Dean is named after his maternal grandmother, Deanna Campbell. Dean has a half-brother, Adam Milligan. Dean was Heaven's only chance at stopping Lucifer and was also the true vessel for Michael, also known as "Michael's Sword."
Dean wears an amulet which Sam had originally intended to give to John, but gave Dean the necklace instead. In Season 5, it was revealed that the amulet can detect God's presence; Castiel borrows it from Dean to track God on Earth. After finding out in "Dark Side of the Moon" that God refuses to help in the fight against Lucifer, Castiel returns it to Dean, who drops it into a trash can.
In addition to the amulet, up until the fifth season episode "Changing Channels," Dean always wore a silver ring on his right ring finger. He sports a MTM-Special Ops Watch (The Black Patriot Model) and wears it in the fourth season with a Velcro band. He also has a small black tattoo on the upper left side of his chest; it is a protective plated pentagram with rays of the sun surrounding it. The symbol is said to ward off demonic possession.
|“||Don't be afraid of the dark? What, are you kidding me? Of course you should be afraid of the dark! You know what's out there!||”|
— Dean to Sam
From an early age, he was trained by his father John Winchester to hunt down and kill things of the supernatural. However, unlike his brother Sam, he shows no resentment toward his father for being "raised like a warrior." Dean feels that after his mother's violent death, his father raised him and his younger brother the only way that he knew how at the time. He seems to prefer "the hunt" to the possibility of a normal life. He is also the only one allowed to call his brother "Sammy".
Dean is a fan of classic rock music. When giving false names, he frequently gives the names of rock musicians. He also appears to be a fan of Jack Nicholson and possibly watches Oprah. He tends to make light of some of his and Sam's adventures and is known to use crude humour, make sexual innuendos and indulge in pornography. Dean frequently uses the word 'bitch' in all kinds of situations. He also has a habit of nonchalant expressions followed by a raised eyebrow or rolls his eyes when someone, usually law enforcement or a doctor, says monsters aren't real.
He has only been in love three times, once with Cassie Robinson, once with Jo Harvelle, and now with Lisa Braeden. But his relationship with Lisa ends when he asks Castiel to erase her memories of him.
Dean avoids any emotional intimacy preferring to just keep his relationship with women as that of sexual partners. He is considered very handsome and is usually successful at obtaining one-night stands; there are also some old sexual partners who he has visited multiple times. The handful of women who become his friends usually give him a hard time and keep him in line. He is devoted to the memory of his mother and to his younger brother Sam. He is also a passionate defender of humanity. Dean values his family's safety over anything else, even going so far as to kill a demon and its human host in order to save Sam's life, as well as sacrificing his very soul and suffering in hell to resuscitate his brother.
Even though Dean is excellent physical shape, Dean is known to have very bad eating habits. He is often shown enjoying greasy, fattening, or otherwise unhealthy food, especially cheeseburgers and pie. Dean is terrified of flying, and claims that it is the reason why he drives everywhere. Despite his working knowledge of the afterlife, Dean is skeptical towards believing in the "good aspects of religion," while he may believe in demons he claims angels don't exist as he only believes in what he can see. However he becomes more open minded after meeting Castiel.
(For more information click on name)
Dean's trademark black 1967 Chevrolet Impala, was passed down to him by his father. Dean protects and cares for the Impala with almost the same devotion he shows to his family and often talks to it as though it were human, (Bloodlust and Simon Said). He often calls it "Baby". When Bela tows the Impala away in Red Sky at Morning, Dean nearly has a heart attack at the loss of the Impala. In a way, the Impala is the third Winchester. Dean is also the very reason he has the Impala. In the episode "In the Beginning" Castiel sends Dean back to the past where he meets his father. His father is about to buy a Volkswagon, when Dean shows up and convinces him to buy the Impala.
WeaponsDean has been seen using a variety of weapons over the course of the series, and is very inventive while improvising weapons from his surroundings, but there are some particular armaments he seems to prefer. Dean tends to use a chromed Colt 1911 with ivory grips, which John is seen using in a flashback, and also uses a sawed-off double barrel shotgun when he needs extra firepower. He has also been seen with an G3 SG1 sniper rifle in "Simon Said" and "All Dogs Go To Heaven" . Dean is shown to possess a large machete in "Dead Man's Blood", and has used a knife in several episodes. He is shown to possess a Desert Eagle loaded with wrought iron in the episode "Something Wicked" and tasers which he and Sam used in the start of "Faith", when he electrocuted himself. Also, bolth Dean and Sam have aquired angel killing Knives in (presumbly from castiel).When weapons are scarce and Dean is in a dangerous situation, he uses hand-to-hand combat or whatever is available as a weapon. During "On the Head of a Pin", Dean is shown with a number of torture implements, including syringes of holy water. The trunk of the Chevy Impala contains numerous weapons which are implied as having been needed in the past, notable examples sheath knives and an DefTech 37mm grenade launcher.
Skills and Abilities
Dean possesses excellent combat and hunting prowess; comprehensively trained by his father from early childhood as a paranormal investigator and hunter of the supernatural, he is established throughout the series as an extremely dangerous individual, and he is more than capable of taking a stand against even the most formidable of opponents, such as demons and vampires. Dean is adept with martial arts and knife fighting as well; he has subdued several human assailants with ease in multiple episodes and bested physically more powerful creatures, often unarmed or equipped with only a blade.
Dean is well-versed with multiple types of firearms; he prefers his Colt 1911 and sawed-off shotgun, but is proficient with most other weapons he might acquire. An expert marksman, he seldom misses his intended target and can efficiently put down anything vulnerable to bullets.
Dean is also a proficient tracker and possesses prudent tactical skills. Highly resourceful, he frequently utilizes improvised weapons and explosive devices; in "Croatoan," he demonstrated in constructing Molotov cocktails and improvised explosive devices.
