up everything for him. Castiel nearly killed Dean but stopped and returned the unconscious Dean to Bobby.
Despite Bobby and Castiel's insistence on keeping Dean from Zachariah, Sam allows him to try to rescue Adam. Castiel dispatches the angelic guards and the brothers attempt to rescue Adam, but Sam's ambush on Zachariah fails and Zachariah causes internal damage to both Adam and Sam to coerce Dean to consent to Michael. Ultimately, he relents, but after Zachariah summons Michael, Dean taunts him into sacrificing himself in order to allow Michael in.
Zachariah angrily refuses, and Dean stabs him and ushers his brothers out of the room.Unfortunately Adam does not escape in time and is locked in the room with the approaching Michael. As they leave, Dean admits that he would have accepted Michael, but because of Sam's faith he decides that he will "take the fight to them".
|“||I don't know if it's being a big brother or what, but to me, you've always been this snot-nosed kid that I've had to keep on the straight and narrow. I think we both know that's not you anymore. I mean, hell, if you're grown up enough to find faith in me, the least I can do is return the favor. So screw destiny right in the face. I say we take the fight to them and do it our way.||”|
— Dean changing his mind about being Michael's vessel
in Point of No Return
In Hammer of the Gods, when Dean and Sam are forced to help several other deities against Lucifer, they team up with Gabriel, who finally decided to support their side. They manage to lure Lucifer to their location, but Gabriel is the one that faces him and ultimately dies in the process. Despite, Gabriel gives them the first real key to defeating Lucifer: find the four "keys" to Lucifer's Cage before luring him there and sealing him back in his cage. The four "keys" are revealed as the four rings of the Horsemen. The brothers already have two from War and Famine so set up to find the last two.
Dean and Sam, with help of the Crowley and a now human Castiel, face off against the Horsemen Pestilence and manage to get his ring. However, trouble brews in Chicago from an epidemic of the Croatoan Virus. Dean locates the last Horsemen, Death, who gives his ring to Dean in hopes of locking Lucifer back in his cage. He's "chained" to Lucifer and wants to be free of him. Sam proposes he say yes, somehow takes control of Lucifer, and throw himself in the cage---sacrificing himself to stop the Apocalypse. Dean opposes it, finding it risky and unwilling to sacrifice his brother, but Sam still believes his choice is right. Bobby talks to Dean, telling him to have faith in his brother whatever happens.
|“||I'm not gonna lie to you though. It goes against every fiber I got. I mean, truth is ...You know, watching out for you ... it's been kinda my job, you know? But more than that ... it's kinda who I am. You're not a kid anymore, Sam, and I can't keep treating you like one. Maybe I gotta grow up a little too. I don't know if we got a snowball's chance. But ... but I do know, that if anybody can do it .. it's you.||”|
— Dean agreeing with Sam's plan for Lucifer
in Swan Song
It is reluctantly decided that the plan to throw Lucifer back in the cage requires Sam to become Lucifer's vessel. Dean knows he will lose his brother, but tries have faith in him and respects his choice. Once Sam says "yes" to Lucifer, the archangel takes Sam over and closes the portal with ease. He leaves Dean alive as he leaves to go fight his older brother, Michael, who is now in Adam's body.
Just as Lucifer and Michael are about to begin, Dean shows up in the Impala to witness the fight as if to try and stop the inevitable one last time. Having had enough of Dean's attempts to save Sam, Lucifer goes on a rampage and begins to beat Dean to a bloody pulp. Lucifer kills Castiel and Bobby as he continues to beat Dean until Sam is able to regain control long enough to open the portal to Lucifer's cage. Sam grabs hold of Michael and falls into the cage. The portal is then sealed, leaving nothing behind but the key. Castiel, now a seraph returns from the dead, having been resurrected by God, heals Dean and resurrects Bobby. Dean is heartbroken at having lost Sam and resentful towards God for letting all of this happen. Since Michael is no longer in Heaven, Castiel disappears to restore order.
|“|| Dean: He brought you back. But what about Sam? What about me, huh? Where's my grand prize? All I got is my brother in a hole!|
Castiel: You got what you asked for, Dean. No paradise. No hell. Just more of the same. I mean it, Dean. What would you rather have? Peace? Or freedom?
— Dean and Castiel's goodbye
in Swan Song
Dean gives a goodbye to Castiel and Bobby, but cuts contact off them for a very long time. In the end, Dean keeps the promise Sam wanted for him: to not resurrect him, quit hunting, and go to live with Lisa and Ben. Unknown to him, Sam watches outside in the last scene, having been released from the cage.
|“||Dean didn't want Cass to save him. Every part of him, every fiber he's got wants to die or find a way to bring Sam back. But he's not gonna do either. Because he made a promise.||”|
— Chuck over Dean
in Swan Song
|“||Do you have any idea what walking away meant for me? [...] I showed up at their doorstep half out of my head with grief. God know why they even let me in. I drank too much. I had nightmares. I looked everywhere. I collected hundreds of books, trying to find anything to bust you out. [...] A damn year?! You couldn't put me out of my misery?!||”|
in Exile on Main Street
Dean relocates Lisa and Ben to a different home and starts acting like his father, getting on edge and limiting their movements to 'protect them'. He is called back to hunting when Sam finds an abandoned baby from a crime scene, and needs help taking care of it. They take the baby to Samuel, where Dean is distrustful of the Campbells. Samuel wants to raise the baby as a hunter which infuriates Dean, but before they can discuss it any further, the Alpha Shifter arrives and kills one of the cousins, also taking down the rest of the Campbells. Then the Alpha defeats Sam and Dean and takes the baby. Dean returns to Lisa and Ben but is conflicted with staying or hunting with Sam. Despite the previous pressure of his hunting life, Dean is still too much of a hunter at his core and can't so easily mesh into a "normal life". Lisa forces him to accept this and suggests a compromise: he can go hunting and come back whenever he can. He agrees and gets the Impala out of the garage.
|“|| Lisa: "Maybe we're safer with you here, maybe gone. I don't know. The one thing I do know is you're not a construction worker. You're a hunter. And now you know your brother's out here, things are different. You don't want to be here, Dean."|
Dean: "Yes, I do."
Lisa: "Okay, but you also want to be there. I get it. You're white-knuckling, living like this. Like what you are is some bad, awful thing. But you're not. But I'm not going to have this discussion every time you leave. And this is just going to keep happening so I need you to go. [...] Me and Ben will be here and you come when you can. Just come in one piece, okay?"
— Dean becoming a hunter again
in Two and a Half Men
They find the child responsible for the deaths and discover that he sold his soul to an angel for the staff. Castiel soul probes the child against Dean's wishes but with Sam's consent. The angel Balthazar is responsible for the transaction and Castiel tracks him down, with Dean and Sam staying behind and fighting Raphael's angel henchmen who have been hunting Cass. They help Castiel trap Balthazar after Raphael is defeated and force him to relinquish the child's soul. Afterwards, Sam joins Dean in the Impala again as his own car was destroyed, and Dean questions Sam's strange behavior and his time in hell, but Sam doesn't want to talk about it at all.
Dean is called to a case by Sam to investigate the mysterious deaths of several cops. Dean suggests they call Castiel, but Sam doesn't believe he'll come. To his surprise, Castiel responds to Dean's call and tells them that the staff of Moses is responsible for the deaths. He also informs them that heaven is embroiled in a civil war as Raphael is trying to take over and resume the Apocalypse that Sam and Dean prevented.
In Weekend at Bobby's, Dean calls Bobby for help with a Lamia. Dean continues to grow more unsettled over Sam's strange behavior and calls Bobby to talk to him about it. Bobby yells at Dean for being selfish and oblivious to Bobby's own problems. Abashed, Dean flies to Scotland with Sam in an effort to help get Bobby's soul back from Crowley. Crowley is forced to give him back his soul and the brothers fly back to America.
Sam and Dean investigate what appears to be a vampire attack, and Dean becomes entangled with the vampire Boris. Sam walks by as Boris attacks Dean, but merely watches as Boris turns Dean into a vampire. Dean notices Sam isn't freaked out about his vampirism, as he can hear Sam's steady heartbeat. Sam tries to reason with Dean, assuring him that Samuel will know what to do. Dean then decides to sneak out to visit Lisa in order to say one last goodbye. While visiting, Dean struggles with his bloodlust for Lisa. He comes close to biting her, but retreats into the hallway. As he is leaving Ben approaches Dean despite Dean's warnings, and Dean shoves Ben into the wall in an effort to put some distance between them. He then leaves and returns to the motel.
Upon Samuel's arrival, Dean demands that he kill him, but Samuel refuses and informs him that there is a cure for vampirism. As long as Dean hasn't fed, then the cure can turn him back. The cure requires blood from the vampire who turned him, so Dean infiltrates the nest, and encounters Boris, who explains to him the vampires' aim. When Boris smells the dead man's blood drop from Dean's syringe, he attacks. Before the vampire can make his move, all the vampires in the nest collapse, including Dean. He has a vision of the Alpha Vampire.
When he awakens, Boris is rallying the coven of the vampire to attack Dean. Dean, however, has the upper hand and takes out the entire nest single-handedly, including Boris. Back at the motel, Dean drinks the cure, and goes through a painful process of turning back. His short time as a vampire flashes before him, highlighting Sam's hesitation to save him from Boris. Dean now has lost trust in his brother completely.
Dean becomes so uncomfortable around Sam, beginning making excuses to stay away from him. He informs Bobby of the situation, and digs up information on whatever could possibly be Sam's diagnosis. He then asks aloud for the truth, and is infected with a truth curse from the goddess Veritas where people tell truths to him against their will. Sam, however, proves to be immune to this, as the curse doesn't affect him and lies to him. Dean believes Sam and feels guilty for suspecting his brother. During this time, Dean's relationship with Lisa ends permanently, as she is unable to deal with his issues stemming from his hunting life and his co-dependence on Sam. In a confrontation with Veritas, Dean admits to her truth spell he did want a family, but now sees himself self-deprecatingly as only being good at hunting and could never be normal. During this, Dean also learns Sam is immune to her truth affect and calls him not human. He loses complete trust in him and puts a knife on his brother. This time, Sam comes clean, fessing up to allowing him to become a vampire to get closer to the alpha and his chilling inability to feel anything ever since he got out of the cage, including the safety of his brother. Dean, emotional, processes the truth about Sam, and responds with beating Sam unconscious.
|“||It's the gig. You're covered in blood until you're covered in your own blood. Half the time, you're about to die. Like right now. I told myself I wanted out ... that I wanted a family. [...] But what I'm good at ... is slicing throats. I ain't a father. I'm a killer. And there's no changing that. I know that now.||”|
— Dean's self-deprecation
in You Can't Handle The Truth
Dean takes matters into his own hands, and calls Castiel for assistance with diagnosing Sam. Castiel confirms that Sam has no soul, and that it is still in the cage with Michael and Lucifer. Dean intends on holding Sam in the motel room, but when Sam unties the bonds he's in and refuses, Dean states he'll be watching every move he makes, which Sam agrees to. The two brothers then chase the only lead they have towards Sam's soullessness: Samuel. Samuel has a lead on the Alpha Vampire, and Dean volunteers himself and Sam to join the hunt. Samuel reluctantly lets Dean join the hunt.
Dean is left with Gwen to stand guard while Sam joins the other Campbells on the hunt. Dean talks with Gwen for a while before they fight some vampires, one of which nearly kills Dean until Gwen saves him. Dean soon sneaks away and witnesses some of the fight between the hunters and vampires, as one of his cousin's calls out to him for help from the mansion before she is killed, to his horror.
Dean soon catches Sam helping Samuel and a few other Campbells loading the Alpha vampire into the van. He later confronts Sam about it, and Sam admits that keeping this from Dean was his own idea because they needed to interrogate creatures, and apparently Dean 'messes it up'. Dean is furious about Sam's lack of instinct, and gives him two options: to work with him, or to go off with Samuel and see how that goes. Dean is shocked when Sam comes back, admitting he gave it a 60/40 prediction of whether his brother would come back.
Sam and Dean follow Samuel via his cell phone's GPS to a warehouse where they are holding the Alpha vampire. When Samuel leaves the room, the vampire calls out to them, revealing he was aware of their presence. The brothers then take the opportunity to question the creature themselves. The Alpha remembers Dean by name, referring to him as 'his child for a time'. When the brothers ask the Alpha what Samuel wants from him, the vampire reveals that it is Purgatory, which Dean was shocked to hear was real. The Alpha reveals that it is a realm with the soul of every monster that ever lived. He tells them Samuel is looking for and that Samuel is merely working for someone else. Dean confronts Samuel about it, but is interrupted by the escape of the Alpha. Christian, revealed as a demon, and a few other demons recapture the Alpha and take it away.
Crowley appears on the scene, and reveals that he's Samuel's boss, and is the one who's looking for Purgatory. He also states he is responsible from raising both Samuel and Sam, and is in possession of Sam's soul. Dean expresses doubt to these claims but Crowley reveals he is now the Ruler of Hell and has the power to do so. Crowley tells them if they cooperate, Sam gets his soul back. If they don't, Crowley shoves Sam back in Lucifer's cage.
Dean is reluctant to work for Crowley, but Sam convinces him it's the only way they'll find a way to get his soul back. Dean is still not convinced that Sam is his brother, and later admits that he doesn't know what he is. When Sam states that he thinks it might be best to go back to being the old Sam, Dean accepts his offer, and says it's 'time to get his brother back.'
Dean and Sam are more on the same page now, but Dean still seems to struggle with Sam's behavior and then starts to act as his 'Jiminy Cricket' to Sam's 'Pinocchio'. They investigate a case of crop circle abductions, leading people to believe it is a UFO sighting. Dean decides to check out the crop circles for himself, but gets abducted.
He returns a while later, and walks in on Sam having sex with a hippie chick. Dean expresses irritation at this, and states that he 'had a close encounter, and won it'. However, it's proven that he didn't exactly 'win' anything, as he starts seeing things that no one else can see. There's one moment when Dean's alone, and the door to the motel bursts open and a "little, glowing, hot, naked lady" flies in and starts hitting him. He traps her in the microwave and cooks her, but when he tries to show Sam her remains, Sam can't see them. Sam then draws the conclusion that the UFO encounters are because of Fairies.
Dean and Sam go to visit Marion, a woman they interviewed earlier who had said that fairies were behind the disappearances. She tells them all about fairies, including that they like cream and that they must count every grain of salt or sugar that is spilled in front of them. After they leave, they see Mr. Brennan loading boxes of cream into his car. Dean breaks into his shop and sees elves working on watches for him. Afterwards, Dean is being stalked by a fairy, a Red Cap in particular, and he mistakenly tackles a midget and is arrested for a hate crime. While in jail, Dean was being beaten by the Red Cap in his jail cell, but is saved by Sam in time and is released from jail the next morning. The midget, who was also the district attorney for Tipton county, dropped the charges against him. Dean learns that the leprechaun struck terms of making a deal with Sam, to lift his soul from the cage (and make him a 'real boy'). He questions Sam's way of thinking, and wonders if Sam is having second thoughts.
Dean quickly becomes tired of working for Crowley, as he sees that it's not getting them anywhere. He tries to reason with Sam that Crowley may not keep his end, but Sam has left the room. When Dean slowly walks the motel room looking for Sam, he gets knocked out by demons, led by none other than Meg. Dean responds emotionally, saying he's been dying to see her again to get back at her for being responsible of Ellen and Jo's deaths. Meg seemingly approves of this, but not before demanding where their "boss" is. While neither of the brothers answer, she puts a knife to Dean's neck, getting impatient. Sam, however, merely laughs at her, and reassures Dean that she can't kill them because she needs them to get her to Crowley so she could kill him. Dean says he hopes they both lose. Sam suggests that she works with them and makes a deal with her, which Dean is not in favor of.
When the demons leave, he confronts Sam about it. He is unsure whether working with a demon again will go anywhere good, and their tendencies to double-cross work against them. Sam assures Dean that they will get the jump on the demons first because he'll be bringing Castiel along for the ride. Dean expresses surprise when Sam actually succeeds in calling the angel.
When Castiel performs a ritual to find Crowley's location and can't find him, Dean suggests they search Samuel's office for a map or any hint on Crowley's base. They are interrupted by Samuel. Dean first suggests that Samuel tells them where Crowley is, which he refuses to do. When all his attempts to obtain the information lead to nothing, Dean consents to ask Samuel what Crowley is holding over him. Samuel takes a picture out of his desk drawer, and hands it to Dean: it's a picture of their mother, Mary. Dean expresses a somber opposition towards working with Crowley to bring Mary back, as he tries to convince Samuel to learn from the brothers' mistakes. When Samuel's had enough of his protests, he asks them to leave. Samuel later knocks on their door to give them the location, despite his wishing for them not to go there.
Before they leave for the prison, Castiel talks to Dean about how he doesn't think retrieving Sam's soul is wise. He believes that Sam will be broken beyond repair if they force his "mutilated" soul back in. Dean doesn't want to believe this, and reassures Castiel that they'll deal with whatever complications come up.
Upon arriving and infiltrating the prison, Dean expresses apprehension on how easy it was getting in, which then comes to fruition when the guards are let out and come after the group. When Meg decides to stay behind to hold off the hounds, Dean, Sam, and Castiel head further in the prison in search for Crowley. Castiel is banished by Samuel, much to Dean's surprise, and the brothers are locked in separate cells by demons. When Samuel later tries to make Dean understand, the two express different ways of seeing the betrayal: Samuel saw it as Dean choosing Sam over Mary, while Dean saw it as Samuel choosing Crowley over his own grandsons. He also challenges Samuel that he's going to escape from the prison and the next time he meets Samuel, he'll kill him. Demons then let him out his cell to be taken to a bigger cell to be eaten alive by Ghouls. Dean fights back, but to no avail. Sam later busts in and kills the ghouls.
Dean then finds where Christian has Meg, kills Christian, and then sets off the fire alarm to get Crowley's attention. When the King of Hell enters the room, the brothers confront him and demand he return Sam's soul. Crowley says he can't, and that he was lucky enough to get his body out of the cage. Crowley breaks from the devil's trap, and flings Sam and Dean pinned to the wall. Castiel soon arrives on the scene and rescues them. Dean watches as Castiel burns Crowley's bones, seemingly killing him.
Later, outside the prison, Dean thanks Castiel for his help. Castiel tells Dean about the civil war in Heaven, and Dean is genuinely concerned, and asks if there's anything they can do to help. When the angel says there's nothing they can do and apologizes, Dean reassures him that there's no need to apologize, that they understand and are his friends. Dean tries to reason with Sam, who now has second thoughts on all this trouble for his soul, saying that he doesn't know how wrong, how messed up he is without a soul. Sam disagrees and walks away without a word.
Dean, now more desperate than ever for Sam's soul, seeks out Death to ask for his help. Dean requests not only for Sam's soul, but for their half-brother Adam as well in exchange for his ring. However, Death tells Dean he knows where the ring but doesn't completely reject his request but forces Dean to pick one brother, in which he tries to protest since he wants them to be free. When Death tells him to choose again, Dean picks Sam as his soul's been there longer. Death hints he has the power to jailbreak Lucifer's cage, and makes a wager with Dean: he will restore Sam's soul if Dean agrees to be Death for a day. He also says he will be able to put a mental wall inside Sam's mind to hold back the memories of the cage, as he also confirms that the results of those memories (or of the wall collapsing) would be fatal. Before the horseman can explain why he wants this from Dean, he is resurrected by Dr. Robert.
Dean informs Sam and Bobby on his deal with Death. Sam is skeptical of the wall but very adamant about keeping his soul out of his body, but later backs down and gives Dean false hope not to mess up. Dean, still very suspicious of his soulless brother, tells Bobby to watch him while he's gone.
Dean slips on Death's ring, giving him some of Death's powers and effectively taking his place for 24 hours. The reaper Tessa is assigned to keep an eye on Dean to make sure he has the "minimum screw-up", despite her dislike for Dean's habits of throwing a wrench in everything. Dean does a fair job and kills a few people with a simple touch, following Tessa's list of people, but becomes hesitant when he is supposed to kill a 12-year-old girl. He refuses to kill her, but this sets up a chain of events. The girl survives, but innocent people die in her place as she is disrupting the natural order by being alive. Dean tries to save one of these innocent people, going as far as taking off Death's ring. Realizing the mistake he's made, he reluctantly accepts defeat, and finally decides to kill the girl.
Meanwhile, Sam has tied Bobby up and intends to kill him to prevent his soul from entering his body. Dean manages to arrive in time and knocks Sam out and chains him to the cot in the panic room. Dean expresses deep sadness at how he's failed to fulfill his lifelong promise of saving his brother: this replicant of Sam could not stay alive; he's dangerous, he's cold, and he's capable of anything.
Dean leaves the basement to let his defeat sink in, and finds Death eating. Dean gives him back the horseman's ring, and claims his loss of their wager. Dean then informs him that his wager was rigged right from the start, as he thinks Death would've known he wouldn't last a day. Death denies this, as he explains the natural order and his duty in caring for it before telling Dean it was a lesson he needed. Death then declares their business is finished, but he offers a bonus: he will still go to Hell to retrieve Sam's soul. He then encourages Dean to keep digging in what he's learning regarding the souls.
Dean quickly heads to Bobby and they make it to the panic room, as they witness Sam struggling to stay away from Death, who has returned with Sam's soul. Despite Sam's protests and pleas to Dean, Death restores Sam's soul to his body, with a conflicted Dean watching as his brother screams in pain. A week passes and Sam has still not woken up. During this time, Dean calls Castiel to check on Sam and asks if Cass thinks Sam will ever wake up. Castiel tells Dean that he doesn't think so, leaving Dean alone. Dean heads up stairs and Bobby offers him a drink and a case. Then, to Dean's joy, Sam wakes up and gives Dean a hug, as well as Bobby. Sam later reveals to Dean that he doesn't remember anything other than jumping into the cage. Dean is surprised but relieved to hear this, despite Bobby's suspicion. Dean and Sam go to work on a case involving dragons, during which Dean is overjoyed to have his brother back.
When Bobby finds a sword that could kill the dragons, he sends Dean goes to visit Dr. Visyak. When Dean tries to pull the sword from the stone he only falls off, and has to resort to blowing up the stone instead. He returns to Sam and the two go after the dragons. They fight off the dragons and save the girls they had held captive. Later on as Dean is happily going through the pile of gold they found at the dragon lair, Sam confronts him about being soulless and apologizes to Dean. Dean is shocked that Sam knows and asks who told Sam (who then answers that it was Castiel). Dean tells Sam about the wall inside his head, and that what Sam became wasn't really him.
Then Sam gets a mysterious text message about a case, which gets Dean worried. As they investigate, Dean finds out that Sam has been in this town before, and wants to leave. Sam doesn't want to, which makes Dean angry and he begins to quote John's rules. But they stick around, and Sam begins remembering what happened, much to Dean's displeasure. They do figure out its an Arachne with a grudge against Sam, and defeat it. Afterwards, Sam and Dean have a talk about what happened and Dean tries to make Sam feel better. Then Sam collapses, and Dean rushes to Sam calling his name.
Minutes pass by as a worried Dean tries to wake Sam up. Sam does wake up and Dean helps him up. Dean and Sam talk about what just happened and Dean tells Sam not to scratch the wall again. With that they head out on a case with a mannequin killing people, but Dean gets called away by an "emergency" call from Ben. When Dean arrives, he finds Lisa going out on a date. He and Lisa have a talk, which later results in him leaving permanently. When he comes back, he helps Sam finish the case.
Then things take a turn for the weird when a wounded Balthazar shows up with someone on his tail. He gives Dean a "key" and sends the two into the world of "Jared" and "Jensen", where their lives are a television show. After a great deal of effort and in end derailing the entire TV show by "quitting" and telling off Bob Singer, they manage to get back to their own world. Castiel informs them he has Balthazar's weapons now.
|“||You heard my brother. That's right, I said "brother". 'Cause you know what, Bob? We're not actors. We're hunters. We're the Winchesters. Always have been and always will be. And where we're from, people don't know who we are. But you know what? We mattered in that world. In fact, we even saved the son of bitch once or twice. And yeah, okay, here maybe there's some---some fans that give a crap about this nonsense. But Bob Singer - if that even is your name - tell me this. What does it all mean?||”|
— Dean telling off Robert Singer in an alternate universe
in The French Mistake
Later on, Dean runs into Samuel again, and it takes Sam and Bobby to hold him back from fulfilling his promise of killing Samuel. In the hall, Gwen goes out to talk to him, and Dean shoots her. It turns out, Dean was possessed by Eve's latest invention. Unsure who its possessing, the group rid themselves of their weapons. In a turn of events, its Bobby who is possessed by the Khan worm, and Dean questions and kills it. Bobby does survive.
