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Dean Winchester is a human and hunter, formerly a demon, a member of the Men of Letters with his brother Sam and one of the lead protagonists, also a temporary antagonist, in Supernatural. He and his brother are members of the Winchester and Campbell families, and Dean is also the destined vessel of the archangel Michael. He and Sam are also the surrogate sons of Bobby Singer. Dean is best friends with the angel Castiel, close friends with the late prophet Kevin Tran and reluctant ally of Crowley. Dean has an ex-girlfriend, Lisa Braeden, who he lived with for a year when Sam was in Hell. She has a child named Ben, who Dean acted as a father for. Dean is also the former apprentice of Alastair. Both Dean and Sam were raised in the hunting life by their father after the demon Azazel killed their mother.
Dean's main role in the series is being the self-appointed guardian of Sam and often going to extreme lengths to protect him regardless of personal cost. Often in these occurrences, Dean finds himself the center of a much larger picture. When he was killed by Metatron whilst using the Mark of Cain, Dean returned as a demon and a Knight of Hell loyal only to himself. He was then cured by his brother using purified blood.
Dean was born on January 24, 1979. Mary Winchester, Dean's mother, was killed by Azazel, a yellow-eyed demon, when she interrupted him while he was feeding demon blood to Sam, Dean's baby brother. Azazel pinned Mary to the ceiling, where she suffered stomach bleeding and was consumed in flames.
Upon witnessing this, John, the boys' father, handed the infant Sam to Dean as the nursery burned and told him to "Take your brother outside as fast as you can! Don't look back! Now, Dean, go!" John left their home in Lawrence, Kansas, with Dean and Sam before Dean's fifth birthday.
When Dean was 6 or 7, John took Dean out shooting for the first time, using bottles as target practice. According to Dean, he bulls-eyed every one of them. Dean has cited this story as one of his fonder memories of his father.
On an occasion when John was hunting a Shtriga in Fort Douglas, Wisconsin and left Dean and Sammy alone in a hotel room, Dean got bored and went out to play arcade games in a flashback of Something Wicked. When he came back, he found the Shtriga feeding on Sammy. John returned in time to scare the Shtriga off. For a long time Dean was haunted by his failure to defend his brother. In 1991, when Dean was in sixth grade, he made his first sawed-off shotgun.
Once when 12 year-old Dean was left to babysit 8 year-old Sam while John was on a hunt, Sam began to interrogate Dean about what it was that their dad actually did. Dean responded with "You know that. He sells stuff." When Sam moved on to ask about their mother, Dean got angry and stormed out after yelling, "Shut up! Don't you ever talk about mom! Ever!" Upon his return, Sam revealed to Dean that he had found and read their dad's journal, and demanded to know if monsters are real. Dean finally resigned himself to telling Sam the truth.
Dean continually excused his father's flaws while the tension between Sam and John was clearly starting to take root. Disappointed with John's lying and absence, Sam gave Dean a Christmas present intended for his father: an amulet. Dean wears the amulet until season 5, with Sam wearing it while Dean was in hell.
In 1995, Dean loses all of his and Sam's food money in a poker game and is caught stealing food. As a result, he is sent to a reform school run by a man named Sonny who is an ex-con who turned his life around and eventually gets the charges against Dean dropped. Living at the home, Dean flourishes, becoming a high school wrestling champion, making friends and doing well in school. Dean met a girl named Robin who gave him his first kiss and shared his desire not to go into the "family business". Dean's dreams at the time were to become a rock star or a mechanic and he was supposed to go to a dance with Robin, but his father returned the night of the dance to pick him up and refused to delay even for one night. Sonny offered Dean the chance to stay permanently, but Dean reluctantly left because he couldn't leave Sam.
While working a haunting in Long Island, NY, Dean and Sam convinced their father to do the sights in NYC. That night at midnight, Dean leaves a zonked Sam and John to go see the club CBGB. He's way underage in this den of drinking, smoking, snorting, and becomes drunk for first time. John tracked Dean down, and saved him. Dean whined about how much John embarrassed him, and how Dean "hated him". John replied, "Son, you don't like me, that's fine. It's not my job to be liked. It's my job to raise you right."
During the summer of 1997, John, Dean, and Sam were hunting a werewolf. In November 1997, John "parked" the kids in a small town in Indiana where they attended Truman High School. While Sam was having trouble with a bully named Dirk, Dean got a girlfriend, Amanda. He became uncomfortable when she asked him to meet her parents. When she caught Dean cheating on her with another girl, she challenged him, charging that his 'cool' persona was just a cover for his pathetically sad loneliness.
Around 1998, Dean and John left Sam alone to go hunt a Kitsune. At this time, Dean also gave Sam advice over the phone on how to talk to girls.
In 1998 or 1999, Dean went on a road trip that was supposed to be "5 states, 5 days" while Sam was "in Orlando with Dad, wrapping up that banshee thing". However, he spent most of his time in Lisa Braeden's loft.
Sometime between 2001-2005, Sam left for Stanford. While there, he became estranged from Dean and his father and didn't speak to them for at least a couple of years. During this time, Dean met Cassie Robinson while he and John were in Athens, Ohio, for a hunt. She and Dean dated for a couple of weeks. Before Dean left, he told Cassie the 'big family secret' about hunting. It was then that Cassie promptly called him 'nuts' and dumped him. During this time, Dean had also tracked down Edward Trenton, a monster and father to Cole Trenton, who would later pledge to hunt Dean down in revenge. Dean also hunted a pair of Vetala by himself during this period.
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.
In Phantom Traveler, the boys receive a call from a previous client, who was referred to them through Dad's cell phone message. This is the first indication Dad was still alive. Dean has trouble with this hunt, for he is afraid of flying and they must board a plane to keep it from crashing and everyone on board dying.
Early in the season (Skin), Dean and Sam battle a shape-shifter responsible for a string of brutal murders in the St. Louis, MO area. During the course of the episode, the shape-shifter assumes Dean's form. It taunts Sam, telling him of Dean's issues - Sam got to go to college, Dean had to stay home, and give up his dreams. He's jealous of Sam's friends, of his life. He knows he's a freak, that everyone will leave him, both Sam and Dad. The police catch the shape-shifter in the act of hurting someone, causing police to believe that Dean is responsible for all the murders. However, Dean kills the shape-shifter while it is still in his form, and the authorities officially declare him dead. Dean apologizes at the end to Sam, wishing Sam could be "Joe College". Sam confesses he's never really fit in at Stanford; Dean half jokes that they are both freaks.
In Home, Dean first becomes aware of Sam's psychic abilities when Sam has a vision of trouble at their old home in Lawrence, Kansas. Later in Nightmare, Sam's abilities grow, even showing Sam a vision of Dean's death.
In Asylum, while influenced by the spirit of Dr. Ellicott, Sam tries to shoot Dean in a spirit-induced rage over Dean's insistence in obeying John's orders like a good little soldier. He's sick of doing what Dean orders. In the following episode, Scarecrow, Sam actually does leave Dean, insisting he won't follow Dad's orders. He doesn't understand Dean's blind faith; Dean states, "It's called being a good son!" Dean called Sam "a selfish bastard". Later Dean tells Sam he is proud of how Sam goes after what he wants, even standing up to Dad. Sam eventually goes looking for Dean when he can't reach his brother on his cell phone, rescuing Dean from the scarecrow.
