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Dean Winchester is the son of John and Mary Winchester, and the older brother (and extreme protective self-appointed guardian) of Sam Winchester. He is also best friends with the angel Castiel, a close friend of the late Kevin Tran, and formerly the boyfriend of Lisa Braeden and father-figure to her son Ben, and he has a reluctant, complex, conflicted frenemy relationship with the King of Hell Crowley. Dean was raised by John as a hunter alongside Sam after their mother was killed by Azazel. Dean was destined to be the archangel Michael's true vessel for the Apocalypse, but he turned from and overcame his destiny. Dean is also a Man of Letters by bloodline, a descendant of Cain. Dean has even possessed the Mark of Cain before its removal, and has afterwards become an interest of the Darkness.
Dean was born to John and Mary Winchester on 24 January, 1979. Dean's childhood started out happy with his mother, father, and baby brother Sam, until on November 2, 1983, when the demon Azazel killed Sam and Dean's mother and burned the family home in Lawrence, Kansas down in the process. John subsequently became a hunter and raised Sam and Dean, the family frequently moving around and living on the road. When John was away on hunting assignments, Dean was left to watch and care for Sam.
By the time Dean was 6 or 7 years old, John began teaching Dean to shoot, which Dean turned out to be accomplished at, and began to bring Dean into hunting. (No Exit) Dean was also initially uninterested in looking after Sam while John was away on hunts, until circa 1989, when a shtriga tried to feed off Sam while Dean left Sam unattended; John's long-term disappointment at Dean's act of irresponsibility and Dean's own failure to protect his brother left him haunted by the shtriga encounter and made Dean more responsible and protective of his brother. (Something Wicked) Over the years, Dean and Sam developed a strong brotherly bond. (A Very Supernatural Christmas) By the time Dean was 16, he was a hunter alongside his father, and they were later joined by a (mostly reluctant) Sam. (Bloodlust)
Eventually, circa 2001 - 2004, Sam left Dean and John and hunting behind, and became estranged from and did not contact John or Dean while at Stanford University for the following two - four years. While Sam was at Stanford, Dean at some point met and dated Cassie Robinson while he and John were on a hunt in Athens, Ohio, and Dean came to genuinely fall in love with Cassie rather than limit their relationship to a physical one. However, when Dean and John were to move on, Dean told Cassie the truth about the supernatural and the family hunting business, but Cassie did not believe Dean and deemed him and John insane. This left Dean deeply hurt and left him feeling that it was foolish to become intimate with sexual partners. (Route 666)
The search for John
In October 2005, when John went missing on a hunt, Dean went to Sam at Stanford on Halloween and tried to get him to come back to hunting and help Dean find John; after Sam's girlfriend Jessica Moore was killed on the anniversary of Mary's death in the same way, Sam agreed to join Dean, (Pilot) and the brothers set out in search of John by following clues and coordinates John left them in his journal, leading to the brothers saving innocents and defeating several supernatural threats along the way.
During Sam and Dean's search for John, they learned that Sam was developing mysterious psychic and demonic abilities from what Azazel did to Sam on the night he killed Mary. (Home) During the brothers' journey on the road, Dean also wanted to continue following John's clues and instructions rather than go straight to John's whereabouts, which caused him and Sam to clash several times and at one point resulted in them briefly separating. (Scarecrow) Dean also hoped that Sam would fully return to the family and hunting, and was upset when he learned that Sam intended to return to Stanford after the brothers found John and killed the creature responsible for Jess' and Mary's deaths. (Shadow)
Fight against AzazelEventually, Sam and Dean finally reunited with John while they were tracking and combatting the demon Meg in Chicago, though John initially chose to prefer to go separate ways with Sam and Dean; (Shadow) this later changed when the Winchesters retrieved the Colt from a vampire nest to kill Azazel with, and the three began working and sticking together. (Dead Man's Blood) After John was captured by Azazel's demons, Sam and Dean went to rescue him and confronted Azazel in a showdown which ended with the demon escaping. (Devil's Trap)
Shortly after this, Sam and Dean were sent injured to hospital after a demon crashed a truck into the Impala with them inside, and there, Dean endured an out-of-body experience as the reaper Tessa attempted to get him to cross over, until Azazel restored Dean to his body. John subsequently warned Dean to protect Sam and to be ready to kill his little brother if Sam couldn't be saved from his dark destiny as one of Azazel's demonic soldiers, before John mysteriously died, (In My Time of Dying) leaving Sam and Dean stunned and devastated. (Everybody Loves a Clown)
Search for the special children
Following John's death, Sam and Dean began working with Bobby Singer and Ellen and Jo Harvelle and Ash to try and track Azazel and learn what his plans were, and to also track down Azazel's other special children like Sam. (Everybody Loves a Clown) Dean also struggled with the grief and guilt over John's death, working out that John had sold his soul to Azazel for Dean's own life at the hospital, and initially had trouble revealing to Sam what John had told Dean about Sam at the hospital. Dean grew increasingly concerned for Sam as the latter's powers progressed and developed further, although he attempted to be supportive.
During the Winchester brothers' search for Azazel and the other special children, Dean's police record obtained due to a shapeshifter framing Dean for its killing spree in the past (Skin) also became a persistent problem for him and Sam when the police learned that Dean was alive, especially after a hunt involving another shapeshifter forced Dean and Sam to hold a bank hostage. (Nightshifter)
Eventually, Azazel initiated his plan for the special children and had all of them, including Sam, abducted, leaving Dean and Bobby searching for Sam. They eventually tracked Sam down to Cold Oak, South Dakota, but just as they did, the last other special child, Jake Talley, literally backstabbed Sam, and Sam then died in a grief-stricken Dean's arms. (All Hell Breaks Loose: Part 1) Devastated by his failure to protect his brother, Dean resorted to making a deal with a crossroads demon to resurrect Sam, and Dean was given only one year to live and warned that attempting himself to escape his end of the bargain would cause Sam to die again.