Things again become strange when Balthazar alters history and saves the Titanic. With history changed, Dean finally wins rock, paper, sissors when trying to see whos going to cheer Bobby up and now drives a mustang. He and Sam investigate a string of strange murders, and make the connect to the Titanic. They summon Balthazar who tells them why he did and leaves. When almost killed by Fate, Castiel saves them. He tells them, it's Fate, and she is trying to kill them. The only way to survive is to kill her. So Dean and Sam draw out Fate, and Castiel rights the past. Only Sam and Dean remember the past.
Dean, Sam and Bobby research how to kill the Mother of All, and they find that the ashes of the phoenix can kill her. Dean finds the diary of Samuel Colt, which en-tales how he killed on. So they enlist the help of Castiel to send them back that time to find the ashes. Dean is beside himself with excitement to go back to the wild west. So they head back, and find out the Phoenix is killing people. So Dean tries to set up posse, but it backfires and he ends up as sheriff. So Dean and Finch end up having a showdown, and Dean wins. As Dean rushes for the ashes, Castiel transports them back. Lucky for them, Samuel Colt got the ashes and mailed it to them after studying Sam's cellphone.
So Sam, Dean, Castiel and Bobby, begin to hunt for Eve. Thanks to Lenore's information, they find out that Eve is in Organ Pass, and they head there. There, they discover Eve's experiments, and Dean even names one of her experiments when Bobby gives him naming rights. So Dean names a cross-breed between a wrath and vampire, Jefferson Starship. Then the police show up (Dean hides), but they too are Jefferson Starships. They eventually find Eve in a diner working as a waitress, and she tries to makes a deal with them. She even turns into Mary Winchester to get them to work with her, but Dean refuses nether less, and tells her to bite him. Which she does, only to find out that Dean had swallowed some phoenix ashes earlier. The bite could've possibly turned Dean into a Jefferson Starship, but Castiel cured the infection before it could spread.
After their encounter with Eve, everyone begins to question Castiel. Everyone but Dean who still believes in Castiel. When Castiel comes to save them, he accidentally gives himself away, and Dean catches this. Dean helps them trap Castiel, and question him. Dean is the most hurt and furious by Castiel's actions but nonetheless still wants him to stop before Castiel goes to far. Castiel still disagrees but tries to maintain his loyalty by revealing he was really the one who saved Sam. When demons come, Dean and the others are forced to flee. Castiel is now free, and later visits Dean to explain himself. Dean does not approve of his actions and chastises him harshly, but admits that Castiel is like a brother to him and that's why he's asking him to stop or else he'll have to "do what he has to." Castiel doesn't budge and disappears, breaking their friendship.
|“|| Castiel: "I did it to protect you. I did it to protect all of you! [...] Raphael will kill us all. He'll turn the world into a graveyard. I had no choice."|
Dean: "No, you had a choice. You just made the wrong one."
Castiel: "You don't understand. It's complicated."
Dean: "No, actually it's not and you know that. Why else would you keep this whole thing a secret, huh? Unless you knew it was wrong. When crap like this comes around, we deal with it! Like we always have. What we don't do is we don't go out and make another deal with the Devil!
Castiel: "It sounds so simple when you say it like that. Where were you when I needed to hear it?"
Dean: "I was there. Where were you?"
— Dean confronting Castiel's actions
in The Man Who Would Be King
After Castiel's visit, Bobby reveals that Castiel also stole a diary from Bobby's house. As they read Bobby's photocopies, Dean gets a call from Ben. Ben tells Dean that men are in the house and killed Lisa's boyfriend. Dean tries to help from the phone, but Ben too is captured. Crowley, now on the other line, tells Dean to back off or he will kill Lisa and Ben. Dean refuses to back down, and begins to hunt down Lisa and Ben. He even begins to torture demons for their location. Sam tries to help him, but Dean tells Sam to back off. Then Dean accidentally breaks the Devil's Trap, and the demon attack. Castiel comes in and saves Dean. Dean doesn't want anything to do with Castiel though. Later, its Balthazar who gives Dean Lisa and Ben's location.
So Balthazar transports them there, and they storm the building. Dean finds Ben and Lisa after taking out some of Crowley's goons. He unties them, only to find out that Lisa is possessed by a demon, and she hold Ben hostage. Dean manages to free Ben by splashing holy water at "Lisa". Then he manages to free the knife from "Lisa's" hand and begins to exorcise her. He continues to exorcise her after the demon stabbed Lisa's body. Once the demon is out, Dean moves quickly to save Lisa's life, and carries her out to the car, and rushes her to the hospital. Dean stays by Lisa's bedside, and then Castiel arrives and heals her. Dean asks Castiel for favor to erase Lisa and Ben's memory of him. Dean approaches them after this and apologizes to them. In the car, Sam tries to help Dean, but Dean tells Sam not to mention Lisa or Ben to him ever again, or he will break Sam's nose.A week later, Bobby, Dean and Sam go looking for Dr. Visyak, and they find her in an alley. She is bleeding and tells them how to open the door to Purgatory. Then Castiel appears, and Dean tells Castiel to leave. Castiel tells him he is done playing nice, and promises to put Sam back. This confuses Dean, until Castiel touches Sam, and breaks down the wall inside his head, sending Sam into a comatose state. Dean stays by Sam's bedside, while Sam is comatose. After Balthazar giving them Castiel's location, Bobby manages to convince Dean to go with him after Castiel. Before Dean leaves, he leaves Sam their location. So Dean and Bobby head out. When they arrive they scope out the place, which is full of angels. Then a demon cloud comes, and Dean and Bobby run back to the Impala. The demon smash into the impala, flipping it over.
When Dean wakes up, he checks on Bobby, who is okay. The two then sneak into the place, and walk in as Crowley and Raphael are doing the ritual. Dean throws an angel blade at Raphael, who catches it and flings Dean and Bobby away. Soon after, Castiel shows up, and shows everyone his new power. With it he kills Raphael while Crowley runs away. Dean tries to talk Castiel into powering down, and even reminds Castiel that he used to be family. But Castiel doesn't want to power down and after Sam stabs him, he is proven to no longer be an angel. Dean is very shocked when Castiel proclaims himself God.
|“|| Dean: "Listen. I know there's a lot of bad water under the bridge, but we were family once. I'd have died for you. Almost did a few times. So if that means anything to you ... please. I've lost Lisa. I've lost Ben. And now I've lost Sam. Don't make me lose you too. You don't need this juice anymore, Cass! Get rid of it before it kills us all!"|
Castiel: "You're just saying that because I won. Because you're afraid. You're not my family, Dean. I have no family."
— Dean's final plea to Castiel
in The Man Who Knew Too Much
|“||This is stupid. Our quality of life is crap. We got Purgatory's least wanted everywhere, and we're on our third 'The World's Screwed' issue in what, three years? We've steered the bus away from the cliff twice already. [...] I think if we didn't take it's belt and all it's pens away each year, that the whole enchilada would've offed itself already!||”|
— Dean losing faith in saving people
in How To Win Friends And Influence Monsters
When Castiel leaves, Dean and the others head back to Bobby's, and Dean begins to fix the Impala, since there is nothing else he can do. Dean is concerned for Sam's mental health since the wall is gone. Dean admits to Bobby that he can't take anymore hits, and will believe that Sam is "fine". Then they manage to summon and bind Death.
Dean tries to appease Death, and then Castiel shows up and Dean orders Death to kill him. Castiel frees Death and leaves. Death tells Dean the only way to stop Castiel is for Castiel to let the souls back into Purgatory. Dean doesn't think Castiel will do this, until Castiel comes asking for help. In turn, Dean helps Castiel and the souls are released back into Purgatory, but the Leviathans remain. Dean watches them destroy Castiel and spread throughout the water, leaving only his trench-coat behind.
He also deals with Sam seeing Lucifer while looking into a Leviathan killing. When he returns, he finds Sam gone. Dean eventually finds Sam and convinces him that his reality is real. He and Sam return to Bobby's, but find it burned down. Dean calls Bobby, but gets Bobby's voice mail, and finally tells Bobby how he is really doing. He and Sam are soon attacked by Edgar, and Dean's leg gets broken. On the way to the hospital, Dean begs them not to take them to Sioux Falls General, but is ignored.
He wakes up with his leg in a cast, and Bobby comes in and saves Dean from the hospital. Dean spends 3 weeks in a cast until Sam takes off, and Dean saws the cast off. Dean soon catches up with Sam, and punches Sam for taking the Impala. Sam explains the situation to Dean about the kitsune Amy and her decision to stop killing with her son no longer sick, but Dean sees her as only a monster that will kill again. Dean seem to eventually agree with Sam, but actually goes behind Sam's back and kills her. Dean finds Jacob, Amy's son, but spares him even against the kid's threats and tells him to "look him up in a few years".
|“||I know, I know. But people ... they are who they are. No matter how hard you try, you are what you are. You will kill again. [...] Maybe in a year, maybe ten. But eventually the other shoe will drop. It always does. I'm sorry.||”|
— Dean as he kills Amy
in The Girl Next Door
Dean feels guilty about the incident with Amy, plus feeling guilty lying to Sam about it and begins drinking more than normal. This guilt is what Osiris hones onto and puts Dean on trial. On trial he encounters Jo's spirit as a witness and so is Sam. It's revealed by Osiris Dean feels Jo died because of him since he let her do her first official hunt with them and blames himself for everything Sam went through since he left Stanford. Before Osiris can call the third witness, Amy, Dean accepts the charges. Jo's spirit is controlled by Osiris to kill him, though Dean apologizes for dragging her and Sam into hunting, admitting he just didn't want to be alone. Dean is saved when Sam stabs Osiris and Jo flickers out.
|“|| Dean: "You were a kid. You and Sam. I just - you know, hunters are never kids. I never was. I didn't even stop to think about it. [...] But I didn't want to do it alone. Who does? No, the right thing would've been to send your ass back home to your mom."|
Jo: "Like to have seen you try. He was right about one thing. [...] You carry all kinds of crap you don't have to, Dean. Kind of gets clearer when you're dead."
Dean: "Well, in that case you should be able to see I'm 90% ... crap. Take away that, and what's left?"
— Dean to Jo's spirit
in Defending Your Life
Dean still has nightmares about Castiel dying and killing Amy along with Sam's mental instability, leading to drink more heavily. Nonetheless, Dean continues working. He and Sam find a case where witches are wreaking havoc in Prosperity, Indiana. When they fail to stop the witches, Sam and Dean manage to get Maggie and Don to calm down. Sam approaches Dean about what's bothering him, but Dean brushes him off.
In Season Seven, Time for a Wedding!, Dean is surprised Sam had him dress up for his wedding to Becky Rosen. When a series of deaths occur, Dean contacts Bobby who sends a hunter named Garth Fitzgerald IV, who is clumsy but does good in helping Dean out. After the case is connected to a innovating Crossroad Demon named Guy, a fight breaks out and ends with Dean threatening Guy before Crowley appeared to the Winchesters. Dean was shocked to see him and threatened to kill Guy though was shocked to hear Crowley say he intends to punish Guy for collecting deals early. Dean is skeptical on Crowley's intentions but is shocked when he reveals he ordered his demons not to interfere with the Winchesters as they fight against the Leviathans. Dean thought on the last few months of the lack of demon attacks and was surprised by Crowley's support in their endeavors. Deciding to agree, Dean soon had Crowley cancel Guy's deals so the people would be spared and the latter complied. Dean then turned Guy over and watched as the demons disappear. Afterwards, Dean and Garth had an amicable farewell with Dean telling him that he doesn't completely suck at being a hunter. Dean notes Sam seems to be coping better at this point with his hallucinations of Lucifer in his own way, but Dean is still privately concerned about his stability.
When Dean is cloned by a Leviathan, Dean is forced to lock the Impala up and it not too happy about it. Although, before he can cut the off his clone, the clone tells Sam that Dean killed Amy. This causes Sam to leave Dean. A week later Dean runs into Sam in Lily Dale. Sam is still angry with Dean, but the two do a case together involving ghosts and psychics. After finishing the case and given some advice from the other side, Dean apologizes to Sam, but says he doesn't feel bad for what he did to Amy and believes all his drinking to be because he didn't like lying to him. Sam and him reconcile.
|“||I went with my gut. And that felt right. I didn't trust her, Sam. Of course, ever since Cass, I'm having a hard time trusting anybody. And as far as I've been acting ... I don't know. Maybe it's cause I don't like lying to you. You know, it doesn't feel right. You got me there. I been climbing the walls.||”|
— Dean explaining his behavior
in The Mentalists
Dean and Sam are forced to lay low, still having to hide from cops and the Leviathans tracking them who they still don't know how to kill. In combined factors of losing Castiel, Sam's broken wall, and their failure to keep Leviathans out (causing yet another apocalypse), Dean's cynicism and frustration skyrockets. In How To Win Friends And Influence Monsters, even goes as far to say the world seems to want to end and he feels like nothing they do seems good enough. Bobby, however, chastises Dean and tells him to find a motivation to keep doing his job, whatever it is, or he'll wind up dead. Sam, Dean, and Bobby get in a confrontation with the leader of the Leviathans---Dick Roman, who secured himself as powerful businessman for further reach. They narrowly escape, though Bobby is fatally shot in the head as they make their escape.
|“|| Bobby: "'The world's a suicide case, we save it, it just steals more pills? [...] I've seen a lot of hunters live and die. You're starting to talk like one of the dead ones, Dean."|
Dean: "No, I'm talking the way a person talks when they had it. When they can't figure out why they used to think all this mattered."
Bobby: "You're not a person. [...] You tried to hang it up and be a person with Lisa and Ben. And now here you are with a mean old coot and a van full of guns. That ain't person behavior, son. You're a hunter, meaning you're whatever the job you're doing today. Now, you get a case of the Anne Sextons, something's gonna come up behind you and rip your fool head off. Now you find your reasons to get back in the game. I don't care if it's love or spite or a ten-dollar bet. I've been to enough funerals. I mean it. You die before me, and I'll kill you."
— Bobby's lecture to Dean
in How To Win Friends And Influence Monsters
In Death's Door, Sam and Dean rush Bobby to the ER where he falls into a coma. Both brothers are stressed over Bobby's critical condition. Sam brings up the possibility that Bobby might not make it, but Dean refuses to consider it. Ultimately Bobby dies, but manages to wake up a moment to write down coordinates he discovered during their last encounter with Dick Roman.
Weeks pass after Bobby's death. Sam and Dean are devastated, though Dean takes his loss the worst. He becomes obsessed with vengeance against Dick Roman and pays Frank Devereaux to help him track the meaning of the numbers Bobby left them with no luck. Eventually, with help from Frank in Adventures in Babysitting, Dean tracks down a new subsidiary of Dick's and manages to tap into its surveillance. Dean's apathy towards hunting heightens considerably after yet another loss, but wants revenge on Dick and couldn't bear to leave Sam hunting alone. After advice from Frank, Dean tries to cover up his private misery and continues doing jobs.
In The Slice Girls, it's revealed Dean keeps Bobby's old flask as a memento and frequently uses it. Sam grows frustrated with Dean's drinking and lack of interest in cases that don't revolve around Dick Roman. During this time, Dean unknowingly sleeps with and has a daughter, named Emma, with an Amazon. The Amazons age and grow in a very short period of time until they reach adulthood, and so the baby is birthed in mere hours, and reaches adolescence in a few days. Amazon teens must go through a rite of passage in which they must kill their fathers - the event that Dean and Sam were investigating in the first place. Dean was shocked to realize he produced a child and didn't like Sam's jokes about being a father. Meanwhile, a clue is given to them by a strange "breeze" in the room. Dean believes it may be Bobby's spirit, but Sam doesn't think so and gets mad at him for the suggestion.
When Dean's daughter comes to Dean, she lies and tells him she needs his help to escape the other Amazons. A wary Dean sees through her scheme and they end up drawing their weapons and stand ready to face one another. Emma was impressed with him as she was told that he was a challenge. Both Emma and Dean knew that Dean was too soft and could not bring himself to kill Emma, his own child and he told her that he wouldn't get in his head and told her to leave the amazons. However, Sam who was recently enlightened to his brother's situation, upon entering the room decides that Dean cannot bring himself to kill his own daughter, and so, after a short confrontation, he kills her. Sam then reminds Dean that he had to do it, just like Dean "had" to kill Amy.
When Sam's hallucinations eventually worsen and he suffers a complete psychotic break he's admitted to a psychiatric ward in The Born-Again Identity, Dean is determined to find a healer for his brother's mind. He stumbles upon a "faith healer" named Emmanuel, but is revealed to actually be an amnesiac Castiel who was resurrected. Dean is shocked to see him alive and is stricken with mixed feelings, still blaming Castiel for his mistakes to Sam's mind and the world.
|“||I just know that ... this whole thing couldn't be messier. You know, I used to be able to shake this stuff off, whatever it was. It might take some time, but ... I always could. What Cass did ... I just can't. I don't know why.||”|
— Dean to amnesiac Castiel
in The Born-Again Identity
Him and Meg take Emmanuel to Sam where Castiel slowly regains his memories. Castiel is almost too ashamed to help Sam, but Dean nonetheless convinces him he still can fix it. Thanks to Dean, Castiel shifts Sam's hallucinations to his own mind and saves his brother, though at the cost of Castiel's own sanity. In the aftermath, Dean made an agreement with Meg to keep an eye on Castiel - who was now insane in psychiatric ward - but hadn't completely forgiven him.
Dean continues to work cases with Sam and tries to stop Leviathans, but the strange activity around them continues. Eventually, the brothers discover in Of Grave Importance, Bobby is a ghost and is tied to his old flask that Dean carries around. He had been helping them in small ways with their hunting for a while. Dean is particularly unsettled, glad to be around Bobby but upset that he chose to stay to help them when he could've found peace. Bobby, however, justified his choice. Unsure what to do next with the situation, the brothers at the moment let it rest.
Soon after, in The Girl With The Dungeons and Dragons Tattoo, Sam and Dean receive an automatic email from Frank, who had been recently killed by Leviathans. The message informs them a hacker of Dick's at Roman Enterprises is hacking into Frank's information about them. The hacker turned out to be Charlie Bradbury, who discovered the truth about Dick Roman and Leviathans after hacking it. It's discovered that the Leviathan's ultimate plan is to turn people into "perfect cattle" for their meals. Sam and Dean rush to location by GPS tracker on Frank's hard drive, managing to get a reluctant Charlie to sneak in Dick Roman's office and get his private information. Bobby, however, set on vengeance follows them despite Sam and Dean's warnings.
Charlie manages to get Dick Roman's information and give the brothers a chance to steal a private package being transported to Dick, but is injured accidentally by Bobby who lost control seeing Dick. Sam and Dean narrowly escape, discovering the package to be an tablet. Charlie survives with a broken arm and departs, leaving the brothers with an unknown tablet and concerns of Bobby turning into a vengeful spirit.
Sam and Dean crack open the tablet in Reading Is Fundamental, unknowingly calling forth Kevin Tran as the next prophet. Simultaneously Castiel awakens in the mental ward. The brothers rush over to him, who manages to decipher it an angel tablet called the Word of God. Dean tries to seek answers from Castiel and is still angry over his actions, but Castiel is clearly insane and has given up fighting even to help them. Meanwhile, Kevin tries to steal the tablet and they discover he's a prophet.
After Kevin is stabilized, he fully deciphers the tablet before leaving and they figure out how to kill Leviathans: "a bone of a righteous mortal dipped three bloods of the fallen". Sam and Dean have the first type of blood---Castiel's, a fallen angel---and set out for the other two.
Dick Roman's power grows. Dean and Sam are resorted to eating organic food on a daily basis as all other foods are infected by Leviathans, something Dean is not happy about. The brothers discover the other blood types are from an alpha and Crowley. Crowley refuses to give his blood right away so Sam and Dean go after the Alpha Vampire. After discovering the Leviathans plan to exterminate not just humans but monsters, the alpha grudgingly gives them his blood. Sam and Dean's plan is successful until they go to the motel to find Bobby gone and the place ransacked. Dean is upset at Bobby's violent and reckless impatience to get Dick, unwilling to admit he was close to being a vengeful spirit.
In Survival of the Fittest, Sam and Dean get a bone of nun and try to summon Crowley but he doesn't show. This makes the brothers doubt his word, though sure enough Crowley appears later with a vial of his blood. He explains the deal Dick tried to make with him to bring them another demon's blood, but this was the real deal. Neither Dean or Sam trust them, but know they don't have another option. Meanwhile, Castiel and Meg rally with them. Crowley indicates Castiel can help against the Leviathans, but he still refuses to actively involve himself in the matter. Dean grows frustrated with this.
|“||We can't leave it. You let these friggin' things in. So you don't get to make a sandwich. You don't get a damned cat. Nobody cares that you're broken, Cass! Clean up your mess!||”|
— Dean to Castiel
in Survival of the Fittest
Afterwards, Bobby reappears after nearly killing a maid and Sam in his obsession with vengeance against Dick. Bobby realizes he's dangerous and wants his flask burned before he loses himself entirely as a vengeful spirit. Both Sam and Dean are sad at losing their surrogate father yet again, but do the right thing and burn it, putting him to res. The day before they infiltrate Dick's base of operations, Castiel transports Dean to his Impala which had been on lockdown all year since Slash Fiction. Castiel shares his reluctance to fight because he fears he's only bad luck. Dean disregards this and tells him he's the only one left who can help. Dean finally forgives Castiel for his actions and motivates him to fight. Slowly more like his old self and as the only one who could identify the real Dick Roman among to copiers at the base of operations, Castiel agrees.
|“|| Castiel: I'm not good luck, Dean.|
Dean: Yeah, but you know what? Bottom of the ninth and you're the only one left on the bench. Sorry, but I'd rather have you. And anyway, nut up, alright? We're all cursed. Do I seem like good luck to you?
— Dean motivates Castiel to fight
in Survival of the Fittest
The next day, Dean, Sam and Castiel infiltrate SucroCorp. Meg stays out in the open to distract the Leviathans, Sam goes to get Kevin, and Dean and Castiel go after Dick. Castiel is able to locate him and they confront the leader. Dean stabs Dick with the bone, but it has no affect. Castiel holds him place from behind while Dean pulls out the real bone, tricking him into lowering his guard. Dean kills Dick by stabbing him through the neck, causing him to convulse and pulse strangely. Sam appears and watches as Dick suddenly explodes in black goo, Dean and Castiel disappearing with him.
Dean wakes up in shadowed plane with Castiel, now trapped in Purgatory as a side-effect of the weapon. Castiel who is now sane again tells Dean their location. Seeing the monsters around, Dean wants to get out, but Castiel grimly tells they're more likely to get ripped to shreds than escape. Castiel suddenly disappears, leaving Dean alone as monsters come up to attack.
|“||It was bloody. Messy. Thirty-one flavors of bottom-dwelling nasties. Hell, most days felt like 360-degree combat. But there was something about being there. It felt pure.||”|
— Dean describing his experience in Purgatory
in We Need To Talk About Kevin
Dean finds a lone vampire and interrogates him on information for Castiel's whereabouts, but gets nothing out of him. He kills the vampire with ruthless primal ease, only to be attacked by another. A vampire named Benny saves him. Dean is hostile, but Benny approaches him with the possibility of escape. There was a portal out of Purgatory only a human could use, but he would only give him the details if he gets him out of there too by using a spell to carry his soul. Dean naturally distrusts him, but agrees to work with Benny if he helps him find Castiel.
Eventually, after interrogating more monsters, Dean and Benny locate Castiel on the far side of Purgatory. Dean is happy to see Castiel alive until Benny reminds him of the angel's sudden disappearance. Dean believes he was just attacked, but Castiel admits he ran away. He explains he left because the Leviathans in Purgatory want him destroyed more than anyone, so he wanted them after him to protect Dean. Castiel requests to stay but Dean has Benny tell him of the portal bur admits he doesn't know if it works on angels, though Dean refuses to leave without him.
|“||We'll figure it out, Cass. Buddy, I need you. [...] And if the Leviathans want to take a shot at us, let 'em. We ganked those bitches once before. We can do it again. [...] I'm not leaving here without you.||”|
— Dean to Castiel
in What's Up, Tiger Mommy?
Dean, Castiel, and Benny trek throughout Purgatory. Dean still shows distrust towards Benny for being a vampire despite working with him. He also clashes with him over Castiel, who was attracting more monsters coming with them. Castiel agrees that he's only cause trouble going with them, not knowing if he can even make it through the portal, but Dean doesn't care. Eventually, Castiel attracts Leviathans. As they're fighting, Castiel is about to be killed. Dean looks in in horror, but Benny saves the angel. This made Dean begin to trust Benny.