In Faith, Dean acquires a fatal heart condition when he is electrocuted during a hunt. Later, he is saved by a faith healer, Roy Le Grange, whose wife is controlling a Reaper. When Dean asks why he was saved, Roy Le Grange says he looked into Dean's heart and saw, "A young man with an important purpose. A job to do. And it isn't finished."
Sam learns of Dean's past relationship with Cassie Robinson during episode Route 666, and figured out Dean loved her but she dumped him. Dean and Cassie have a stormy relationship, "working things out". He confesses that he was honest with her, but he doesn't really know why. He tells Sam that he and Cassie will be "working things out until they're 90." Dean asks Cassie, "Don't leave the house, please" when she tells him she hates him getting all authoritative on her, which shows Dean submitting meekly for her. Getting ready to leave, Dean hopes it's less permanent this time, although she says she's a realist and tells him "Goodbye Dean". Dean claims he's seen stranger things happening, telling her, "See you Cassie". Sam wonders if putting everything on hold to hunt is worth it, after meeting Cassie.
In Shadow, as they prepare to battle Meg, Sam confesses to Dean that he will return to Stanford after they kill Azazel, the demon who killed their mother and Sam's girlfriend, Jessica Moore. Dean becomes upset with Sam and insists that they keep fighting together.
John sends Dean and Sam on a mission in Something Wicked, knowing Dean would want to finish the Shtriga hunt. Dean is finally able to defeat it, something which has haunted him since he first saw it snacking on little Sammy when they were kids.
In Salvation John tells the boys all the information he has on the demon, so the Winchesters head for Salvaton, Iowa, to hunt it down. Meg sets a trap for John, which worries Dead, but with an admonition for the boys to finish the demon, John leaves. In the confrontation with the demon, the boys save the family. Afterwards Sam sees the demon and wants to go back in the burning building to kill it, but Dean prevents him, telling him it's suicide. Back at the motel Dean reiterates he's not going to let Sam kill himself over this demon, because it's not worth dying over. Sam pushes the point, and Dean confesses that Sam and Dad are all that he has left. Trying to call Dad again, Meg answers the phone, telling Dean that he's never going to see his father again.
In the last episode, Devil's Trap, Azazel possesses Dean's father in an attempt to get The Colt for his own. After Dean realizes this, The Yellow-Eyed Demon pins him and Sam to a wall and reveals that John favors Sam over Dean. The demon also tells Dean that he was responsible for sending the demon's children back to Hell, so he sees this as justice. After Dean makes a sarcastic remark about the situation, the demon tortures him and Dean pleads for his father's help before losing consciousness. John takes control over the demon briefly, allowing Sam to escape the hold and shoot John in the leg, releasing Dean. Dean's concern is for Dad, begging Sam not to kill Dad while the demon is inside. The demon escapes, leaving John furious with Sam, although Sam understands Dean better - the family comes first. While Sam is driving to the hospital after Dean and John were injured, a demon-possessed driver T-bones his truck into the Impala, causing massive damage to the car and the Winchesters inside.
All three of the Winchesters survived the wreck, although Dean was more severely injured than his father or brother. In the first episode, In My Time of Dying, Dean is in a coma. Sam realizes Dean's spirit is near, and is able to communicate through an ouija board. Spirit Dean explains a reaper is after him, so Sam works hard to help. Spirit Dean begs his father to help him, to bring him back, but John only sits there. Tessa, the reaper, tries to convince him to cross over. In an effort to save Dean, John makes a deal with Azazel, and Dean wakes up. John tells Dean he's sorry for putting too much on Dean growing up, and that he's proud of Dean. He reiterates to take care of Sammy, and then tells Dean a secret which shook him. John leaves, and dies, shocking both brothers.
Dean and Sam gave their father a hunter's funeral in Everybody Loves a Clown. While the body was burning, Sam asks Dean if Dad had said anything to him before he died. Dean lies, saying no. While trying to deal with his grief in fixing up the Impala, an old message takes the boys to a roadhouse where they meet Dad's friends Ellen and Jo Harvelle, and the computer genius Ash. Ash puts in all the information into his computer, and promises to call them if he gets anything. Sam jumps to work a case, surprising Dean by saying he wouldn't go back to school but continue to hunt. At one point Sam pushes Dean to deal with Dad's death, and Dean pushes back by telling Sam he spent his entire life fighting with Dad and that Sam only wants to make it right now because Dad is dead. After the case is closed, Sam admits to Dean that he was right. He pushes back at Dean, pointing out that Dean isn't all right either, before walking away. Dean takes out his hurt, anger, and grief by hitting his beloved Impala's trunk over and over and over again.
Over the first half of the second season, Dean struggles with the death of his father and the resulting guilt that he should have died instead. In Bloodlust, he meets up with Gordon Walker, a vampire hunter whom he bonds with after a successful hunt. Dean admits to a hole after his indestructible father died, and he can't talk with Sammy about it. Gordon advised him to put that hunger towards his job - killing monsters. When Sam returns, he tries to get Dean to see they don't kill supernatural, they hunt evil. After locating the nest, Dean realizes Sam is correct and ties up Gordon, making Gordon their enemy.
In Children Shouldn't Play with Dead Things, Dean is antsy the entire hunt, on edge, blowing up, telling everyone, "What was dead should stay dead!" Sam can see Dean is not dealing very well with their father's death, but cannot get him to open up. At the end Dean apologizes to Sam for his behavior, as he finally admits to Sam that he should not even be alive, but that Dad had given up his life and the Colt to save him. He does not tell Sam what John said, preferring to shoulder the burden himself. He has a firm conviction that he must save Sam, because killing him is unthinkable.
During an investigation in Baltimore, MD, (The Usual Suspects), Dean is arrested in connection with another series of murders. It is revealed that Dean has a rather impressive police record with charges including credit card fraud, breaking and entering, and grave desecration. Although Sam and Dean are able to prove that the murders were actually committed by one of the detectives on the case, it is unclear whether or not the charges against Dean were ever officially dropped. However, the problem still remains that the authorities have realized that Dean is not dead as they had previously believed. 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.
At the end of All Hell Breaks Loose Part 1, just as Dean arrives to rescue his younger brother, Sam is stabbed and collapses into Dean's arms. Amidst his brother's pleas to stay with him, Sam dies, leaving Dean alone as the last living Winchester. Inconsolable, Dean outright refuses when Bobby Singer suggests they burn Sam's body, prompting Bobby to leave the cabin. After his monologue with Sam, during which he confesses his failure as an older brother, Dean storms out of the cabin in a furious rage. At his wits end, he travels to a crossroads to make a deal with a "crossroads demon" for Sam's life in exchange for his soul. In the end, Dean is allowed one year to live and Sam is resurrected. At first, Bobby is the only one to know about Dean's deal as Sam can't remember anything past the point when Jake Talley stabbed him to death. Bobby yells at him for what he did and Dean pleads with him not to tell Sam about the deal, as he knows it will upset Sam.
Later, the The Yellow-Eyed Demon asks Dean if he knows what he brought back to life is the real Sam, considering he killed Jake Talley in cold blood and without hesitation. Sam finds out what Dean did by the end and Dean pleads with him saying that he couldn't let Sam die, "not like that." Sam vows to find a way to get him out of the deal.
At the end of the second season Dean kills The Yellow-Eyed Demon with the Colt, freeing his father's soul. During the battle, however, hundreds of other demons escaped from the door to Hell and now Dean and Sam must hunt and kill all of them.