Dean also possesses extensive knowledge of the supernatural and mythology. He is versed with how police, fire departments and various government agencies (FBI, CDC) typically operate and conduct investigations, and knows how to both impersonate and evade them effectively. An accomplished mechanic, he maintains his Impala in tip top condition and has maintained an intimate knowledge of automobiles and engines since childhood.
Dean is a virtuoso of escape, evasion and silent movement, when the situation requires subtlety and stealth. Lastly, he is also alarmingly skillful in many areas frowned upon by the law: lock picking, breaking into security systems (not so much computers, which often falls to Sam), car jacking and gaining an 'advantageous purchase' comes naturally to him.
Due to his time spent in Hell as Alistair's "student", Dean has an in-depth knowledge of torture, able to inflict the maximum amount of pain and agony on a victim while keeping them alive as long as possible. In the season 5 premiere, Dean revealed he had learned the banishing spell from Castiel that sends angels back to heaven.
In Live Free or Twihard, Dean was turned into a vampire and possessed all their basic abilities, notably enhanced hearing and superhuman strength, as well as could also smell vampires from miles away. However, when Dean took the cure that reversed the transformation, his enhanced abilities were lost and back to normal human status.
Dean is born in January, 24 1979 prior to Mary's death, Dean played T-Ball. Mary Winchester is killed by Azazel when she interrupts him feeding demon blood to Sam. John hands the infant Sam to Dean as the nursery burns and tells him to "Take your brother outside as fast as you can! Don’t look back! Now Dean, go!" John leaves Lawrence with Dean and Sam before Dean's fifth birthday (see The Journal (diary entries)). In 1985-86 (approx) When Dean is "6 or 7", John takes Dean out shooting for the first time, using bottles as target practice. According to Dean, he "bullseyed every one of them." (Story told by Dean to Jo in 2.06 No Exit.) Dean cites this story as one of the fonder memories of his father.
In 1.18 Something Wicked Dean recounts to Sam of an occasion when John is hunting a Shtriga in Wisconsin and leaves Sam and Dean alone in a hotel room. Dean gets bored and goes out, and comes back to find the Shtriga attacking Sammy. John returns in time to scare the Shtriga off. Dean is haunted by his failure to defend his brother. In 1991 When Dean is in sixth grade he makes his first sawed-off shotgun.
Events told in flashback scenes in 3.08 A Very Supernatural Christmas. Dean is left to babysit Sam (8 years old) while John is on a hunt, and Sam begins to interrogate Dean about what it is that their dad actually does. Dean responds "You know that. He sells stuff." When Sam moves on to asking about their mother, Dean gets angry and yells "Shut up! Don't you ever talk about mom! Ever!" before storming out. Upon his return, Sam reveals to Dean that he found and read their dad's journal, and demands to know if monsters are real. Dean finally resigns himself to telling Sam the truth.
"Dean: I swear, if you ever tell dad I told you any of this, I will end you.
Dean: First thing you have to know is...we have the coolest dad in the world. He's a superhero.
Sam: He is?
Dean: Yeah. Monsters are real. Dad fights 'em. He's fighting them right now.
It is hinted at that Dean still believes that his father is a "superhero" at this point, and continually excuses his flaws, while the tension between Sam and John is clearly starting to take root. Disappointed with John's lying and absence, Sam gives Dean the present intended for his father: the amulet.
Dean: ... So, I picked up this crossbow, and I hit that ugly sucker with a silver-tipped arrow, right in his heart. Sammy's waiting in the car and, uh, me and my Dad take the thing into the woods, burn it to a crisp. I'm sitting there and I'm looking into the fire, I'm thinking to myself... I'm sixteen years old. Kids my age are worried about pimples, prom dates... I'm seeing things they'll never even know. Never even dream of. So right then I just sort of...
Gordon: Embraced the life?
In summer 1997 John, Dean and Sam are hunting a werewolf. After School Special. In November 1997, John "parks" the kids in a small town in Iowa, where they attend Truman High School. While Sam is having trouble with a bully called Dirk, Dean gets a girlfriend, Amanda, although he becomes uncomfortable when she wants him to meet her parents. When she catches him cheating on her with another girl, she challenges him, charging that his 'cool' persona is a cover for his loneliness.
In 1998 or 1999, Dean is 19 or 20 years. In The Kids Are Alright, Dean says it has been "8 years ago", then edits himself to say it has been "8, almost 9 years". The episode is based in 2007, therefore, depending on when "8, almost 9 years" ago was precisely, he was either 19 or 20 at the time. Dean goes on a road trip that was supposed to be "5 states, 5 days" while Sam (15 or 16) was "in Orlando with dad, wrapping up that banshee thing". However, Dean reveals in 3.02 The Kids Are Alright that he spent most of his time in Lisa Braeden's loft. "She was a yoga teacher. It was the bendiest weekend of my life."
Sometime between 2001-2005. Sam leaves for Stanford. While there he becomes estranged from Dean and his father, and doesn't speak to them for at least a couple of years. During this time, as Dean tells Sam in 1.13 Route 666, he met Cassie Robinson while he and John were in Athens, Ohio for a hunt. She was "finishing up college" (she was therefore approximately 21 or 22) and they "went out for a couple of weeks". Dean was in love with Cassie, who was the first person he'd ever seriously dated (as Sam says "for more than one night") and the first person he'd ever felt that way about. When he found out he was leaving, he told Cassie the 'big family secret' about hunting because, as Dean says in the episode, he "just couldn't lie to [her]". Cassie, however, called him 'nuts' and dumped him. This, as Dean also revealed in the episode, really hurt him, and he decided at that point that it was "stupid to get so close" and that he didn't need to open up to anyone. It is likely that it was around 2003 or 2004, during the "almost two years" that Dean did not speak to Sam, because Sam claimed that Dean hadn't told him anything about it. That means Dean was approximately 24 or 25.