Eventually, Dean, Castiel, and Benny make it towards the portal Dean can activate. Using a spell, Dean successfully transports Benny's soul in his arm and is ready to leave with Castiel. As they make their escape, Dean and Castiel are attacked by Leviathans. Going through them, the portal opens for Dean. Castiel lets go of Dean just as they're about to make it. Dean is sucked up by the portal and returned to Earth.
|“||I can't believe what I'm hearing. Sam, we have an opportunity to wipe the slate clean. We take Kevin to the tablet, he tells us the spell, we send every demon back to hell - forever. Every single bastard that destroyed our lives, killed our mother, killed Jess, and you're not sure?||”|
— Dean's determination to close the gates
in We Need To Talk About Kevin
Sam and Dean catch up, though Dean refuses to disclose the fate of Castiel. Dean is disapproving that Sam retired from hunting and even more upset Sam made no attempt to look for him. He checks Sam's old mobiles (which he had ditched) where he played voicemails of Kevin over the course of months that had escaped Crowley and was in hiding. Dean is angry Sam left Kevin alone. It becomes clear Dean's perspective on hunting changed significantly since Purgatory and he now holds tighter responsibility on saving lives than ever. Sam and Dean find him and discover Crowley wanted him to read another Word of God which detailed different ways to defeat demons, including a spell to shut the gates of Hell. Dean is motivated to close the gates of Hell forever through Kevin's help, though Sam is less sure and needs to be convinced. Crowley appears for Kevin, but they escape.
After escaping, Dean gets a call from Benny. Dean tells his friend not to call him for a while, hiding their friendship from Sam. Despite being out of Purgatory, Dean is still continually on edge and seems more guarded than he ever has been before.
In What's Up, Tiger Mommy?, Sam and Dean go to Kevin's mother's house under Kevin's request to see if she was safe. After rescuing Ms. Tran from demons, she decides to go with the group to help protect her son. When they discover the tablet was stolen from the place Kevin was hiding it, they track it down ultimately to an auction house. The group ends up in a bidding war when Crowley shows up, and Kevin ends up being auctioned off along with the tablet. Ms. Tran offers up her own soul in order to save her son. When that offer is accepted Crowley possesses Ms. Tran's body to steal the tablet. Dean fights against Crowley and nearly killed him despite being inside Ms. Tran's body, highlighting Dean's more ruthless nature since Purgatory. Crowley, however exits out of her body just in time and manages to escape with the tablet. After asking for a moment alone with his mother, Sam and Dean find Kevin and his mother gone and note from Kevin saying he didn't want to end up killed being useless to them like Crowley warned.
Dean continues to hop on every hunting case he can find with remarkable enthusiasm. Sam tags along reluctantly, missing his year of normal and only interested in finding Kevin. This creates strain between the brothers. Eventually Dean's suddenly intense sense of purpose alienates Sam so much he admits after closing the gates of Hell, he wants to quit and live normally. Dean doesn't believe he means it, but Sam insists.
|“||All right, man. Look, I get it. You took a year off to do yoga and play the lute. Whatever. But I'm back. Okay, we're back, which means that we walk and kill monsters at the same time. We'll find Kevin. But in the meantime, do we ignore stuff like this? Or are innocent people supposed to die so that you can shop for produce?||”|
— Dean's newfound purpose
After another failed attempt to locate Kevin in Blood Brother, Dean receives a call from Benny who needs help taking down the vampires that turned him. Dean leaves without telling Sam about where he's going and finds the vampires' nest. Eventually, Dean gives into Sam's calling and tells him he's with his friend and needs help taking down the nest. Sam shows up after they take down the nest and officially meets Benny, but quickly realizes he's a vampire.
Sam is angry with Dean trusting a vampire in Southern Comfort, but Dean insists he's good. Sam still doesn't trust it. While doing a case with Garth, Dean gets possessed by a specter that forces you to kill the people you have a grudge against. Dean goes after Sam, revealing he still holds resentment for Sam not trying to find him in Purgatory and all his other past mistakes. Dean also highlights his disappointment in both Sam and Castiel, who he feels both betrayed him so trusts Benny because he's the only that hasn't.
|“||Mistakes? Well, let's go through some of Sammy's greatest hits. Drinking demon blood? Check. Being in cahoots with Ruby. Not telling me that you lost your soul. Or how about running around with Samuel for a whole year, letting me think that you were dead while you were doing all kinds of crazy. Those aren't mistakes, Sam. Those are choices! [...] Yeah, I might've lied, but I never once betrayed you. I never once left you to die. And for what a girl? You left me to die for a girl?!||”|
— Dean's hidden resentment towards Sam
in Southern Comfort
When specter is defeated, Dean tries to brush off what happened between him and Sam. Sam, however, knows he had meant everything he said. Sam stands up to him and tells him he needs to get over it before he drives him away.
In A Little Slice of Kevin, Castiel mysteriously returns to Earth with no memory how while Sam and Dean are examining a case of strange kidnappings. Dean is shocked to see Castiel back, but is wary of his sudden return. They discover Crowley is kidnapping future prophets after losing Kevin in hopes they can analyze the tablet. Soon Crowley kidnaps Kevin and the brothers get a call from Mrs. Tran asking for help. Castiel, Sam, and Dean inflitate Crowley's hideout. With Castiel's help, they manage to secure Kevin tough the tablet breaks in half and half is missing. It's revealed Dean blames himself for not bringing back Castiel, but Castiel shows and tells him he always planned to be trapped in Purgatory for punishment and chose to stay. Dean didn't fail.
|“||You can't save everyone, my friend ... though you try.||”|
— Castiel to Dean
in A Little Slice of Kevin
In Citizen Fang, Sam confronts Dean on a trail of a bodies leading towards Benny in Louisiana that Martin Creaser tracked. Dean doesn't believe Benny did it, but is willing to do what he has to only if Sam and Martin give him time to get Benny's side. Benny explains he didn't do it, but another vampire from his past did and he's trying to clean up his mess. Dean trusts Benny and tries to convince Sam and Martin of the same. Martin knocks him out and they go after Benny themselves. Desperate, Dean uses the fake number of Amelia's he swapped on Sam's phone with one of his phones and sends a fake S.O.S protect Benny. Dean tries to help Benny escape, but ultimately Benny is forced to kill Martin in self-defense. Sam, who had left the scene and rush to the rescue as Dean guessed, figures out it the truth later. Sam is angry with his brother, but Dean believes he did the right thing.
In Torn and Frayed, Sam and Dean argue about Benny and the fake text on Amelia. The brothers take a break, but are brought back together to help Castiel rescue the angel Samandriel who was kidnapped by Crowley. Dean and Sam are suspicious over Castiel's strange behavior after seeing Samandriel suddenly dead beside him. They also sort out their issues. Dean admits he could never separate himself from hunting for normal the way Sam could and, tired of arguing with him, gives him his blessing to be with Amelia if it makes him happy.
|“||I'm just tired of all the fighting. [...] And y'know, maybe I'm a little bit jealous. I could never separate myself from the job the way you could. Hell, maybe it's time for at least one of us to be happy.||”|
— Dean gives Sam his blessing to be with Amelia
in Torn and Frayed
Ultimately, Sam realizes there are too many important things he has to take care of and choses to stay with Dean. Dean, out of loyalty to Sam, is forced to end direct contact with Benny.}}
In As Time Goes By, Dean and Sam meet their grandfather, Henry Winchester, who travelled in time on the run from the Knight of Hell Abbadon protecting a vital key. The brothers also discover the Winchester bloodline were composed of the Men of Letters---chroniclers with vast knowledge of the unexplained and supernatural which they passed on to hunters that they deemed worthy. At first, Dean resents Henry for leaving John to grow up alone, as he had disappeared doing Men Of Letters duties, but ultimately comes to respect him and forgives after finally seeing he wasn't at fault. They help Henry capture Abbadon and manage to protect the key, but at the cost of Henry's life. Henry slowly dies but not before expressing pride in them and their father. The brothers bury their grandfather with his fallen Men of Letters comrades. The two were left understanding the significance of the Campbell and Winchesters being paired together and wondered over how their father's life would of been if he had his father.
The key left behind by Henry leads Sam and Dean to the Men of Letters headquarters in Everybody Hates Hitler, which is remarkably well-preserved despite being abandoned. After doing a case about the Judah Initiative, Sam and Dean adopt the place as their home and base of operations, becoming official Men of Letters.
In Trial and Error, Dean receives a call from Kevin who deciphered part of the tablet that would close the Gates of Hell forever: three trials completed by somewhere worthy and the first was killing a hellhound. Dean is enthusiastic about this and automatically elects himself to do it. Sam and Dean track down ten-year contracts to find a hellhound and are lead to a farm where Crowley made multiple deals. Dean recklessly sets out to kill the hellhound. Dean expresses his jaded picture of his future and knows these trials will have a fatal consequence, but wants Sam safe and to have a family. Dean is determined to do the trials because he feels he has nothing left to lose.
|“||I'm a grunt, Sam. You're not. [...] And you told me yourself you see a way out. You see a light at the end of this ugly-ass tunnel. I don't. But I'll tell you what I do know. It's that I'm gonna die with a gun in my hand. 'Cause that's what I have waiting for me. That's all I have waiting for me. I want you to get out. I want you to have a life- become a Man of Letters, whatever. You with a wife and kids and grandkids, livin' 'til you're fat and bald and chugging Viagra. That is my perfect ending and that's the only one I'm gonna get. So I'm gonna do these trials. I'm gonna do them alone. End of story.||”|
— Dean' s resolve to do the trials
in Trial and Error
Dean finds the hellhound and is nearly killed until Sam comes to his rescue, killing it and becoming the person for the trial. Dean refuses to let Sam do this, but Sam expresses his faith in both of them. Dean reluctantly lets Sam carry out the rest of the trials.
In Man's Best Friend With Benefits, Dean is still concerned over the trials and continues to try to convince Sam he can do them instead. Sam, frustrated, admits he believes Dean can't trust anyone but himself. Dean and Sam are infected fight a witch named Spencer Wallis who infected them with some of their worst memories. Dean is affected by remembering everything they went through and decides to stand by Sam's choices to do the trials.
In Goodbye Stranger, Dean spots a bloody tissue of Sam's and realizes he's been hiding the toll the trials have on his health. Castiel returns, telling them Crowley has been searching for Lucifer's crypts. He lies and says he's looking for parchment to decipher the tablet, but Sam and Dean later find out he's searching for an angel tablet. The brothers; distrust over Castiel heightens, but they nonetheless work with him and find Meg who knows about the location of the crypts.
When finding the tablet, Dean wants to give it to Kevin, but Castiel wants to take it to Heaven. Dean refuses and Castiel, under control of Naomi, proceeds to attack him and says Naomi's name which Dean overhears before Castiel beats him brutally. Dean knows Castiel isn't himself and desperately tries to snap him out of it. Just as Castiel is about to kill him, Castiel stops and heals Dean. Castiel apologizes, but leaves with the tablet to protect it from Naomi - and them. Outside, Crowley is there for the tablet. He kills Meg, but the brothers escape. Soon after, Dean confronts Sam about lying and that he's there for him. Dean, still shaken about Castiel, doesn't want to be lied to anymore.
In Taxi Driver, Kevin translates the second trial which is to "rescue a soul from Hell." The brothers contact a rogue reaper Ajay and find out from him that Bobby's soul is in Hell. Hearing this, Dean wants to help Sam save Bobby, but Sam tells him it's his trial and convinces Dean to stay. As Sam rescues Bobby, Dean visits Kevin, who hears Crowley in his thoughts and is convinced he knows where he is. In a panic, Kevin hides the tablet and Dean is visited by Naomi who tries to convince him she's trustworthy.
|“|| Kevin: "Just tell me when this all ends 'cause that's the only thing I want to hear."|
Dean: "No. Like I told you before, this isn't going to end. Look, man. Other guys, they got it easy, y'know? It's all backyard barbeques ... and bowling teams, but you and me? We got to carry a little extra weight."
Kevin: "I can't take it."
Dean: "Yes, you can. Hey, look at me. Now, this whole thing sucks. I know. But you suck it up and push through because that's what we do. And when you get on board with that, the ride is a lot smoother."
— Dean motivates Kevin
in Taxi Driver
When finding out Sam is in Purgatory, Dean contacts Benny and asks him if he can help get him out to get them both out. Dean is guilty, but has to save his brother. Benny agrees, admitting he didn't like being on Earth and Dean reluctantly kills him. Benny rescues Sam and Bobby's soul is sent to Heaven, completing the second trial. Dean is upset Benny didn't come with even though according Sam he chose to stay and decides not to burn his bones, in hopes that one day he'll be able to bring him back. The brothers visit Kevin, only to find him missing.
In The Great Escapist, Dean continues to take care of Sam who's health is rapidly declining from the trials. The brothers receive an automatic message from Kevin, who assumes he's dead and sends them notes from his deciphering of the tablet. This leads Sam and Dean to meet Metatron, the scribe of God. With come convincing needed, he saves Kevin from Crowley. Kevin has the other half of the tablet and has figured out the third trial: to cure a demon.
In Clip Show, Sam and Dean watch a serious of old exorcism videos on the Men of Letters files, proving a curing a demon is possible. The brothers dig up Abaddon's body and intend to cure her, but are distracted when Crowley calls detailing his plans to kill everyone they ever saved if they didn't surrender the tablet. Abbadon escapes and with no demon to cure, Sam and Dean go after Crowley. Crowley massacre is lead to Sarah Blake Sam's old fling. Sam and Dean do everything in their power to save her, but are too late. Sam considers surrendering, but Dean is determined and convinces him to push on.
In Sacrifice, Dean and Sam seem to give in to Crowley's demands after nearly killing Jody Mills. However, when the deal is made, Dean handcuffs Crowley which has a devil's trap on it, steals the angel's tablet, and traps him to use for him to the third trial. Dean is called away by Castiel and gives Kevin the tablet to translate as Sam cures Crowley. Ultimately, it's revealed Castiel's deal with Metatron was a trick and Sam will die if he completes the trials. Dean rushes to the scene just as Sam is about to completely cure Crowley. Sam wants to carry out the trials even if he dies, admitting he feels like all does is let Dean down and it hurts him to watch his brother to trust Castiel or Benny more than him. Dean tells him none of that is true and there's no one else in the world he cares about more than Sam. Dean convinces Sam to stop and they agree to save people their own way.
However, Sam is still affected by trials and falls to the ground in pain. Dean calls out for Castiel, but he's nowhere. The brothers watch as angels fall from the sky, Metatron's plan to self-destruct Heaven completed.
|“||Listen, man. I know we've had our disagreements, okay? Hell, I know I've said some junk that sets you back on your heels. But Sammy ... come on. I killed Benny to save you. I'm willing to let this bastard and all those sons of bitches that killed Mom walk because of you. Don't you there think that there is anything past or present that I would ever put in front of you! It has never been like that! Ever! I need you to see that. I'm begging you.||”|
— Dean's final appeal to Sam
|“||This is nuts. I mean, you're Sam, but you're not Sam, and normally he's the one I'm talking to about all this stuff. I'm trusting you, Zeke. I just gotta hope that you're one of the good guys.||”|
— Dean's uneasy alliance with "Ezekiel"
in Devil May Care
When Sam falls into a coma in I Think I'm Gonna Like It Here, he takes him to a local hospital and finds out that Sam is going to die. Dean then goes to a church and prays to all the angels for help. As a consequence, Dean is attacked by several angels looking for Castiel and is forced to banish them all save for one named "Ezekiel". Ezekiel tells him Sam's condition is too severe to be healed and he must possess him to heal both Sam and himself fully. Dean at first refuses, knowing Sam would never agree, but desperate to save his brother, gives in. Ezekiel casts an image of Dean in Sam's head to get him to say yes and it works. Dean guiltily keeps his possession by Ezekiel a secret from his brother.
In Devil May Care, Dean and Sam work together to use Crowley for information to kill all the demons loose on Earth. Meanwhile, they discover Abaddon is still alive and kidnapping hunters for them to give up Crowley. The brothers team up with Irv and Tracy Bell where Dean gets in a violent confrontation one-on-one with Abaddon. She flees from Ezekiel, who took control of Sam to save them from demons. Dean is uncomfortable with the situation and admits he also feels guilty about not closing the gates of Hell after seeing the damage the demons are causing, but Ezekiel reassures him. He is still skeptical about the angel's motives, who only asks him to trust him. Dean also stops Kevin from leaving them, and calls him family.
|“|| Dean: "This is on me. I was the one that talked Sam out of boarding up Hell. Okay? So every demon deal, every kill that they make ... well, you're looking at the person that let it happen."|
Zeke: "You were protecting your brother. I am in Sam's head. Everything he knows, I know. And I know what you did, you did out of love."
— Dean and "Zeke"
in Devil May Care
In I'm No Angel, Dean is alerted by Ezekiel the faction that is after Castiel and fears for his safety. He makes an excuse to Sam about his knowledge and together they search for their friend, leading them to a rogue reaper. She kills Castiel, but Ezekiel takes over Sam and brings him back to life. Sam questions again Dean's knowledge about angels and Castiel on how he survived, but he lies to both of them. They take Castiel back to their bunker, only for Ezekiel to possess Sam and warn that Castiel can't be here without drawing attention to himself. Dean initially refuses, but when Ezekiel warns he'll be forced to leave Sam's body if he stays, he reconsiders. Dean reluctantly forces Castiel to leave without explanation.
In Slumber Party, Sam and Dean fight to stop The Wicked Witch from entering Oz. They meet up again with Charlie. After she gets killed by the Witch, Dean begs "Ezekiel" to save her, which he reluctantly does. Later, Dean and Sam get possessed from the Witch and are turned into minions of hers. They then hunt down Charlie and Dorothy to try and kill them. They aren't turned back until Charlies saves them by killing the Witch.
In Dog Dean Afternoon, Sam and Dean solve two bizarre cases in which a dog is the sole witness. Dean uses a spell that gives him the ability to talk to animals. He gets along quite well with their witness The Colonel, despite the fact that he doesn't really like dogs.
In Heaven Can't Wait, Dean works with Sam and Kevin to research ways to undo Metratron's spell on the angels and return them to Heaven. Dean is called away by Castiel for a case where he greets his friend working a mediocre job at a place called Gas-n-Sip. Dean at first believes it's beneath him and encourages him to get back on track, but after facing off against a dangerous angel type Zit Rein, he encourages Castiel to live normal. Dean finds out by Sam through Crowley's there's no reversal for the angels who got expelled for Heaven, but doesn't tell Castiel this and tells him to just leave it to them.
InRock and a Hard Place, he and Sam catch up again with Sheriff Mills. Dean and Sam also renews their virginity and join a chastity group to get closer to the source of mysterious kidnappings. Dean has sex with an ex-porn star chastity counselor after the meeting. This causes them to get abducted by Vesta, a goddess after virgins that broke their vows. Sam and Jody arrive as Dean tries to free himself and the other victims. Jody kills Vesta and they say their goodbyes. Dean feels increasingly guilty after Sam admits he thinks there's something wrong with him---that he'll never be normal---and is close to telling him about Ezekiel, but the angel stops him and warns the consequences if Sam ejects him. Dean lies to his brother yet again.
In Holy Terror, Dean is still unsure of the idea to not tell Sam about "Ezekiel", but is convinced by the angel to still use the trials as an excuse. Sam and Dean work a case with Castiel, where it becomes apparent Dean didn't tell Sam why Castiel left. Dean finds out from Castiel — now an angel again by stealing another one's grace — that "Ezekiel" died during the fall and the one possessing Sam isn't him. Determined to expel the unknown angel, Dean works with Kevin to perform a ritual weakening the angel for Sam to expel him. Dean performs the ritual and explains to Sam quickly, including his motivations for lying and that he was trying to save him. Sam, actually still possessed and nearly acting, punches Dean and kills Kevin under request of Metatron.
Dean wakes just in time to see Kevin die. It's revealed the ritual had been altered by the angel, making it useless. Dean tries to attack "Ezekiel", but the angel overpowers him and leaves with full possession over Sam. Dean is left alone, having lose both Kevin and Sam.
In Road Trip, Dean is devastated by grief and guilt. He gives Kevin a hunter's funeral and is determined to kill the angel possessing Sam in revenge. Castiel appears and they reluctantly work with Crowley for him to help them expel the angel from Sam. They discover the angel is Gadreel, the angel that first let Lucifer out of his cage and into the "garden". After torturing Gadreel to bring out Sam doesn't work, Crowley temporarily possesses Sam to connect to his mind and expel the angel in exchange for his freedom. Sam expels the angel and Castiel heals the rest of his damage from the trials.
Sam is furious with Dean for tricking him by letting Gadreel possess him, but Dean stands by his reason to save him. Dean brokenly leaves to hunt Gadreel on his own, convincing himself all he does is hurt the people around him. Sam doesn't try to stop him.
|“||Kevin's blood is on my hands, and that ain't ever getting clean. I'll burn for that. I will. But I'll find Gadreel and I'll end that son of a bitch. But I'll do it alone. [...] I'm poison, Sam. People get close to me, they get killed. Or worse. You know, I tell myself I-I help more people than I hurt, and I tell myself I'm doing it for the right reasons, and I-I believe that. But I can't. I won't ... drag anyone through the muck with me. Not anymore.||”|
— Dean's decision
in Road Trip
In First Born, alone in a bar, Dean is approached by Crowley for help with finding the First Blade, the only weapon that can kill Abaddon. Dean reluctantly allies himself with the demon and begins the search by looking for information on a hunt his father did where he captured, interrogated and exorcised a demon who claimed to know about the Blade. The information they find leads them to a hunter named Tara and eventually to the biblical Cain who Dean is shocked to learn is now a very powerful demon. Dean asks for Cain's help in locating the Blade, telling him they need to kill a Knight of Hell. Dean is pissed at Crowley when Cain reveals that he created the Knights which Crowley knew, but is surprised to learn that Cain was the one that killed them all. When Cain refuses to help, Dean sneaks back with Crowley to search for the Blade only to be caught by Cain. When four demons show up, Dean is left to fight three of them single-handedly. He wins and Cain tells him how he slaughtered the Knights after they kidnapped his wife who was killed by Abaddon. Cain still refuses to help and is unimpressed by Dean's threats. Cain leaves as a demon army arrives, but returns willing to help and explains that the Blade is useless without the Mark of Cain which he can transfer to someone worthy, such as another killer. He'd let Dean fight alone to see if he was worthy and offers him the Mark, trying to warn him that it comes with a terrible price. Dean takes the Mark anyway without learning what the price is and after telling them that the Blade is at the bottom of the ocean, Cain teleports Dean and Crowley to safety while he takes on the demon army, asking for Dean to return after he kills Abaddon to kill him too. Outside, Dean is shocked to see Cain slaughter the demons alone. However, he pissed at Crowley as he realizes Crowley used him to get access to the Blade. Crowley confirms this, but while Dean threatens to kill him when everything is over, he recognizes he still needs Crowley and sends him after the Blade.
Sam and Dean run into each other in Sharp Teeth after working on the same case involving Garth (now a werewolf) and a werewolf cult. They work together reluctantly, Sam still furious and Dean still guilty. After the case, Dean again apologizes to Sam and tries to suggest they work together again in hopes they can patch it up. Sam agrees to work with him, but insists to keep it professional because he doesn't think he can't trust Dean. Dean resignedly agrees to his terms.
In The Purge, after another tense case, Dean finally erupts and insists he did the "right thing" saving him. Sam disagrees and believes Dean simply didn't want to let him go if it meant he was alone. Dean challenges Sam that he would've done the same thing if the roles had been reversed. Sam says he wouldn't, shocking Dean.
|“|| Dean: "You know, Sam. I saved your hide back there. And I saved your hide at that church ... and the hospital. I may not always think things all the way through, okay? But what I do, I do because it's the right thing. I'd do it again."|
Sam "And that is the problem. You think you're my savior. My brother, the hero. You swoop in, and even when you mess up, you think what you're doing is worth it 'cause you're convinced you're doing more good than bad ... but you're not.[...] Please tell me, what is the upside of me being alive?"
Dean: "Are you kidding me? You and me. Fighting the good fight together."
Sam: "Just once, be honest with me. You didn't save me for me. You did it for you. [...] I was ready to die. I should've died, but you ... you didn't want to be alone. And that's what this all boils down to. You can't stand the thought of being alone. [...] I'll give you this much. You are certainly willing to do the sacrificing. As long as you're not the one getting hurt."
— Sam's outlook on Dean
in The Purge
In Captives, it's revealed Kevin's spirit is haunting the bunker due to an after-affect of Metatron's spell. Dean is still stricken with guilt over his death and apologizes to him, though Kevin doesn't blame him. By Kevin's last request, Sam and Dean search for Kevin's mother and find her still kidnapped by Crowley. The boys rescue her and Linda reunites tearfully with her son, deciding to take him with her until Kevin can move on. The brothers make peace with him and vow to find a way to send Kevin to Heaven.
In Blade Runners, Sam and Dean work with Crowley to track down the First Blade. Their search leads them to a rogue member of the Man of Letters named Cuthbert Sinclair a.k.a. "Magnus" who tries to keep Dean as a "collectible" upon discovering he has the Mark of Cain. Dean uses the First Blade to kill Magnus, uncharacteristically beheading him as he's pulled by the dark power of the Blade. Sam snaps Dean out of his aggression. The brothers decide to kill Crowley now they have the blade, but Crowley steals it and will only give it back when it's time to kill Abbadon.