In the third season premiere, The Magnificent Seven, Dean decides to make the best of his final year, indulging in various acts of hedonism while Sam tries desperately to find a loophole in the crossroads demon's deal. While searching for the 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 later learns that Ruby is a demon, and she promises to help him free Dean from his contract. She "fixes" the Colt so that it can again kill "anything" and also shows them a knife that can do the same. Later, Dean and Sam learn from Ruby that all demons used to be human but had their humanity burned away in the fires of Hell. Dean begins to train Sam to fight demons alone for after Dean's contract is up.
Over the course of the season, the brothers meet up with another beautiful woman, Bela Talbot. Bela acquires magical objects and sells them for a large profit, is unscrupulous and seemingly amoral. In Dream a Little Dream of Me, when Bobby falls into a coma, Sam and Dean investigate the murder of a scientist. While viewing Dean's dreams it becomes clear that Dean believes Sam was their father's favorite but only thought of Dean as a tool. Dean encounters a future, demonic version of himself in a nightmare, which shocks him into starting to fight for his life. After waking up, Dean admits to Sam that he doesn't want to die. Meanwhile, Bela steals the Colt, meaning they won't have it when the hellhounds come for Dean.
In Mystery Spot, Sam is forced to relive the same day, a Tuesday, over and over again. On each new day, Dean dies a different way despite Sam's frantic efforts to save him. Sam later discovers that the culprit is the Trickster, a villain from Season 2. It finally becomes Wednesday, but this time, Dean dies and doesn't come back. Sam spends months trying to hunt down the Trickster, who reveals that he has been trying to get Sam to understand that he and Dean can't keep making sacrifices for each other, and that Dean is going to die no matter what Sam does. The Trickster then sends Sam back to Wednesday, despite Sam failing to learn the Trickster's lesson. Sam is warned by Ruby that Dean might not make it back from hell.
In Jus In Bello, the FBI and Agent 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 Ruby ultimately tells him 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.
Dean, with 30 hours left, still 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 was hiding, the three quickly manage to locate her. However, Dean discovers that Lilith has switched bodies as Sam is about to kill the little girl. As the clock strikes midnight, Dean smiles and tells Sam to be brave and to continue what he's doing. The brothers and Ruby run from the hellhounds and place a salt barrier to protect themselves. However, Dean realizes Lilith is in Ruby. Too late. The demon uses her powers to subdue the two, opening the door for the hellhounds. Sam watches as his brother is mauled to death by the hellhounds, pleading that Lilith stop. As Lilith leaves an unconscious Ruby, Sam holds the dying Dean in his hands, frantically yelling out to him. Now in Hell, Dean is desperately yelling for help, calling out for Sam.
Dean was in Hell for a total of four months, which he later tells Sam "felt like 40 years", as in Hell, time is different from the mortal world. He was tortured by Alastair every day, and was even offered the option to torture other souls instead. Dean refused his offer for thirty years until finally giving in, triggering the first seal to Lucifer's Cage. Dean spent his last 10 years in Hell torturing other souls until Castiel pulls him out and declares that Dean is the only one who can stop Lilith from freeing Lucifer from Hell.
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 and a powerful whine that shatters the gas station's windows. Dean calls Sam but learns that Sam's number has been disconnected. He calls Bobby who hangs up on him. As a last resort, he hot-wires a parked car and goes to Bobby's house. A fight ensues until Dean is able to prove to Bobby that it is really him. Dean and Bobby then find Sam in a town right near where Dean was buried-he's in a hotel with a girl, but claims he is in town searching for a demon.
The Winchesters soon attempt to track down the force that 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 vessel, and it becomes clear that Sam lied to Dean when he told him he didn't know where Ruby was. To Dean's dismay, Sam also confesses that he has been using his powers to exorcise demons in the hunt for Lilith. In the episode Wishful Thinking, Dean confesses that he remembers Hell.
In Are You There God? It's Me, Dean Winchester, Dean is haunted by the spirits of Meg Masters, Henricksen and Ronald Reznick who want to kill Dean for not saving them. Dean, with guidance from Bobby, ultimately lays their souls to rest.
Later when Dean is asleep, Castiel, the angel who rescued Dean, re-appears and tells him that they must stop Lilith from opening the 66 Seals because if they fail, Lucifer will bring the Apocalypse. 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.
In In The Beginning, it takes us to 1973 where Dean learns about the Winchester history. He meets his parents, John Winchester and Mary Campbell, before he is born. Although tempted to stop Azazel from killing his mother, he realizes that he and Sam will no longer be hunters and all the people they saved will die. Dean learns that his mother was a hunter from a long line of hunters. Teaming up with his future mother and grandfather, they plan to take out Azazel with a borrowed Colt. Azazel, however, is one step ahead and possesses Samuel, Dean's grandfather. Dean fails to stop him and the possessed elder finds John about to propose to Mary. Samuel kills John. A heartbroken Mary confirms a deal with Azazel, allowing him "permission" in 10 years. Dean arrives 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. 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 and torture them. Dean resisted for thirty years (three months), but eventually gave in and spent ten years torturing people in Hell to escape being tortured himself. In Family Remains, Dean confesses to Sam that he enjoyed torturing souls, as he finally had the chance to dish out the same pain that he'd endured for the past thirty years.
In Death Takes a Holiday, Dean meets up again with the reaper, Tessa, who wakens his memories of their previous encounter with a kiss; Dean confesses that there has been a "hole" in him since that time and realizes that it is related to her. Soon after, Tessa is taken by Alastair in his quest to break another of the 66 seals; breaking the current seal involves killing reapers. The boys ask their psychic friend Pamela Barnes to help them astral project so that they may find the kidnapped reapers. Once they have, they are captured, but Sam is able to break them out and Tessa is able to continue reaping souls. However, before Dean is able to return to his body, Alastair corners him only to be captured by the angels; Castiel then appears and informs Dean that they have won this seal. As Dean awakes in his body, Pamela is dying from the injuries she obtained during a fight with a demon, while the boys were "out." 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 Angel form when they were looking for who pulled Dean out of Hell.
Dean, along with Sam and Ruby, defends 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 the 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.
Since he was Alistair's "student" in Hell, Dean is pressed into service by Castiel and Uriel, who need him to torture Alastair for information on who is killing angels in On the Head of a Pin. Dean refuses at first, but eventually agrees. Dean 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 when Sam, having grown stronger in his demonic abilities, arrives and uses his powers to torture Alastair in to revealing he does not know who is killing the angels; Sam kills Alastair shortly thereafter. Later, as Dean recovers in the hospital, Castiel informs him about Uriel's betrayal; Uriel had been killing angels who did not join his cause to free Lucifer from Hell. Castiel also confirms Alastair's claim that Dean was the first seal, but adds that because of this, Dean is the only man capable of averting the Apocalypse. However, Dean does not believe he is able to do it and tells Castiel to find someone else as tears run down his face.
In It's a Terrible Life, in an effort to put Dean back on the "right path," Zachariah, Castiel's superior, re-writes Dean and Sam's memories to remove their knowledge of supernatural creatures, making them believe they are average people working regular jobs, and drops them in a haunted building. After the brothers proceed to defeat the ghost behind the hauntings, Zachariah (who posed as Dean's boss) restores Dean's memories to show him that hunting is in his blood. This only renews Dean's resolve.