In October 2005 Dean is 26 years. In Pilot, Sam asks Dean why he didn't go with John when he left to check out the hunt in Jericho. Dean explains that before he showed up in Palo Alto to get Sam from Stanford, Dean was "working [his] own gig ... this, uh, voodoo thing down in New Orleans".
Sam asks, "Dad let you go on a hunting trip by yourself?" to which Dean replies, "I'm twenty-six, dude." This implies that before Sam left for college when Dean was 23 (see again Canon Discrepancies: How long did Sam spend at Stanford?), Dean had not gone on a hunting trip by himself. Considering the two men had not spoken in "almost two years", as Dean points out in 1.01 Pilot, it could mean that Dean hadn't hunted alone until he was 24 or 25.
|“||I swore I was done hunting for good. Come on, it wasn't easy, but it wasn't that bad. Yeah? When I told Dad I was scared of the thing in my closet, he gave me a .45. Well, what was he supposed to do? I was nine years old. He was supposed to say, "Don't be afraid of the dark." Don't be afraid of the dark? What, are you kidding me? Of course you should be afraid of the dark! You know what's out there!||”|
— Sam and Dean
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.
|“||You know I gotta say... I'm sorry I'm gonna miss it. Miss what? How many chances am I gonna have to see my own funeral?||”|
— Dean and Sam
In Home, Dean first becomes aware of Sam's psychic abilities, when he has a vision of trouble at their old home in Lawrence, Kansas. In Asylum while influenced by the spirit of Dr Ellicott, Sam tries to shoot Dean in a spirit indused 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, who insists he and John are both selfish because all they care about is revenge then later who 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, an accident while hunting leaves Dean with a fatal heart condition when he is electrocuted, but he is saved by a faith healer 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, Dean confesses to Sam anounces he will return to Stanford afther Azazel is kill to which Dean says he wishes Sam would stay with him and keep hunting, even if they kill the demon that killed their mom, and Jess.
|“||Don't say just in case something happens to you, I don't want to hear that freaking speech, man. Nobody's dying tonight, not us, not that family, nobody. Except that demon. That evil son of a bitch ain't getting any older than tonight, understand me?||”|
In the last episode of this season "The Yellow-Eyed Demon" possessed 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 his children back to hell, after Dean makes a sarcastic remark about the situation, the demon tortures him, Dean pleads for his father's help before losing consciousness. Sam manages to get free and shoots the demon/John in the leg, releasing the demon from John's body.
The season finale concluded with Sam, Dean, and John escaping from a clash with The Yellow-Eyed Demon in Salvation, Iowa. While Sam was driving to a hospital after Dean and John were injured, a demonically possessed driver drove his truck into the Impala, causing massive damage to the car and the Winchesters inside.
|“||Come on, Dad. You've got to help me. I've got to get better, I've got to get back in there. You haven't called a soul for help, you haven't even tried. Aren't you going to do anything, aren't you even going to say anything?! I've done everything you've ever asked me, everything. I've given everything I've ever had. Now you're just going to sit there and watch me die? What the hell kind of father are you?!||”|
in In My Time Of Dying
All three of the Winchesters survive the wreck, although Dean is 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 die. In order to save him, John makes a deal with The Yellow-Eyed Demon, trading his life for Dean's. Before he dies, John whispers something in Dean's ear, which shocks him.
Throughout the first half of the second season, Dean struggles with the death of his father, as well as with the knowledge that he was the one who was supposed to have died. Furthermore, he is haunted by his father's last words to him, and at the midpoint of the season, it is revealed that John told Dean that The Demon intends to turn Sam evil, and if Dean can not save Sam, Dean must kill his brother.
|“||My name is Dean Winchester. I am an Aquarius. I enjoy sunsets, long walks on the beach, and frisky women. And I did not kill anyone.||”|
— Dean giving his cofession to the police
in The Usual Suspects
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 over the years 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. A team of FBI agents, led by Special Agent Victor Henricksen catches up with Dean and Sam in Milwaukee, WI ("Nightshifter"), where attempted bank robbery and several more murders are added to Dean's list of supposed crimes.
|“||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
|“||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? [screams] What am I supposed to do?||”|
— Dean to Sam
in All Hell Breaks Loose - Part 2
However, the The Yellow-Eyed Demon questions Dean if he is sure what he brought back in Sam is "pure" after Sam unhesitatingly kills Jake, unloading several bullets into his head without any sign of remorse. Sam figures out what Dean did by the end, and Dean tells him not to be mad, that he couldn't let Sam die, not like that. Sam vows to get him out of this, no matter what. At the end of the second season Dean kills The Yellow-Eyed Demon with the Colt freeing his father's soul but during the battle hundreds of other demons escaped their prison and now Dean and Sam must kill all of them, as well as find a way to save Dean from dying in a year's 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 we raise a little hell, huh?||”|
— Dean to Sam
in The Magnificent Seven
In the third season premiere "The Magnificent Seven," Dean decides to make the best of his final year, indulging in many pleasures and refusing to even think about saving himself, while Sam tries desperately to find a loophole in the Crossroads demon's deal. While searching for escaped demons to send back to Hell, Sam encounters Ruby, a mysterious blonde who assists him but who also informs him that, for some reason, demons are killing all of his mother's old acquaintances. Sam learns that Ruby is a demon, and she promises him help in freeing Dean from his contract. She "fixes" the Colt so that it can again kill "anything" and also shows them a knife in her possession that can kill anything. Later, Dean and Sam learn from Ruby that all demons used to be human, but had their humanity burned away slowly in the fires of Hell. Dean begins to train Sam to fight demons alone once he is gone.