In Mother's Little Helper, Dean grapples with the after-effects of holding the First Blade. He struggles between wanting it's power or just using it to kill Abaddon. Dean becomes uneasy over taking up the First Blade again even it means killing Abaddon, afraid of what it'll turn him into. Crowley pushes Dean to accept his role and eventually he reluctantly decides he'll have to do what he'll have to.
|“||I want to kill Abaddon. That's what I want. So whatever happens with the Blade, I can't worry about that. [...] What I want, what I fear, none of that means squat. Because this is the one chance we have to kill Abaddon. So I'm all in, no matter what the consequences.||”|
— Dean taking on the burden of The Blade
in Mother's Little Helper
In King of the Damned, in the presence of the First Blade, the Mark grants Dean immunity to Abaddon's powers at first with great concentration and then no effort. He also displays telekinesis and strength great enough to lift Abaddon off her feet effortlessly. However, the Mark and Blade's effects cause him to go overboard and repeatedly stab the dead Abaddon after he kills her. Sam confronts Dean about this and Dean explains he knew from the start he had to kill Abaddon alone and whatever else he had to kill it with. Worried about what it's doing to him, Sam tries to tell Dean to stash the Blade away, but Dean refuses.
In Stairway to Heaven, the brothers investigate a case of angels blowing themselves up along with innocent people supposedly in the name of Castiel. Under influence of the mark, Dean is quick to blame Castiel for the crimes and is shown aggressive in his dealings with the angels and Tessa. Despite telling Sam he hadn't, Dean brings the First Blade with him and accidentally kills Tessa, wanting to be free of hearing the lost souls. Castiel is forced to give up his army after refusing to kill Dean under their orders. It's revealed the martyring angels were Metatron's double-agents and used for this very reason. Dean slips in deeper control of the mark and tries to kill Gadreel who arrives to join their side, having to be held back by Sam and Castiel.
|“||The Blade's the only thing that can kill Metatron, and I am the only one who can use it. So from here on out, I'm calling the shots. [...] Until I jam that blade through that douchebag's heart, we are not a team. This is a dictatorship. Now you don't have to like it, but that's how it's gonna be.||”|
— Dean to Sam
in Stairway to Heaven
In Do You Believe In Miracles?, Dean is shown to be over-aggressive and has no control over his desire to kill Metatron. His need for the First Blade is also very detrimental to his health. He even works with Crowley to hunt down Metatron. When he does find Metatron, he tries to kill him but fails. Metatron then stabs Dean in the heart, killing him. Crowley approaches Dean and tells him that Dean is a lot like Cain who also died because he wasn't willing to kill innocents but Cain's very sacrifice is what made him become a demon. Crowley then tells Dean to open his eyes. Dean does so, but returns as a demon (more specifically a knight of hell).
|“||It's better this way. The Mark. It's turning me into something I don't wanna be. [...] I'm proud of us.||”|
— Dean's last words to Sam as he dies
in Do You Believe In Miracles?
|“|| Crowley: "What are you doing?"|
Dean: "Oh, whatever I want."
Crowley: "Really? Because I think you don't know what you want. Tell me, Dean. What are you? A demon? If so, why isn't Lester's wife dead? Did you feel sorry for her? So maybe you're human. Except you have those pretty black peepers and you're working alongside me. Why don't you do us all a great big favor and PICK A BLOODY SIDE?!"
Dean: "Or what? Make a move. See how that ends. I ain't your friggin' bestie and I ain't taking orders from you. When I need to kill, I'll call. Until then, stay out of my way."
— Dean and Crowley
In Reichenbach, Dean continues his carefree and aggressive activities. Crowley grows concerned the mark on Dean will act up if he doesn't kill soon and gives Dean a job to kill a woman her husband sold his soul to be killed for. Dean reluctantly goes to her house, but after seeing Lester outside to "watch the hit" Dean instead kills him. Crowley is appalled Dean ruined his deal (he could no longer get the soul now that Lester was killed without his wife dead) and challenges Dean for not knowing whether he's good or bad. Dean humiliates Crowley and ends their partnership.
Shortly after, Crowley betrays Dean by telling Sam where he is. Dean rejects Sam's attempts to bring him back to cure him and is finally found by Cole, who followed Sam. Dean shows no apparent remorse for Cole's dead father and mercilessly beats him. Sam traps Dean with Devil Trap handcuffs while Crowley takes the First Blade and hides it far away. Sam questions Dean's decision not to kill Cole and believes he showed mercy. Dean replies letting him live with the knowledge he could never get his revenge was the worst thing he could've done to him.
In Soul Survivor, Dean is tied inside a Devil's Trap as Sam starts the curing ritual. Dean expresses his condescension towards hunting monsters ("the natural order") and is completely jaded over any point it ever had. He also calls out Sam for being responsible for Lester's deal and believes him to be just as bad as himself if not worse. As the ritual continues, Dean starts to be in pain, causing Sam to fear if it was killing him. As a demon Dean shows true resentment towards Sam and their family, telling Sam he was the reason their mother died and their father wasted their entire lives hunting for nothing.
|“||You notice I try to get as far away from you as possible? Away from your whining, your complaining. I chose the King of Hell over you! Maybe I was just ... tired of babysitting you. Or always having to yank your lame ass out of the fire since ... forever. Or maybe ... maybe it was the fact that my mother would still be alive if it wasn't for you. That your very existence sucked the life out of my life! [...] You never had a brother! Just an excuse for not manning up. But guess what. I quit.||”|
— Demon Dean taunting Sam
in Soul Survivor
Eventually, Dean is less demon enough to escape the Devils' Trap and tries to kill Sam with a hammer, still not wanting to be human again. Castiel saves Sam and restrains Dean, letting them continue the rest of the ritual. When Sam is upset that a barely demon Dean still didn't want to be human, Castiel comments it was because it was easier for Dean to stay that way in favor of feeling human pain. The ritual is a success and Dean is human again, but with a heavy conscience over everything he did as a demon.
In Paper Moon, Sam and Dean are taking a break from hunting. They relax by a lake, but Dean is quickly motivated by a case. Sam is concerned it's too soon for Dean to get back to work, but Dean insists. The attacks turn out to be werewolf and they run into Kate whose now werewolf sister Tasha is killing people. Meanwhile, Dean tries to get Sam to open up about killing Lester while Sam tries to get him to open up about his actions as demon, but neither succeed. After Tasha is dead, Dean admits to Sam he's not alright and it's too soon for him to hunt, but he has to because he wants to do the right thing.
In Fan Fiction, Dean and Sam stumble across an all-girls school that is putting on a musical of the Supernatural books. Dean is put off by the events and becomes more so when Sam reveals that he was a theater kid, and it is all very jarring for the boys. They meet Marie and Maeve who are big fans and tell them of little details, as a result they search around. Dean also tries to tell Marie of events after the Apocalypse but she doesn't believe him and they find no trace of monsters but soon do when hearing of Marie seeing a bizarre kidnapping. The girls tell Sam and Dean she wants to believe in ghosts and demons, and Sam and Dean encourage it, since those things are real and reveal they are the Winchesters though the girls accept monsters are real, they seemingly deny any possibility that Sam and Dean are the real ones because they are too old. Regardless, they research and learn it is the goddess Calliope behind the kidnappings and decide to play go on after learning that she will eat Marie who they use as bait to draw her out. In the midst, Dean watches as Sam is kidnaped and fights Calliope's prop of a monster before it explodes when Sam kill the goddess. With the case over, Dean speaks to Marie who implies she now believes he and Sam are the real deal by handing Dean a makeshift Samulet, which Dean later hangs on the mirror of the Impala, after telling her 'I don't need a symbol to remind me how I feel about my brother'. The brothers then watch the play and are nostalgic before being disturbed at remembering their captive brother Adam. The episode ends with the boys driving off into the sunset in the Impala.
During Ask Jeeves, Dean and Sam learn that a recently deceased rich woman left Bobby money but with his death, it goes to them. They arrive at the mansion, where they find themselves put off by the rich lady's relatives. However, a string of murders occur and soon they are accused when they tried to help. While captive, Dean sees it was the maid and the rich lady's daughter Olivia (Shapeshifter) who committed the murder. The two break out and Dean confronts Olivia and proceeded to fire several more rounds into her body, possibly as a result of the Mark of Cain. Though Dean cast it aside, it showed Sam that Dean is still plagued by the mark's effects.
In Girls, Girls, Girls, Sam and Dean run into a dangerous witch named Rowena who is trying to train other girls to be to be witches. Dean corners her, but is trapped by Cole, allowing her to escape. Cole quickly realizes he's no longer a demon. Dean tries to apologize for their last meeting and explain he's no longer the same, but Cole attacks. Dean wins the fight, telling Cole his father had been a monster and he had killed him working a case. Dean gives Cole the choice whether to shoot him or spare him, describing himself already as a "lost cause". Cole hesitates, but believes Dean and lets him live.
|“||I get it. That was your story. Look, man, I've got one of those too. But those stories we tell to keep us going? Sometimes they blind us. They take us to dark places. The kind of place where I'd beat the crap out of a good man just for the fun of it. [...] Cole, once you touch that darkness ... it never goes away. Now, the truth is ... I'm past saving. I know how my story's gonna end. It's the edge of a blade or the barrel of a gun. So the question is, is that gonna be today? That gonna be that gun?||”|
— Dean's speech to Cole
in Girls, Girls, Girls
In The Things We Left Behind, Dean is having nightmares of killing people from the mark. He and Sam help Castiel connect with Jimmy's long-lost daughter Claire who's been taken in by a man named Randy to makes her steal to help him pay off his debts. In a conversation with Castiel, Dean makes him promise to kill him if the mark gains too much control, not wanting to be what he was before. Randy betrays Claire after being found out by thugs and they come to her rescue. Castiel and Sam take Claire to safety, but the mark on Dean acts up. Dean's nightmares becomes reality when he mercilessly slaughters all the thugs, causing all three to realize things have finally gotten worse.
In The Hunter Games, Dean is now desperate to have the mark removed. Castiel takes Metatron briefly out of prison to be used for information, only getting that they need the First Blade. Dean is reluctant to take back the Blade, but goes along with it as long as the Blade is kept directly away from him. They enlist Crowley, who takes the Blade out of hiding but refuses to give it back until needed. Dean goes to Metatron for information, but is provoked and nearly kills him. Sam and Castiel stop Dean while Metratron is returned to prison. Dean is upset at how easily he lost control and only has one hint from Metatron ("the river ends at the source"). Sam encourages Dean to fight the mark harder.
In There's No Place Like Home, Dean is trying a series of methods to keep the mark under control. Sam and Dean discover Charlie returned from Oz and was split between her good and bad selves. Dark Charlie gets revenge on the man that killed her parents and tries to stop Good Charlie from conjoining them again. Dean loses control while fighting Dark Charlie, seriously wounding her and causing harm to Good Charlie in the process. Charlie becomes herself again and forgives Dean, but Dean doesn't forgive himself.
During Angel Heart, when Castiel catches sight of Claire, he calls Dean and Sam to help him deal with Claire.
Dean, Sam, and Castiel arrive, while Claire is not happy to see Dean for killing Randy but tells them of her search before fleeing the hospital when they leave the room. However, she made the mistake of telling them where she was staying as well as checking in under her own name and Sam is waiting for her while Dean and Castiel interrogate Ronnie. Dean starts to get aggressive because of the mark and Cass has to calm him but they get news of a healer that Ronnie works with. Much later, Dean and Castiel to investigate Ronnie's murder. When they return to the motel, Sam is able to figure out that the man Amelia was supposed to meet, Peter Holloway, has a farm that Amelia had been spending time around. When Claire tries to leave with them, Dean tells her to stay put but Sam and Castiel do to the same to him because the Mark of Cain is starting to affect Dean worse.
Things between Dean and Claire are awkward at first, so Dean takes Claire to play mini-golf which they bond over. When Claire puts her putter in the last hole to demonstrate how the ball gets taken there, Dean realizes that the angel who has her mother used an angel sword instead of an angel blade and he and Claire research angels. By doing this, Dean earns respect from Claire for figuring out this clue from a golf game and she finds information on the Grigori, a class of angels that preys on humanity and when they are unable to reach Sam or Castiel. Dean prepared to go as Claire expected Dean to leave her behind while he goes to rescue them. However, Dean instead gives her a gun and instructions on how to use it and takes her with him, to her joy.
Arriving to Sam and Castiel's location, Dean watched as Claire reunited with her mother before he and Cass go to find Sam. When Sam tries to tell them what they are dealing with, Dean reveals that he figured out already. He soon learned from Sam of what Grigori have been doing. They go to the barn and find Amelia stabbed but stop Tamiel from killing Claire. A fight breaks out, with Dean using the mark to injure the angel but is overpowered. However, he watched as Tamiel prepared to kill Cass, though Claire catches him off-guard and stabs him from behind. Afterwards, Dean tells Sam that he felt like himself, to his joy. He speaks with Claire and gives her a copy of Caddyshack and a lore book, having noticed her keeping Tamiel's sword. He advises her against becoming a hunter, telling her how dangerous it is and that she got her revenge when she killed Tamiel. Claire jokingly tells him he's pretty old when he tells her about how hunters don't live long and leaves in a taxi.
During About a Boy, Dean researched the mark of Cain before Sam told him of a case. Dean went to a bar in Oregon. After questioning the bartender, Dean starts talking with Tina, a woman at the bar, about JP. They begin drinking together and reminiscing about crappy childhoods. Sam calls Dean, as Tina leaves the bar, and Dean watches as a mysterious man follows Tina out. Dean explains to Sam that he may have something so he hangs up and goes outside. Dean hears a scream and when he goes to investigate he finds a pile of clothing. The mysterious man approaches Dean, and with a flash of bright white light, Dean wakes up in a basement and discovers that he is a teenager. Dean looks like his 14-year-old self, but he has all his adult memories. A 14-year-old Tina is in the room next door, while Dean reassures Tina, they discover JP who is then taken away by the mysterious man. After snacking on cake, Dean finds a way out of the basement, and Teen Tina tells him to go for help while she remains behind as a distraction. Going to the motel, Dean knocks on the door and greets a confused Sam with a "Hi'YaSammy." Dean explains what happened, and the boys head out to save Tina. In the car, Dean tells him that what he'd going through feels weird, as he states that he liked a Taylor Swift song, he's puberty again, and only good thing came out. He reveals that the Mark of Cain is gone. Sam says he found yarrow, flowers used in rituals, so the boys assume they are hunting a witch. Sam wants to get Dean changed back, but Dean isn't so sure; believing that while not ideal, they've found a cure for the Mark of Cain.
Sam and Dean arrive at the house where Tina is being kept, Dean sneaks in the same way he got out, but Sam is too big to enter that way. Dean is attacked by the mysterious man, but Sam comes up behind him and saves Dean. The mysterious man explains that he is Hansel of Hansel and Gretel, and that the evil witch, Katja made him and his sister do terrible things. When Sam and Dean reveal to him they are hunters, he agrees to help the kill her. However, if Hansel wants to help, Sam first demands to know how to turn Dean back to his proper age. Hansel explains that the hex bag around his neck is the key. Hansel and the boys enter the kitchen, and she orders Hansel to take care of the Sam and Dean who think Hansel is on their side. Katja explains that she never made Hansel do anything, and then Hansel knocks Sam down and takes his gun.
Katja explains to Sam and Dean that she loves to eat delicious children, and Sam questions why she changes adults to children instead of taking children. She explains that stealing children has become more difficult since the olden days, and it is much easier to just transform an adult no one will miss than attempt to kidnap a child. She explains that the Grand Coven sent her here to take care of Rowena. While Dean is distracting Katja with conversation, Sam breaks free and attacks Hansel, Sam then goes after Katja but she easily throws him against the wall. Meanwhile, Dean is being beaten by Hansel. Katja orders Hansel to turn Sam, but when Hansel reaches for the hex bag around his neck, it is gone. Dean has taken it, and he uses it to turn back into an adult. He picks up the witch's knife and kills Hansel, Dean then shoves the hex bag in Katja's mouth, keeping her from reciting any spells and pushes her into the fiery oven.
Afterwards, Sam and Dean explain to Tina that the hex bag was destroyed, but there is a chance they can figure out how to reverse the spell, but Tina sees her renewed youth as a second chance at life, and is willing to make the best of it. The next day, Sam and Dean give Tina a lift to the bus station and all the cash they have, and they depart. Sam and Dean now know that the Grand Coven may become an issue, however, Sam is more concerned about the Mark of Cain. Dean felt he had to change back to save Sam, which Sam understands: Dean saved them –- Dean pulled a "Dean Winchester." After thanking Dean, Sam admits that he wants the Mark gone, but Sam also wanted Dean back. Sam counts it as a win because he has Dean back and Dean didn't "Hulk out." Again, Sam reassures Dean that they will figure it out. Dean agrees, and they drive off while listening to a Taylor Swift song, much to Sam's befuddlement.
In Halt & Catch Fire, Sam and Dean find a case revolving around college students getting killed by a vengeful spirit through the internet. The brothers save the last of the four students and get rid of the ghost. While Sam is still hopeful for getting rid of the Mark of Cain, Dean gives up on the search and decides that he'll just keep fighting the mark until he can't anymore. Sam protests, but Dean can't invest in anymore "false hope".
|“||My peace is helping people. Working cases. That's all I want to do. [...] I'm done looking for a cure, Sammy. [...] I appreciate the effort, okay? I do. But the answer is not out there. It's with me. I need to be the one calling the shots here, okay? I can't keep waking up every morning with false hope. [...] So I'm gonna fight it until I can't fight it anymore. And when all is said and done ... I'm gonna go down swinging.||”|
— Dean giving up on removing the mark
in Halt & Catch Fire
When Cain starts killing off his descendents to "purify" the world of a bloodline made mostly of killers in The Executioner's Song, Dean takes responsibility for this and reluctantly decides he needs to kill Cain with the First Blade. Dean tricks Crowley into giving him the Blade and with Sam and Castiel, follows Cain's trail to a 12-year-old boy who they manage to save. Dean is scared of fighting Cain, fearing losing control again, but is adamant on going alone. Dean stands off against Cain while Sam, Crowley, and Castiel wait. Cain declares Dean is living his story in reverse and that eventually he'll kill Crowley, Castiel, and Sam himself before becoming a complete monster.
Cain nearly kills Dean, but Dean manages to immobilizes him. He pleads if there was any chance Cain could stop killing, wanting hope for himself, but Cain knows he won't stop. Dean kills Cain and gives the Blade to Castiel to hide, but is devastated by the bleak future that awaits him.
Dean's fear of becoming a demon and killing again steadily heightens. He's having terrible nightmares in the middle of the night, but tries unsuccessfully to hide this from Sam. After Sam goes out on his own in Inside Man, unbeknownst to Dean to try to find out a way to remove his Mark. Dean gets in a confrontation with Rowena. She uses the Attack Dog Spell on college students. Dean stops himself from killing them just in time for Rowena to try to kill him in a flash of light, but it doesn't work. It's revealed bearing the Mark of Cain gives Dean limited immunity to certain types of attacks. Dean wants to kill Rowena, but choses not to she can end her spell on the rabid college students.
In Book of the Damned, Charlie comes to the brothers on the run from the Styne family. She stole the Book of the Damned from them, a powerful dark magic book that might be able to remove the mark from him. Dean starts to think there's hope for him, but when in the contact with the book he senses it's darkness and the mark reacts to it. Sam and Charlie try to translate it, but Dean decides he doesn't want to use it because of the consequences it might have. Sam protests, but Dean is firm and demands he burn it. They're attacked by the Stynes, but make it out. Dean thinks Sam burned the book, but Sam actually burned another and is working with Rowena to translate it.
|“||The book's been calling to me ever since I laid eyes on it, okay? Calling out to the mark. I can hear it like it's alive. It wants me to use it, but not for good. [...] This is my cross to bear, Sam. Mine. And that book is not the answer. Now we got to destroy it before it falls into the wrong hands, and that includes me.||”|
— Dean rejecting the Book of the Damned
in Book of the Damned
In The Werther Project, Dean takes down a nest of six vampires by himself. When Sam goes alone to an address, Dean follows him. Sam explains the backstory of the Werther Box and the Men of Letters without giving away why he came there (working with Rowena). Sam opens the box, which drives the people around them to suicide. Dean imagines himself in Purgatory with Benny who tries to get him to die and come here so he wouldn't kill anymore. It's also revealed Dean knows neither Sam or Castiel will do what they have to when he gets out of control. Dean refuses to kill himself because of the mark, but admits he would if he really had to. He breaks out to save Sam, who's trying to shut down the Werther Box with his blood. Dean shuts down the box with some of his own and destroys it, but still doesn't know Sam is lying to him.
In Dark Dynasty, Dean starts to become suspicious of Sam and senses he's hiding something from him. The brothers find a case revolving around the Stynes and they manage to capture one, learning more about their history and abilities. Dean finds out the Book of the Damned can't be destroyed and realizes Sam lied to him. Dean confronts his brother, but the Styne escapes. When Charlie is put in danger decrypting notes from the book, Dean is furious at Sam and they both rush to her rescue. Sam and Dean arrive, only to see Charlie dead.
In The Prisoner, Dean gives her a hunter's funeral and is very devastated by Charlie's death. He blames Sam for her dying and lying to him, separating from his brother to go hunting for the Stynes. His emotions fed by the mark, Dean gets arrested but attacks the deputy for the location of their headquarters. Once there, he coldly kills every guard but is captured by the family. Dean wakes up on the operating table in the Stynes lab where they plan to take him apart for pieces for themselves. Monroe is amused that Dean believed he could come in "guns blazing" and win. Dean warns them that if they kill him, he will be resurrected as a demon by the Mark of Cain and kill all of them; if they let him go, he might or might not let a few of them live, but at least he will be human. The Stynes are undaunted, seeing a man that doesn't die as the perfect lab rat. As Monroe goes to cut him open, Dean breaks free of his restraints, cuts Eli's throat with a bone knife and overpowers a nurse, killing her with a lethal injection she attempts to use on him. Dean then grabs Monroe and begins strangling him, informing Monroe that he took something from Dean who will take everything from him in return. Monroe gasps out that its too late as Dean's family and home will be gone before Dean snaps his neck. Taking Monroe's gun, he kills every last member of the American Styne family. Returning the bunker, he finds Eldon, Roscoe preparing to burn his possessions but kills Roscoe and confronts Eldon. He is silent at Eldon taunts about Charlie until he taunts him back with the massacre of his family and proceeds to execute him by shooting him in the head. Dean then kills Cyrus Styne, a non-violent teenager that didn't want to follow in his family's footsteps. Castiel and Sam are shocked at his uncharacteristic brutality, leading Castiel to confront him. Dean also blames Castiel for lying and intending to go forward with using the Book of the Damned despite the risks. Dean ends up attacking Castiel and nearly kills him, but stops at the last minute. Dean leaves Castiel, bloodied and beaten, telling him and Sam to stay away from him.
In Brother's Keeper, intent on getting rid of the Mark of Cain, Dean summons the Horseman Death to help him. Death agrees on the ground that Dean kills Sam to prevent his brother from trying to rescue him.
Sam and Dean get into a fight with Dean coming out the winner. Sam accepts his fate and Death gives Dean his scythe to use as a weapon. However, Dean is unable to go through with the plan, and stabs Death instead, killing the Horseman, proving that Dean holds his brother higher than he does to mankind and vice versa, since Sam desperately tries to save his brother while knowing the darkness would be the consequence. Both brothers hold each other higher than they do to mankind.
Dean and Sam do manage to remove the Mark by using Rowena and the Book of the Damned, but this causes Amara to be released from its prison. Sam and Dean are both hit by the giant black fog, that is The Darkness' true form.
The massive dark cloud washes over the Impala, and Dean soon finds himself confronted by a woman wearing a dark dress inside it. She reveals herself to be Amara, whom Dean set free, and she informs Dean that they will always help each other. Dean then finds himself a few miles away from where he originally was. He and Sam soon regroup. They discover that the dark cloud has transformed various people into what they call "Rabid". The brothers are forced inside a hospital, where Dean meets a baby girl named Amara, who later turns out to be The Darkness herself, but Dean is unable to do anything as Crowley eventually disappears with the child.
A couple of weeks after the incident, Dean and Sam drive to Quaker Valley, Oregon. Unable to figure out what monster they are up against, Dean calls Castiel and discusses the case with him. In the middle of their conversation, Dean is attacked by Deputy Donelly, who turns out to be responsible for the murders Although Dean manages to defend himself, he fails to execute Donelly for he does not know the correct method. Upon providing Castiel with a photograph of the monster's teeth, Castiel is able to give Dean the right information, revealing the monster to be a Nachzehrer. One night, though, Sam wakes up from a vision of their father, and while Sam is rather enthusiastic about believing it was God leaving a massage, Dean disagrees.