Dean, Bobby, Ellen and the resurrected Sam subsequently tracked Jake down to an old cemetery in southern Wyoming as Jake was opening a devil's gate to release Azazel's demon army. During the ensuing fight against Azazel, Dean successfully killed Azazel with the Colt and avenged the boys' mother. After having a silent moment with John's freed spirit, Sam and Dean set about preparing for the ensuing war between hunters and the demons released from the devil's gate. (All Hell Breaks Loose: Part 2)
Last year on Earth
Following Azazel's defeat and during the subsequent war against the demon army, Dean chose to make the best of his final year alive, indulging in many pleasures and acts of hedonism, and refusing to consider saving himself (due to pain that breaking that part of the deal would kill Sam) while Sam desperately search, with the supposedly good demon Ruby's help, for a loophole in Dean's deal to save him. (The Magnificent Seven) Dean also trained Sam to be ready to fight the demons once Dean was gone and in Hell after his contract was up, and Bela Talbot became a frequent ally, enemy and annoyance to the brothers during this time.
Over time, as Dean's one-year time to until his contract was up began to run out, he started to realise that he didn't want to die and go to Hell and become a demon, and so began to hope that Ruby would succeed in saving him from his contract. (Dream a Little Dream of Me) Shortly before Dean's contract was to come due, he and Sam learned from Bela that the demon army's new leader Lilith held Dean's contract, (Time Is on My Side) and so set about getting her to release Dean from the contract. However, Lilith ultimately defeated Sam and Dean as Dean's contract came due, and Dean was clawed and mauled to death by Lilith's hellhound, and his soul sent to Hell. (No Rest for the Wicked)
Time in Hell
Dean's soul spent four months in Earth time in Hell, but due to time differences between Hell and the physical plane, for Dean it was closer to forty years. While Dean was in Hell, he was terribly tortured, being torn apart in horrific manners and put back together for the torture to start all over. At the end of each day of torture, the grand demon torturer Alastair would approach Dean and offer to end his torture if Dean would take up torturing other damned souls in Hell. For the first thirty years in Hell time, Dean refused, but eventually he couldn't bear the torture anymore and took up Alastair's offer so that his torment would stop.
Alastair subsequently tutored Dean in torturing and had Dean torture Hell's other souls, and Dean found that he enjoyed venting his suffering on the other souls in Hell regardless of who they were, by torturing them. (Heaven and Hell) After ten years in Hell time of this, on September 18, 2008 (four months in Earth time after Dean was killed and taken to Hell), Dean was rescued and pulled out of Hell by the angel Castiel, and resurrected back on Earth. (Lazarus Rising)
Return from Hell and the 66 sealsAfter his resurrection from Hell and the discovery of angels and the circumstances of his resurrection by Castiel, Dean returned to Bobby and Sam. (Lazarus Rising) The team were initially overjoyed to be reunited, but when Dean learned that Sam was consuming demon blood and attempting to use and control his demonic powers, this began to cause a rift between the brothers until Sam supposedly agreed to stop using his powers. (Metamorphosis) Sam, Dean and Bobby also learned that Lilith and her demons were attempting to start the Apocalypse by breaking the 66 seals keeping Lucifer imprisoned in his cage in Hell. (Are You There, God? It's Me, Dean Winchester) Following his return from Hell, Dean was initially reluctant to discuss or even admit that he remembered his time in Hell, out of guilt, horror and shame at what he had done torturing under Alastair during his last ten years in Hell, although he eventually confessed the truth to Sam. (Heaven and Hell)
Eventually, Castiel and Uriel went to Dean to get him to torture Alastair into revealing who was behind a recent string of angels' deaths, which Dean did using the brutal torturing skills he had learned under Alastair in Hell. After the mystery was solved and Alastair killed by Sam, Dean learned to his shame and distress that he had started the Apocalypse by breaking the first seal when he'd tortured in Hell. (On the Head of a Pin) This initially caused Dean to lose his confidence in his ability to do good and help the angels stop Lilith freeing Lucifer, until Zachariah restored Dean's resolve by showing Dean how capable he was at fighting evil even without his proper mind and memories. (It's a Terrible Life)
As Lucifer's seals continued to break, Dean eventually learned firsthand that Sam had lied about stopping using his demonic powers and had become addicted to demon blood, (The Rapture) forcing an upset Dean and Bobby to attempt an excruciating detox on Sam. Sam escaped and returned to Ruby, and Dean trapped them down and got into a fight over what Sam was doing which ended with Sam choosing Ruby and his demonic nature over Dean. (When the Levee Breaks) Castiel and Zachariah subsequently took Dean and held him in a safe room against his will to protect him from the Apocalypse, as Zachariah and the archangels had in actuality wanted the Apocalypse to happen so that the remains of Earth would afterwards become Paradise. Dean managed to get Castiel to turn on the Host of Heaven and free Dean, and Dean went to Sam at St. Mary's Convent to stop Sam from breaking the final seal by killing Lilith. However, Sam once again chose Ruby over Dean, destroying Dean's trust and faith in Sam and releasing Lucifer from Hell. (Lucifer Rising)
The ApocalypseAfter being teleported to safety by God as Lucifer rose from the cage, Sam and Dean set with Bobby about discovering a means of killing Lucifer to stop the Apocalypse, and discovered that Dean was to be the archangel Michael's predestined true vessel for the Apocalyptic war between Heaven and Hell; determined to find a means of stopping Lucifer that would not destroy most of Earth and humanity, Dean turned his destiny down and he, Sam and Castiel began fighting against both Heaven and Hell in their efforts to stop the Apocalypse. (Sympathy for the Devil)
Due to Dean having become distant from and less trustful of Sam due to Sam's actions, the brothers initially parted ways (discovering during this time that Sam was to be Lucifer's true vessel for the Apocalypse), (Good God, Y'All!, Free to Be You and Me) but after Zachariah showed Dean a very bleak, terrible Apocalyptic future that this course of action would bring, Dean instead chose to rejoin and reunite with Sam in the fight against the forces of Heaven and Hell. (The End)
