Dean Winchester/Synopsis

History

Early Life

Dean holding infant Sam

Dean Winchester was born on January 24, 1979 in Lawrence, Kansas. He was the eldest child of John and Mary Winchester.

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.

Dean holding a trench gun

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.

Dean and Sam celebrating Christmas together

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." Sam: "Promise." 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.

Dean as a 16 year old.

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.

In New York, Dean, Sam and John were working on a haunting in Long Island when Dean and Sam asked John to let them go out into the city and enjoy the sights. After convincing John, they all go out, see the sights, ride on the subway, eat a lot of pizza, etc. Then one night at midnight, when Sam and John are tuckered out and sleeping, Dean snuck away from them and went to CBGB where he gets completely drunk 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." He saw people drinking, smoking, etc. Dean says he saw a "500-pound guy on stage with a mohawk just screamin'." Dean's mind was blown and was not sure of what to do. 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 drunk, 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, forever. 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 was freaked out because John was just standing there not saying anything. Even a boy with a safety pin through his nose and a "Kill Everything" tattoo says to John, "Sorry, Sir". So after getting him out of there, Dean yelled at him 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 in Bloodlust

Dean and his girlfriend

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!"	”
	— Dean 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.

Season 1

Dean asks Sam if he will hunt with him

“	I think he wants us to pick up where he left off. Saving people, hunting things, the family business.	”
	— Dean to Sam after John goes missing in Pilot

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 Skin

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?	”
	— Dean in Salvation

Dean confronts Azazel possessing John.

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.

Season 2

“	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

Dean watching over his dying body.

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

After Sam suddenly disappears, whisked away with other "special children" by Azazel to an old ghost town, Dean is desperate to find him. He learns from Ash something major is happening and visits, only to find the Roadhouse burned down and Ash dead. Andy manages to transmission an image in his head of their whereabouts and both him and Bobby immediately leave. Just as Dean arrives to rescue his younger brother, however, Sam is suddenly stabbed by Jake Talley and collapses in Dean's arms. Amidst his brother's pleas to stay with him, Sam dies, leaving Dean alone as the last living Winchester.

“	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.

Dean fires the last original Colt bullet at Azazel

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

Season 3

“	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 exorcising the demon "Lust"

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.

A possessed Dean from the future confronts himself in a nightmare

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

One of Dean's many death scenes in "Mystery Spot"

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.

Agent Henriksen and the Winchesters meet again, thanks to Bela.

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.

Dean dies by Lilith and her hellhounds

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.

Dean suffering in Hell.

Now in Hell, Dean is tortured and desperately yelled out for help, calling out to his brother Sam but receives no help.

In Hell

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.

Dean spent his last 10 years in Hell torturing other souls until Castiel pulls him out and declares that Dean is the only one who can stop Lilith from freeing Lucifer from Hell.

Season 4

“	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 in Metamorphosis

Dean climbs out of his coffin after having been mysteriously pulled out of Hell

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.

Dean gazes at Cass's holy visage

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 only to be silenced when Castiel reveals his Angel's Wings, proving his story. Though shocked, Dean berates him for what he did to Pamela, as Castiel brings up he did warn her as his true form was overwhelmming. 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.

Dean is confronted by Meg's vessel

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.

“	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

Bobby's suspicions are later confirmed by Castiel, who visits Dean in the middle of the night. He 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.

Dean meets a younger John

In In The Beginning, it takes us to 1973 where Dean learns about the Winchester 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 mother was a hunter from a long line of hunters. 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. Samuel kills John. A heartbroken Mary confirms a deal with Azazel, allowing him "permission" in 10 years. Dean arrives home shortly and realizes he can't change destiny. Castiel warns Dean of Sam's dark actions behind his back and they must stop before the angels have to kill him.

“	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, but 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, Dean introduced Sam to Castiel and met Uriel who were prepared to wipe out an entire town to stop it from happening, but 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 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 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 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 now threaten to kill Sam. Dean reluctantly gives up their location, but demons appear too and a battle between both sides take place. With them distracted, Anna takes her grace and becomes an angel again, disappearing in a white light.

Dean tells Sam what happened in Hell

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, Dean meets up again with the reaper, Tessa, who wakens his memories of their previous encounter with a kiss; Dean confesses that there has been a "hole" in him 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.

Dean interrogates Alastair on Cass's orders

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, not wanting 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 John was originally meant to break it, 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.

Dean complains to Cass

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, 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.

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.

Dean and Sam meet their half-brother

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 and Sam realize it was all true as they stare at a picture of their father and Adam together with Dean trying somewhat unsuccessfully to contain his ire when 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, Sam and Dean 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 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.

Dean and Bobby stage an intervention.

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, Dean and Bobby trick Sam and lock him in Bobby's panic room to detox him from the demon blood.