In the episode The Monster at the End of This Book, 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, Dean confronts Sam about drinking demon blood when Sam receives a request to go to Bobby's house. Once there, Dean and Bobby trick Sam and lock him in a demon-proof panic room 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. Sam escapes the panic room after Castiel releases him, and Dean tracks him down to a hotel, despite Sam's efforts to shake him. They argue over whether or not Ruby is corrupting Sam, if Dean is supposed to stop the Apocalypse, and if Sam is turning into a monster. The argument leads to a fight that Sam wins. On the floor and in pain, Dean calls to Sam, "If you walk out that door, don't you ever come back" -- the same ultimatum John gave Sam when he left for college years before -- after which Sam leaves the room.
Towards the end of the season, Dean and Sam have a strong confrontation which leads to a separation. Soon afterwards, Sam learns Lilith's location and sets out to destroy her that evening. Around the same time, Dean swears his alliance to serve Christ and is then held captive by Zachariah. After having once again been freed by Castiel, Dean finds Sam only to realize he's too late. Before killing Ruby, who had been manipulating Sam all along, Sam kills Lilith. As a result, the final seal is broken and the Apocalypse begins.
The fifth season picks up right where season 4 ends when the portal to Hell opens. As Lucifer escapes, the brothers are teleported into an airplane by an unknown force (later revealed to be God). 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 Ruby's 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 are Ellen, Jo, and Rufus all trying to hunt the demons, who turn out to be normal people War has altered to make look like demons. Once the brothers cut the ring finger off of war, sending the town back to normal, Dean worries that Sam cannot control his urge to drink demon blood. The brothers then agree to go their separate ways because Sam is a liability with his demon blood lust. Later, Castiel finds Dean and they capture the Archangel Raphael to ask the location of God.
In the fourth episode of the season, The End, 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 becomes possessed by Lucifer and is the reason the world was in such disarray. Later, the future Dean is killed by a Lucifer-possessed Sam. After being told by his future self to agree to be Michael's vessel, Dean is transported back to his own time where he comes face to face with Zachariah. He clearly refuses to become Michael's vessel when prodded by Zachariah. At the end of the episode, the brothers meet up again and decide they should stay together to "keep each other human."
In the episode Changing Channels, the brothers learn from the Trickster, a disguised 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.
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, but Ellen insists on staying 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 failed to kill Lucifer and lost two allies and friends, Dean becomes more disillusioned and hopeless. With his experience in Heaven during Dark Side of the Moon, where he spends time in heaven and finds 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.
During Point of No Return, Dean prepares for his possession by Michael before he's found by Sam and Castiel who return him to Bobby's house. They convince Dean to allow them some more time in order to research another method of stopping Lucifer; however, the resurrection of their brother Adam Milligan (who agreed to be Michael's vessel) forces Sam, Bobby and Castiel to keep both Adam and Dean from Zachariah. When Dean escapes and tries to lure the angels, both Castiel and Sam leave to find him, allowing Adam to be removed by angels. Despite Bobby and Castiel's insistence on keeping Dean from Zachariah, Sam allows him to try to rescue Adam. Castiel dispatches the angelic guards and the brothers attempt to rescue Adam, but Sam's ambush on Zachariah fails and Zachariah causes internal damage to both Adam and Sam to coerce Dean to consent to Michael. Ultimately, he relents, but after Zachariah summons Michael, Dean taunts him into sacrificing himself in order to allow Michael in. Zachariah angrily refuses, and Dean stabs him and ushers his brothers out of the room. Unfortunately Adam does not escape in time and is locked in the room with the approaching Michael. As they leave, Dean admits that he would have accepted Michael, but because of Sam's faith he decides that he will "take the fight to them".
It is reluctantly decided that the plan to throw Lucifer back in the cage requires Sam to become Lucifer's vessel. Dean, defeated and heartbroken, promises Sam he'll return to Lisa and Ben once this is all over. Once Sam says "yes" to Lucifer he loses control and closes the portal, then takes his leave to fight his older brother, Michael.
Just as Lucifer and Michael are about to begin, Dean shows up in the Impala to witness the fight as if to try and stop the inevitable one last time. Having had enough of Dean's attempts to save Sam, Lucifer goes on a rampage and begins to beat Dean to a bloody pulp. Lucifer kills Castiel and Bobby as he continues to beat Dean until Sam is able to regain control long enough to open the portal to Lucifer's cage. Sam grabs hold of Michael and falls into the cage. The portal is then sealed, leaving nothing behind but the key.
Castiel, now a seraph returns from the dead, having been resurrected by God, heals Dean and resurrects Bobby. Unsurprisingly, Dean is heartbroken at having lost Sam. Since Michael is no longer in Heaven, Castiel disappears to restore order.
In the end, Dean keeps his promise to Sam and goes to live with Lisa and Ben, but unknown to him, Sam watches outside, having been released from the cage.
One year later, Dean is living a normal life with Lisa and Ben, having a normal job and having the Impala covered up with his weapons locked away in the garage. He seems somewhat happy until he notices supernatural occurrences around his neighborhood. As he prepares to fight, he has an impossible encounter with Azazel, but it turns out to be a hallucination created by djinns and he is snapped out of it by none other than his brother, Sam. Dean is happy to see Sam alive but is soon enraged when he learns that Sam has been out of Lucifer's cage and back on earth for over a year and didn't tell him. Soon, he is reunited with his resurrected grandfather Samuel Campbell and other members of the Campbell Family.
Dean takes Lisa and Ben to Bobby's for safety, and discovers that Bobby knew Sam was back as well and didn't tell him. Dean and Sam use themselves as bait to lure the djinns in but Dean becomes affected again with hallucinations of Azazel killing Lisa and feeding Ben demon blood. Sam is able to snap Dean out of it as the Djinn are captured. Sam leaves after Dean decides to stay with Lisa and Ben.
Dean relocates Lisa and Ben to a different home and starts behaving like his father. He is called back to hunting when Sam finds an abandoned baby from a crime scene, and needs help taking care of it. They take the baby to Samuel, where Dean is distrustful of the Campbells. Samuel wants to raise the baby as a hunter which infuriates Dean, but before they can discuss it any further, the Alpha Shifter arrives and kills one of the cousins, also taking down the rest of the Campbells. Then the Alpha defeats Sam and Dean and takes the baby. Dean returns to Lisa and Ben but is conflicted with staying or hunting with Sam. 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.
Dean is called to a case by Sam to investigate the mysterious deaths of several cops. Dean suggests they call Castiel, but Sam doesn't believe he'll come. To his surprise, Castiel responds to Dean's call and tells them that the staff of Moses is responsible for the deaths. He also informs them that heaven is embroiled in a civil war as Raphael is trying to take over and resume the Apocalypse that Sam and Dean prevented.
They find the child responsible for the deaths and discover that he sold his soul to an angel for the staff. Castiel soul probes the child against Dean's wishes but with Sam's consent. The angel Balthazar is responsible for the transaction and Castiel tracks him down, with Dean and Sam staying behind and fighting Raphael's angel henchmen who have been hunting Cas. They help Castiel trap Balthazar after Raphael is defeated and force him to relinquish the child's soul. Afterwards, Sam joins Dean in the Impala again as his own car was destroyed, and Dean questions Sam's strange behavior and his time in hell, but Sam doesn't want to talk about it at all.