In their efforts to defeat Lucifer, Sam and Dean first attempted to kill Lucifer with the Colt, losing Jo and Ellen in the process, but this mission against Lucifer failed. (Abandon All Hope...) The team next attempted to seek out God and get him to stop Lucifer, but when Sam and Dean were killed and sent to Heaven, they learned before being resurrected that God would not help in stopping the Apocalypse. (Dark Side of the Moon) As Sam and Dean began to lose hope of stopping the Apocalypse, Dean eventually came to believe that consenting to possession by Michael as his true vessel was the only way of stopping Lucifer and saving as much of humanity as possible, but through Sam's faith in Dean, the latter pulled out of this and escaped from possession by Michael. (Point of No Return)
Sam and Dean eventually learned from Gabriel that the rings of the Four Horsemen of the Apocalypse could reimprison Lucifer in his cage, (Hammer of the Gods) and began tracking down the horsemen to defeat them and take their rings. (The Devil You Know) When Sam decided that the only way to send Lucifer back into Hell using the rings was if Sam allowed Lucifer to possess him and then retook control of his body to jump into the cage and take Lucifer with him, Dean was strongly against allowing Sam to do this, but brought himself to realise that it was not his choice. (Two Minutes to Midnight)
After gathering all four of the horsemen's rings, Sam and Dean tracked Lucifer down to Detroit, where Sam said yes to Lucifer but was still taken over by Lucifer. Dean refused to give up on Sam or on hope of still stopping the Apocalypse, and so he, Bobby and Castiel located Michael and Lucifer at Stull Cemetery and intervened before the two archangels could begin the Battle of Armageddon. Dean's interference enraged and irritated Lucifer into viciously attacking Dean and beating him to near-death, until Sam retook control from Lucifer and sent himself and Lucifer into the cage with Michael as Dean sadly watched. (Swan Song)
In the aftermath of the end of the Apocalypse, Dean went to Lisa and Ben Braeden, and successfully built a normal, happy life free of hunting and the supernatural with them over the following year, to uphold Dean's last promise to Sam that he would have a normal life rather than attempt to bring Sam back from the cage.
Sam's returnA year after Sam's sacrifice and the stopping of the Apocalypse, Dean discovered when he was targeted by a group of djinns that Sam had been back from Lucifer's cage virtually the entire time, and that their grandfather Samuel Campbell had also been resurrected and hunting alongside Sam and the rest of the Campbell family. (Exile on Main St.) Dean quickly found himself beginning to return to hunting with Sam and the Campbells, and Dean initially tried to balance it out with his life with Lisa and Ben, but he soon had to leave Ben and Lisa and fully return to hunting, although he was still allowed to visit them whenever he could, (Two and a Half Men) until an incident in which Dean shoved Ben away to save him ended his and Lisa's relationship. (You Can't Handle the Truth)
At the same time, Dean began to become more suspicious and uncertain of Sam when the latter began displaying unusual cold and calculating behaviour and cunning; (The Third Man) until eventually, when Dean was temporarily turned into a vampire and Sam stood by and allowed Dean to be turned in hopes that Sam and the Campbells could use Dean's vampirism to find the Alpha Vampire, (Live Free or TwiHard) Dean became completely convinced that it was a supernatural doppelganger impersonating Sam, and began to distance himself from Sam and work out what it could be. Eventually, Dean began to soften and warm back up to Sam and think he was probably just being paranoid, only for the brothers to then discover in a hunt for Veritas that Sam indeed wasn't human. (You Can't Handle the Truth)
Through Castiel, Sam and Dean learned that it was indeed Sam, but without his soul, which was still in Lucifer's cage, and the brothers subsequently set about finding a means of retrieving and restoring Sam's soul, resorting to helping Crowley reach Purgatory in hopes that Crowley would return Sam's soul in exchange. Dean was also disturbed on the way by soulless Sam's behaviour and the thought of what was happening to Sam's soul in Hell. (Family Matters, All Dogs Go to Heaven) Eventually, Dean managed to get Death to restore Sam's soul by taking Death's place reaping people for twenty-four hours, (Appointment in Samarra) and Sam recovered with his soul restored after a week. (Like a Virgin)
Following the restoration of Sam's soul, Dean remained concerned for Sam, and the brothers worked to find a means of defeating Eve, the Mother of All Monsters, when she threatened to overrun the Earth with her monsters. (...And Then There Were None, Frontierland) Castiel's civil war in Heaven against Raphael was also an obstacle for Sam and Dean on occasions. (The Third Man, The French Mistake, My Heart Will Go On) Sam and Dean eventually succeeded in tracking Eve down and killing her with phoenix ash and stopping her plans, (Mommy Dearest) but they and Bobby discovered shortly afterwards that Castiel was in an alliance with Crowley to open Purgatory and use the power of the deceased monster souls there. This horrified and upset Dean, who tried without success to get Cass to not do this. (The Man Who Would Be King)
After an attack on Lisa and Ben by Crowley forced a heartbroken and devastated Dean to have Castiel wipe the Braedens' memories of him, (Let It Bleed) he, Sam and Bobby went to stop Crowley and Raphael from opening Purgatory, but they failed when Cass absorbed all of Purgatory's souls and used them to decide to replace God as a powerful universal ruler. (The Man Who Knew Too Much)
Sam, Dean and Bobby worked to find a means of stopping Castiel, and eventually succeeded in getting him to return all the monster souls to Purgatory when the Leviathans that Cass had also absorbed from the monster realm threatened to break free of him. (Meet the New Boss) However, many Leviathans remained inside Castiel and escaped onto the Earth and took human form, killing Cass in the process. (Hello, Cruel World) Shortly afterwards, the Leviathans hunted Sam and Dean, forcing them and Bobby into hiding at Rufus Turner's cabin, where they set about finding a means of killing the Leviathan and learning what their secret conspiracy plans for humanity were. (The Girl Next Door)