During the course of the season, the brothers meet up with another beautiful woman, Bela Talbot, numerous times. Bela acquires magical objects and sells them for a large profit, and is unscrupulous and seemingly amoral. In "Dream a Little Dream of Me," when Bobby falls into a coma, Sam and Dean investigate the murder of a scientist. In the course of viewing Dean's dreams, it becomes clear that Dean believes that Sam was their father's favorite, but only thought of Dean as a tool. Dean encounters a future, demonic version of himself in a nightmare, which shocks him into starting to fight for his life and to realize he is not worthless. 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 to fight with when the hellhounds come for Dean.
In "Mystery Spot," Sam is forced to relive the same day, a Tuesday, repeatedly. On each new day, Dean dies a different way despite Sam's frantic efforts to save him. Sam realizes 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. He is warned by Ruby that he might not make it back from hell.
In "Jus In Bello," the FBI and Agent Henricksen 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. 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 continues to search for a means to save himself from his fate, but ultimately is told by Ruby that there is no way to get him out of his deal. 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, and she has been taken 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, stills desperately tries to free himself. He uses his last resource, Ruby, and takes 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 hiding, the three quickly manage to locate her. However, Dean discovers that Lilith has switched bodies as Sam is about to kill the little girl. As the clock strikes midnight, Dean smiles and tells Sam to be brave and to continue what he's doing. The brothers and Ruby run from the hellhounds and placed a salt barrier to protect themselves. However, Dean realizes Lilith is in Ruby. 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 Lilith to stop. As Lilith leaves an unconscious Ruby, Sam holds the dying Dean in his hands, frantically yelling out to him. Now in "Hell", Dean is desperately yelling for help, calling out for Sam.
In HellDean was in hell for 40 years because in hell time goes faster. He was tortured by the demon [[Alastair|Alastair]] who, every day, gave Deant the chance to torture other souls but every day he said no to Alastair, until one day after 30 years when he said yes to to the offer and triggerd the first seal to Lucifer's Cage. For the last 10 years in hell, Dean tortured souls until the Angel Castiel pulled Dean out because he was the only one that could stop Lilith from freeing Lucifer from Hell.
|“||Who are you? Castiel. Yeah, I figured that much, I mean what are you? I'm an Angel of the Lord. Get the hell out of here. There's no such thing. This is your problem, Dean. You have no faith.||”|
— Dean and Castiel
in Lazarus Rising
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 sees the television and radio flicker on, with static, and a powerful whine that shatters all of the glass and hurts Dean's ears. Dean calls Sam, but finds his number disconnected. He calls Bobby, who hangs up on him, so 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. Dean and Bobby track down Sam in a town right near where Dean was buried—he's in a hotel with a girl, but he claims he did nothing to bring Dean back and is in town because he is searching for a demon. The girl acts puzzled by all of this and leaves, while Dean tells Sam he remembers nothing from Hell.
The Winchesters track down whatever force ripped Dean from Hell. By the end of the episode, it is revealed that an angel named Castiel pulled Dean from Hell on God's command; Castiel tells Dean that God has work for him. The girl in Sam's room, it turns out, is Ruby in a new body, and Sam had lied to Dean when he told him that he didn't know where Ruby was and that he wasn't using his demonic powers. Dean, in turn, was lying to Sam about Hell; in the episode "Wishful Thinking," Dean confesses that he does remember every second of Hell.
In "Are You There God? It's Me, Dean Winchester", Dean is haunted by the spirits of Meg Masters, Henricksen and Ronald Reznick, wanting to kill Dean for not saving them. Dean, with guidance from Bobby, ultimately puts their souls to rest.
Later, as Dean is asleep, Castiel, the angel that rescued Dean, re-appears and tells him that they must stop Lilith from opening all 66 Seals. If they fail, Lucifer will bring the end to the world. Dean believes that Lucifer is a fairy tale told in "Demon Sunday School". But Castiel objects and tells him that Lucifer is all too real.
|“||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 The Beginning", takes us to 1973 where Dean learns about the Winchester history. He meets his parents, John and Mary Winchester before he is even 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. 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 tempted, heartbroken Mary confirms a deal with Azazel, allowing him "permission" in 10 years. Dean arrives shortly and realizes he can't change destiny.
In "Heaven and Hell," Dean 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 put on the rack and "cut, carved, and torn" apart until there was nothing left of him, only to be made whole again just so the demons could start over on him. Dean reveals that, at the end of every day, the demon Alastair would offer to take him off the rack if Dean would put souls on it and torture them. Dean resisted for thirty years, 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.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 leave their bodies 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." Pamela also 'saw' what Sam did to the Demons that tried to kill her. This worried Sam because Pamela became blind whilst trying to catch a glimpse of Castiel in his true form when they were looking for who pulled Dean out of Hell.
|“||That’s another question why would you fall? Why would you want to become one of us? You don’t mean that. I don’t? I mean a bunch of miserable bastards; eating crapping confused afraid- There’s loyalty forgiveness love- Pain- Chocolate cake- Guilt- Sex. Yeah you got me there.||”|
— Dean and Anna Milton about being human
in Heaven and Hell
Dean, along with Sam and Ruby, defend Anna Milton from Castiel, Uriel and Alastair as both Heaven and Hell want Anna for their own personal gain. Anna takes her grace from Uriel and, for the moment, vanquishes the angels and Alastair, who at that time, was supposedly dead.
Both Dean and Sam overcome new obstacles such as fighting an abandoned girl in Family Remains, defeating a tricky Magician in "Criss Angel is a Douche Bag", facing his past in "After School Special" and killing a seductive siren in "Sex and Violence"
Dean realizes that everyone is cheating death in a small town and finds out that the demons are kidnapping Reapers to open another seal. Dean and Sam ask Pamela for help and she brings them into the Spirit World, where they find Alastair as the mastermind of the plan. Dean also teams-up with Tessa and learns how ghosts interact with the living world.
|“||[singing:] Heaven. I’m in heaven. And my heart beats so that I can hardly speak. And I seem to find the happiness I seek when we’re out together and dancing cheek to cheek. [laughing] I’m sorry. This is a very serious, very emotional situation for you. I shouldn’t laugh, it’s just that, I mean, are they serious? They sent you to torture me? You’ve got one chance. One. Tell me who’s killing the angels. I want a name.||”|
— Alastair and Dean
in On the Head of a Pin
In the next episode "On the Head of a Pin," Dean is pressed into service by Castiel and Uriel, who need him to torture Alastair for information on who is killing angels, since Dean was his "student" in Hell. Dean refuses at first, but eventually agrees. However, he only 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.")