Sam detoxes from 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 and Sam witness the release of Lucifer

Dean swears his alliance to serve Christ and is then held captive by Zachariah. Dean 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. Sam as well plays a part. Dean horrified at their lack of concern for the lives of innocent people and is desperate to get free. Castiel, after much resisting, admits Lilith is the final seal and rebels to give Dean a chance to escape. Dean goes after Sam, but arrives too late. Ruby, who had been manipulating Sam all along for this moment, is later killed by Dean. 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

Season 5

“	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

Dean sent on the plane by God

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). Bobby gets possessed by a demon and instead of killing Dean he kills the demon inside himself, using Ruby's knife, in turn paralyzing himself from the waist down.

The brothers soon meet Becky Rosen, a fan of the books about them who tells them that Michael's sword is on earth. At their father's lockup, they are confronted by Zachariah and Dean is told that he is the "Sword of Michael", which means the Archangel Michael will use his body as a vessel to lead the forces of heaven, but Dean must consent to this. Dean refuses as he and Sam are tortured by Zachariah 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 were connected. 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.

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. Later, Castiel finds Dean and they capture the Archangel Raphael to ask the location of God. Dean also grows closer to Castiel, admitting he had more fun with him in 24 hours than he had with Sam in years.

In The End, Dean is transported five years in the future by Zachariah to the year 2014. He 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 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.

Despite Zachariah and Future Dean's protests, Dean still refuses to become Michael's vessel. Nonetheless shaken by his grim future, Dean calls Sam and decides they should stay together to "keep each other human".

Dean confronts The Trickster in Dr. Sexy M.D.

In the episode Changing Channels, 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" to "accept" their roles as Michael and Lucifer.

Dean angers the "trickster"

They are warned by Castiel that trickster may be something else before he banished by him but this along with his reaction to a comment Dean made causes them to realize the trickster was an angel all along. After trapping him, 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

Dean, Ellen, Jo, Bobby, Sam, and Castiel.

Sam and Dean 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.

Dean shoots Lucifer with the Colt.

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.

When Anna travels back in the year 1978 to kill John and Mary, resolving to prevent the Winchesters' birth to stop the Apocalypse and Lucifer, Sam and Dean 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.

Dean finally meets Michael.

Ultimately, Anna succeeds in landing a fatal blow on Sam, but Michael at last appears (in John's body) and burns her alive. Recognizing 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 resurrects Sam and sends the brothers back to the future. The brothers help a weaken Castiel 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, but is quickly 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.

Dean tries to save Adam

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.

Dean kills Zachariah.

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 returns to Lisa and Ben

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

Season 6

“	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?!	”
	— Dean in Exile on Main Street

Dean's normal life with Lisa

One year later, Dean is living a normal life with Lisa and Ben, having a normal job and having the Impala covered up with his weapons locked away in the garage. He seems somewhat happy, though still struggles with his grief over losing Sam. Despite retiring, he retains his old hunting habits such as keeping guns handy, hiding a Devil's Trap under Lisa's rug, and sleeping with salt and holy water under his bed. Dean's "apple pie" life is halted when he notices supernatural occurrences around his neighborhood. As he prepares to fight, he has an impossible encounter with Azazel, but it turns out to be a hallucination created by Djinns and he is snapped out of it by none other than his brother, Sam. Dean is happy to see Sam alive but is soon enraged when he learns that Sam has been out of Lucifer's cage and back on earth for over a year and didn't tell him. Dean's "normal life" was far from happy, ranging from having frequent nightmares to excessively drinking. It's revealed he tried finding ways for Sam to get out his Cage despite Sam telling him not to. Soon, he is reunited with his resurrected grandfather Samuel Campbell and other members of the Campbell Family. Dean is distrustful of Sam and Samuel both being brought back and by extension greatly distrusts the Campbells.

Dean takes Lisa and Ben to

Dean hides Lisa and Ben at Bobby's

Bobby's for safety, and discovers that Bobby knew Sam was back as well and didn't tell him. Dean and Sam use themselves as bait to lure the djinns in but Dean becomes affected again with hallucinations of Azazel killing Lisa and feeding Ben demon blood. Sam is able to snap Dean out of it as the Djinn are captured. Sam leaves after Dean decides to stay with Lisa and Ben.

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

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.

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

Dean questions Sam

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.

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.

Dean becomes a vampire

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 you, 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.

Dean takes out a vampire nest and their leader Boris

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 sneaks away

Dean spies on the Campbells

and 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.

Dean and Sam interrogate the Alpha vampire

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 brothers take the opportunity to question the creature themselves. The Alpha remembers Dean even 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 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. 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 versus a Fairy

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.

"Remember when we used to gank demons?" - Dean to Sam

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, and 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.

Dean assures Castiel that they will find a way to deal with Sam's complications

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 argues with Sam about getting his soul back

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 makes a wager with Death

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 chooses 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 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 puts Death's ring on

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 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.

Dean peeking in on a chained, unconscious Sam

Meanwhile, Sam has tied Bobby up and intends to kill him. 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 and Death discussing the natural order

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, and declares their business is finished, but he offers a bonus: he will still go to Hell to raise Sam's soul. He then encourages Dean to keep digging in what he's learning regarding the souls.