Shortly after, Dean learned of a Kitsune, Amy Pond, that Sam had hunted and spared in the past after falling in love with her, and though Dean pretended to Sam to leave her alone, he secretly killed her anyway due to the risk that she would kill again. (The Girl Next Door) Following this, Dean began to become overwhelmed by worry over the Leviathan situation and Sam's worsening hallucinations of Lucifer and guilt and repercussions over killing Amy. Sam eventually learned that Dean had killed Amy while the brothers were hunting two Leviathans framing the brothers for a killing spree, and this enraged Sam and caused the brothers to briefly separate, (Slash Fiction) before reuniting and making up while working on the same case in Lily Dale. (The Mentalists)
While Sam, Dean and Bobby were investigating murders in New Jersey and uncovered a Leviathan food additive part of their secret plans for humanity and conspiracy, (How to Win Friends and Influence Monsters) Bobby was fatally injured by the Leviathan leader Dick Roman and died afterwards, (Death's Door) leaving Sam and Dean emotionally stunned and mourning for weeks before they resumed hunting and investigating the Leviathans' plans. (Adventures in Babysitting) Over time, when Sam's illusions of Lucifer worsened until they began to severely torrure him and threaten to kill him, Dean began desperately seeking out help. He eventually discovered a resurrected Castiel and, with Meg, got Cass to save Sam by shifting Sam's hallucinations into Cass' own mind. (The Born-Again Identity)
After Sam was saved from his Lucifer illusions, while Castiel recovered, he and Dean began to suspect but were reluctant to believe that Bobby had stayed behind with them as a ghost, (Party on, Garth) and they eventually discovered that Bobby's spirit had indeed remained to help and watch over the brothers. (Of Grave Importance) Dean in particular was worried for Bobby about this, and feared that Bobby would become a vengeful spirit, (The Girl with the Dungeons and Dragons Tattoo) and they were eventually forced to put Bobby to rest when Dean's concern was confirmed. (Survival of the Fittest)
After Sam and Dean learned that the Leviathans intended to overthrow and farm humanity as cattle, they, with Meg and an insane but recovered Castiel, learned through the prophet Kevin Tran from the Word of God how to create a bone of a righteous mortal washed in the three bloods of the fallen that could kill a Leviathan. (Reading Is Fundemental) Sam and Dean subsequently assembled all the components and created the bone, (There Will Be Blood) and afterwards launched an attack on the Leviathan-occupied SucroCorp to kill the Leviathan leader Dick Roman with the bone. The team succeeded in killing Dick and collapsing the Leviathans' plans and hierarchy, but as a side-effect of the bone's use, Dean and Castiel were sent with Dick's essence to Purgatory and marooned there with the predatory monster souls. (Survival of the Fittest)
Time in Purgatory
Dean was abandoned by Castiel in Purgatory immediately after they arrived there (unbeknownst to Dean at the time, this was to throw the remaining Leviathans in Purgatory off Dean's trail), and overall spent a year in there. Dean became immersed in his warrior fighting skills in Purgatory, regularly fighting for survival against the deceased monsters there, and attempted to locate Castiel by interrogating the monsters in Purgatory. Dean eventually joined with the deceased vampire Benny Lafitte in Purgatory, and the two developed a strong bond in their time together against Purgatory's other inhabitants. (We Need to Talk About Kevin)
Dean and Benny eventually located Castiel and then travelled to an escape portal for humans back to Earth which they hoped all three of them could escape Purgatory through via Dean. (What's Up, Tiger Mommy?) Although they lost Castiel, Dean successfully transported himself and Benny's soul in his arm back to Earth through the portal, and resurrected Benny there before parting ways with him. (We Need to Talk About Kevin)
Return from Purgatory and the Trials of God
Shortly after his return from Purgatory, Dean reunited with Sam, but learned to his shock, hurt and disgust that Sam had chosen to attempt to give up hunting rather than attempt to find Dean or rescue or protect Kevin, which in turn initially caused a rift between the brothers, (We Need to Talk About Kevin) though they eventually made up. (Torn and Frayed) After Sam and Dean reunited with Kevin, they learned that there was another Word of God which recorded the three Trials of God which could permanently seal all demons in Hell. (We Need to Talk About Kevin) After the team retrieved the tablet, they had Kevin translate the Trials so that Sam and Dean could perform them to seal all the demons in Hell forever.
Meanwhile, Sam and Dean learned of the Men of Letters and their relation to them by bloodline from an encounter with their time-travelling paternal grandfather, (As Time Goes By) and the brothers subsequently gained possession of the Men of Letters' old bunker and adopted it as a home and headquarters. (Everybody Hates Hitler) Castiel also returned from Purgatory and reunited with Sam and Dean. (A Little Slice of Kevin)
Eventually, when Kevin began translating the Trials of God to seal Hell, Dean intended to complete the Trials himself out of fear that Sam would die if he did, but Sam was forced to be the one when the latter completed the first trial of killing a hellhound. (Trial and Error) Sam subsequently completed the second trial of sending a damned innocent soul to Heaven, although Dean was forced to reluctantly sacrifice Benny in the process to save Sam and Bobby from Purgatory. (Taxi Driver) Dean grew worried and concerned for Sam when the Trials' purifying effect began to dangerously damage Sam. (The Great Escapist)
Eventually, Sam and Dean reached the third trial of curing a demon, and Dean reluctantly left Sam to complete the trial by restoring Crowley's humanity, while Castiel and Metatron worked to complete the Trials of God to close the gates of Heaven. When Dean learned that completing all three of the Hell Trials would kill Sam, he stopped Sam from fully curing Crowley and convinced his brother to let go of the Trials of God and his attempts to redeem himself for his past mistakes; and shortly afterwards, Dean and Sam watched in horror as Metatron's spell, instead of sealing all angels in Heaven, banished them all to Earth, causing the Fall. (Sacrifice)
Lying to Sam
Just after the Fall, when Sam began to die from the effects of the Trials of God, Dean resorted to having the angel Ezekiel (actually Gadreel in disguise) possess Sam to repair the damage from inside. Gadreel agreed to allow Sam to remain in control of his body for most of the time, but warned that Sam would be able to fatally eject the former if he knew he was possessed by an angel, so Dean and Gadreel agreed to keep this a secret from Sam until Sam was healthy enough for Gadreel to leave. (I Think I'm Gonna Like It Here)