The distraction is enough for Alastair 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, but 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 afte . 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 up to such a task and tells Castiel to find someone else as tears run down his face.
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. 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 renews Dean's resolve.
In the episode "The Monster at the End of This Book," it is revealed that Dean is aware that Sam used his demonic powers to kill Alastair, but neither Castiel nor Dean know how Sam is getting stronger. In "The Rapture," Dean witnesses Sam drink the blood of a demon he is about to kill. Later, in the Impala, Sam tells Dean to get it over and yell at him for drinking demon blood when Sam gets a request from Bobby to head to his house. Once there, Dean and Bobby trick Sam and lock him in the demon-proof panic room for his own safety as he detoxes from the demon blood.
While Sam is going through painful withdrawal symptoms from the demon blood, Dean asks Castiel for help. He takes an oath to serve God and the angels if it would mean that Sam wouldn't have to kill Lilith, to which Castiel says "If that gives you comfort." 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. Dean yells at Sam by saying, "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, resulting in Sam's four-year estrangement from his father -- after which Sam leaves the room.
|“||It's the Archangel! I'll hold them off; I'll hold them all off! Just stop Sam!||”|
— Castiel to Dean
in Lucifer Rising
Towards the end of the season, Dean and Sam have a strong confrontation which leads into a seperation. Dean telling him never to return. He swears his alliance to serve Christ and is then held captured as Zachariah prevents him from stopping the Apocalypse. After being freed by Castiel, he finds Sam, only to realize he's too late. Before killing Ruby, who had been manipulating the brothers all along, Sam kills Lilith, and in doing so, brought on the Apocalypse.
|“||I'm not sure if he's my brother any more. If he ever was.||”|
— Dean to Bobby Singer
in Lucifer Rising
The fifth season begins right where season 4 ends with the portal opening. As Lucifer escapes, the brothers are teleported into an airplane by an unknown force (Later revealed to be God). Dean is told by Zachariah 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 and Castiel saves him when Zachariah tries to force Dean to agree by harming him and Sam. Bobby gets possessed by a demon and instead of killing Dean he kills the demon inside himself, using Rubys knife, in turn paralyzing himself from the waist down.
Dean and Sam fight the Horseman War in a town where the people think that their neighbors are demons. In this town is Ellen, Jo, and Rufus all trying to hunt the demons, who turn out to be just people that War has made eyes seem black. 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, and the brothers agree to go their separate ways because Sam is a liability with his demon blood lust. Castiel finds Dean and they capture the Archangel Raphael to ask the location of God.
|“||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 with your family. Don’t say I never did anything for you.||”|
— Dean to Gabriel
in Changing Channels
In the fourth episode of the season, Dean is transported forward in time, this time by Zachariah to see what the future will be like. He finds himself in 2014, eventually meeting up with his future self, as well as the survivors and victims of the Croatoan Virus from season 2. Dean finds out that Sam let Lucifer into his body, and this was the reason the world was in such disarray. Later, the future Dean is killed by Lucifer, while in Sam's body. After being told by his future self to accept Michael into his body, Dean is transported back to his own time, where he comes face to face with Zachariah. He refuses to become Michael's vessel. In the end of the episode, the brothers meet back up again, and decide that they should stay together, to "Keep each other human." In the episode Changing Channels, it is revealed to Dean and Sam by the Gabriel (who reveals that he is the Archangel Gabriel) that their relationship (Dean, the older brother loyal to an absent father, and Sam the younger brother, rebellious to the father's plan) mirrors the relationship between Lucifer and Michael, and has been told to the angels since the beginning to bring about Judgment Day.
|“||Oh, uh, excuse me for asking, but aren't you kind of signing your own death warrant? I mean, what happens to you if we go up against the devil and lose? Number one, he's going to wipe us all out anyway. Two, after you leave here, I go on an extended vacation to all points nowhere. And three, how about you don't miss, okay! Morons!||”|
The tenth episode of the season shows Sam and Deans plans to find Lucifer and kill him, with help from Castiel, Jo, Ellen, and Bobby. They find out that the Colt is in the possession of a demon named "Crowley," who gives the Winchesters the gun to kill Lucifer and end the Apocalypse. 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. 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, in turn Ellen stays with Jo and both die in the blast. The Winchesters then find out that Lucifer is one of the five things in the universe that the colt cannot kill by using it on him, with no effect. Having lost another plan, Dean becomes more disillusioned and hopeless, and with his experience in Heaven during "Dark Side of the Moon" where after spending time in heaven and finding out God doesn't see the battle with Lucifer to be his problem, he begins to see little reason to deny his destiny as Michael's vessel, deciding to take on the role at the end of the next episode.
|“||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
To use a plan to get Lucifer back in the cage provided by the fallen archangel Gabriel, they reluctant need Sam to become the vessel so he can jump back in the cage with Lucifer. Dean is against this but knows it has to be done. Sam makes him promise to return to Lisa and Ben to live a normal life once this is all over and he promises to do just that once this all plays out. Once Sam says "yes" to Lucifer, he loses control and closes the portal, then takes his leave to fight his older brother, Michael, who is possessing Adam.