In Our Little World, Dean and Sam hunt down Amara at Crowley's lair. Dean finds a teenage Amara, but is unable to attack her, for reasons he cannot understand. When Crowley threatens Dean's life, it is Amara who demands Crowley to release Dean or else die. Crowley complies, and Dean regroups with Sam at the bunker, where they discover from Castiel that Amara is in fact God's sister.
Dean and Sam handle a case involving possessed costumes, and work together to save the people the spirit is after. They are assisted by Sheriff Donna. During another case, Dean meets Sam's childhood imaginary friend, Sully, who is in need of their help.
In O Brother, Where Art Thou? Sam manages to convince Dean to follow his visions and contact Lucifer. Although heavily against the idea, Dean relents so long as Sam is able to remain safe during the encounter. The brothers then contact Crowley and Rowena, who can use the Book of the Damned to find a means to summon Lucifer. While Sam watches over Rowena, Dean investigates a massacre at a church, which they correctly assume was caused by Amara. At a park, Dean senses The Darkness and is taken away by her to a countryside. This prevents Dean from meeting up with Sam, who goes to face Lucifer without him.
The Darkness tries to explain herself to Dean, though Dean remains steadfast in his conviction to fight against her, but an attempt to stab her with a knife proves fruitless. The Darkness makes a move to consume his soul, but doesn't seem able to, instead she kisses Dean passionately. Their meeting is interrupted by the arrival of angels. Although The Darkness successfully kills all three, Heaven prepares to attack her with a powerful blast. For his safety, The Darkness teleports him back to the park.
In The Devil in the Details, Dean attempts to drive back to the location where The Darkness was, but the smiting caused by the angels poisoned the air. Dean falls out of his car and starts to throw up. Castiel arrives just in time to warn Dean not to proceed any further and that he will go himself. Dean returns to the Men of Letters' bunker hoping to find Sam. There is no one present. He calls Crowley and finds out that Sam is trapped in Hell with Lucifer. Dean then makes his way towards Billie, who provides him with the witchcatcher and a means to get into Hell and Limbo.
Together with Crowley, Dean traps Rowena in the witchcatcher and forces her to return Lucifer to his Cage. Castiel arrives shortly after bearing a message from The Darkness, promising her arrival. Dean then hears noises and rushes to go check on Sam along with Castiel. When the two of them arrive just outside the cage, Lucifer teleports them into it and a battle ensues. Lucifer proves to have the upper hand against all three, knocking them about and then strangles Dean to convince Sam to say "yes". Castiel pushes the archangel off of Dean, who then rushes over to Sam. While sitting next to Sam, Dean watches as a bright light signals the archangel's return to the Cage. Dean and Sam leave Hell at Crowley's demand. Dean remarks that it was a rough day for all of them.
A few days later, Dean presents Sam with a new case for them to work on. When asked if Castiel is alright, Dean reassures him that Castiel "always is". The brothers arrive at a retirement home and investigate the strange death of a patron there. They question one of the residents, Mildred Baker, when a second death occurs. Midred shows an interest in Dean. Mildred, a witness to the death of Arthur, explains the incident in enough detail that the brothers realize it was a banshee attack. Upon returning to the Bunker, Dean hears noises and prepares his handgun. To his surprise, he finds Castiel among a pile of books and sheets. Castiel tells him he is in search of a way to trap the Darkness. When Dean reveals his own failed attempts to kill Amara, Castiel prompts him to explain further, which he does. Dean reveals he has an irresistible attraction towards Amara and that it scares him, though Castiel comforts him, believing this to be a good thing.
When Sam comes up with a plan to use Mildred as bait against the banshee, Dean rejoins with him at the retirement home and stays with Mildred until the sun sets. Mildred tells him how to live happily, and that is by following "your heart". Suddenly, Dean hears the banshee's screams and it turns out that it's targeting him. Sam and Eileen Leahy arrive and with Mildred's assistance, they defeat the banshee before Dean cracks his skull on the wall. Case closed, Dean and Mildred walk out the building, arms linked. Mildred tells Dean that she can tell that he has his eyes on someone, and offers to be his woman if he ever wants. At the Bunker, Sam inquires as to why the banshee attacked him, since its victims are weak people. Dean is unable to give an answer.
In Don't You Forget About Me, Sam and Dean get a call from Claire about a possible monster problem. They reunite with Jody and Alex who both claim Claire has not been hunting real monsters as she claims to be. When Claire reveals Alex's intent to have sex with her boyfriend, Jody initiates a sex talk which leaves everyone - including Dean - uncomfortable. Claire's concern for monsters lurking around proves true, when she, Jody and Alex get kidnapped by vampires intent on getting revenge on Alex. Sam and Dean arrive soon enough to stop one of them from hurting Claire. In the ensuing battle, both vampires are killed and the women are saved.
In Love Hurts, Dean hooks up with a woman in Kansas, who leaves a hickey on his neck, which Sam notices. The brothers then investigate the death of a babysitter, and afterwards, her lover. When the wife of the lover comes to them and reveals a spell she used, the brothers realize the deaths are caused by a curse. When a qareen comes for the wife, Dean kisses her to take on the curse. With Dean as its new target, the qareen shapeshifts into the form of Dean's darkest desire, which is revealed to be Amara. "Amara" proceeds to attack Dean, intent on ripping his heart out, but Sam locates the qareen's heart in time and stabs it, killing the monster. Back at their motel, Dean reveals his attraction to The Darkness to Sam, and he admits that he cannot help defeat her, for whenever they are near, he cannot control himself. Sam doesn't blame him for this, since it is not Dean's fault.
In The Vessel, Dean agrees to go back in time to retrieve a Hand of God, a weapon to use against Amara. Dean doesn't allow Sam to join him in case "things go sideways", adding that Dean can't kill Amara anyhow. Dean calls Castiel to be taken aboard the USS Bluefin, but finds himself alone inside the submarine. Dean hides under the beds as some of the crewmen enter, and spots a warding on the wall near the door. After stealing the clothes of one of the crewmen, Dean goes after Delphine and introduces himself to her. He warns the captain of the submarine's fate and the importance of his mission. Delphine eventually comes to trust Dean since they are both from the Men of Letters. She opens the box and shows Dean the Hand of God, which is a piece from the Ark of the Covenant. Delphine removes the wardings keeping Castiel from entering the submarine, but reveals that the last warding is carved into her chest. She convinces Dean to kill her to let his friend in, but before Dean can proceed, the submarine gets attacked by a German Destroyer.
Delphine uses the Hand of God to destroy the submarine and the Destroyer. Before her body erupts, she gives Dean back the weapon and Castiel arrives to take Dean away. Dean returns to the present. Sam, lying on the floor, yells at Dean, telling him that "Castiel" isn't Cass. The angel responds by throwing Dean across the room and taking the weapon. Dean realizes then that it is in fact Lucifer. However, the Hand of God was depleted when used by Delphine. Furious at Dean over the loss of its power, Lucifer stalks towards Dean, who he has pinned to the wall, but before he can lay a hand on Dean, Sam banishes the archangel from the Bunker. Dean and Sam later make an agreement to hunt down Lucifer and rescue Castiel, though Sam warns Dean that Castiel might not want to be saved. Dean doesn't listen.
A week later, Dean decides they need a break and takes a case that involves boxing. Dean is highly enthusiastic about meeting Gunner Lawless, whom he was a major fan of since childhood. The brothers get to watch a match while there. Dean and Sam later discover that Lawless is behind the death of one boxer and the disappearance of another. They track him down to his hideout and Dean finds out that Lawless is working with a crossroads demon. The demon Duke orders Lawless to attack Dean, however, Dean manages to convince the boxer to do the right thing. Lawless disobeys his master and kills Duke. To Dean's misery, Lawless chooses to die for his sins, and lets the hellhound take him to Hell.
Two weeks after, Dean and Sam pick up a case Bobby once dealt with years before. They find out they are hunting a Soul Eater and through the Men of Letters' archives they discover a way to kill it. Dean lets the Soul Eater take him to its nest so he can draw a sigil inside the nest while Sam draws one inside the house. Once the spell is completed, Dean catches a glimpse of Bobby from the past, before they are both transported out of the nest.
During a werewolf hunt, Sam gets shot and seemingly dies from the wound. Desperate, Dean chooses to overdose on drugs so he can "die" and speak with Billie, in order to have her revive Sam and let them trade places. He claims that Sam is the one who can defeat the Darkness, but when asked how, he is unable to provide an answer. Billie nonetheless rejects his offer and the people watching over his body revive him. Dean soon discovers that Sam wasn't really dead, and is relieved by the fact.
Sometime later, Dean receives a call from Crowley to meet up with him at a secret location. Dean and Sam learn that Crowley has not only escaped imprisonment, but also possesses a Hand of God, but he plans to get their help in using it against Lucifer. The brothers decline since they want Lucifer out of Castiel first. When Rowena joins their side, Dean and Sam prepare a trap for Lucifer and Dean summons him through an incantation. Using the angel suppressing sigil, Dean attempts to talk to Castiel but he only manages a few seconds before Lucifer regains control, and proceeds to mock Dean over his demand for his friend.
Crowley opts to speak with Castiel directly by possessing the angel's vessel. Dean waits for the demon's return but much to his dismay, Crowley instead gets trapped inside and requires their assistance to get out. As Sam begins exorcising Crowley from Castiel's vessel, Dean reluctantly sprays holy water, which does the trick. Lucifer, in retaliation, starts suffocating the brothers but he is soon interrupted by Amara. The two face off but Lucifer proves incapable of harming his aunt, even with a Hand of God. Before the pair leave, Dean shouts to Castiel one last time, much to the surprise of both Amara and Lucifer.
Dean is later shown at the bunker drinking heavily, but is nevertheless determined to get Castiel back. During a hunt involving a bisaan, Dean understands the task will not be easy, and that it's best that the two of them do not ask for help, especially from other hunters. When a case possibly involving Amara catches their attention, Sam and Dean drive into a town soon attacked by a giant fog that turns people into a new version of the rabids. They try to escape and end up locked inside a police station with a few other survivors, but Sam becomes sick from the fog, and briefly falls under its influence.
Like a previous victim, the rabid-infected Sam accuses Dean of choosing Amara, which Dean denies. In the midst of their desperation, Dean shouts for God to stop the fog as he tends to Sam. Dean then spots something glowing in Sam's jacket pocket, and finds his amulet inside. Suddenly, the fog disperses and Sam recovers completely. Realizing that it must be God, the brothers walk outside and discover other infected victims healed and the people dead now alive. Walking along the road, Dean and Sam spot the presumably deceased Chuck Shurley, whose presence causes the amulet to burn hot, as it would do in God's presence, thus revealing to them who Chuck really is.
At first Dean is skeptical, until the man they knew as Chuck teleports them back to the Bunker and reveals Kevin Tran's ghost as having been in the Veil this entire time. Kevin greets them and requests that they trust God, before Chuck sends him up to Heaven where he belongs, thus sealing Dean and Sam's belief. While Sam acts enthusiastic and almost happy about finally meeting God, Dean is less thrilled and God calls him out on it as Dean goes on about how he felt the world had been abandoned by God who was always around even shedding tears over how it made him feel. God assures that he did try to help, time and time again, until he chose to just allow his children to decide for themselves. Dean tells God that he feels that God is just trying to justify his leaving. God then tells he knew the pain that he went through Dean not to shift his abandonment issues with his father on him, as Dean can only look in sadness. They go over a plan but come up with nothing before God steps out for the brothers to discuss a plan stating he had faith in them, as he pokes fun at Dean's previous lack of faith towards him, to Dean's surprise.
However, God proves less interested in dealing with his sister than they do, going so far as to shower, sleep, wear Dean's robe and watch porn from his laptop. Dean and Sam later find out why from Metatron, who calls them and reveals his meeting with God and shows them a "suicide note" God wrote.
Frustrated, Dean confronts God at a park to tell him to change his mind, with success. Meanwhile, Sam and Dean encounter another prophet, Kevin's successor, who is a survivor of a town engulfed and destroyed by Amara's fog. With the assistance of both Donatello and Metatron, the brothers form a plan to rescue Lucifer while Dean distracts Amara.
Dean calls out to Amara, and meets up with her in a forest. Amara is overjoyed to see him again, but Dean brushes off her hopes of the two of them being together. Amara informs of him that some day, he will give up his humanity and be a part of her, and urges him to stop resisting. When Amara touches Dean, she realizes that she can no longer read his thoughts and it's because Dean has been in contact with God. Feeling betrayed, Amara abandons Dean and goes after Lucifer's rescue party. The plan succeeds regardless, thanks to God.
At the Bunker, Dean and Sam are forced to become counselors for Lucifer and God when Lucifer begins demanding an apology. The brothers fail in their task but God does manage to give what Lucifer wants. The four then plan an attack on Amara, and agree to use demons, witches and angels in the absence of the three other archangels. Dean is tasked with getting Crowley to join. During discussion, Dean believes it is best to just kill Amara, seeing it as a rational decision since it would mean Amara would not escape prison again. Lucifer points out that Dean just wants to get rid of Amara because of their attraction, so Sam points out that for once, they can finally leave the decision-making to God, and not worry about the decisions themselves. Dean finally relents.
The group arrive at a warehouse where they are joined by Crowley and Rowena. God then reveals the plan to give Sam the Mark since Dean was already tainted by it. Dean is enraged, and drags Sam away to talk to him privately. Again, Sam convinces Dean to accept the plan because it is God's plan. Amara soon arrives outside their location, where witches, angels and demons each attack her in order to weaken her. Her vessel severely damaged, Amara still manages to stumble into the warehouse, and is stabbed by Lucifer. Dean attempts to approach, but Sam holds him back.
The two watch as God and Amara exchange words, and Dean holds onto Sam when the Mark begins to form on his arm. Unfortunately, Amara manages to lash out and attack God. Dean tries to stop her, but Amara simply flings him away and leaves God dying and unconscious on the floor, and promises the end of all of God's creations, before leaving. Sam goes to check on God, while Dean carefully approaches Lucifer, who was flung away in his attempt to rescue God. Dean wakes what he presumes is still Lucifer, only to discover it's Castiel, who explains that Lucifer was expelled.
Rowena returns from outside to tell them about the state of the sun. Because of God's condition, the sun is slowly dying, which would mean the end of everything. This causes everyone including Dean to grow depressed and hopeless, and they start drinking. Sam tries vigorously to get everyone to figure something out. Castiel offers using souls to fight Amara. This sparks Rowena to suggest creating a soul bomb. Dean and Sam thus go to Waverly Hills Sanatorium to collect souls for the bomb. However, the souls prove insufficient. Luck comes in the form of Billie the Reaper, who saw the boys collect the souls and offers to help by raiding the Veil for more.
With the crystal packed, Rowena reveals to the group that she will turn Dean into the bomb itself, since he is the only person who can get close to Amara. Dean accepts, and eventually heads out to Amara's location. At the park, Dean and Amara discuss about what Amara truly wants, because Amara is not happy about what is happening to the Earth as a result of what she did to her brother. Dean tells her that in truth, she does not wish to kill her brother despite how angry she is at him, because he is still family and she still cares about him.
Dean's words dig deep and Amara decides to summon her brother to their location. The two manage to reconcile, and Amara heals God, thus restoring the sun. The two decide to depart, leaving Earth to the Winchesters. In thanks, Amara promises to give Dean a gift which Dean soon finds out is the resurrection of his mother Mary Winchester.
In Keep Calm and Carry On, Dean is shocked by Mary's resurrection. Mary, not remembering her death or anything that came after it, is confused by Dean's presence and claim that he is her son. Dean tells Mary that he's not four anymore since she has been dead. This causes Mary to suddenly remember her death at the hands of Azazel and she lets up Dean who tells her that she has been dead for 33 years. Dean convinces Mary of his identity by reciting her family history and her history with John. Convinced, Mary hugs Dean and they sit on a bench in the park. Dean fills her in on all that she's missed over the last 33 years. Dean watches as Mary is stunned by the news that they met through time travel twice and met Dean while she was a ghost which she is unable to remember either. After she was shocked to hear she was resurrected by God's sister, Dean remarked he knew it was hard to handle but they'll get her up to date.
Afterwards, Dean takes her to the Men of Letters bunker to meet Sam. Mary is shocked to find out that the Men of Letters are real as she'd only known them as a hunter's myth. Noticing blood on the ground, Dean hands Mary a gun and tells her to stay behind as he searches the bunker. Instead, Mary explores and hides when she hears someone enter. Emerging from hiding, Mary threatens Castiel at gunpoint until Dean defuses the situation. Dean explains to a shocked Castiel who Mary is and to the shocked Mary that Castiel is in fact an angel. After Castiel explains what happened before Lady Toni Bevell banished him, Dean searches through traffic cameras on the Winchester's laptop for the kidnapper's car. Mary is confused by the size of the computer before Dean locates the vehicle. Joining Dean and Castiel in the hunt for Sam, Mary goes with them to the bunker's garage where she recognizes the Impala as John's car and comments on how beautiful the car still is, treating the car in a similar manner to how Dean does.
Tracking the kidnapper's vehicle to the airport, the three question a man there about the kidnappers and Mary is surprised by Castiel acting violent when he's an angel. The man gives up the tail number of Toni's plane and Mary sits in a café and watches the changed world as Dean searches for information on the plane. When Castiel joins her, Mary tells him about how strange everything is to her, from the fact that she was resurrected at all to the world around her. Dean rejoins them and explains that the plane has a diplomatic registry, meaning that they can't access the flight plan. After Castiel spots a nearby veterinary clinic, the three realize Sam could've been treated there and kidnap the doctor for answers. After the man admits he treated Sam's leg wound for $100,000 but clearly holds something back, Mary orders Castiel to beat the answers out of him. The doctor finally tells them that he has Toni's phone number as she called to ask about the sedative he used on Sam and Mary watches with Castiel as Dean calls Toni.
Having failed to get anything from the phone call, the three make their way back to the bunker when the Impala is rammed by Ms. Watt in an SUV, knocking Mary unconscious. Castiel is able to determine that Mary is not seriously hurt before he and Dean are forced to fight Ms. Watt who has the upper hand due to a set of enchanted brass knuckles. As Ms. Watt prepares to kill Dean with his own gun, Mary regains consciousness and stabs Ms. Watt through the back with Castiel's dropped angel blade, killing her and saving Dean. As Dean and Castiel push Ms. Watt's SUV off the road, Mary sits inside the Impala door and stares at her hands before Dean tells her that they have a lead from Ms. Watt's cellphone. Mary tells him that she's not alright as she never wanted her children to become hunters, but Dean tells her that he and Sam have done a lot of good and the world is a better place with them in it as hunters. The three then set out for Aldrich, Missouri where Ms. Watt's cellphone points to Sam being.
In Mamma Mia, Mary arrives at the location Sam is being held, and finds both her sons being held captive by Lady Toni Bevell. Mary surprises Sam by her appearance before she gets into a fight with Toni. They are interrupted by the arrival of Toni's colleague, Mick Davies, who accuses Toni of misbehaving and apologizes to the gang for her behavior. Mick takes Toni away, allowing the trio, plus Castiel, to return to the Bunker.
In The Foundry, Dean and Sam take on a case Mary found. The brothers initially believe they are dealing with a Myling, but thanks to Mary, they realize it is a vengeful spirit. Together they manage to defeat Hugo Moriarty and free the children he had murdered and trapped as spirits. Back at the Bunker however, Mary reveals that she is having difficulty coping with the present, having lost 33 years of her life and that she still remembers Sam as the baby he once was. Dean is resentful of her choice chooses not to hug her and watches her leave.
In American Nightmare, Dean and Sam, investigate a case involving the deaths of two people and the possibility of a vengeful spirit. Dean reveals that Castiel and Crowley are working together in hunting down Lucifer, who has taken possession of rock star Vince Vincente. Dean is disgusted when Sam reveals he actually likes Vince's songs. While searching for the spirit, Sam finds out after eavesdropping on a conversation between Abraham and Elijah Peterson that the daughter, Magda, is still alive.
The two men capture Sam and show him Madga's powers, believed to be the work of the Devil. Sam reveals to Magda that she is not the Devil, but a psychic. He relates to her through his time as a Special Child, and promises her that she can learn to control her powers and stop hurting people. When Gail decides to murder her entire family, Sam manages to convince Magda to spare her mother and allow the police to take her away. Sam then bids Magda farewell.
In The One You've Been Waiting For, Sam and Dean discover the Thule Society's plan to resurrect Adolf Hitler. Although the brothers fail to stop the ritual, Dean manages to kill the Führer. Meanwhile, Sam tries to comfort the Führer's descendant, Ellie Grant, who was forcibly used in the ritual to bring her ancestor back to life. Unfortunately, she does not believe in his story about freeing The Devil and being his vessel.
In Rock Never Dies, Sam joins Dean, Castiel and Crowley in stopping a concert hosted by Lucifer in Los Angeles. Once they have the location, Sam and Dean try to remove the fans from the bar, and succeed when Dean scares everyone off with gun shots. As the fans run out, Sam fights to keep the door opened while Lucifer tries to close it. Sam wins and he, Dean and Castiel confront Lucifer who is on the stage. Sam questions Lucifer's motive for trying to kill these people when he and God already reconciled. Sam is disturbed to hear that Lucifer does not accept God's apology since God has once again abandoned him. In retaliation, Lucifer has decided to smash up God's already broken toys and force the brothers to watch.
Since Lucifer's vessel is deteriorating, he departs it, leaving Vince Vincente dead. This leaves a bad feeling in Sam, who finds that they have lost the battle and are losing slowly, since people are dead and Lucifer without an actual plan is more dangerous than Lucifer with one.
In LOTUS, Sam, Dean and Castiel track Lucifer to President Jefferson Rooney's location. They discover that Lucifer has conceived a child and Sam considers it the antichrist. They are surprised to receive help from British Man of Letters Arthur Ketch, who came in response to Sam's call for help to Mick Davies, though Sam had hung up before Mick could answer, alerting him that the Winchesters might be in danger. Arthur Ketch offers the brothers a special weapon for expelling angels and demons from their vessels. Sam and Dean decide to use Lucifer's lover as bait and expel him from the president with this device. Crowley brings Rowena and she personally banishes Lucifer back to his Cage. In their final confrontation, Sam orders Lucifer to go to Hell, and is relieved once he has been forcibly sent there.
Convinced by Lucifer that they had planned to kill Jefferson, Dean and Sam get arrested and by First Blood, they have been imprisoned at Site 94 for six weeks. Dean makes a deal with Billie to escape by having her kill them temporary. After their deaths, they are able to successfully escape and manage to outsmart the Secret Service, who they detain and tell them what really happen to the president. Afterwards, the brothers are soon reunited with Mary and Castiel, and on their way home Billie confronts them on the road demanding they uphold their end of the deal; one Winchester must go to the Empty.
Before either Dean, Sam or Mary can offers themselves up, Castiel stabs Billie to death and angrily tells the trio to realize how important the Winchesters are to the world, and to him. Dean watches in awe at Castiel's declaration, before resuming their journey home.
In the aftermath, Dean is both angry and worried about Castiel, who had done something very dangerous. In Lily Sunder Has Some Regrets, Dean discovers that a flight of angels Castiel once worked with is in danger, despite his warnings they accompany him to ensure he doesn't do a reckless stunt. The angel garrison were being hunted down by a vengeful woman. Dean and learn from Ishim that the woman had birthed a Nephilim with an angel who was sent to observe humanity and it was their flight that executed both the angel and the child. Dean and Sam try to protect Castiel and Ishim, but the woman, Lily Sunder, reveals to the brothers that her daughter May was not a Nephilim, but an ordinary human and that Ishim had committed the murder out of jealousy.
Dean and Sam are convinced by her story and Dean passes it onto Castiel, who is currently tending to Ishim's wounds. Dean warns Castiel about Ishim's real colors and confronts the latter about this, Lily's words are confirmed as Ishim becomes angry and assaults Dean and Castiel, intent on killing the former whom he views as a weakness to the latter. Dean was unable to banish Ishim without doing the same to Castiel who might be killed in the process in his state. Nevertheless, Dean is surprised when Sam brings Lily who fights Ishim before Castiel manages to kill Ishim, thus avenging Lily's husband and daughter. Afterward, Dean told Lily to retire from her vendetta but Castiel stepped in and apologized but she thanked him for allowing her to move on. Back at the Bunker, Sam learns from Castiel that he is now hesitant to murder Lucifer's child despite the threat the unborn child poses.
In Stuck in the Middle (With You), Dean is called upon by Mary to help with a demon case. He, Sam and Castiel go to meet her at a diner, where they encounter a hunter named Wally. While there, Dean tries to get the waitress and Castiel to flirt with each other, much to the latter's annoyance.