Afterwards, while Dean tried to alleviate any reason for Sam to suspect something was amiss, Gadreel would usually let Sam remain in control; but would occasionally briefly take control, to protect Sam's life or to talk to Dean. Gadreel advised Dean against calling on him too much as it would slow down Sam's healing process, (Slumber Party) and he also persuaded Dean to send Castiel (who'd been rendered human after the Fall due to Metatron taking his grace for the spell) away from Sam rather than let Cass stay at the bunker. (I'm No Angel) In the meantime, Sam, Dean and Kevin worked to try and find a means of reversing the Fall and sending the fallen angels back to Heaven, (Heaven Can't Wait) and also had to deal with Abaddon; who was usurping control of Hell with Crowley absent and imprisoned at the bunker. (Devil May Care)
While Sam and Dean were investigating angel slaughters caused by angel civil war on Earth, when Dean learned from Castiel after the latter had become an angel again that Gadreel wasn't Ezekiel since the real Zeke had died in the Fall, he tried to depower Gadreel (with an unaware Kevin's help) long enough to tell Sam the truth so Sam could expel the angel. However, Gadreel had preplanned ahead of this, and took full control over Sam's body, then killed Kevin and left the bunker with the demon and angel Word of God tablets. (Holy Terror)
Afterwards, with the help of Castiel and Crowley (the latter in exchange for his freedom), Dean tracked down and captured Gadreel, and the angel was expelled from Sam with Crowley's help. However, though Sam was freed from Gadreel's control, when neither he nor Dean himself were able to forgive Dean for what his actions had resulted in Gadreel doing to Sam and to Kevin, Sam and Dean initially parted and went separate ways - Dean going to find a way of stopping Abaddon, and Sam to find and punish Gadreel and Metatron. (Road Trip)
Taking on the Mark of Cain
While working separate ways from Sam, Dean partnered with Crowley in search of the First Blade - the one weapon capable of killing a Knight of Hell like Abaddon - and the search led them to Cain himself. In order for Dean to be able to activate and wield the First Blade's power, Cain transferred the Mark of Cain from himself on to Dean, and Dean was afterwards left waiting while Crowley went off to find and retrieve the First Blade. (First Born) Shortly after Dean took on the Mark, he and Sam reunited on a werewolf case concerning Garth; (Sharp Teeth) Sam afterwards agreed that he and Dean could go back to hunting together, but Sam made clear that it would be strictly as unclose co-workers, and the rift between the brothers over Kevin's death remained. (Sharp Teeth, The Purge)
After a time, when Crowley failed to make contact with Dean for a status update on the search for the First Blade, Dean and Sam tracked Crowley down and found that the effects of Sam's incomplete demon-curing ritual in the final Hell Trial had caused Crowley to sink into an addiction to human blood (which degenerated Crowley into a soppy, inattentive mental state). After Sam and Dean detoxed Crowley, the three tracked the First Blade down to the surviving Man of Letters-turned-witch, Cuthbert Sinclair. When Sinclair intended to torture Sam and make Dean a part of his collection, Dean killed Sinclair with the Blade (activating the Mark of Cain by using the First Blade, and causing Dean to feel the Mark's effects), and Crowley afterwards took the First Blade to 'safekeep' until Dean had a chance to kill Abaddon. (Blade Runners)After killing Sinclair with the First Blade, the murderous urge the Mark's activation had induced in Dean did not fade, resulting in Dean taking on a more aggressive, ruthless and withdrawn persona. Though Sam became concerned for the effects of the Mark on Dean, Dean continually denied that anything was wrong with him. (Mother's Little Helper - Alex Annie Alexis Ann) Dean eventually succeeded in killing Abaddon with the First Blade and putting an end to her threat; (King of the Damned) but the aggressive and murderous effects from the Mark of Cain continued to worsen from there, and Dean refused to go anywhere without the First Blade. (King of the Damned, Stairway to Heaven)
War against Metatron
At the time of and just after killing Abaddon, Sam and Dean became involved with Castiel's and his angel army's war to retake Heaven from Metatron, (King of the Damned) and with investigating a deep-rooted conspiracy among the angels' ranks. Castiel eventually lost all his angel followers over to Metatron when he refused to kill Dean to prove himself to them, and Dean afterwards single-mindedly set about finding Metatron on his own to try and kill him with the First Blade, without letting Sam or Cass try to help him. (Stairway to Heaven)
When Dean became completely out of control due to the worsening effects of the Mark of Cain, Sam and Cass tried to lock him up, but Dean escaped with Crowley's help, and tracked Metatron down as the latter began making his move to rule over humanity as their new Messiah. While Dean was fighting against Metatron with the First Blade (unsuccessfully, due to Metatron having empowered himself using the angel Word of God), Metatron was defeated and imprisoned after Cass depowered him by breaking the angel tablet, but not before Metatron managed to mortally stab Dean. Despite Sam's efforts to save Dean, Dean chose death instead of living to let the Mark of Cain turn him into a monster, and subsequently died of his injury. However, due to the effects of the Mark, instead of being free of its curse in death, Dean was transformed into and brought back as a demon, just like Cain. (Do You Believe in Miracles?)
- In the time loop created by Gabriel in which Sam relived the same Tuesday over and over, Dean died in each replay of the loop, each time in a different way. When Gabriel ended the aforementioned time loop, Dean was shot and killed the following Wednesday. After six months, Gabriel released Sam and reset events to the Wednesday, and this time Dean avoided death. (Mystery Spot)
- In the alternate future which Zachariah sent Dean into where he and Sam had remained separated after defeating War and thus Lucifer had ravaged the Earth with the Croatoan virus; Dean had, by 2014, become the cold and ruthless leader of Camp Chitaqua, and had by now lost almost all hope and faith in stopping the Apocalypse and had no moral code or qualms over killing his own friends anymore. This future’s version of Dean was killed by Lucifer in August 2014 during a failed assault on Lucifer's location. (The End) Present Dean immediately set about preventing this future after returning to his time, teaming back up with Sam to stop Lucifer without Armageddon.