Dean is about to lose hope until Castiel and Bobby help pull back together and he goes to the battlefield and interrupts the destined battle between Lucifer and Michael. Michael is enraged that Dean interrupted their battle as he is no longer a part of the story and then Castiel takes him out to give Dean enough time to talk to Sam. Then Lucifer kills Castiel and Bobby as he continues to beat Dean into a bloody pulp until he is able to reach towards Sam and then he opens Lucifer's cage but is stopped by Michael from jumping in. But then Sam pulls him in with him and they both fall into the pit.
|“||Al I got is my brother in a hole!||”|
— Dean to Castiel
in Swan Song
Season 6One 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 is truly happy until he notices supernatural occurrences around his neighborhood and in the garage when he was getting ready to fight, he has an impossible encounter with Azazel, the Yellow Eyed Demon, but it turns out to be a hallucination created by Djinns and is snapped out of it by none other than Sam, his brother. They are filled with joy to see each other again but Dean is soon enraged when he figures out that Sam has been back this entire time and didn't tell him. Soon, he is reunited with his thought deceased Grandfather Samuel Campbell and other members of his family from his mother's side who were all thought to be dead. They teamed up to take down the dijinns who went after Lisa and Ben so Dean took them to Bobby's who was enraged even more when he found out that Bobby knew Sam was back as well and didn't tell him. Then Dean and Sam used themselves as bait to lure the dijinns in and Dean was affected again with hallucinations of Azazel killing Lisa similar to how his mother died and feeding Ben demon blood, but eventually snapped out of it by Sam. Sam leaves after Dean decides to stay with Lisa and Ben.
Dean relocates Lisa and Ben to a different home and starts to take on traits of his father that were similar in his childhood. He is called back to hunting by Sam as shapeshifters were murdering parents and taking the babies from them and Sam needs help to take care of an abandoned baby from a crime scene and soon find out that the baby is the shifter's boy and killing the parents in order to recollect.
They take the baby to Samuel after a shape shifter attacked them at the store and motel, and Dean is distrustful of the Campbells and has a rocky start with his cousins. Samuel wants to raise the baby as a hunter, which enrages, Dean but before they can discuss it any further, the Alpha Shifter arrived and killed one of the cousins, also taking down the rest of the Campbells, then the Alpha defeated Sam and Dean and took the baby.
Dean is conflicted with either leaving and go hunting with Sam, or stay with Lisa and leave that life behind for good. Then Lisa suggests a compromise, he can go hunting and come back whenever he can. He agrees and gets the Impala out of the garage and gets back on the road with a smile on his face.
Dean has some guilt of leaving as he has erotic dreams about Lisa and is called to a case by Sam to investigate the mysterious deaths of cops and decide to call for Castiel, but Sam doesn't believe he'll come. To his surprise, he did show and tells them that the staff of Moses is responsible for the deaths and an angel stole the item along with others from heaven and that heaven was in civil war as Raphael is trying to take over and resume the Apocalypse that they prevented last season.They find the child responsible and discover that he sold his soul to an angel for the staff as he wanted revenge for the cops did to his older brother. Castiel soul probes child against Dean's wishes but strangely Sam is fine with this. The angel Balthazar was responsible and they track them down, with Dean and Sam staying behind and fighting Raphael's angel henchmen. They help trap Balthazar after Raphael is gone and forces him to relinquish the child's soul and give back the stolen items of heaven, which gets him released by Castiel and both angels vanish without saying a word.
Sam joins Dean again as his car was destroyed when Castiel destroyed it by landing on it, as Dean questions Sam's strange behavior and his time in hell, but Sam doesn't want to talk about it at all.
Later, they help Bobby claim his soul back as Crowley turned his back on him and they travel to Scotland and used his bones as bargaining chips to get his soul back. Crowley agreed as the burning of demon bones can kill them and returns Bobby's soul with him collecting the bones from Dean and Sam.Things seem to be going well for Dean until a case of missing girls comes to the brothers. Sam and Dean investigate what appears to be a vampire attack, and Dean becomes entangled with the vampire Boris and he attacks Dean. Sam walks by, but merely watches as Boris turns Dean into a vampire. Once Sam interferes, the deed has been done. Dean is now a vampire. Dean asks Sam why he 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, which turns out to be, as Dean says, a lousy decision. Dean tries to tell Lisa what has happened, but struggles with his words due to his bloodlust for Lisa. He comes close to biting (or killing) her, but retreats into the hallway. Ben enters the hallway, and Dean warns Ben to stay back. Ben approaches, but Dean shoves him to the wall. He then leaves back 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 it. As long as Dean doesn't feed, then the cure can turn him back. All he needs is the blood of the vampire who turned him. Dean infiltrates the nest, and encounters Boris, who explains to him the vampires' aim. When Boris smells the dead man's blood drop from Dean's syringe, he attacks. Before the vampire can make his move, all the vampires in the nest collapse, including Dean. He has a vision of the Alpha vampire.When he awakens, Boris is rallying the coven of the vampire to attack Dean. Dean, however, has the upper hand and takes out the entire nest single-handedly, including Boris. Back at the motel, Dean drinks the cure, and goes through a painful process of turning back. His short time as a vampire flashes before him, highlighting Sam's hesitation. Dean now has lost trust in his brother completely.
Dean becomes so uncomfortable around Sam, it gets to the point where Dean makes excuses to stay away from him. He informs Bobby of the situation, and digs up on information on whatever could possibly be Sam's diagnosis. He then asks aloud for the truth, and is infected with a truth curse where people tell truths to him against their will. Sam, however, proves to be nulled towards this, as the curse doesn't affect him. He lies to Dean at first, but then comes clean after Dean pulls a knife on his brother. Dean processes the truth about Sam, and responds with beating Sam unconscious.
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, and Dean expresses to Sam that he doesn't trust Samuel, much to Sam's surprise.Dean is left with Gwen to stand guard while Sam joins the other Campbells on the hunt. Dean sneaks away 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. Sam and Dean follow Samuel via his cell phone's GPS to a warehouse where they have 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 in truth, he doesn't really care about it, but he's 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 is also 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 works the cases anyway, as he sees no other option. Dean is still not convinced that Sam is his brother, and later admits that he doesn't know what he is. When Sam comes clean to Dean that he thinks it's best to go back to being the old Sam, Dean accepts his offer, and says it's 'time to get his brother back.'