Dean joins the gang in infiltrating the target demon's house. However, they get attacked by two demons while they are there. One of them manages to kill Wally, only for Dean to stab her to death with an angel blade. Both Mary and Castiel are attacked by the demon they were after, Ramiel, who severely wounds Castiel before the four are able to escape. While there, Dean tends to Cass before Crowley appears. Through him and Castiel, Dean learns that the demon Ramiel is a Princes of Hell like Azazel, who were Hell's most powerful generals and the Lance that Castiel got stabbed with was a weapon for Michael to kill Lucifer and the latter will die soon. Crowley then leaves as the Winchesters set a trap for Ramiel. Dean is horrified when Crowley is soon thrown through the barn by Ramiel and is knocked unconscious while the Winchesters successfully trap Ramiel. Dean and Sam demand for Ramiel to tell them how to cure Cass but are told there is no cure and Ramiel wants a possession they stole but they are oblivious to this. Unfortunately, Ramiel's weapon, the Lance of Michael, enables him to break free and he proceeds to brutally attack each Winchester. Dean attacks Ramiel and holds his own but is overpower, Ramiel tries to kill Dean but Sam stops him from killing him as they fight over the spear before Mary stabs Ramiel with an angel blade, this leaves him distracted long enough for Sam to kill him with the Lance.
However, the Lance's effects are slowly killing Castiel, much to Dean's horror. Castiel does not recover, and thinking this is the end, Castiel professes his love for all of them. Dean and Sam are touched, but Crowley awakes in time and destroys the Lance, which restores Castiel to full health. Dean and Sam help him get to his feet and the three return home together.
In The British Invasion, Dean tries to contact Castiel, who is mysteriously absent, but only gets a voicemail response. Thanks to Eileen, Dean and Sam get a lead on Kelly Kline. Sam pretends to be Kelly's doctor and lures Kelly back to the doctor's clinic. Dean waits for Kelly to arrive and captures her, taking her to the docks where Sam, Eileen, Mick and a Man of Letters Renny Rawlings are waiting for them.
While they discuss what to do with Kelly's Jack, Kelly's protector Dagon arrives and takes Kelly away. Eileen tries to intervene but ends up killing Renny by accident. The British Men of Letters' protocol urges Mick to kill Eileen in retaliation, but Sam convinces him not to. Sam and Dean take Eileen back to the bunker. While there, Sam gives Dean the Colt, and Dean is pleased to have it back, though he doesn't know where Sam got it from.
In The Memory Remains, Dean and Sam investigate disappearances in a small town and discover that the Bishop Family had earned their wealth by giving blood sacrifices to the deity Moloch. A member of the Bishop Family, Pete Garfinkle captures Dean and tries to sacrifice him as well, but Sam comes to the rescue and kills Pete, as well as Moloch, the latter using the Colt.
In The Future, Castiel finally returns to the bunker after a very long, unexplained absence. Dean is displeased and gets angry at Castiel for not receiving any of Dean's calls. Their argument soon dies down and Dean is back in his room. Castiel visits him in hopes of returning a mixtape Dean made for him, only for Dean to demand that he keep it, since it was a gift. Dean tries to remind Castiel that they should stick together, since they are members of Team Free Will.
After Dean returns to the bedroom from getting a drink, he finds Castiel gone again, and the Colt - which he kept under his pillow - missing. Thanks to Sam, they manage to track Castiel using GPS. The brothers find Castiel at a motel, with The Colt, and Kelly Kline. On the orders of the angels, Castiel plans to take Kelly to the Heavenly Portal which will kill both Kelly and her unborn child. Sam and Dean disagree with the plan and force the two to wait in The Impala.
However, Dean had handed Castiel the keys to the car so he could unlock it and get inside, and by doing so, the two were able to drive off. Dean is forced to repair Castiel's truck and explain to Sam that Dean believes Castiel's actions are based on a desire to get a win, since Castiel has had little success so far.
By the time Dean has fixed the truck and driven it to the Portal, Dagon has returned and is about to kill Castiel. The two brothers try to intervene but Dagon knocks them aside easily and destroys the Colt, much to Dean's horror. Dagon then moves on to kill Castiel as well. Dean cries out as Dagon prepares to strike the angel, but Castiel somehow manages to grab Dagon's wrist and incinerate her. Castiel heals Dean's arm and informs them that he was granted power by the child in Kelly.
When Castiel tries to leave again, Dean and Sam resist, forcing Castiel to knock them out and leave them in the park as he and Kelly drive off.
Confronting Castiel about his actions, the latter apologizes and heals Dean after a brief argument. Dean and Sam are shown the alternate reality, which Castiel deduces that the portal was created by the Nephilim's powers. Entering the portal, Sam and Dean learn that Castiel's new friend is the other world's Bobby Singer who they are happy to see before they learn they were never born there. The trio soon meet Crowley who followed them and decide to confront Lucifer outside the cabin after he arrive. After tossing Castiel aside, Sam and Dean lure Lucifer to the rift where they work with Crowley in sealing the rift, hoping to imprison Lucifer inside.
Dean holds Lucifer off with angel killing bullets which Alternate Bobby gave him however, Lucifer tosses Dean away. Crowley then confronts Lucifer and bids the brothers goodbye as he commits suicide to complete the spell meant to seal the rift. Castiel arrives while ignoring Dean's protests, Castiel charges at Lucifer again and stabs him with an angel blade.
Sam and Dean return to their world as emerges to their relief only to be met with horror as Lucifer followed him and stabbed Castiel right before their very eyes. The angel collapses dead on the ground, his wings imprinted on the sandy ground. Lucifer is defeated moments after when Mary attacks Lucifer, sending them both tumbling into the rift right before it finally closes.
Sam goes into the cabin to check on Kelly who had gone into labor during the conflict, leaving Dean to stand over Castiel's corpse.
In Lost & Found, Dean briefly stands over Castiel's corpse, grieving, before heading inside the cabin. He goes outside and prays to God to resurrect Castiel and everyone who died but it fails and Dean is left upset at result. Dean decides to hold a Hunter's Funeral for Castiel. Alongside Jack, who sees Castiel as his father instead of Lucifer, the Winchesters burn Castiel and Kelly Kline's bodies outside the cabin.
In The Rising Son, Dean spends his time with Sam and Jack who he treats rather coldly which doesn't go unnoticed by Jack who tries to emulate him in order to appear more favorable. Jack eats a burger and drinks beer the same way (and the same time) as Dean does, but this only serves to annoy Dean. The trio are soon visited by Donatello Redfield. After Donatello notices that Jack's presences isn't toxic like Lucifer, Dean comments not yet to Sam.
When Jack goes missing the brothers and Donatello search for him, they find him with another "Donatello" using his powers to open a rift. They inform Jack the impostor was a demon which they prove by shooting him and he reveals his true form and he has yellow eyes like the Princes of Hell. The demon uses his powers to choke them but an angered Jack realizing he was tricked makes an attempt to attack Asmodeus but the latter flees.
During the night, Dean and Sam do research and realize the demon was Asmodeus, the last of the Princes of Hell. Dean later approaches Jack and tells him that while he is unsure of being evil if he turns then he will be the one to kill him.
During Patience, he is contacted by Missouri Moseley who requests his aid. Dean also sees Jody Mills was called as well and they learn a monster was attacking psychics and Missouri was next and she tells them to protect her son James Moseley and granddaughter Patience Turner. After her death, Dean and Jody tried to warn her son of the danger he and his daughter were in but they were rebuffed.
When Patience is taken by the monster, James reveals he studied a little magic and tracks Patience to an abandoned building. After finding her, they fight off the Wraith as they do Patience helps them by telling it will strike allowing them to survive. Dean ultimately kills the monster, avenging Missouri's death. Jody tells Dean he still has it but he is still bitter and tells Patience that she should listen to her father and continue on with a normal life as she may never get the chance again as he lists his own experience as a Hunter.
He returns to the bunker where he argues with Sam about how trusting Jack cost Castiel his life.
In The Big Empty, the brothers get news about a series of people dying because of their former loved ones after they went to see a therapist named Mia Vallens. Pretending to be a trio of brothers with Jack, they say that they are mourning their late mother. Dean and Sam have an argument with Dean telling him to accept their mother's death before he angrily walks out the room. Sam then returns and holds her at gunpoint revealing he discovered Mia is a Shapeshifter as Dean joins him in pointing a gun. Mia states she did not hurt anyone as the brothers tell her that some of her patients have ended up dead which surprises her. Knowing they are hunters, Mia proclaims her innocence and tells them she has an alibi and to check it out to confirm it.
Dean goes to do so and returns confirming she is telling the truth, to her relief. They then ask if she isn't killing anyone who was as she deduces it to be her old lover Buddy who is also a shifter that enjoyed killing just to torment others. However, she is trying to atone for her past by helping people get through their grief. Understanding, the Winchesters state if Buddy is doing so then he must be taking on the forms of her patients to get information and kill them. Dean and Jack go to a possible lead, but find nothing useful and head back. Once they return, Mia tells them Sam has found out Buddy's disguise and has left while Dean goes to call Sam but while doing so, he is knocked out by Buddy who takes on his form and calls Sam who was heading back. Buddy subdues Jack and ties up him and Dean while speaking to Mia, being angry she abandoned him to start a new life and proclaims his intention of destroying the life Mia has made by having her kill the hostages but she refuses and tells him to kill her. Dean wakes up and tries to get Jack to free them as Buddy notices this and moves into kill them but sees Sam return, to Dean's worry. When Sam enters the house, Dean tries to yell it was a trap but Buddy silences him and leads Sam upstairs using Dean's voice. Just as he's about to shoot, Mia tries to stop Buddy but is pushed aside though Jack uses his power to cause the bullet to ricochet into the wall. This saves and allows Sam to shoot Buddy, killing him.
Mia apologizes for the trouble she has caused and promised to do something about Buddy. She laments that all her attempts to help people were for naught but Jack states she helped him in his time of need. This somewhat relieves her spirits as she smiled at him in thanks.
At the bunker, Dean meets Jack and congratulates him on his actions in the mission as Jack accepts it. Dean goes to talk to Sam and apologizes for his recent behavior and tells Sam to maintain his faith in bringing back their mother, after the latter starts to doubt his thoughts.
During Advanced Thanatology, Dean and Sam investigate a case in which Sam tries to move Dean past his depression. The brothers soon learn the monsters killing people is a ghost and after killing the ghost, Dean decides to temporarily kill himself and have Sam resuscitate him in a short time. Carrying out his plan, Dean travels the house and encountered Jessica who promises to take him to a better place but he shrugs her off as she realizes who he is and notifies her superiors of him being dead. Dean continues on and encounters the ghost of Shawn who explained that Meadows before him and possessed him. Meadows forced Shawn to put on the stolen plague mask and return it to the Meadows' house. The possessed Shawn was then forced to kill himself with a drill through the head. Meadows hid Shawn's body somewhere in his house while Shawn himself became a ghost trapped in the house.
With the three minutes done, Sam tries to resurrect Dean but nothing works as Dean wonders what is halting him as Billie appears before Dean who is surprised at her being alive, knowing Castiel killed her. She freezes time after being annoyed by Sam's pleas for Dean to awaken and explains that Castiel indeed killed her but she was resurrected by a cycle of reapers after the death of the Death which allowed her to be reincarnated and take his place. Billie brings Dean to her domain where she questions him over the recent rift between dimensions as she knows of his involvement.
Dean promises to tell her if she will allow the ghosts of the abandoned building to finally pass on, as she is shocked while he tells her that they will both get what they want that way. She complies and has Jessica gather all the souls of the building and tells them they are going to a better place.
Billie then tells Dean that she has lived up to her end of the bargain, as she has him tell her about the rift and he explains it is due to Lucifer's son Jack who opened it. Billie then explains the importance of the cosmic and quantic fabric of order.
Billie soon notes on his change in demeanor as she brings up his request since it was not for himself. Dean explains he knew he couldn't win with her, as Billie brings up his previous attitude and actions as Dean states he and his actions don't matter. Billie notes that Dean actually wants to die permanently and he explains that he has lost and failed so much. He states while Sam is still trying, he is just tired and done with everything, he ends his rant by telling her she can reap his soul if she wants.
Amused by this, she refuses and tells him that while she would be satisfied at the thought, she explains that her eyes have been opened by her new position and sees the importance of the Winchester Family. She goes over every one of his possible death but says he is not meant to die this way and tells him that if he wants to die, she tells him to keep living as he has work to do before she sends him back as he tries to ask about his mother.
After that, Dean awakens as Sam is relieved at his being alive as he processes what happened to him.
Morning comes, as the police gather the bodies as Sam questions what happened to Dean as he tries to shrug it off for later. Sam sees that won't happen as Dean tells him about Billie being resurrected as the new Death and Sam is surprised to hear this. Dean then bitterly lists all the things they went through and how he needs a win to get over his pain of losing loved ones.
The brothers leave while Penny identifies the dead body of her son and breaks down at seeing him gone.
While Sam sleeps during the drive, Dean gets a call from someone and is shocked to hear who it is from as Sam wakes up and asks him about it as Dean only looks at him stunned. The Winchesters then travel to a small town and are surprised to see Castiel alive again as he greets them with a nod.
In Tombstone, Dean and Sam are still shocked at seeing Castiel alive again as he confirms its really him and explains he annoyed an ancient cosmic being so much that it sent him back. With that, he is embraced by the brothers who questioned if he was in Heaven but Castiel replies that he was actually in The Empty. After telling them that the realm was an afterlife for angels and demons and what its like, Castiel stated that he was awoke by a voice and believed they did something but they state it wasn't them nor God as he had no power there before they deduce it was Jack. Returning to the bunker, they greet Jack and reveal the resurrected Castiel to him as he was surprised to see him. The brothers asked if he had a role in bringing Cass back as he mentions begging for the latter's return and they suggested it was the cause. Jack then goes over a hunter's case about a zombie as he describes the details of it which seem supernatural.
While Dean seems to be humoring him, he agrees since it in a place where he can act out a cowboy fantasy as he adjourns the meeting excited. The group head to Dodge where they rest at a motel with pictures of cowboys which Dean happily identifies while his team goes over his love of the old west. Sam soon asks Dean about his good mood as he explains with Cass back and their team whole, he has the win he was waiting for as Sam accepts his brother moving on from his depression.
The next day, Dean and Cass went out to investigate the crime. They dressed up like cowboys from the movie Tombstone which Dean made Cass watch, before meeting the officers he told his friend it was good to have him back. Dean then met Joe Phillips and claimed that they were investigating a series of grave robberies which were possibly connected to the one in Dodge City. Joe had suggested that Carl's investigation into the robbery led to his death and made it clear to the two men that if he found the killer, he would kill the man instead of arresting him since the deceased officer was his nephew which Dean understood.
When Sam and Jack returned, the team went over the evidence. Cass showed suspicion towards Athena's position and possible connection with the grave robbing's, which Sam agrees with although this was quickly dismissed by Dean since she would have full access to the bodies and would not need to dig them back up. Jack soon gets a video of the stolen truck being driven by an outlaw who Dean recognizes as a dead outlaw and realized its a Ghoul. Jack soon deduced the ghoul's identity as the mortician's boyfriend from a picture he had seen there.
After tracking the Ghoul to a bank which he was robbing, a gunfight breaks out. In an attempt to stop it, Jack unleashes a telekinetic blast that throws the Ghoul and a security guard back. The security guard hits his head on a pole and dies while Dave gets away. Jack is grief-stricken at his accidental casualty as Dean tells Sam and Cass to take him to the bunker as he goes after the ghoul.
At night, Dean returned to the mortuary where he was met by Joe Phillips who had linked Dave to the crime of the robbery and murder of his nephew. Seeing his determination, Dean and Joe teamed up and Dean told Joe to aim for the head.
They attempted to find Dave in the graveyard where Dave avoided being caught by them. After Dean moved away from Joe to flush Dave out, Dave grabbed Joe from underground and dragged him through a tunnel to the mortuary. Dean followed the tunnel to the mortuary, where he found Dean Athena Lopez tied to a chair in the mortuary, and upon seeing her panic, he revealed that Dave was not human, to which she responded with clear upset and fear. He then found Joe beaten but alive. Dave then showed up and held Dean at gunpoint, demanding his surrender. Dean taunted Dave after he was dumped by his scared girlfriend as Dave prepared to shoot. However, unnoticed by Dave, Dean had slipped Joe his shotgun. After Dean moved out of the way, Joe used Dean's shotgun to blow Dave's head off, killing him.
The following morning, Dean is questioned by Joe on what exactly had happened. Dean gave Joe the story that a guy named Dave had killed Carl and tried to kill him before Joe shot him dead while Dean was never there. Joe agreed that the story was "fair enough." Dean covered for Jack as he told Joe that Dave was responsible for the death of the security guard at the bank as well.
He then went back to the bunker, saying he took care of everything as Jack has an outburst regarding the dead man and is scared that he will hurt the others stating he must be a monster. Dean spoke up by saying that he believed Jack was a monster but he was wrong though Jack rebuked this as he said they are all he has and he can't hurt them. Jack throws them back saying he is sorry and teleports out of the bunker.
In War of the Worlds, Sam and Dean continue their search for Jack to no avail. There are no signs of any Nephilim activity which Dean is skeptical about since Jack could cause a tsunami with a hiccup. Cass goes out to meet a contact who doesn't trust strangers. Dean tells him not to do anything stupid as he and Sam head out on their own. Dean tells Sam he has found a case where witches are being killed and suggests that they work a case as their search for Jack is proving fruitless. The brothers review the security footage of one of the witch abductions and spot someone who looks like Arthur Ketch in the video. They are shocked by this as they wonder how he is alive with Dean promising to kill him. A witch named Daniela approaches them and asks for their help noting that while they don't like witches, they do help people in trouble. Daniela takes them to a hidden cabin in the woods which witches use as a safe house. There she revealed she was a victim of the witch killer by showing them the scars he inflicted on her before she was able to escape. She says that the killer wanted to know the location of Rowena MacLeod, but as everybody knows she is dead. Dean asks her if he had a British accent as she says yes and asks if they know him before Sam shows her a photo of the Arthur Ketch lookalike, who she confirms was her torturer.
Later, the Winchesters use Daniela as a bait to successfully lure Arthur and capture him after Dean tranquilizes him.
Dean and Sam take him to the bunker where Dean takes delight in beating up the Ketch lookalike, in retaliation for what he did to his mother. The man claims that he is really Arthur Ketch's twin brother Alexander who fled the British Men of Letters after refusing to complete initiation. He works as a freelance mercenary hunting Supernatural creatures. Dean doesn't buy it even when Sam brings up documented proof of his claim.
Dean is annoyed to see Sam has allowed Ketch to walk around, albeit in chains. Dean tells Sam that he thinks something happened with Cass and the two leave Ketch but re-chain him up.
They arrive at a bar, where they discover evidence of a fight and wondered what happened to Cass. The two are then attacked by demons until they are saved by Alexander who used a lockpick in his mouth to escape and drove after them on a motorbike in the garage. Dean points a gun at him and states he knew that despite Alexander's claims he knows that he is really Arthur. He explains that the moves he used resembled that of Arthur's from when they fought alongside each other and against each other. The man admits his identity as Arthur and explains that the British Men of Letters captured Rowena a few years ago and discovered the spell she had sewn into herself that revived her. In exchange for her escape, she did the same for Arthur but the spell needs recharging so he is seeking her out. Dean says that Lucifer killed Rowena, something Ketch is skeptical of, and raises his gun. Ketch throws something that causes a burst of light and escapes but not before Dean shoots him in the shoulder.
On the way back, Dean calls Castiel who tells him that he didn't have a signal but he has found a lead on Jack and is following it.
In The Scorpion and The Frog, Dean calls Cass who is going on a lead to find Jack. Dean is soon contacted by an unknown man who requests a meeting. The brothers go to a diner and meet Barthamus, the new Ruler of the Crossroads who asks them for help. They immediately refuse to aid a demon, though this does not deter Barthamus who reveals a Nephilim tracking spell which helped them find Jack but he will only give it after they help. After doing research, they find the spell can actually track down Jack and agree. Barthamus wants them to steal something from an old man named Luther Shrike. He states this required a man who had been sent to Hell which he remarks on Dean fitting since he has been.
They go to Luther's home where they come up with a plan to sneak in, Sam will serve as a distraction Dean and the others will go through the manor.
Hiding in the backseat of the Impala under a tarp alongside Alice to be smuggled into Luther's property. Dean makes a crack about Alice's shoes, leading Alice to shush him. Once they are past the gate, Sam lets them out.
After separating from Sam, Dean and Alice make their way to a barn on the property where Dean begins setting up a spell to summon Grab. While they wait, Alice's behavior causes Dean to label her weird. When she drinks a Nerve Damage, Dean recognizes it as something that he had loved as a kid and Alice gives him one. As Dean continues setting up the spell, he warns Alice that working for demons is a bad idea, but she points out that he is too. Alice admits that she has no choice but to work for Barthamus, but dodges questions as to why.
Dean is able to summon Grab and watches as Grab admits that he doesn't know where the vault is, but that Dean's blood will lead them to it. Dean understands Grab's explanation as to how that will work, Grab casts a spell that causes Dean's arm to point in the direction of the vault and the three begin following it there. As they travel, Dean complains before he and Grab argue.
After Grab's spell leads the group to a cellar, Grab refuses to join them as Dean and Alice enter the cellar alone where they find the vault door. Alice quickly guesses that Dean must stick his hand in the ornament of a head on the door to open it and the two banter briefly about Dean's reluctance to stick his hand in. Finally, with a lot of dramatics, Dean sticks his hand in which is promptly held in place before the mechanism inside the ornament extracts a drop of blood, opening the door.
Dean is made fun of by Alice who moves to enter the vault room, but is almost hit in the head by a dart booby-trap. Dean quickly pulled Alice to safety and as Grab asks them for an update, she admits that Barthamus never told her anything about the booby-traps. Dean complains about the bobby-traps which Alice notices Luther enter and flees the area. Seeing Luther, Dean asks about his brother as Luther states he is alive for now and was surprised Dean was a lackey for a demon.
Drawing his gun, Dean suggested that Luther just hand over the safe, but Luther refused and advanced on Dean. Dean shot Luther several times, causing him pain but failing to stop Luther. As Luther went to stab Dean, Sam entered and told Dean that Luther was immortal. Dean responded by punching Luther in the face, knocking him out.
The brothers tied Luther to a pillar and questioned him on how to get past his bobby-traps and into the safe. However, Luther refused to comply, stating that they would never crack the riddle and if they tried, they would be hit by "a thousand tiny darts, each tipped with silver and filled with arsenic, holy water and holy oil." Amused, Luther laughed and wished them good fortune, leading to Dean gagging Luther with a piece of masking tape.
As they struggle to find a way, Sam came up with the idea to use Luther himself to bypass the traps since he was immortal. Tying the man to a chair on top of a rolling platform, they sent him rolling through the vault. As a gagged Luther screamed, the brothers watched as he was pelted by all of his own. With Luther having been used to effectively disarm his booby-traps, he was tied to the pillar again by Dean who noted to Sam that Luther was pissed.
After opening the safe and retrieving the trunk with Alice's help, the Winchesters discovered that Luther had escaped his bonds and disappeared. The Winchesters drove away, before Luther appeared in the middle of the road in a truck to stop them. A chase ensued, but Luther was closed in on the smaller car, with Sam opening fire and shooting out Luther's driver-side tire, forcing Luther's truck off the road.
The brothers armed themselves but Luther emerged without a fight since he was defenseless off his property. Luther soon told them what had happened with Barthamus and his son in the past, which earned their sympathy as the Winchesters believed Luther's story. Luther revealed to them that he had leverage over Barthamus and provided Sam with the key to the trunk to look inside. When the Winchesters found a set of human bones, which Luther explained Barthamus' bones. To their horror, Barthamus appears and decapitates Luther. The demon confirmed Luther's story to the Winchesters, showing a callous attitude about what he had done to Luther and his son. Utterly disgusted with Barthamus' treatment of Luther and his son and deeply sympathetic to both of them, the Winchesters refused to turn over Barthamus' bones to him. Barthamus then took Alice hostage and demands that the Winchesters turn over his bones in exchange for Alice's life, promising to kill her if they try to burn his bones and kill him. Reluctantly, they slide Barthamus' bones out and he sends a terrified Alice out to retrieve them and decides to keep the spell.
As Barthamus gloats, Alice apologized to them but Dean brings up her past words and gestures to his eyes to Barthamus' bones where Dean has left his lighter. Noticing this, Alice realized his meaning as Barthamus ordered Alice to hurry up as Alice walks over to the bones, and uses Dean's lighter to set them on fire. With a scream, Barthamus catches on fire and burns to ash along with his vessel, killing Barthamus. Dean ordered Sam to get the spell as he runs to retrieve it but the fire from Barthamus' destruction ignites the tracking spell, destroying it as well.
Afterwards, the brothers bid Alice farewell and decide to keep looking for Jack in a new way.
During The Bad Place, Dean and Sam continue to track down Jack with Dean even contacting Patience Turner for some help. The two soon get an alert from Jody who tells them she has a lead in their search by telling them a man named Derek Swan had met Jack but he is dead. This causes them to believe Jack had killed the man, Sam was hesitant to believe this as Dean had to tell him to consider it while stating he liked Jack but he had gotten out of hand before.