Dean looks on, troubled by Sam's screams of pain

Dean and Bobby quickly head 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.

Dean tries to wake Sam

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 is the Sheriff

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.

Dean confronts Castiel

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.

A possessed Lisa holding Ben hostage

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.

Dean tells Sam where he's going

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

Season 7

“	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

Dean fixing the Impala

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.

Dean on crutches

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.

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. 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 eventually sees through her scheme and they end up drawing their weapons and stand ready to face one another. Sam, 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. 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 in Purgatory.

Dean wakes up in shadowed plane with Castiel, now trapped in Purgatory as a side-effect of the weapon. 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.

In Purgatory

“	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

Following Castiel's mysterious disappearance, Dean survives his brush with gorilla-wolves after arriving and sets out to find his friend. Some time passes and already Dean is changed by paranoia and survival instinct. He was constantly targeted by monsters, never had sleep, and was completely on his own. At some point early on, Dean forged a personal weapon from the environment in Purgatory and used it on nearly every monster he came across. It's a implied a part of Dean even enjoyed Purgatory for it's simplicity and the "pureness" of relying on his darker, survival instincts. Dean later states "I always did like this place" while hallucinating Purgatory, showing further his enjoyment of his time there.

Dean and Benny

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 spell out of Purgatory only a human could do, but he would only give him the details if he gets him out of there too. Dean naturally distrusts him, but agrees to work with Benny if he helps him find Castiel.

Dean reunites with 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 and Benny admits he doesn't know if the spell works on angels, but 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?

Attacked by Leviathans.

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.

Dean leaves Purgatory through the portal.

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.

Season 8

“	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

After spending a year in Purgatory (it is unknown how time differs in Purgatory, so it's possible Dean was there for a significantly longer period of time), Dean uses a spell to return to Earth with help of Benny. Dean carries Benny's soul out of Purgatory and resurrects him on Earth. Dean bids goodbye to Benny and they go their separate ways. Dean travels to the safehouse in Whitefish, Montana and reunites with Sam.

Dean after a year in Purgatory.

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 in Heartache

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 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. thumb|Dean and Sam meet their grandfather Henry}} 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. Dean at first 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 dies in 2013 and the brothers bury him with his fallen Men of Letters comrades.

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 brother's 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. Castiel, under control of Naomi, proceeds to beat 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 and find out Bobby's soul is in Hell. Dean wants to help him 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 in Sacrifice

Season 9

“	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

Dean by Sam's bedside

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

Dean being tested by Cain.

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 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. Dean is 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

Dean dies in Sam's arms.

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?

Season 10

“	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

In Black, six weeks have passed since Dean became a demon. He left Sam a note telling him not to look for him and formed somewhat of a partnership with Crowley. Dean lives in excess---drinking, doing drunk karaoke, sex, and brawl fights---and resists Crowley attempts to monitor him. Dean receives a call from Cole Trenton, a man who devoted his entire life to revenge on Dean for killing a father during a hunt two years before the pilot. Cole has Sam tied up and threatens to kill him if he doesn't come. Dean callously tells him Sam isn't his responsibility anymore, but nonetheless promises to kill Cole next time he sees him.

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 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.

Dean tortures Metatron

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.

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 is 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 attacks their headquarters and coldly kills every last member of the American Styne family - including 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.

Season 11

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.

Dean being suffocated by Lucifer.

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.

Dean with Mildred.

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.

Dean and Lawless in a bar.

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 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. God ends his monologue by telling Dean not to compare him to his own father, as he knew the pain that he went through. God then steps out for the brothers to discuss a plan as he pokes fun at Dean's previous lack of faith towards him.

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 encounters Mary in the woods.

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 gives Dean a gift which Dean soon finds out is the resurrection of his mother Mary Winchester.  

Season 12

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. Castiel is unable to heal his injuries and he slowly dies. When Ramiel reaches their location, Sam, Dean and Mary work together to defeat him, with Sam eventually stabbing him with his own weapon, a lance. 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 arrives just then and decides to break the lance, which heals Castiel. 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 unborn child, 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.

Season 13

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 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 comment not yet.

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 demons 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.

Dean reunites with Missouri

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.

Dean helps James search for Patience

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.

Learning she is a shifter, Dean and Sam hold Mia at gunpoint

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.

Dean attacked by the ghost

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.

Dean and Castiel reuniting.

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.

Dean and Cass as cowboys

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.

Sam and Dean investigating Witch murders

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.

Alice and Dean in Luther's cellar.

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.

Sam and Dean find Jack

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 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 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. 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.

Dean and Sam in the Bad Place

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.

Having seen him lose his mind, Sam and Dean have Donatello restrained

During Good Intentions, Dean and Castiel go off to face some ancient warriors for their hearts.

In A Most Holy Manthe 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.

Dean and Sam in the world of Scooby Doo

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.

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 god from another world and 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. To their shock, Arthur reveals the battered Gabriel in his possession and are at loss as they believed him dead but Arthur says that wasn't the case. Seeing his state, Dean asks what Arthur did to him 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 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.