- In an alternate universe where the supernatural and the Winchesters and their lives are fictional, Dean’s counterpart in this reality is an actor called Jensen Ackles, who portrayed Dean in the show Supernatural. (The French Mistake)
- In an alternate timeline created when Balthazar saved the Titanic from sinking, Dean possessed a Mustang instead of the Impala. The alternate timeline versions of Sam and Dean helped Castiel and Balthazar fight Atropos, until Atropos threatened to kill them and Balthazar restored history to normal (although Castiel made sure Sam and Dean remembered those events from the alternate timeline). (My Heart Will Go On)
- Originally, after Dean was sent back with Chronos to 1944, he was strangled and killed in 1944 New York by Chronos. This was changed when Sam and Jody Mills performed the spell to bring Dean and Chronos back to the present just before Chronos could kill him. (Time After Time After Time)
Dean was kind, sometimes understanding, mischievous, funny and slightly immature, and was an avid fan of cheap Hollywood movies and classic rock music; and, despite being and remaining in excellent physical shape, Dean was known to have a very poor diet and disgusting eating habits, preferring fattening, greasy and unhealthy foods such as pie and cheeseburgers, and considering salad and other food in Sam's more healthy diet to be 'rabbit food'. Dean enjoyed and preferred the uncomplicated things in life, such as television, pornography and food, and he regularly displayed humorous behaviour even in tense situations, often in the form of crude humour and remarks and sexual innuendos. This habit of humour in light of tense situations could sometimes make Dean appear foolish, although it seemed to be more his own way of dealing with the stress of hunting than actual foolishness. Dean was also terrified of flying, and claimed it to be the reason he always travelled around by car.
Despite Dean's foolish and immature behaviour, beneath his arrogant-seeming demeanour he showed many signs of self-loathing; he would downplay his achievements and put up with abuse from others as he felt he deserved it, and he would blame himself when things went seriously enough wrong if he played any indirect role at all in the incidence. Dean also saw himself as nothing more than a brute and a grunt, and often felt his life to be largely worthless to the point that he was willing to throw his life away when he thought it was necessary. Sam and Bobby both called Dean out for these self-loathing feelings, though these feelings usually afterwards returned.
Normally, Dean preferred to engage with women solely as sexual partners and avoid any emotional intimacy or long-term relationship with them, although he did have several long-term and intimate relationships. After the tragic events that led to Dean having to have himself wiped from Ben and Lisa's memories and leave them behind for their safety, Dean became more hesitant and reluctant to resume his original habit of one-night stands in each town the Winchester brothers visited; and after Dean had one one-night stand which led to him fathering an Amazon daughter which Sam was forced to kill, Dean became more reluctant to have even a physical relationship, and he seemed to have given up on having any family beside his brother following the incident with Lisa and Ben.
Outside of hunting, Dean was very well-disposed and laid-back; but when Dean and Sam were hunting, Dean was typically more ruthless, aggressive and merciless than Sam, though he was capable of recognising and acknowledging when he and/or other hunters went dangerously too far in their hunting tasks. Dean possessed a semi-bigoted hatred of supernaturals, especially demons, and was prepared to kill them without question; although when hunting, Dean was still much more logical and reasonable and less dangerous than more rash and dangerous hunters such as Gordon Walker. Dean was very competent and intelligent despite his somewhat impulsive and arrogant behaviour, although he could become more irrational when his family was threatened. Unlike Sam, Dean did not resent John for raising him and Sam as warriors and hunters, and Dean actually originally preferred life as a hunter to a normal life, which he considered dull. However, after all the things he saw and the tragedies and losses he suffered as a hunter, Dean came to resent his life as a hunter and admitted that he would give it up for a normal, happy life if he could.
Dean deeply loved his family and strongly valued their safety over anything else, being willing to sacrifice himself and in rare instances even others to protect his family, and considering it his greatest responsibility to help and protect Sam. Dean was originally deeply, almost blindly, loyal to John over nearly anything else and would follow all of John's commands and instructions without question; but Dean realised over time that John was not always right and that the safety of their family was more important than their crusade against Azazel, and after John died, Dean seemed to have lost faith in his father and realised that he was capable of doing better than John did.
Dean has displayed a soft spot for children and he was also very good with them, able to talk to them with ease and warmth and sympathy. Dean was more willing to put his life in danger for children than he was for nearly any others. Dean's affection even extended to monster children despite his hatred for monsters, and despite his ruthless standards he was usually unwilling to kill monster children unless he has a crucial need, and he recognised with born monster children that what they are isn't their fault.
Dean was known to have a more bitter and pessimistic view of things and the world than Sam; Sam saw the Winchesters' brains and the Campbells' brawns working together in their family tree, while Dean admitted to seeing nothing but death in their family, and before the Apocalypse, Sam believed in and privately prayed to God and angels while Dean had no faith. Dean was forced to accept that angels existed during the Apocalypse, and he afterwards became more open-minded to the possibility that creatures hunters had previously thought non-existent, such as dragons and phoenixes, could indeed be real; although angels' tendency towards smug, arrogant an manipulative actions and behaviour meant that Dean still possessed a low opinion of them as nothing more than 'dicks' and 'monsters with wings.' Because of all the bad things in the world, such as the ones Dean himself experienced, happening to people who don't deserve it, Dean had a negative view of God as a callous deadbeat due to God's apparent inaction in all the evil and misery plaguing the world and the many times of great crises.
After his resurrection from Hell, Dean suffered chronic anxiety and was left with a deep emotional mark from his time in Hell, and he felt deep shame and guilt for immersing himself in his darkest thoughts and committing horrible torture under Alastair. This overwhelming sorrow and shame made Dean more obsessed than before with saving and protecting people, and reluctant to talk about when he was in Hell to anyone; completely hiding the truth that he remembered Hell from Sam and Bobby alike from the start.
The year Dean spent in Purgatory also had a heavy and profound effect on him: the constant threat of death in Purgatory combined with losing Castiel left Dean deeply hardened, emotionless and humourless, embracing the inner-warrior he'd been trained all his life to be and adopting a slightly ruthless and volatile, until Cass also returned. Dean's time in Purgatory also made Dean much firmer in his belief of hunting and protecting people, and he viewed it as their duty to protect others and considered quitting out of hunting selfish and out of question. Despite his greater ruthlessness, Dean's year in Purgatory also gave him more faith in monsters retaining/recovering their humanity and avoiding killing humans, although it would seem that after Benny's second and final death, Dean reverted to his original preference to kill all monsters. Following Castiel's return, Dean began to gradually readjust back into his previous, more laid-back personality.