In Weekend at Bobby's, Dean calls Bobby for help with a lamia and later on to discuss Sam's behavior. Bobby later yells at Dean for being selfish and oblivious to Bobby's own problems. Abashed, Dean flies to Scotland with Sam in an effort to help get Bobby's soul back from Crowley.
Sam and Dean investigate what appears to be a vampire attack, and Dean becomes entangled with the vampire Boris. Sam walks by as Boris attacks Dean, but merely watches as Boris turns Dean into a vampire. Dean notices Sam isn't freaked out about his vampirism, as he can hear Sam's steady heartbeat. Sam tries to reason with Dean, assuring him that Samuel will know what to do. Dean then decides to sneak out to visit Lisa in order to say one last goodbye. While visiting, Dean struggles with his bloodlust for Lisa. He comes close to biting her, but retreats into the hallway. As he is leaving Ben approaches Dean despite Dean's warnings, and Dean shoves Ben into the wall in an effort to put some distance between them. He then leaves and returns to the motel.
Upon Samuel's arrival, Dean demands that he kill him, but Samuel refuses and informs him that there is a cure for vampirism. As long as Dean hasn't fed, then the cure can turn him back. The cure requires blood from the vampire who turned you, so Dean infiltrates the nest, and encounters Boris, who explains to him the vampires' aim. When Boris smells the dead man's blood drop from Dean's syringe, he attacks. Before the vampire can make his move, all the vampires in the nest collapse, including Dean. He has a vision of the Alpha Vampire.
When he awakens, Boris is rallying the coven of the vampire to attack Dean. Dean, however, has the upper hand and takes out the entire nest single-handedly, including Boris. Back at the motel, Dean drinks the cure, and goes through a painful process of turning back. His short time as a vampire flashes before him, highlighting Sam's hesitation to save him from Boris. Dean now has lost trust in his brother completely.
Dean becomes so uncomfortable around Sam, Dean begins making excuses to stay away from him. He informs Bobby of the situation, and digs up information on whatever could possibly be Sam's diagnosis. He then asks aloud for the truth, and is infected with a truth curse from the goddess Veritas where people tell truths to him against their will. Sam, however, proves to be immune to this, as the curse doesn't affect him. 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.
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 are holding the Alpha vampire. When Samuel leaves the room, the brothers take the opportunity to question the creature themselves. The Alpha remembers Dean even by name, referring to him as 'his child for a time'. When the brothers ask the Alpha what Samuel wants from him, the vampire reveals that it is Purgatory Samuel is looking for and that Samuel is merely working for someone else. Dean confronts Samuel about it, but is interrupted by the escape of the Alpha. Christian, revealed as a demon, and a few other demons recapture the Alpha and take it away.
Crpwley 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 states that he thinks it might be best to go back to being the old Sam, Dean accepts his offer, and says it's 'time to get his brother back.'
Dean and Sam are more on the same page now, but Dean still seems to struggle with Sam's behavior and then starts to act as his 'Jiminy Cricket' to Sam's 'Pinocchio'. They investigate a case of crop circle abductions, leading people to believe it is a UFO sighting. Dean decides to check out the crop circles for himself, but gets abducted.
He returns a while later, and walks in on Sam having sex with a hippie chick. Dean expresses irritation at this, and states that he 'had a close encounter, and won it'. However, it's proven that he didn't exactly 'win' anything, as he starts seeing things that no one else can see. There's one moment when Dean's alone, and the door to the motel bursts open and a "little, glowing, hot, naked lady" flies in and starts hitting him. He traps her in the microwave and cooks her, but when he tries to show Sam her remains, Sam can't see them. Sam then draws the conclusion that the UFO encounters are because of Fairies.
Dean and Sam go to visit Marion, a woman they interviewed earlier who had said that fairies were behind the disappearances. She tells them all about fairies, including that they like cream and that they must count every grain of salt or sugar that is spilled in front of them. After they leave, they see Mr. Brennan loading boxes of cream into his car. Dean breaks into his shop and sees elves working on watches for him. Afterwards, Dean is being stalked by a fairy, a Red Cap in particular, and he mistakenly tackles a midget and is arrested for a hate crime. While in jail, Dean was being beaten by the Red Cap in his jail cell, but is saved by Sam in time and is released from jail the next morning. The midget, who was also the district attorney for Tipton County, dropped the charges against him. Dean learns that the leprechaun struck terms of making a deal with Sam, to lift his soul from the cage (and make him a 'real boy'). He questions Sam's way of thinking, and wonders if Sam is having second thoughts.
Dean quickly becomes tired of working for Crowley, as he sees that it's not getting them anywhere. He tries to reason with Sam that Crowley may not keep his end, but Sam has left the room. When Dean slowly walks the motel room looking for Sam, he gets knocked out by demons, led by none other than Meg. Dean responds emotionally, saying he's been dying to see her again to get back at her for being responsible of Ellen and Jo's deaths. Meg seemingly approves of this, but not before demanding where their "boss" is. While neither of the brothers answer, she puts a knife to Dean's neck, getting impatient. Sam, however, merely laughs at her, and reassures Dean that she can't kill them because she needs them to get her to Crowley so she could kill him. Dean says he hopes they both lose. Sam suggests that she works with them and makes a deal with her, which Dean is not in favor of.
When the demons leave, he confronts Sam about it. He is unsure whether working with a demon again will go anywhere good, and their tendencies to double-cross work against them. Sam assures Dean that they will get the jump on the demons first because he'll be bringing Castiel along for the ride. Dean expresses surprise when Sam actually succeeds in calling the angel.
When Castiel performs a ritual to find Crowley's location and can't find him, Dean suggests they search Samuel's office for a map or any hint on Crowley's base. They are interrupted by Samuel. Dean first suggests that Samuel tells them where Crowley is, which he refuses to do. When all his attempts to obtain the information lead to nothing, Dean consents to ask Samuel what Crowley is holding over him. Samuel takes a picture out of his desk drawer, and hands it to Dean: it's a picture of their mother, Mary. Dean expresses a somber opposition towards working with Crowley to bring Mary back, and tries to convince Samuel to learn from the brothers' mistakes. When Samuel's had enough of his protests, he asks them to leave. Samuel later knocks on their door to give them the location, despite his wishing for them not to go there.
Before they leave for the prison, Castiel talks to Dean about how he doesn't think retrieving Sam's soul is wise. He believes that Sam will be broken beyond repair if they force his "mutilated" soul back in. Dean doesn't want to believe this, and reassures Castiel that they'll deal with whatever complications come up.
Upon arriving and infiltrating the prison, Dean expresses apprehension on how easy it was getting in, which then comes to fruition when the guards are let out and come after the group. When Meg decides to stay behind to hold off the hounds, Dean, Sam, and Castiel head further in the prison in search for Crowley. Castiel is banished by Samuel, much to Dean's surprise, and the brothers are locked in separate cells by demons. When Samuel later tries to make Dean understand, the two express different ways of seeing the betrayal: Samuel saw it as Dean choosing Sam over Mary, while Dean saw it as Samuel choosing Crowley over his own grandsons. He also challenges Samuel that he's 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 Ghouls. Dean fights back, but to no avail. Sam later busts in and kills the ghouls.