Dean and Sam are more on the same page now, but Dean still seems to struggle with Sam's behavior and then starts to act as his 'Jiminy Cricket' to Sam's 'Pinocchio'. They investigate a case of crop circle abductions, leading people to believe it is a UFO sighting. Dean decides to check out the crop circles for himself, but gets abducted.
He returns a while later, and walks in on Sam having sex with a hippie chick. Dean expresses irritation at this, and states that he 'had a close encounter, and won it'. However, it's proven that he didn't exactly 'win' anything, as he starts seeing things that no one else can see. There's one moment when Dean's alone, and the door to the motel bursts open and a "little, glowing, hot, naked lady" flies in and starts hitting him. He traps her in the microwave and cooks her, but when he tries to show Sam her remains, Sam can't see them. Sam then draws the conclusion that the UFO encounters are because of Fairies.
Dean and Sam go to visit Marion, a woman they interviewed earlier who had said that fairies were behind the disappearances. She tells them all about fairies, including that they like cream and that they must count every grain of salt or sugar that is spilled in front of them. After they leave, they see Mr. Brennan loading boxes of cream into his car. Dean breaks into his shop and sees elves working on watches for him. Afterwards, Dean is being stalked by a fairy, a Red Cap in particular, and he mistakenly tackles a midget and is arrested for a hate crime. While in jail, Dean was being beaten by the Red Cap in his jail cell, but is saved by Sam in time and is released from jail the next morning. The midget, who was also the district attorney for Tipton county, dropped the charges against him. Dean learns that the leprechaun struck terms of making a deal with Sam, to lift his soul from the cage (and make him a 'real boy'). He questions Sam's way of thinking, and wonders if Sam is having second thoughts.Dean quickly becomes tired of working for Crowley, as he sees that it's not getting them anywhere. He tries to reason with Sam that Crowley may not keep his end, but Sam has left the room. When Dean slowly walks the motel room looking for Sam, he gets knocked out by demons, led by none other than Meg. Dean responds emotionally, saying he's been dying to see her again to get back at her for being responsible of Ellen and Jo's deaths. Meg seemingly approves of this, but not before demanding where their "boss" is. While neither of the brothers answer, she puts a knife to Dean's neck, getting impatient. Sam, however, merely laughs at her, and reassures Dean that she can't kill them because she needs them to get her to Crowley so she could kill him. Dean says he hopes they both lose. Sam suggests that she works with them and makes a deal with her, to 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 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, to which he refuses to tell them. When all his attempts lead to nothing, Dean then 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 (unsettled by Castiel watching porn) to give them the location, despite his wishing for them not to go there.Before they leave for the prison, Castiel talks to Dean about how he doesn't think retrieving Sam's soul is wise. He believes that Sam will be broken beyond repair if they force his "mutilated" soul back in. Dean doesn't want to believe this, and reassures Castiel (and by extension, himself) 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 gonna make it out of 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 demons. Dean fights back, but to no avail. Sam later busts in and kills the demons.
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. When Castiel intervenes, he asks again if he can restore Sam's soul. Crowley repeats that he can't, and Castiel burns his bones to ash.Later, outside the prison, Dean thanks Castiel for his help. Castiel expresses his failures in 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. When Castiel leaves, Dean then assures Sam that they will figure something else out to get his soul back, to which Sam claims they won't (and shouldn't). Dean tries to reason with Sam, saying that he doesn't know how wrong, how messed up he is without a soul. Sam disagrees and walks away without a word. He doesn't even respond to Dean's calling. Dean, now more desperate than ever for Sam's soul, seeks out the pale horseman Death to ask for his help. Dean requests not only for Sam's soul, but for their half-brother Adam as well (Death however forces Dean to pick one, in which he chooses Sam). 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 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, as Tessa states, knocks over a domino. 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, but finally decides to kill the girl.Meanwhile, Sam's going to the limit trying to survive as a soulless being, and is getting ready to sacrifice Bobby for a spell, before Dean intervenes. He 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 life-long promise of saving his brother: this replicant of Sam could not stay alive; he's dangerous, he's cold, and he's capable of anything. Dean leaves the basement to let his defeat sink in, when he is approached by Death, who invites him to join him for a little treat. Dean gives back the horseman's ring, and claims his loss of their wager. Death, however, finds himself amused by Dean getting a hard look behind the curtain about the natural order, even stating that his brother Sam and himself keep coming back, and cause a disruption on a global scale.
Dean then assumes 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 (possibly referring to the search for Purgatory).Dean then demands Bobby to open the door to the panic room, as they witness Sam struggling to stay away from Death, who has returned with Sam's soul. Despite Sam's pleas, Death restores Sam's soul in his body, with a conflicted Dean watching as his brother screams in agony. A week passes and Sam has still not woken up. During this time, Dean calls Castiel to check on Sam and asks if Cas 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 doesn't remember anything other than jumping in the hole. Dean is surprised at glad at this information, despite Bobby's suspicion. So he and Sam go and go work a case involving dragons, which makes Dean happy to work with soulful Sam.
When Bobby finds a sword that could kill the dragons, so Dean goes to visit Dr. Visyak. When Dean tries to pull the sword from the stone he falls off and resorts to blowing it up instead. He returns to Sam and the two go after the dragons. There they fight off the dragons and save the girls they held captive. Later on as Dean is happily going thought the pile of gold they found at the dragon lair, Sam confronts him about him being soulless and apologizes to Dean. Dean is shocked that Sam knows and asks who told Sam (who answers Castiel). Dean tells Sam about the wall inside his head, and that what Sam did wasn't him. Sam disagrees and wants to fix it. Dean is about to disagree, but Sam argues that Dean would do the same thing. Then Bobby arrives and tells them about the Mother of All.