After Kevin was killed by Gadreel as an indirect consequence of Dean's actions, Dean became highly angry and guilt-ridden with himself for what his actions had caused for Sam and Kevin, and Dean became more quiet, serious and determined than ever. After Dean took on the Mark of Cain and began to suffer the Mark's effects, he developed symptoms of addiction to use of the First Blade. Initially, he grew increasingly ruthless and aggressive, became even more cold and withdrawn towards even his closest friends, acted highly rash, distrustful and imprudent when it came to using the Blade, and he refused to admit that he wasn't thinking or acting clearly at all.
Following Dean's brief time as a demon, he realised how serious and dangerous the Mark's effects and the First Blade were, and the lingering threat of the Mark taking him over brought him to force himself to take up a more ordered, healthy lifestyle to recover and maintain control against the Mark. However, as the Mark's effects only continued to worsen and proved in the long run undefeatable, Dean decided to leave finding a cure alone even if it meant him eventually losing himself to the Mark's bloodlust, out of concern of what the consequences of such magic would be for others, and out of shame and self-loathing over how he was harming the ones he loved under the Mark's influence.
After Dean learned Sam had still persisted with looking for a cure behind Dean's back, and when Charlie died as a direct result of Sam's actions, this was the last straw for Dean; prompting him to all but give in to the Mark and slaughter the Stynes in revenge, and bringing Dean to lose his already-shaken faith in his and Sam's brotherly bond and his conviction in protecting Sam no matter what. Dean declared to Sam that he thought it was Sam who deserved to be dead instead of Charlie, Dean deemed his and Sam's devotion to fighting for their family to be selfish and more about themselves than everyone else, and Dean was even fully resolved to kill Sam himself to ensure Sam's conviction to saving Dean as family couldn't unleash the consequences that would ensue. However, when Sam reminded Dean of all the family they'd had and lost over their lives, and through it what family had meant to him, Dean changed his mind about killing Sam to save everyone else, and he and Sam became a team again.
During Dean's time as a demon after he was resurrected by the Mark of Cain, the demonization of his soul caused his personality to alter drastically; retaining several of his human self's traits such as his love for flings with women, drinking, and hitting roadhouses, but becoming much more dark, arrogant, selfish and vicious. Demon Dean found that he enjoyed both the sense of power he had, and the sense of freedom and clarity from lacking all his human self's emotional pain as a demon, due to which he acted like a hedonist; doing whatever he wanted whenever he wanted on little more than a whim, without any thought or regard for anyone or anything else. His 'freedom' from emotional pain as a demon also meant that Dean wanted to avoid, and possibly even feared, being cured by Sam and going back to his old, human self.
Demon Dean didn't empathize at all with others, and unlike the human Dean, he only cared about his own needs and wants over others matters (no matter how important, and he wouldn't listen to or even at all be intimidated by even the King of Hell). He also seemed to be laid-back about and enjoy taking his time with his tasks, seen with how he stalked Sam in the bunker in a taunting, 'cat-and-mouse' manner. As a demon with the Mark of Cain, Dean was also extremely wrathful, violent, aggressive and uncontrollable; he would brutally and relentlessly beat both humans and demons who were no threat to him, on little more than a whim. Dean was also immensely sadistic and evil, even for a demon; he spared Cole during their fight so that Cole would have to live with the rage and humiliation of getting his chance to take his vengeance and failing (in Dean's own words, it was the "worst thing [he] could have done to [Cole]"), and he relentlessly verbally tormented Sam with taunts and claims that they were never really brothers at all. While much colder than his human self, Demon Dean could still be highly charismatic and confident with women, but when said women in any way didn't fully cooperate with his wants, he could instantly turn extremely vicious and psychologically-abusive. When Ann Marie rejected Dean's advances, the latter completely shamed and humiliated her for sleeping with him, in spite of knowing that he had left her broken and near tears; and when a stripper Dean was watching refused to let him touch her, Dean put a dollar note down and demanded that she degradingly pick it up off the floor.
Dean's transformation immensely twisted, contorted and blackened his brotherly love for Sam, so that he no longer cared about his brother's life when Sam got himself into a deadly situation; Dean refused to do anything to help or save Sam when the latter was captured by Cole, coldly declaring that it was Sam's own problem, and he attempted to kill Sam without any emotion or aversion when the latter brought him back to the bunker and tried to cure him. However, Demon Dean may have still retained some slight trace of his human self's reluctance to harm his brother; after his transformation, Dean left Sam a message asking the latter to let him go and leave him alone to live out his new life as a demon, and when Sam finally tracked Dean down, Dean even restrained himself and gave Sam a second chance to let him go and walk away. Similarly to his lack of care about Sam's life, Demon Dean also lacked his human self's love and affection for the beloved Impala; letting the car's condition deteriorate, and nonchalantly remarking about this, "It's just a car."