Dean then finds where Christian has Meg, kills Christian, and then sets off the fire alarm to get Crowley's attention. When the King of Hell enters the room, the brothers confront him and demand he return Sam's soul. Crowley says he can't, and that he was lucky enough to get his body out of the cage. Crowley breaks from the devil's trap, and flings Sam and Dean pinned to the wall. Castiel soon arrives on the scene and rescues them.
Later, outside the prison, Dean thanks Castiel for his help. Castiel tells Dean about the civil war in Heaven, and Dean is genuinely concerned, and asks if there's anything they can do to help. When the angel says there's nothing they can do and apologizes, Dean reassures him that there's no need to apologize, that they understand and are his friends. Dean tries to reason with Sam, saying that he doesn't know how wrong, how messed up he is without a soul. Sam disagrees and walks away without a word.
Dean, now more desperate than ever for Sam's soul, seeks out Death to ask for his help. Dean requests not only for Sam's soul, but for their half-brother Adam as well (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, sets up a chain of events. The girl survives, but innocent people die in her place, as she is disrupting the natural order being alive. Dean tries to save one of these innocent people, going as far as taking off Death's ring. Realizing the mistake he's made, he reluctantly accepts defeat, and finally decides to kill the girl.
Meanwhile, Sam has tied Bobby up and intends to kill him. Dean manages to arrive in time and knocks Sam out and chains him to the cot in the panic room. Dean expresses deep sadness at how he's failed to fulfill his 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, and finds Death eating. Dean gives back the horseman's ring, and claims his loss of their wager. Dean then informs him that his wager was rigged right from the start, as he thinks Death would've known he wouldn't last a day. Death denies this, and declares their business is finished, but he offers a bonus: he will still go to Hell to raise Sam's soul. He then encourages Dean to keep digging in what he's learning regarding the souls.
Dean quickly heads to the panic room, as they witness Sam struggling to stay away from Death, who has returned with Sam's soul. Despite Sam's protests, Death restores Sam's soul to his body, with a conflicted Dean watching as his brother screams in pain. A week passes and Sam has still not woken up. During this time, Dean calls Castiel to check on Sam and asks if 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 he doesn't remember anything other than jumping into the cage. Dean is surprised but relieved to hear this, despite Bobby's suspicion. Dean and Sam go to work on a case involving dragons, during which Dean is overjoyed to have his brother back.
When Bobby finds a sword that could kill the dragons, he sends Dean goes to visit Dr. Visyak. When Dean tries to pull the sword from the stone he only falls off, and has to resort to blowing up the stone instead. He returns to Sam and the two go after the dragons. They fight off the dragons and save the girls they had held captive. Later on as Dean is happily going thought the pile of gold they found at the dragon lair, Sam confronts him about being soulless and apologizes to Dean. Dean is shocked that Sam knows and asks who told Sam (who then answers that it was Castiel). Dean tells Sam about the wall inside his head, and that what Sam became wasn't really him.
Then Sam gets a mysterious text about a case, which gets Dean worried. As they investigate, Dean finds out that Sam has been in this town before, and wants to leave. Sam doesn't want to, which gets Dean angry and he begins to quote John's rules. But they stick around, and Sam begins remembering what happened, much to Dean's displeasure. They do figure out its an Arachne with a grudge against Sam, and defeat it. Afterwards, Sam and Dean have a talk about what happened and Dean tries to make Sam feel better. Then Sam collapses, and Dean rushes to Sam calling his name.
Minutes pass by as a worried Dean tries to wake Sam up. Sam does wake up and Dean helps him up. Dean and Sam talk about what just happened and Dean tells Sam not to scratch the wall again. With that they head out on a case with a mannequin killing people, but Dean gets called away by an "emergency" call from Ben. When Dean arrives, he finds Lisa going out on a date. He and Lisa have a talk, which later results in him leaving permanently. When he comes back, he helps Sam finish the case.
Then things take a turn for the weird when Balthazar shows up with someone on his tail. He gives Dean a "key" and sends the two into the world of "Jared" and "Jensen", where their lives are a television show. After a great deal of effort they manage to get back to their own world, 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 Dean shoots her. It turns out, Dean was possessed by Eve's latest invention. Unsure who its possessing, the group rid themselves of their weapons. In a turn of events, its Bobby who is possessed by the Khan worm, and Dean questions and kills it. Bobby does survive.
Things again become strange when Balthazar alters history and saves the Titanic. With history changed, Dean finally wins rock, paper, scissors when trying to see who's going to cheer Bobby up and now drives a mustang. He and Sam investigate a string of strange murders, and make the connect to the Titanic. They summon Balthazar who tells them why he did and leaves. When almost killed by Fate, Castiel saves them. He tells them, 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 phoenix can kill her. Dean finds the diary of Samuel Colt, which en-tales how he killed on. So they enlist the help of Castiel to send them back that time to find the ashes. Dean is beside himself with excitement to go back to the wild west. So they head back, and find out the Phoenix is killing people. So Dean tries to set up posse, but it backfires and he ends up as sheriff. So Dean and Finch end up having a showdown, and Dean wins. As Dean rushes for the ashes, Castiel transports them back. Lucky for them, Samuel Colt got the ashes and mailed it to them.
So Sam, Dean, Castiel and Bobby, begin to hunt for Eve. Thanks to Lenore's information, they find out that Eve is in Organ Pass, and they head there. There, they discover Eve's experiments, and Dean even names one of her experiments when Bobby gives him naming rights. So Dean names a cross-breed between a wrath and vampire, Jefferson Starship. Then the police show up (Dean hides), but they too are Jefferson Starships. They eventually find Eve in a diner working as a waitress, and she tries to makes a deal with them. She even turns into Mary Winchester to get them to work with her, but Dean refuses nether less, and tells her to bite him. Which she does, only to find out that Dean had earlier swallowed some phoenix ashes earlier.
After their encounter with Eve, everyone begins to question Castiel. Everyone but Dean who still believes in Castiel. When Castiel comes to save them, he accidentally gives himself away, and Dean catches this. So Dean helps them trap Castiel, and questions him. Dean also tells Castiel he is like a brother to him, and asks him to stop. When demon come, Dean is forced to flee, but takes one last look at Castiel and leaves. Castiel is now free, and visits Dean. After a talk, Dean and Castiel's relationship breaks, and Castiel leaves.
After Castiel's visit, Bobby reveals that Castiel also stole a diary from Bobby's house. As they read Bobby's photocopies, Dean gets a call from Ben. Ben tells Dean that men are in the house and killed Lisa's boyfriend. Dean tries to help from the phone, but Ben too is captured. Crowley, now on the other line, tells Dean to back off or he will kill Lisa and Ben. Dean refuses to back down, and begins to hunt down Lisa and Ben. He even begins to torture demons for their location. Sam tries to help him, but Dean tells Sam to back off. Then Dean accidentally breaks the Devil's Trap, and the demon attack. Castiel comes in and saves Dean. Dean doesn't want anything to do with Castiel though. Later, its Balthazar who gives Dean Lisa and Ben's location.