The two met Derek's girlfriend who told them that Derek was a Dreamwalkers as Sam spoke to her, Dean found a portrait of a world that resembled the one that Lucifer was sealed in. They come to the conclusion, Jack is trying to link with his father and bring him back to their world. After finding Jack with a girl named Kaia Nieves, they learn that he didn't kill Derek and that he disappeared to master his powers to see other worlds, to prove that he is good. Jack then reveals to the brothers that their mother is still alive, which surprises Dean before Jack shows them the world Mary was trapped in and how she was suffering in a cage. Dean was visibly shocked to see that his mother was really alive, even feeling guilty about not considering it. They soon learn Kaia is a more powerful Dreamwalker which was why Jack was with her but she refused to help.
On the way, he apologizes for doubting Sam's beliefs and they agree to get their mother back no matter what happened. Dean then talks to Jack and apologizes for thinking he killed someone as they thought he was looking for Lucifer. When Jack says that he only views them and Castiel as his family, Dean firmly agrees with this statement and compliments on finding his and Sam's mother.
They are then alerted after Jack hears angels talking and reveal they have Kaia. Dean holds one of Kaia's Abductors hostage and watches as Jack refuses to join the angels before a fight breaks out. It ends with Jack saving dean from angel as the latter go resolve to find his mother was so extreme he held a Kaia at gunpoint and was willing to let the angels go extinct when they tried to take Jack.
In Wayward Sisters, Dean and Sam wander the new realm which was a giant forest of monsters. The brothers searched for the rift which they believed would be opened. Dean adopted to eating some of the creatures there which disgusted Sam. Very soon, the Winchesters are confronted by a hooded figure who proceeds to attack them and knock them out with its spear.
They awoke to find themselves captured by their attacker who was planning to have them fed to a giant monster but they are saved by Claire Novak and Kaia Nieves who arrived through the rift. Seeing Kaia caused Sam to ask about Jack, Dean heard from her Jack was sent to the other world with Mary. The girls free them as they run to the rift as the hooded being finds them and throws a spear at Claire but Kaia sacrifices herself to protect her. The brothers bring a stunned Claire back to their world after crossing the rift.
Now back in their world, they thanked Jody for her part in saving them and she assures them that she'll deliver their thanks to Claire. Dean watched as Sam warned Jody that the rift was opened for a while and there could be other strange monsters still roaming but Jody says they can handle it and the brothers head home.
During Breakdown, Dean notices that Sam is now in a depression as the latter states its because they've now lost Jack as well as their mother. They are soon contacted by Donna Hanscum who asks them to help her find her missing niece Wendy Hanscum and they agree to help. While checking out the last place she was seen, they meet FBI agent Terrance Clegg, who was investigating a connection to a serial killer. His presences causes Sam worry as he is real law and the law are still looking for him and Dean but the latter shrugs it off.
They meet Doug Stover again, Dean tells him that he and Sam are Donna's cousins to avoid suspicions. As they investigate a series of suspects, they soon get info from Marlon, a clerk at the station Wendy was at and are led to a building where they meet with Clegg who believes he could find the killer there. Dean and Donna revealed to Doug that every monster he heard of is actually real.
When Dean and Donna go off, Marlon is revealed to be a vampire and attacks Doug turning him into one as well. Dean and Donna subdue Marlon, as Dean tells her there is a cure for it which requires Marlon's blood. Donna later interrogates Marlon about everything he knows before she kills him and he tells here where to find the victims.
They also learn that Terrance is responsible and he has begun his illicit business by using Sam for the auction. As Terrance prepared to kill Sam, Dean showed up in time and killed Terrance with a fatal shot to his heart, saving his brother. Meanwhile, Donna had killed The Harvester after locating her niece and saving her from being a victim.
After Doug wakes up, they explain to him what they do and Dean offers him a chance to help but he refuses though compliments what they do for people. Dean watches as Sam comforts Donna after he breaks up with her.
At the bunker, Dean asks Sam what's been up with him as he states that he realized from their time in the Bad Place as well as losing Jack and their mother that the people around them all die. He ends it by stating their job ends bloody before going to his room.
During Various & Sundry Villains, Dean goes into town where he helps a woman but its a trap as her sister uses a hex bag to activate the spell on him. Dean returns stating he is in love this confuses Sam but he gets worried when Dean grabs the Black Grimoire. Sam tries to stop him thinking it was a love spell like the one Becky Rosen put on him but Dean has forgotten this event and knocks Sam out with a punch and leaves. Dean meets with his love as Sam catches up but Dean is still insisted on giving the book and nearly kills Sam as the woman takes the book and leaves them. However, Rowena suddenly reappears to break the love spell cast on Dean by Jamie Plum and they are shocked to see her.
Rowena later goes with them to the bunker where she explains her return and asked about her son. They informed her of Crowley's death, which shocked her as she couldn't believe his change in attitude and his act. Rowena then decided to help them after she reveals she put a tracking spell on the Black Grimoire which forces the brothers to take her along.
In Stillwater, Oklahoma; Rowena explained to the Winchesters that she is after a ritual in the book that will remove the magical binding placed upon her by the Grand Coven upon her expulsion. Dean searches for information from the locals, he talks with a clerk who gives him an address and hopes he deals with the troublesome witch sisters which he agrees to.
Dean then returned with the location of the witch sisters but refused to take Rowena with them, Rowena suddenly tosses a hex bag at the Winchesters' feet and magically immobilizes them. Sam soon found a way to remove the bag which freed them and they go after Rowena.
They arrive in time to find Rowena attacked by the Plum sister's zombie mother. A fight ensued between the brothers and witches where the two hunters are overpowered with Sam correctly deducing that it was a spell that had enhanced their strength to superhuman levels. Rowena soon shot Mrs. Plum in the head as the Plum sisters were able to pin the Winchesters to a table. Distracted by their mother's death, Rowena cursed the Plum sisters with Attack Dog Spell, commanding them to kill each other. Under the command, the sisters savagely attacked the other. They both later died due to the inflicted wounds.
In the aftermath, Dean once again refuses to leave Rowena with the Black Grimoire. Still terrified, Rowena pleads with Sam who takes the book from her.
At the end, Dean later questioned Sam's reason for sympathizing with Rowena as he knew he gave her the spell to unbind her. Sam told her he could relate to how she felt about Lucifer even though she isn't a friend and promised to kill her if she went out of line.
In Devil's Bargain, Dean and Sam are told by Castiel that he was captured by Asmodeus and the latter had his phone and spoke to Dean to monitor them. Castiel soon tells them that Lucifer has returned due to the alternate Kevin Tran using his grace in a spell to open a rift, which surprises Dean. However, Castiel tells them another problem is coming which is Michael who wants to invade and conquer their world as Dean is more surprised. Dean reprimands Castiel for still meeting with Lucifer but the latter states this situation called for it and brings up Lucifer's weak state. They decide to make a plan before asking about Mary and Castiel reveals she's alive but knows very little of her well-being.
Dean has some sincere words over Castiel's capture as he tells him that they must put their rescue plan into action. Summoning Donatello Redfield, the group plan to have him read a spell on an angel tablet that could open a rift to the other world so they could locate their mother and Jack before Michael harms them.
While Donatello reads, they get word from Castiel about angel's dying and realize Lucifer is responsible and decide to search for Lucifer him in his weakened state. They travel to his last location and are told by a man that Lucifer went to see a faith healer Sister Jo.
During Good Intentions, Dean and Castiel go off to face some ancient warriors for their hearts.
In A Most Holy Man, the brothers then get the ingredient of a most holy man. At the bunker, they are relieved but Sam tells Dean even if they are successful in their efforts there will still be monsters. Dean told his brother to have faith, a choice of words that surprise Sam.
In Scoobynatural, Dean and Sam are attacked in store by a living dinosaur toy which they soon kill by blowing it up. After the store owner thanks them, he lets them have anything they want which causes Dean to ask for a flat screen television which annoys Sam as they carry it.
Later on, Dean calls Sam into a room which is revealed to be a leisure spot for Dean that is complete with the TV. After hooking up the monitor, the screen glows and the brothers are sucked into the television, now as 2-dimensional cartoons. They find Baby in the cartoon world and drive it to the local hangout, the Malt Shop, and find the Mystery Machine, concluding they were in a Scooby Doo cartoon. Dean, fawning over his childhood heroes, greets them and they allow him and Sam to join them in their adventure, which Dean recalls the episode and they decide to play it out.
Dean then challenged Fred to a race, he is asked by Sam as to why he can't stand Fred and explains it his attitude and how Daphne is settling for him. The two start the race but Dean ends up losing the race and is embarrassed that his car lost to a van as Sam tells him to let it go.
However, unlike in the original run, they discover that one of the victims, Cousin Simple, was murdered when they discovered his dead body. Despite the brutal circumstance, the Scooby Gang treat it like a normal mystery. Dean and Sam soon tackle a figure who is revealed to be Castiel, having been sucked into the television as well, joins them on their case to figure out the mystery.
The group splits up to investigate with Dean choosing Daphne and Fred joining them, to his annoyance. Dean continues to flirt with Daphne, but she continues to remain ignorant of his flirtations. He soon finds a book in the library that triggers a trap door, that they fall into before fleeing from the ghost.
They all meet up, and the Phantom attacks them, with Fred getting injured, and Shaggy getting thrown out through the balcony door. Sam and Dean drive off the Phantom, using iron candlesticks and find Shaggy holding on for his life. Scooby jumps to save Shaggy and Castiel jumps and slows their descent to the ground, but Shaggy's arm gets broken. With Shaggy's injury and the unexplainable abilities displayed by the Phantom, the Scooby Gang is confused by the unusual circumstances. Dean and Sam decide to tell them that all the paranormal stuff is real, including the ghost. The Gang begin to have a nervous break down by this revelation, but Dean stops them by mentioning their past acts to encourage them, which gets Sam to reveal he watched the show as well. Dean showed them their equipment which causes an amazed Fred to ask to help, now being able to stand him he has him set a trap for the Phantom.
Before they leave, the three find the Scooby Gang suffering a second nervous break down which Dean states they can't leave them in. To set their minds at ease, they have the ghost disguise itself as Cosgood Creeps in the Phantom costume, making the cartoon heroes believe the whole thing was just another staged set up by a normal human.
The child returns Castiel and the Winchesters to the real world, and they destroy the knife in the television, putting the kid to rest. Afterwards, they go back to the pawn shop, finding Alan about to sign his store over to Jay, and confront the Real Estate Developer of his crimes, knowing he used the ghost to drive off owners to buy their property and then on Sam and Dean when they got to close to discover his plan. While they knew he would never be arrested for those actions, they hacked his finances and had him arrested for tax evasion.
As Jay is arrested, he uses the meddling kids quote from Scooby Doo and Dean uses Scooby's phrase but Sam and Cass tell him to cut it out.
During The Thing, Dean pulls pranks on Sam as he sleeps before he wakes up and they go over Solomon's seal as the next ingredient for the spell. As they look through books, Dean soon found some noteworthy that is located in Rhode Island.
They arrive in Rhode Island where they find a building which they discover is a Men of Letters' bunker. They use their key and enter the area finding it is no different from their own. The two soon hear screaming, they follow it and find a strapped woman who begs them to free her. They release her and question her as she reveals some of what she remembers and asks where she is. After seeing her license, they are shocked that she is over a hundred years old and reveal to her she is in the future which understandably leaves her in disbelief. They decide to take her with them and find out the cause.
At a diner, they speak to the woman whose name is Sandy and promise to figure out how she is alive after a hundred years.
As Dean investigate the bodies, Sandy appeared and a tentacle shoots out of her mouth as she knocks Dean out. Dean awakes to find Sandy who reveals her true name is Yokoth and she stole the original Sandy's body. She explains her past as a goddess from another world and how her mate Glythur was trapped there after she came through. She reveals she has abducted Dean so she could reopen the rift between universes and have Glythur take his body as his vessel for them to devour the world. Dean protests this but Yokoth silences him as she succeeds in reopening the rift and performed a Summoning Spell for Glythur. Dean was horrified as Glythur's tentacles emerged through the rift and attempted to latch onto him as he managed to dodge the tentacles despite being chained down. Dean's struggle ended as Glythur's tentacles started to wrap around him to hold him down, though Sam arrived with Marco and Ophelia Avila and attacked Yokoth. As Yokoth was distracted, Dean managed to free his right hand, snatch the Seal of Solomon and toss it to Ophelia who casts a reversal spell to close the rift. As the rift closed, Glythur was sucked back into its own universe but before the rift fully closed, Glythur wrapped his tentacles around Yokoth and dragged the screaming Yokoth back with him. The brothers explained to the Avila siblings they needed the seal to open a rift and they knew the repercussions but were prepared as they were given the item.
The Winchesters returned to the Men of Letters bunker with the Seal of Solomon, they note the last ingredient is grace of an Archangel before they realize someone is waiting for them and aim their guns only to see its Arthur Ketch. To their shock, Arthur reveals the battered Gabriel in his possession and they are at loss, having believed him dead but Arthur says that wasn't the case. Seeing his state, Dean asks what Arthur did to Gabriel as the latter explains that Asmodeus had been holding Gabriel prisoner until Arthur rescued him. After Arthur tells them that he heard they need an archangel for a spell, a concerned Dean watched as Gabriel reacted in terror as Sam admitted to needing his grace. Arthur then presents a vial containing Gabriel's grace, stolen along with the Archangel blade. In return, Arthur asks for sanctuary at the bunker since Asmodeus will chase him to the ends of the Earth for his actions. To both Sam and Arthur's obvious shock, Dean agrees to Arthur's proposal since it can potentially help them get their mother and Jack back.
Afterwards, Dean readies his gear and tells Sam to prepare to open the portal to Apocalypse World, as he wanted to save their loved ones quicker. Dean tells Sam he's going alone as he needs Sam to be there in case he gets trapped and because he needs him to keep an eye on things. Arthur then arrives and announces that he'll join Dean, stating he wanted to be a world away from an angry Asmodeus. To Sam's surprise, Dean instantly agrees to allow Arthur to join him on his journey when he won't allow Sam. Dean tells Sam that he doesn't care if Arthur survives or not unlike Sam and in fact hopes he doesn't, something that Arthur takes in stride. Once the rift opens, Dean entrusts Gabriel into Sam's hands as he and Arthur pass through into Apocalypse World together, leaving Sam and Gabriel behind.
In Bring 'em Back Alive, Dean and Arthur wander the area with Dean being put off by him practicing stealth. The two soon witness a squad of angels lining up humans and executing them on the bridge in Michael's name. He is angered at this act and tries to stop but is told by Arthur not to get involve before he is shocked by a familiar face who is taken away by the angels.
Dean and Arthur then continue on as Dean ignores Arthur's questions about Charlie before he is grazed by a bullet. He is then attacked by a crazed man who restrains him and states he will sell Dean for a good price but Arthur comes to his aid and tackles the man for answers. Taking advantage of the distraction, Dean frees himself as the man manages to pin Arthur and hold a knife to his neck but Dean shoots bullets in the air to stop him. Dean repeats Arthur's question and after shooting the man in the leg, he learns there is a camp for human prisoners.
Dean and Arthur head in the direction of the camp but Dean is weakened and Arthur examines him and sees the bullet Dean was grazed with was laced with poison. Fortunately, Arthur was familiar with it and treats his wound as he proceeds to treat the wound and Dean gives him his answer about Charlie and how he failed her.
Eventually, they make it to the camp where they see Charlie taken out to the middle of the camp where she was to be executed by decapitation. However, Dean threw a grenade as he and Arthur storm the camp kill the guards before proceeding free Charlie from her binds. Dean ignores her questions of who they are and told her to run which she complies.
After getting a safe distance from the camp, Dean talks with Charlie and tells her that he and Arthur are from another world, which is not a war zone and that another version of her was there but says she is dead. He told her of the close bond he had with her counterpart and the latter was pleased to learn she preferred females.
Dean then asked Charlie about Jack and Mary Winchester who he told her was his mother. Dean then learns that Jack and Mary are now resistance leaders against Michael and the angels and last she heard, were fighting in Dayton, Ohio. When Charlie questions if he is telling the truth, he shows her the Rift, which confirms his words to her amazement.
Dean sees the rift is closing as Arthur and Charlie both tell Dean to return to his world, to his shock. Arthur tells him they need to learn Michael's plans before they locate Jack and Mary before telling him to get reinforcements. Dean wanted Charlie to accompany him but she declines his offer, as she wants to defend her world and tells him to come back with a way to defeat Michael as Dean voices he can't lose her again. Though she is touched by his words, she tells him it wasn't his call. Seeing her resolve, Dean tosses her his gun as angels appear and Dean goes back to the main world as Arthur and Charlie defend him.
Returning to the bunker, the rift closes as Dean sees the mess and questions Sam and Castiel on what occurred in his absence. Dean is then informed Asmodeus attacked with some demons but Gabriel regained his wits and killed the latter. Though he is surprised, he questions where he is as they needed the rift opened as he explains his own journey. Dean's surprise turns to rage after he hears Gabriel's refusal to help and he bemoans that he shouldn't have left Apocalypse World if he knew about that. Castiel swore to Dean that they'd find Gabriel again as Dean agrees to it.
In Funeralia, Dean, Sam and Castiel try to track down Gabriel but have no luck. They contact Rowena who ignores their pleas and goes about killing people. They suspect its Rowena and Dean tells Sam that he doesn't want to state he warned him but they have to be ready for anything. Dean then stops the car after Jessica appears.
Jessica greets Dean who recalls their meeting while telling Sam Winchester who and what she is. Jessica reveals her assignment and that she has seen their possessions, such as an old hamburger Dean has in his room and love movie, which annoys him before they question her and she reveals Rowena is killing people ahead of time, as Dean becomes worried. Sam then sends Jessica off. Dean stated they could of use her help explaining they don't know what Rowena got them into as reapers are involved.
They investigate the death scene and do research on the victim but nothing fits Rowena's motive. They notice a scorch mark and Sam reveals to Dean that is the remains of a reaper. Acting on this, Dean calls Jessica and questions her about the reapers dying and she states this was why she was called as someone later revealed to be Rowena MacLeod is killing reapers. She explains what consequences that Rowena's actions will cause and how they should stop her since Billie ordered the reapers not to get involved directly. Jessica soon mentions to Dean's list of deaths as he comments its a shelf before Jessica reveals that Sam is always the one to kill Rowena permanently.
Rowena later calls the brothers for a meeting, they question her motives as Rowena revealed she was doing all this to get Death's attention so she would resurrect Crowley for her, as she went onto state it was her fault as to how he turned out. The brothers state it won't be possible and threaten her with the fact that Sam is always the one to permanently kill her.
Dean goes after them and finds Rowena's hideout where fights Bernard who he fails to convince of Rowena's intentions. As they fight, Dean is choked by Bernard as Jessica appears and he asks her for help but she says she can't help because of her orders. Dean soon defeats Rowena's follower as Jessica congratulates him but he ignores her and goes after Sam. Dean and Jessica enter the room, where he sees Billie who greets Dean before stating she'll see him again shortly before disappearing with Jessica.
Afterwards, Dean tends to Sam as they ask Rowena if she is okay as she replies she doesn't know. Sam comforts her before telling her Lucifer is back and they may need her help in stopping him, which she agrees to, pointing out that she now knows Lucifer won't be the one to ultimately kill her. Both brothers express hope that Rowena can be redeemed and that they can help her change her fate.
In Unfinished Business, Dean and Sam have Rowena search for Gabriel by using a tracking spell to narrow down his location. Dean complains about the search as Gabriel doesn't want to be found as they have to worry about their mother and Jack. As he complains, Gabriel appears at the door wounded and greets them, as they are shocked to see him.
As he tries to leave, two men named Sleipnir and Narfi arrived and demanded for Gabriel and they attacked the hunters. Dean fought Sleipnir who was armed with a whip while Narfi fought Sam. Dean eventually managed to disarm Sleipnir and throw him to the ground. Moments later, Narfi was killed by Gabriel who threatened to do the same to Sleipnir. Terrified, Sleipnir fled, followed by Dean who quickly lost him.
Afterwards, the brothers disposed of Narfi's body and once again questioned Gabriel who refused to answer them but Dean handcuffed him for answers. Dean and Sam learn the two men they fought were pagans and that Gabriel killed their brother which was they were hunting him down. Gabriel continued on by revealing his past with the pagans' father Loki and the deal the two made after Gabriel faked his death, Dean noted Gabriel left out certain details in the story as Gabriel corrected it. Gabriel then revealed his life of luxury before Loki and his sons had him kidnapped and sold to Asmodeus. Dean listened to Gabriel reveal his intentions to settle the score and tried to talk him out of it but saw he was insistent on finishing it but he saw Gabriel was insistent on finishing it. They offered him help but only if he will help them in their endeavors and he begrudgingly agreed.
Later, they went to a motel where they fought with two bodyguards. As the nearby elevator opened with the Winchesters and Gabriel inside, Sleipnir was shocked to see them but quickly ordered his bodyguards to get the three. With a snap of his fingers, Gabriel turned out the lights and a gunfight ensued in the dark. During the fight, the Winchesters killed Sleipnir's bodyguards and Sam hit Sleipnir himself in the right shoulder with a silver bullet, sending Sleipnir to the ground. In the chaos, Dean slipped away and decided to confront Loki alone with Gabriel's sword.
He went to the pent house where he found him sitting in wait, Dean claimed not to care why Gabriel wanted Loki dead, Loki recognized that Dean did "a little bit" and explained that his treatment of Gabriel stemmed from the death of his father Odin. Though Dean pointed out that Lucifer killed Odin, Loki told him that Odin was at the hotel in the first place because he was there to deal with Gabriel's brothers. Dean brought up that the world was ending as Loki told Dean about Gabriel's promise when Gabriel took on the persona of Loki and how Gabriel broke the promise when he showed up at the hotel which cost Odin his life. Loki pointed out that despite their differences, Odin was still his father and he didn't want Odin dead.
As Loki asked what Dean would do for his father, he approached Dean who stabbed Loki with the sword. However, Loki proved to be merely a projection that Dean couldn't harm, but that could hurt Dean. The projection was dissipated when Sam arrived and shot it.
Later, Dean and Sam went down the hall where they watched Gabriel fight the real Loki and was overpowered. As Loki grabbed Gabriel again, Dean slid him the correct sword and watched the two share words before Gabriel killed Loki.
Afterwards, Gabriel thanked the brothers for their help even though he knew they weren't keen on it. Gabriel then decided help them in defeating Michael, as they question his change in mind which he states is because he promised.
Returning to the bunker, they wait for Gabriel's grace to recharge, Dean was sitting the front when Sam appears and mentions that Rowena is "boning up" on the Demon Tablet and Castiel is helping Gabriel settle in for their upcoming mission to Apocalypse World. Dean is then confronted on his leaving to kill Loki alone as he states that they could handle it. Sam tells him that's a lie and asks about his recent treatment to him lately such as going to Apocalypse World with Ketch and having him miss out. Dean voices his lack of concern for himself and that he only cares about what happens to Sam and mentions the last time the Apocalypse occurred Sam died and that he doesn't want that to happen again as Sam tells him no matter what happens they will do things together even if it means death. Dean watches Sam leave as he thinks about things.
In Beat the Devil, Dean and the others prepare the spell and he is dismayed to hear Gabriel is extracting his grace in his room. However, it wasn't enough grace to open the rift and this caused the others to reconvene about the plan. Castiel suggested tracking down Lucifer as he is the only choice, Sam was against this since they had too much experience with him until Castiel convinces Dean they have no choice. Dean then tells Sam they deal with Lucifer afterwards. Agreeing Sam tells them he has plan, they go to notify Rowena and Gabriel who just finish having sex of Sam's plan.
After Gabriel and Rowena ambushed Lucifer and brought him to the bunker. Dean watches as Sam tells Lucifer his plan was to use Lucifer to continuously keep the rift open until they find Mary and Jack. Dean then leaves Lucifer with Rowena as they travel through the rift.
Traveling through Apocalypse World, Dean asked Sam about how he feel and is told that his spirits are lifted since they can save their mother and Jack. They find a girl and man attacked by a vampire and they intervene with Sam killing the vampire with decapitation. Dean then learns that since the angels have exterminated most of humanity, the monsters are getting hungry and wilder for humans to devour. They are soon told that Jack and Mary are at a camp which is where they are headed and there is a shortcut but vampires are there, Gabriel wanted to avoid it but everyone tells him it is the best way.
Unfortunately, as they travel the tunnels Sam was attacked by vampires and was dragged off by the vampires screaming. Castiel went after him and was horrified to find him dead and told Dean not to look to look at the carnage.
The group found an area with warding and met with armed humans but Dean was surprised to see his mother. Happy to find her, Dean embraced her but he was unable to her of Sam's fate though his tears gave it away and the two mourned Sam. At the camp, Dean reunited with Jack as well before he decided to retrieve Sam's body however, the latter arrived alive but with Lucifer, which shocked Dean.