- Cain (ancestor; deceased)
- Henry Winchester (paternal grandfather; deceased)
- Millie Winchester (paternal grandmother)
- Samuel Campbell (maternal grandfather; deceased)
- Deanna Campbell (maternal grandmother; deceased)
- John Winchester (father; deceased)
- Mary Winchester (mother)
- Sam Winchester (brother)
- Adam Milligan (biological paternal half-brother)
- Emma (biological daughter; deceased)
- Gwen Campbell (maternal third cousin; deceased)
- Christian Campbell (maternal third cousin; deceased)
- Mark Campbell (distant maternal "something twice removed;" deceased)
- Johnny Campbell (distant maternal relative; deceased)
During Dean's time as a demon, he possessed most if not all of the basic demon powers and abilities, but Dean's were greatly strengthened and far surpassed those of most other demons due to his status as an uber-demon. Dean possessed superhuman levels of strength far above low- and mid-level demons', which allowed him to easily overpower and brutally beat up both demons and well-built humans in physical combat; Dean was even able to toy with and then easily subdue Cole, in spite of the latter's extensive combat skills and training, during a fight, and Dean was even able to push Crowley, the King of Hell, to the ground with ease. (Black, Reichenbach) However, Castiel was able to restrain Dean when re-strengthened by replenishing his borrowed grace (although Dean's demonic strength may have been weakened at this time due to being partially cured). (Soul Survivor)
Dean also couldn't be harmed or killed by conventional means as a demon; he was able to completely regenerate stabs, cuts and slashes to his body within seconds, and was unaffected by tear gas. Also, while Dean wasn't immune to holy water, he did seem to be more resilient to it than regular demons, as he only took a couple seconds to recover. Dean could, however, be fully restrained and incapacitated by the supernatural handcuffs. Also, while Dean was initially affected differently by the demon cure and was much more resistant to its effects than other demons, Dean's transformation into an uber-demon still was not irreversible; repeatedly injecting him with purified blood on consecrated ground could eventually fully restore Dean to his human self. (Reichenbach, Soul Survivor)
Other special abilities
Besides his transformation into a demon, as a human, Dean has gained or briefly possessed several supernatural powers and abilities over the years.
- The Mark of Cain made Dean, even when he was human, the master of the First Blade and the one person other than Cain who could wield the First Blade's power; which in turn allowed Dean to kill all kinds of supernaturals with the Blade, including Knights of Hell and other Mark-bearers. The Mark also gave Dean the ability to, when the Mark was activated by the First Blade's presence, telekinetically call the Blade into his hand, and it gave Dean enhanced strength and stamina. (King of the Damned, Stairway to Heaven, Do You Believe in Miracles?)
- Dean temporarily became a ghost via astral projection at one point. He learned to use the ghostly abilities of teleportation, intangibility, telekinesis and invisibility as a spirit. (Death Takes a Holiday)
- Dean was at one point temporarily turned into a vampire, although he was cured and fully reverted to his human state before he could succumb to his bloodlust and render the transformation permanent. As a vampire, Dean possessed extreme sensitivity to light and sound, and an immensely-improved sense of smell, as well as increased strength and superhuman agility. (Live Free or TwiHard)
- Dean is able to see fairies past their invisibility on Earth, after having been briefly abducted to their world in 2011. (Clap Your Hands If You Believe...)
- When wearing Death's ring, Dean took Death's place in the natural order as the horseman representing Death. He existed in the Veil as a reaper-like entity, and had the ability to reap the dying's souls from their bodies with a touch. (Appointment in Samarra)
- Dean once temporarily gained the ability to communicate with animals, along with the enhanced olfactory sense of a dog, by consuming a human-animal mind meld potion to communicate with the Colonel. However, he lost both these abilities when the spell naturally wore off. (Dog Dean Afternoon)
Dean has died and resurrected numerous times.
- In Gabriel's time loop in which Sam kept reliving the same Tuesday over and over, Dean died on each replay of the Tuesday, in a different way each time, until Gabriel ended the loop: (Mystery Spot)
- Shot at the Mystery Spot
- Run over by a car in the street
- Crushed by a falling piano in the street
- Choked on a sausage at a diner
- Slipped in the motel shower
- Food poisoning from a taco breakfast
- Electrocuted by his razor
- Accidentally hacked with an axe by Sam at the Mystery Spot
- Mauled by a golden retriever in the street
- Hit by an arrow (implied)
- Numerous other unknown deaths in the loop
- In the Wednesday after Gabriel ended the time loop, Dean was shot and killed by a bar patron. Gabriel later reset events back to the start of this Wednesday, and Dean avoided death. (Mystery Spot)
- On 2 May, 2008, Dean was mauled to death by a hellhound and taken to Hell, due to his crossroads deal to resurrect Sam. He was rescued and resurrected by Castiel four months later. (No Rest for the Wicked)
- In the alternate 2014 where Lucifer had ravaged humanity with the Croatoan virus, the Dean of this future was killed when Lucifer broke his neck. (The End)
- Dean was shot and killed by Walt and his soul sent to Heaven. He was sent back to Earth and resurrected some time later by Joshua. (Dark Side of the Moon)
- Dean was temporarily killed so he could speak with Tessa and Death about retrieving Sam's soul, before being revived. (Appointment in Samarra)
- Dean was originally strangled to death by Chronos when hunting him in 1944. This was changed when Sam and Jody Mills brought Dean back to the present. (Time After Time After Time)
- Dean was mortally stabbed through the chest by Metatron while attempting to kill the latter with the First Blade. Due to the effects of the Mark of Cain, Dean was shortly afterwards brought back as a demon, (Do You Believe in Miracles?) but would be restored to his human self several weeks afterwards. (Soul Survivor)
- Dean apparently knows very little about pop culture such as Myspace and H.P. Lovecraft, although he may have improved over time.
- Dean was revealed in Man's Best Friend with Benefits to be allergic to cats.
- Though not confirmed onscreen, fans have suggested after First Born was broadcast that the reason Dean is Michael's true vessel could be because his biblical ancestor Cain killing his younger brother Abel mirrors Michael's destiny in the Apocalypse to kill his fallen younger brother Lucifer. It was indicated by Gabriel in Changing Channels that Dean is Michael's true vessel because his relationship with John and Sam mirrors Michael's with God and Lucifer respectively.
- As hinted in In the Beginning and confirmed in The Song Remains the Same, Dean is named after his maternal grandmother Deanna Campbell.
- Dean's demon self in Season 10 has been nicknamed 'the Deanmon' not only by fans but also in trailers and promotionals.
- Dean has been nicknamed Squirrel or Not-Moose by Crowley, in reference to the nickname of one of the two title characters of The Rocky & Bullwinkle Show.
- Dean has been occasionally compared to David Hasselhoff; he'd signed a receipt under the alias D. Hasselhoff in All Hell Breaks Loose: Part 1, and Claire Novak called him Hasselhoff (earning an oddified and thinking expression from him) in The Things We Left Behind.
- Dean initially had a stronger connection with the forces of Heaven from Season 4 to 8; but this has been inverted from Season 9 onwards, so that he has a stronger connection with the dark forces such as the demons and later the Darkness.