So Balthazar transports them there, and they storm the building. Dean finds Ben and Lisa after taking out some of Crowley's goons. He unties them, only to find out that Lisa is possessed by a demon, and she hold Ben hostage. Dean manages to free Ben by splashing holy water at "Lisa". Then he manages to free the knife from "Lisa's" hand and begins to exorcise her. He continues to exorcise her after the demon stabbed Lisa's body. Once the demon is out, Dean moves quickly to save Lisa's life, and carries her out to the car, and rushes her to the hospital. Dean stays by Lisa's bedside, and then Castiel arrives and heals her. Dean asks Castiel for favor to erase Lisa and Ben's memory of him. Dean approaches them after this and apologizes to them. In the car, Sam tries to help Dean, but Dean tells Sam not to mention Lisa or Ben to him ever again, or he will break Sam's nose. A week later, Bobby, Dean and Sam go looking for Dr. Visyak, and they find her in an alley. She is bleeding and tells them how to open the door to Purgatory. Then Castiel appears, and Dean tells Castiel to leave. Castiel tells him he is done playing nice, and promises to put Sam back. This confuses Dean, until Castiel touches Sam, and breaks down the wall inside his head, sending Sam into a comatose state. Dean stays by Sam's bedside, while Sam is comatose. After Balthazar giving them Castiel's location, Bobby manages to convince Dean to go with him after Castiel. Before Dean leaves, he leaves Sam their location. So Dean and Bobby head out. When they arrive they scope out the place, which is full of angels. Then a demon cloud comes, and Dean and Bobby run back to the Impala. The demon smash into the impala, flipping it over.
When Dean wakes up, he checks on Bobby, who is okay. 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.
When Castiel leaves, Dean and the others head back to Bobby's, and Dean begins to fix the Impala, since there is nothing else he can do. Dean is concerned for Sam's mental health since the wall is gone. Dean admits to Bobby that he can't take anymore hits, and will believe that Sam is "fine". Then they manage to summon and bind Death.
Dean tries to appease Death, and then Castiel shows up and Dean orders Death to kill him. Castiel frees Death and leaves. Death tells Dean the only way to stop Castiel is for Castiel to let the souls back into Purgatory. Dean doesn't think Castiel will do this, until Castiel comes asking for help. In turn, Dean helps Castiel and the souls are released back into Purgatory, but the Leviathans remain. Dean watches them destroy Castiel and spread throughout the water, leaving only his trenchcoat behind.
He also deals with Sam seeing Lucifer while looking into a Leviathan killing. When he returns, he finds Sam gone. Dean eventually finds Sam and convinces him that his reality is real. He and Sam return to Bobby's, but find it burned down. Dean calls Bobby, but gets Bobby's voice mail, and finally tells Bobby how he is really doing. He and Sam are soon attacked by Edgar, and Dean's leg gets broken. On the way to the hospital, Dean begs them not to take them to Sioux Falls General, but is ignored.
He wakes up with his leg in a cast, and Bobby comes in and saves Dean from the hospital. Dean spends 3 weeks in a cast until Sam takes off, and Dean saws the cast off. Dean soon catches up with Sam, and punches Sam for taking the Impala. Sam explains the situation to Dean, and Dean appears to agree but later kills Amy behind Sam's back. Dean feel guilty about this, plus feeling guilty lying to Sam about it and begins drinking more than normal. This guilt is what Osiris hones onto and puts Dean on trial. On trial he encounters Jo again, and before Osiris can call the third witness, Dean accepts the charges. Dean is saved when Sam stabs Osiris.
Dean still has nightmares about Castiel dying and killing Amy, which causes him to wake up and start drinking. But he continues on and he and Sam go to work on a case where witches are wreaking havoc in Prosperity, Indiana. When they fail to stop the witches, Sam and Dean manage to get Maggie and Don to calm down. Sam approaches Dean about what's bothering him, but Dean doesn't tell Sam anything.
When Dean is cloned by a Leviathan, Dean is forced to lock the Impala up and it not too happy about it. Although, before he can cut the off his clone, the clone tells Sam that Dean killed Amy. This causes Sam to leave Dean. A week later Dean runs into Sam in Lily Dale. After some advice from the other side, Dean apologizes to Sam but says he doesn't feel bad for what he did to Amy. He and Sam soon reconcile.
In The Slice Girls, Dean unknowingly sleeps with and has a daughter, named Emma, with an Amazon. The Amazons age and grow in a very short period of time until they reach adulthood, and so the baby is birthed in mere hours, and reaches adolescence in a few days. Amazon teens must go through a rite of passage in which they must kill their fathers - the event that Dean and Sam were investigating in the first place. When Dean's daughter comes to Dean, she lies and tells him she needs his help to escape the other Amazons. A wary Dean eventually sees through her scheme and they end up drawing their weapons and stand ready to face one another. Sam, recently enlightened to his brother's situation, upon entering the room decides that Dean cannot bring himself to kill his own daughter, and so, after a short confrontation, he kills her. Sam then reminds Dean that he had to do it, just like Dean "had" to kill Amy.
Presently, Dean is trapped in Purgatory with Castiel, after having killed the Leviathan leader Dick Roman.
Season 8 starts with Dean coming back from Purgatory after spending one year there (it is unknown how time differs in Purgatory, so it's possible Dean was there for a significantly longer period of time). He came back with the help of a friend, Benny, who is a vampire. Dean carries Benny's soul out of Purgatory and resurrects him on earth before the both of them go their separate ways. Dean travels to the safehouse in Whitefish, Montana where he bumps into Sam. The brothers reunite. When Sam asks Dean where he had been and what happened to Castiel, Dean replies saying that he had been in Purgatory and as far as he knows Castiel didn't make it. When Dean asks about what Sam has been doing Sam truthfully tells him that he has quit hunting and has been in an relationship with a girl, Amelia. When Dean asks if Sam ever tried to find him he replies that he just drove away. Dean starts checking Sam's old mobiles (which he had ditched) in which he found voicemails of Kevin Tran who had managed to escape from Crowley and is in hiding. Sam and Dean find him and they discover that he was taken to Crowley to read another Word of God. The tablet is entitled Demons, and details different ways to kill or banish them, including a spell to shut the gates of Hell. Sam and Dean decide to to seal the Gates of Hell forever and they bring Kevin into this plan. Kevin agrees, but his girlfriend then appears possessed by Crowley. Crowley tells Kevin to come with him but instead he escapes with the Winchesters. Driven mad by losing the opportunity of having Kevin read the tablet, Crowley kills Kevin's girlfriend. After a while Dean gets a call from Benny who is seen to be taking a break. Dean talks to Benny and says that he can't call just to get an update but if he needs help he will be there.
When Sam falls into a coma, he takes him to a local hospital and finds out that Sam is going to die. Dean then goes to a church and prays to all the angels for help. He later lets "Ezekiel" possess Sam so that they both may heal.
In Devil May Care, Dean teams up with Sam, when the latter is a lot healthier, to hunt Abaddon. When Sam is knocked unconscious by three demons, Ezekiel rescues him. Dean is still skeptical about the angel's motives, who only asks him to trust him. He also stops Kevin from leaving them, and calls him family.
In I'm No Angel, Sam and Dean try to reach Castiel before the angels can get their hands on him. Fortunately, they're able to save Cas, so they take him back to the HQ. When learning that Cas had finally had sex, he makes a joke about it. Later on, Dean is given the choice of having the angel heal Sam or keep Cas around. Dean makes the hard decision of having the angel, so he ended up having to kick Cas out of their lives.
In Slumber Party, Sam and Dean fight to stop The Wicked Witch from entering Oz. They meet up again with Charlie. After she gets killed by the Witch, Dean begs "Ezekiel" to save her, which he reluctantly does. Later, Dean and Sam get possessed from the Witch and are turned into minions of hers. They then hunt down Charlie and Dorothy , to try and kill them. They aren't turned back until Charlie saves their asses by killing the Witch.