Then Sam gets a mysterious text 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. But Sam doesn't want to, which gets Dean angry and 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 a Arachne with a grudge against Sam, and defeat it. After 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.Couple of minutes pass by, and Sam is still out. Dean is very scared for his brother, and 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 maniquin 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 permanetly. When he comes back, he helps Sam finish the case.
Then things a turn for the werid when 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. But they do get back, and Castiel tells them he has Balthazar's weapons now. 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 confirms this and shoots her. It turns out, Dean was possessed by Eve's latest invention. So they spilit up, and in the end, its Sam who kills Samuel. Unsure who its possessing, they rid of their weapons. In a turn of events, its Bobby who is possessed by the Khan worm, and Dean questions and kills it (despite Bobby's life in danger). Bobby does survive.Things take a turn for the werid 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. At a scene of a murder Sam, notices a girl, and they go investigate, only to be saved by Castiel from thier looming death. He tells them, its Fate, and she trying to kill them. The only way to survive is to kill her. So Dean and Sam draw out Fate, and Castiel rights the past. Only Sam and Dean remember the past. Dean, Sam and Bobby research how to kill the mother of all, and they find that the ashes of the phoniex 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 excited to go back to the wild west. So they head back, and find out the Phoniex 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.
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.
|“||Jefferson Starships…because they're horrible and hard to kill.||”|
in Mommy Dearest
After Castiel's visit, Bobby reveals that Castiel also stole a diary from Bobby's house. As they read Bobby's photocopies, Dean gets a call from Ben. Ben tells Dean that men are in the house and killed Lisa's boyfriend. Dean tries to help from the phone, but Ben too is captured. Crowley, now on the other line, tells Dean to back off or he will kill Lisa and Ben. Dean refuses to back down, and begins to hunt down Lisa and Ben. He even begins to torture demons for their location. Sam tries to help him, but Dean tells Sam to back off. Then Dean accidentally breaks the Devil's Trap, and the demon attack. Castiel comes in and saves Dean. Dean doesn't want anything to do with Castiel though. Later, its Balthazar who gives Dean Lisa and Ben's location.So Balthazar transports them there, and they storm the building. Dean finds Ben and Lisa after taking out some of Crowley's goons. He unties them, only to find out that Lisa is possessed by a demon, and she hold Ben hostage. Dean manages to free Ben by splashing holy water at "Lisa". Then he manages to free the knife from "Lisa's" hand and begins to excorise her. He continues to excorise 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 Casteil appears, and Dean tells Castiel to leave. Castiel tells him he is done playing nice, and promises to put Sam back. This confuses Dean, until Castiel touches Sam, and breaks down the wall inside his head, sending Sam into a comatose state. Dean stays by Sam's bedside, while Sam is comatose. After Balthazar giving them Castiel's location, Bobby manages to convince Dean to go with him after Castiel. Before Dean leaves, he leaves Sam their location. So Dean and Bobby head out. When they arrive they scope out the place, which is full of angels. Then a demon cloud comes, and Dean and Bobby run back to the Impala. The demon smash into the impala, flipping it over.
When Dean wakes up, he checks on Bobby, who is okay. So the two sneak into the place, and walk in as Crowley, and Raphael are doing the ritual. Dean throws Angelic Blade at Raphael, who catches it and flings Dean and Bobby. Then Castiel shows up, and shows his new power. With this he kills Raphael, and Crowley runs away. Dean tries to talk Castiel to powering down without making Cas angry, and even reminds Castiel that he used to be family. But Castiel doesn't want to power down and after Sam stabbing him, proves he is no longer an angel. Dean is very shocked to hearing Castiel proclaiming himself to be god.
Through the course of the series, Dean has died many times.
In the episode, "Mystery Spot", Dean has died over a hundred times. All in a completely different way which includes being shot, hit by a car, poisoned, choking, vicious dogs and a lot more. However, whenever Dean dies, the day starts over again. They find Trickster is behind this game and forces him to stop. Trickster tells Sam that this is how it's going to be like after Dean dies and it he can't do anything to protect Dean.
In the Season 3 finale "No Rest for the Wicked", Dean has almost spent his year. Desperately trying to find a way out, he goes after Lilith, the demon holding his deal. The attempt fails and Dean is viciously mauled by Hell Hounds. Now deceased, a heart-broken Sam decides to continue his job as a hunter, wondering if there's a way to help his brother escape Hell.
In Season 5 he dies again, killed by hunters who are angry at the brothers for starting the apocalypse. So they corner Sam and Dean in their motel room and shoot them.
Dean and Sam- Sam and Dean relationship to date
Dean and John- Dean and John's Relationship.
Dean and Castiel- Dean and Castiel's Relationship.
Dean and Bobby- Dean and Bobby's relationship over the years.
Minor Relationship- Other relationships Dean has had throughout his lifetime.
- "Phantom Traveler"
- "Bloody Mary"
- "Route 666"
- "Hell House"
- "Devil's Trap"
- "In My Time of Dying"
- "The Usual Suspects"
- "What Is And What Should Never Be"
- "All Hell Breaks Loose - Part 1"
- "All Hell Breaks Loose - Part 2"
- "The Magnificent Seven"
- "The Kids Are Alright"
- "Mystery Spot"
- "Long-Distance Call"
- "Time Is on My Side"
- "No Rest for the Wicked"
- "Lazarus Rising"
- "Are You There God? It's Me, Dean Winchester"
- "In The Beginning"
- "Yellow Fever"
- "On the Head of a Pin"
- "99 Problems"
- "Free to Be You and Me"
- "The End"
- "The Curious Case of Dean Winchester"
- "Dark Side of the Moon"
- "Point of No Return"
- "Swan Song"