In Exodus, Dean told Jack to not approach Lucifer as he didn't want Jack to turn evil. He ordered Gabriel to kill the latter as Lucifer brings up he resurrected Sam and they need him to fight Michael but this causes an argument and Jack disappears. Dean congratulates Lucifer on this as the latter allows himself to be taken in by Supernatural Handcuffs. Dean is called on by Sam who apologizes for letting Dean's fear come true but Dean tells his brother that he's alive and that's what matters. They go to talk to Mary and are pleased when she punches Lucifer in the face as Castiel escorts him.
Dean and Sam talk to their mother but she tells him that she wants to defend the world after fighting with the humans. Dean is shocked when Sam supports this and says they will take the survivors to their world which pleases Mary.
Afterwards, Dean and Sam went to the resistance's leaders for his proposal and they are skeptical until Mary vouches for them.
On the road, Dean is not to pleased to see Lucifer and Jack bonding, as Mary tells him that Jack will see Lucifer for who he is. Dean is even more upset when Lucifer smites angels and reveal the cuffs didn't work. The brothers reunite with Bobby and Dean is told about Arthur and Charlie going on a mission together and becomes worried.
Dean takes part in the interrogation of an angel and they learn Charlie and Ketch are being held captive. He goes with the others and kills the angels before helping a wounded Arthur out of his shackles, Arthur remarks on Dean saving him by telling him it was about time as Dean helps him out. Much later, Dean learns everyone decided to evacuate with them but they had no way to transport them until Dean noticed a bus and they fixed it up and drove everyone to the rift.
As he and Sam were evacuating the humans from Apocalypse World through the Rift, Michael appeared. Dean was shocked to finally see the latter and witnessed Lucifer step forward to attack him but Michael easily tossed aside Lucifer before he approached the Winchesters but noticed Gabriel who he was surprised to see. Gabriel told Dean and Sam to retreat as he wanted to make up for his past and engaged Michael. Dean watched as the two archangels fought before Michael managed to kill Gabriel, to his horror. Dean was told by Sam to retreat as Michael tried to go after them but to no avail. The rift closed leaving Michael and Lucifer stranded in Apocalypse World.
During Let the Good Times Roll, Dean went with Sam, jack, and Castiel on a werewolf hunt. During the hunt, Jack used telekinesis to hold the werewolves in place, allowing the Winchesters to easily kill them.
Afterwards, Dean spoke with Sam about how their hunting is going and expresses hope that with Jack's help, they may actually be able to win over the forces of evil in the long run and even retire. Dean soon comforts Jack over his nightmares about the people that Jack has lost.
After the murder of Maggie, Dean and the others talked to her friend and they learn it might have been a boy she liked who did. When Jack went after the supposed attacker, Dean and the others went to stop him Dean is forced to shoot him to get Jack's attention. After the Winchesters point out Nate's innocence, Jack departs, further distraught by his actions.
Angel radio is heard, Dean tells Nate to run before he and his group leave out the store as the windows shatter. Michael suddenly appears in a gas station to the shock of the Winchesters and Castiel. Unable to defeat Michael, Dean ignites a trail of holy fire, holding Michael back long enough for the Winchesters and Castiel to escape in the Impala.
They return to the bunker where they find Maggie resurrected and are told by Mary that Lucifer was the one who brought her back before he left with Jack. Dean and Sam are confused by how the archangels got to their world and Dean decides to contact Jody for help. The bunker is soon attacked by Michael who attacks the Winchesters and Castiel who prove to be no match for him. Dean is picked up by Michael who wants him to be the first he kills as the latter questions how he arrived. Michael states he made a deal and begins to slowly strangle Dean to death as he gloats about his plan to cleanse the Main Universe. Dean remains defiant towards Michael before Jack was alerted of this by Sam's prayer and arrived in time to save Dean. Dean watched as Jack tortured Michael and watched as he nearly killed the Archangel but was prevented when Michael revealed his deal with Lucifer. Dean then watched the confrontation which ends with Lucifer stealing Jack's power and taking him as well as Sam away.
With his brother and Jack gone, Dean and Castiel turn on Michael who, severely weakened, explains that Lucifer won. Michael explains that having consumed a Nephilim's grace, Lucifer is "super-charged" and can now end the whole universe if he wishes. Michael admits that he no longer possesses the strength to defeat Lucifer in his current state with a "banged-up" vessel and appears to accept that they are facing the end of everything. Dean remembers that he is the Michael Sword, Michael's perfect vessel who will make Michael stronger than he has ever been. Michael admits that together, he and Dean have a chance against Lucifer and seeing no other choice, Dean offers Michael a one-time deal: Dean remains in control while Michael powers him so that together they can fight Lucifer. Michael accepts the deal and Dean becomes his vessel.
At a church, Dean appears just Lucifer was forcing Sam and Jack to fight. With Michael now powering Dean who remains in control, Dean battles Lucifer, using several of Michael's powers in battle. Finally, thanks to having Michael inside of him, Dean is able to kill Lucifer with an archangel blade.
Dean was then congratulated on his victory by Sam as he took it in stride before he felt pain as Michael decided to go back on their deal and take full control over Dean who brought up the promise before he lost control of himself. Michael then left the church in Dean's body and changed his outfit as he walked the streets in thought of his plans.
In Gods and Monsters, Dean manages to manifest himself in a mirror as Michael adjusts his tie. Dean orders the archangel to get out, but Michael refuses and shatters the mirror, telling Dean that he owns him and he should enjoy the ride. After Sam, Mary and Bobby deal with Michael's enhanced werewolves, a weakened Dean arrives to the others shock. Dean tells them that he couldn't kick Michael out and the archangel left on his own for an unknown reason.
During The Scar, Dean and Sam return to the bunker while Bobby and Mary clean up the mess left by their hunt. Dean makes fun of Sam's new beard and sees that in his absence that the bunker has frequented by other hunters and relieves them that he is not Michael before being shocked to hear Sam being called Chief. He reunites with Jack and Castiel who are more than happy to see him. After going to his room, Dean finds himself with a scar on his arm and has no memory of it along with his possession by Michael, Castiel accesses his memories to find out why Michael left Dean and what left a strange scar on Dean's left arm. This triggers a memory of Michael being stabbed in the arm by the hooded figure with their spear. Dean remembers the person from the Bad Place and realizes that their spear must be able to harm Michael and could be the key to defeating him. The Winchesters contact Jody Mills who has been investigating three murders she thought were done by a human serial killer but realizes were done by the mysterious person when they describe the weapon.
The Winchesters and Jody search the woods near Sioux Falls for Kaia, finding three decapitated vampire heads, confusing them as Alex had determined that the murder victims didn't react to any of the usual monster tests. They eventually realize that the vampires are some of Michael's enhanced monsters that he sent to kill the assailant and get their spear after they injured him. The three find hooded person's camp where Dean recalls Michael was there with the hooded figure. Dean is soon attacked by the hooded person but in the struggle, their hood falls off, revealing their face as Kaia to the shocked hunters before she escapes. Dean thinks it might be Kaia from another world just like Castiel and Bobby's counterparts, they decide to go after her for answers. Dean ambushes the Alternate Kaia manages at an abandoned cabin, he soon knocked her out. Tying her up, they interrogate Kaia, they realize that she is indeed the alternate reality counterpart of their Kaia. and she admits that Kaia's death was an accident as she was aiming for "the blonde one." Kaia refuses to explain how she opened up a rift between the worlds or where her spear is but remembers how Dean had once threatened the Main Universe Kaia with a gun to get her to comply. After Kaia reveals she is also a dreamwalker and she confirms it. When Kaia refuses to give up the location of her spear, Dean threatens to torture her to get it, leading Kaia to taunt him that Dean is no better than Michael. Dean remembers that Michael approached Kaia to form an alliance, but she refused and attacked him instead. The interrogation is cut short by the arrival of four of Michael's enhanced vampires who demand Kaia and the spear. The hunters prove to be no match for the vampires, but Dean manages to shoot out the leg on Kaia's chair, freeing her in the hopes that she will help them. Instead, Kaia flees out a window but unexpectedly returns with her spear to kill the four vampires and save Dean, Sam, and Jody. Sam points out that Kaia saved them when she didn't have to, but she claims that by killing the werewolves she was only helping herself. Though the Winchesters warn her that if she keeps her spear, she will be a target for Michael's monsters, she departs saying that she has been running from monsters successfully all of her life.
In the aftermath, they part ways with Jody and Dean apologizes to Sam about being reckless before he relates his possession and calls it like clawing for air after being plunged in water.
During Mint Condition, Dean hasn't come out of his room and Sam asks if he is alright since he has been watching horror movies. To get Dean back on his feet, Sam has him join on a case at a comic shop and where Dean gets excited about movies, with his brother jokingly calling him a geek. After the person interviewed is attacked, the brothers become suspicious since it was by a toy and rush him to a hospital.
At the hospital, he is called by Sam and learns it is a Vengeful Spirit and its possessing a mannequin of his favorite movie villain. He reveals to Dirk that monsters exist and what's after them. Dean tries to fight the mannequin but is overpowered and forced to run and the mannequin chases Dirk who distracted him. Dean later found Dirk and they fled the scene but were found by the ghost and forced to fight until Sam arrived along with Samantha. He watched as Sam put the ghost to rest. Afterwards, he asks Sam about his dislike of Halloween and learns he went through an embarrassing moment as a child.
In Nightmare Logic, Dean approaches Sam on resting since he has been running himself ragged. Dean and Sam receive a report that Maggie went missing and they go off to find her. At the funeral home (the spot she was last seen), they find their mother and Bobby Singer as well. They agree to work together, Dean watched Bobby insult Sam before he and the latter were sent to investigate the area. Dean encountered a vampire but saw it die in a strange way. Dean later recounted this to everyone and wondered what was lurking about. Very soon, Dean recognized a blood rig that a previous djinn had drained his blood with did he realize it was a Djinn named Neil. Dean ordered the daughter of the funeral home to leave after telling her the threat. Dean confronted the Djinn who had been enhanced by Michael and has been acting as a trap for hunters. Neil had thought Dean was Michael testing him but he explained he wasn't the angel anymore, before he learned that Neil's new enhanced abilities enable him to sense the fears of a victim by touching them and to bring their fears to life in the real world. Neil reveals that he is one of dozens of traps set up for hunters by Michael and attacks Dean who mysteriously proves immune to Neil's powers. Lacking lamb blood, Dean bashes Neil's head in and then shoots him several times in the head after he's dead, ending Neil's manifestations. Dean saw that Sam found Maggie and that everything was done.
Afterwards, he and Sam decide to get word out about Michael's plans. Dean specifically calls Garth to warn him of Michael's enhanced monsters and traps for hunters. He and Sam talk about the endgame of a plan to stop the corrupt Archangel.
In Optimism, Dean is at the bunker and is told by Jack that Sam is on a hunt with Charlie Bradbury while Bobby and Mary are on leave. He talks with Dean about a recent case and asks to join him since Cass said he was making progress. After some reluctance, Dean agreed and they traveled to a town where Jack seemed to be inept but this changed as he improved. They got some info on a recent librarian named Harper Sayles.
Dean tried to asked Harper questions, though Jack was able to get him to leave while Harper took an interest in him, as a way to get her attention. At the apartment, Jack talked with her and she tried to entice Jack but he was called by Dean and he told him that she wasn't a demon but that she may like him, to Dean's disbelief. While investigating the area, Dean was attacked but he managed to escape. He arrived at Harper's apartment and saw a portrait of a man, which was Harper's old boyfriend Vance who was now a zombie that chased him. Dean was left by Jack to handle the threat while the latter ran off with Harper. Dean soon arrived at the library where he and Jack both told Harper and Vance, their supposed love was a sham and attempted to get through to them but were ignored. After Vance was restrained, Harper took the opportunity to run while leaving Vance to be put to rest.
Jack later talked with Dean about the case and was congratulated about his progress, before his sickness acted up. He watch Jack coughed up blood again before he soon collapsed as Dean tended to his unconscious form.
As of Unhuman Nature, Dean and the others tend to Jack with Castiel detecting that something is wrong with his body. After Jack collapses, they rush him to the hospital with the doctors telling that Jack's body is shutting down and the worse may come. Hearing this, they have Jack discharged and call in Rowena for help. She reveals that Jack needs Archangel grace since his body needed to be stabilized. As they search for ways, Jack tells Dean that he wants to get enjoyment out of his remaining days, Dean decides to help him with this and joins him on the trip. Dean teaches Jack how to drive using the Impala and the latter has Dean take him fishing, something that Jack knew was the one thing that Dean had enjoyed doing with his own father.
In Byzantium, Dean is so devastated by Jack's deteriorating condition that he can't maintain his composure as Jack tries to comfort him by resigning to his fate but Dean is not accepting of it and leaves the room. Jack asks Sam to tell Dean it'll be fine though Sam wants Jack to do it as he succumbs and dies. Sam told Dean and Castiel of it, with them being sad at the untimely end.
Dean is later told by Cass that Sam left and they follow him, worried at what he might do. After finding him, Dean asked Sam if he was making a deal with a Crossroads Demon but Sam tells him he was readying a hunter's funeral for Jack, though he didn't finish it out of grief at his death. Much later, Dean calls Mary to reveal Jack's death before he sees Sam and Cass have gotten Lily Sunder to help revive Jack. Dean is skeptical but lets them continue on as it might work.
In The Spear, Dean and the others contact Arthur for the Hyperbolic pulse generator and he reveals he had it mailed. Dean expresses worry when Sam reveals he had Garth infiltrate Michael's army and the latter is passing off info about the latter's plans of invading. Afterwards, he and the others split up with him and Castiel going after Alternate Kaia. Dean reveals his desire to Castiel of revenge on Michael and declares he will kill him. Having been tipped off by Garth, Dean and Castiel search the plant for Kaia, finding her hideout and warm food, but no Kaia. Kaia is able to get the drop on Dean, holding her spear to his back, but Dean stops Castiel from attacking, telling Kaia that they have come to ask for the spear, not to try to steal it. Dean explains how they need it to kill Michael and stop him from hurting more people.
Kaia finally agrees to give them the spear, but asks for their help in returning to the Bad Place in return. Desiring to return home and unable to reopen the rift herself, Kaia asks that they have Jack do it as he did with her Main Universe counterpart, explaining that in the Bad Place, her home, she at least knows what to expect and she also has loved ones she wants to protect. Dean promises to help Kaia return home once Michael is dead and Kaia hands over her spear, threatening to hunt Dean down and kill him if he doesn't return it to her. Kaia tells Dean and Castiel that they can find her again the same way they did this time and then vanishes as they are distracted by a phone call from Sam.
When facing him, Dean is armed with the spear and attacks, making sure to pay him back for using him. Knocking Dean aside, Michael tells Dean that all the imminent deaths will be because of Dean. The hunter regains footing and continues to attack before cornering him with a strike.
As he readies to deliver the final blow, Dean ends up having dizzy spells as Michael's vessel collapses and Dean is repossessed. Michael reveals when first having Dean as a vessel, the latter resisted in accepting it and he decided to leave him but "left the door open a crack" in his mind so that he could return at will. He soon announces that his plan all along had been to break Dean's spirit and that it has worked with Dean trapped in his subconscious. Destroying the spear, he unleashes his army of monsters on the city.
During Nihilism, Michael is revealed to have kept Dean in a imaginary bar that Dean dreamed of owning with Pamela Barnes and keeps him in a loop of still hunting with the same event occurring, that Dean starts to notice.
While in reality, Michael tried to turn everyone against Dean by telling them his thoughts and regarded Dean as trapped. After Sam and Castiel enter his mind, they warned Dean of the loop and he is reluctant to believe it until they used the word Poughkeepsie. Dean then recalls Pamela's death and Michael's actions when controlling him. The illusion disappeared after Michael appears, as Dean orders him out but he refuses and tries to get him to accept the possession. Once Michael is revealed to be powerless in Dean's mind and turns out to be stalling, a fight breaks out. Dean lands several blows on Michael who gains the upper-hand though his boasting and warning of Dean's condition should he leave, gave Dean an idea where he decides rather than eject him but keep him locked away, as he did to Dean. With help from the others, Dean puts Michael behind a locked door, stating he has to have his mind act as The Cage to keep Michael trapped as he regains control of himself. In his room, Dean keeps reminding himself to be in control, though senses Michael continuously screaming and struggling to be released. Billie appears and he notes on her intervention and she warns Dean that Michael most likely won't stay trapped for long because of his potential release in Dean's possible deaths and he is worried. Dean also learned that only one death is different and he is horrified by it and she tells him the choice is his before disappearing with Dean left stunned.
As of Damaged Goods, Dean is going over research to stop Michael and his behavior causes Sam to notice something up with him when given a hug. Sam tells his mother that's something Dean never does and soon deduces Dean's moves. After dealing with Nick and his revenge quest, Sam learns of Dean's plans to lock him and Michael away. Of course, Sam doesn't like the idea but decides to help.
During Prophet and Loss, Dean has a nightmare about his plan with Sam tries to talk Dean out of this mad course of action though Dean is insistent. Sam even breaks a promise to him by calling Castiel to tell him of the plan. When learning of Donatello Redfield's condition, they both share opposing views on it while discreetly relating it to Dean's intentions. After Donatello is healed, Sam relates it to what could happen if Dean doesn't give up but this doesn't sway Dean. At the end, Sam punches his brother before embracing him and mentions that Dean saved him from his fate in The End and persuades him to not give up and Dean thinks on it.
In Lebanon, they do normal cases and decide to use a charm to expel Michael from Dean's mind. However, this results in them bringing their father to the future and they reconnect with Dean what's been occurring in his absence.
After the dinner, Dean shares one last embrace with John before Sam destroys the pearl and John disappears back to 2003. Dean was sadden to witness this but accepted that it was the right choice. Meanwhile, John wakes up in the Impala during 2003. He gets a call from the Dean of that year and believed the events were a dream, before telling Dean that he's coming home. Though John was sent back to the past, it is hinted that he still remembers everything and is pleased with the outcome.
During Ouroboros, Dean and the others were on case for an elusive creature that they had been trailing for weeks with help from Rowena. Later on break, he reveals to a curious Castiel that Michael is continuing to try to break free from his mind with Dean telling Castiel that its taking all of his concentration to keep Michael contained. As a result, Dean is barely even sleeping anymore, showing how stressed he was. Much later, they learn from Maggie that the creature is a Gorgon and its ability to see them is the foresight it gains from victims. Dean was impressed to learn this but wondered how they'd catch it.
Afterwards, Dean and Cass go to a truck depot where they see the Gorgon struck again and left a note to Dean. It told Dean that the Gorgon's name was Noah Ophis and that he saw him reading the note and informed Dean that he saw him with Sam and Rowena before telling him to back off. Dean reported this to Sam who realized that Noah can't see Cass or Jack as angels aren't affected by it. Using this to their advantage, they send the pair to confront him. Once Noah tries to escape after fighting them, Dean and Sam arrived where they met Noah formally, Noah greets Dean who attacks him but is knocked aside along with Sam. Noah then grabs Dean and bashes his head on a counter, knocking him out. With the hunters occupied, Noah tried to escape but is promptly beheaded by Jack, who slipped away and ends his killing spree.
As a result of being knocked out by a Gorgon, Dean lost concentration on his mind and Michael was able to escape his mind. After Dean woke up, he questioned where Michael was and stated that they should have sealed him away in the box before they hear screaming. The group witnessed Michael slaughter the hunters in the bunker in Rowena's body. Michael taunted Dean on not sealing him away in the box but Dean wanted to do so anyway though Michael tortured Dean and his friends. Dean was saved by Jack and witnessed him fight Michael and expel him from Rowena, before incinerating him and taking his grace to replenish his own. Dean was shocked to see Jack was normal and that he is now forever freed of Michael's influence.
During Back and to the Future, Dean and the others fight off the zombies and until they see there are too many and flee. However, Jack's body suddenly reanimates and they believe he was revived until they learn from Cass that a demon is possessing him. The demon is Belphegor, one Hell's torturers and he tells them that he wants to help them contain the souls. They reluctantly agree and put the souls to rest.
They go into town and Dean learns from Belphegor that God has opened all gates to Hell, including the Cage. Dean expressed worry at the Archangel likely coming after him and Sam for revenge but didn't seem relieved to hear Michael is sitting idle.
In Proverbs 17:3, Dean and Sam investigate a case in which a woman was attacked by werewolves. Dean comforted the woman over her friend's death and told her of the supernatural and they talk for a while. The brothers tracked the werewolves to their home and fought them but ultimately one of the werewolves shot his brother for his violent nature before turning the bullet on himself. The woman was freaked out and tripped, ending up impaled on deer antlers until she mysteriously gets up. It is revealed that it was Lilith who masqueraded as a helpless person and deceived the brothers. Lilith reveals she was resurrected from her slumber in the empty by God. She also brings up on how she put Dean to sleep to sneak away and was suppose to seduce him, while realizing that won't happen now and he confirmed it. She soon revealed God resurrected her to steal The Equalizer. Dean refused her demands and attempting to attack her with an Angel Blades, as she was impressed at his upgrade but she easily repelled him and Sam. Dean watched as Lilith threatened Sam, until making her an offer to spare his brother. While he was getting the gun ready she remarked on how she should've focused on him rather than Sam the While he was getting the gun ready she remarked on how she should've focused on him rather than Sam the first time. However, Dean's compliance was a lie and Lilith begins inflicting wounds on him, threatening to cause a death by a thousand cuts. Sam enters and shoots Lilith in the head with a devil's trap bullet, immobilizing her, but Lilith causes the ground to shake and pushes the bullet out of her head with telekinesis. Intercepting the Winchesters outside, Lilith correctly predicts that they have kept the gun in The Impala and retrieves it from the glove compartment. Sam promises that they will get the gun back, but Lilith causes it to melt and vanishes after promising to see them again.
In Our Father, Who Aren't in Heaven, Dean is the adamant about seeking out Michael's help when they learn that he might know something that can help defeat God. While God and Lucifer claimed Michael to be insane, Dean believes that they were simply lying. Dean wanted Donatello to help but God possesses the prophet and threatens their friends. Despite the threat, Dean wants to go through with it and sends Donatello home. After a long day, Donatello contacts Dean to tell Michael is on the move. Castiel was able to distract Michael and Dean and Sam appear with supernatural handcuffs. Taking the Archangel to the bunker, where Michael isn't pleased to see Dean again, angry that Dean abandoned Adam in the Cage while letting Lucifer free upon the world. Dean is then shocked to learn Michael gives Adam control and talks with his half-brother. However, Michael takes back control and refuses to turn on his father. Later on, Cass goes to speak with him and shows him the truth. Dean soon asks how Michael took it, to which Cass describes his order to leave. After Michael has an outburst, he becomes more cooperative and provides Dean and Castiel with the spell they need to trap God and the rift they need to Purgatory. Dean then releases Michael from the Supernatural Handcuffs, letting the archangel go despite his refusal to help them out anymore. On Dean's request, Michael relinquishes control to Adam so that Dean can apologize to his brother.
In The Gamblers, Dean and Sam return to the bunker, with Dean annoyed Fortuna didn't give him luck to win the lottery. He and Sam notice Cass, who is behaving oddly before they are shocked to see Jack with Castiel. After Castiel confirms that its really Jack, Sam pulls him into a hug before Dean holds him close and stares Jack in the eyes. Drinking beers, Jack explains that he wanted to return every day since his resurrection, but he couldn't as Jack can't use his powers without God knowing he's back and trying to kill Jack again. Billie kept Jack hidden in the Empty until God left the Earth at which point it was safe for Billie to resurrect him. Jack explains that eating the angel hearts is making him stronger, but he's not strong enough yet and so they must wait. If Jack follows Billie's plan, he will eventually become strong enough to kill God. This declaration shocked the Winchesters.
During Galaxy Brain, Dean and Sam are wondering what Billie's plan is to kill God.
After Billie arrives by killing Merle, Dean along with Sam confront her on Jack killing God. He is shocked to hear God has a book too, as Billie states that everything dies in the end the books write themselves rather than be written by God. To keep the world going, God had no choice but to build himself into the framework of it which is God's only weakness. Billie reassures them that not even God can read what's in his book unless she lets him. Billie reminds Dean of his time in the library and how she told him he had work. She then reveals that Jack, Sam and Dean are all in God's book and their destiny is to be the messengers of God's destruction, something that shocks them.
- ↑ Pilot
- ↑ Something Wicked
- ↑ Bad Day at Black Rock
- ↑ A Very Supernatural Christmas
- ↑ Bad Boys
- ↑ 'Bloodlust'
- ↑ Sympathy for the Devil
- ↑ There Will Be Blood
- ↑ We Need To Talk About Kevin
- ↑ The Werther Project
- ↑ We Need To Talk About Kevin
- ↑ What's Up, Tiger Mommy?
- ↑ Blood Brother
- ↑ A Little Slice of Kevin
- ↑ We Need To Talk About Kevin