In Dog Dean Afternoon, Sam and Dean solve two bizarre cases in which a dog is the sole witness. Dean uses a spell that gives him the ability to talk to animals. He gets along quite well with their witness, despite the fact that he doesn't really like dogs.
In Bad Boys, it is revealed that Dean was sent to a boys home, from his father, because he lost all their money. The episode showed a couple flashbacks about him there. He was sassy when he first got there, mad that his father left him there. But, towards the end he was upset to go. Also, when there, he met a girl Robin, that he developed a crush on.
In Rock and a Hard Place, he and Sam catch up again with Sheriff Mills. In this episode, Dean also renews his virginity and joins a chastity group. In the classic Dean fashion, he has sex with an ex-porn star, after the meeting. This then causes him to get abducted by the Vesta, the brothers originally came to hunt down. At the end, Dean was about to tell Sam about the angel inside him, but then gets stopped.
In Holy Terror, the mid-season finale, Dean is still unsure of the idea to not tell Sammy, but because of "Ezekiel", he still uses the Trials as an excuse. He also reveals to Cas, that he didn't tell Sam that he had asked Cas to leave them, and continues lying.
Dean also finds out that Ezekiel isn't actually "Ezekiel", but is actually Gadreel, a good angel from Heaven that's doing bad things on Earth.
At the Man of Letters base, shit goes down. Dean gets help from Kevin's tablet to expel an angel from the body. He uses the ritual to remove Gadreel. Doing what he knows is right, he tells Sam all about how he wanted to save him, so he used an angel. But, the angel wasn't who he said he was, and is actually a bad guy, and needs to go.
Sam punches him and knocks him out for a minute. Upon waking, Dean follows Sam in the next room to see Kevin's body falling to the floor, lifeless. Sam then tells Dean that he isn't actually Sam and is instead, Gadreel, still, because the he messed up the ritual. Then, he leaves, leaving Dean alone, having lost both Kevin and Sam.
In Road Trip, after burning Kevin's body, Dean prepares to go after Gadreel for revenge before Castiel shows up and convinces him to work with Crowley to expel Gadreel instead. Dean does so reluctantly and with Crowley's help, tracks Gadreel through the Impala which he has stolen. Dean confronts Gadreel who knocks him out, but causes enough of a distraction that Castiel is able to subdue the rogue angel. After tying up Gadreel, Dean confronts him about his actions and betrayal, but Gadreel refuses to leave Sam and insists he is doing what he has to. Dean allows Crowley to start torturing Gadreel to try to bring out Sam's mind, but eventually can't watch anymore and leaves with Castiel comforting him. When Crowley breaks into Gadreel's "factory settings," Dean has to restrain Castiel from harming him when he learns who the angel actually is. As Gadreel is resistant to torture, Dean agrees to allow Crowley possess Sam to help him expel the angel in exchange for his freedom. The plan works and Gadreel is expelled. After Castiel heals Sam of the damage from the torture and some more of his injuries from the Trials, Dean tries to apologize and then leaves on his own to hunt Gadreel, not wanting anyone else to get hurt. Sam is so furious he doesn't even try to stop Dean.
In First Born, alone in a bar, Dean is approached by Crowley for help with finding the First Blade, the only weapon that can kill Abaddon. Dean reluctantly allies himself with the demon and begins the search by looking for information on a hunt his father did where he captured, interrogated and exorcised a demon who claimed to know about the Blade. The information they find leads them to a hunter named Tara and eventually to the biblical Cain who is now a very powerful demon. Dean asks for Cain's help in locating the Blade, telling him they need to kill a Knight of Hell. Dean is pissed at Crowley when Cain reveals that he created the Knights which Crowley knew, but is surprised to learn that Cain was the one that killed them all. When Cain refuses to help, Dean sneaks back with Crowley to search for the Blade only to be caught by Cain. When four demons show up, Dean is left to fight three of them single-handedly. He wins and Cain tells him how he slaughtered the Knights after they kidnapped his wife who was killed by Abaddon. Cain still refuses to help and is unimpressed by Dean's threats. Cain leaves as a demon army arrives, but returns willing to help and explains that the Blade is useless without the Mark of Cain which he can transfer to someone worthy, such as another killer. He'd let Dean fight alone to see if he was worthy and offers him the Mark, trying to warn him that it comes with a terrible price. Dean takes the Mark anyway without learning what the price is and after telling them that the Blade is at the bottom of the ocean, Cain teleports Dean and Crowley to safety while he takes on the demon army, asking for Dean to return after he kills Abaddon to kill him too. Dean is pissed at Crowley as he realizes Crowley used him to get access to the Blade. Crowley confirms this, but while Dean threatens to kill him when everything is over, he recognizes he still needs Crowley and sends him after the Blade.
In King of the Damned, in the presence of the First Blade, the Mark grants Dean immunity to Abaddon's powers at first with great concentration and then no effort. He also displays telekinesis and strength great enough to lift Abadddon off her feet effortlessly. However, the Mark and Blade's effects cause him to go overboard and repeatedly stab the dead Abaddon after he kills her.
In Do You Believe In Miracles?, Dean is shown to be over-aggressive and has no control over his desire to kill Metatron. His need for the First Blade is also very detrimental to his health. He even works with Crowley to hunt down Metatron. When he does find Metatron, he tries to kill him but fails. Metatron then stabs Dean in the heart, killing him. Crowley approaches Dean and tells him that Dean is a lot like Cain who also died because he wasn't willing to kill innocents but Cain's very sacrifice is what made him become a demon. Crowley then tells Dean to open his eyes. Dean does so, but returns as a demon (more specifically a knight of hell).
In Black, Dean is seen at a bar drinking with Crowley. Dean later has sex with a waitress called Ann Marie.
In Reichenbach, Dean tries to touch a stripper therefore a security guard tries to stop him, as demon Dean, he violently assaults him. Sam later locks up Dean after he attacks Cole Trenton.
In Soul Survivor Dean gets handcuffed by Sam showing that Dean has true hatred against Sam, he tells Sam that he was the reason Mary Winchester, their mother, died. Dean manages to escape, he looks for Sam with a hammer, the angel Castiel, stops Dean with his new grace. Sam cures Dean and they hit the road. Dean is a human once again.
In Paper Moon Dean relaxes with Sam as they sit by a lake, when they read about unknown killings caused by a unknown creature. That creature turns out to be Kate the werewolf from Bitten.
Dean has green eyes, freckles on his face and short-cropped hair that is dark blonde. He is 6'1" - ironically making him shorter than his younger brother Sam - and muscular. Dean is noted to be "handsome" or even "pretty" by other characters on multiple occasions.
He usually wears a plaid shirt over a T-shirt, jeans, and boots, unless he has to wear a disguise in order to impersonate someone. Until Season 6, Dean often wore his father's leather jacket. He also used to wear a watch and a silver ring. As of Season 4, Dean has a hand-shaped burn scar on his left shoulder from where Castiel pulled him out of Hell. This mark has since disappeared from his body.
For the first four seasons, Dean also wore an amulet around his neck that resembled the head of a bull made of brass, attached to a black cord. This amulet was given to him by Sam as a Christmas gift when they were children. Throughout the first half of Season 5, Castiel attempts to use this amulet to find God, as its claimed power is to burn hot in God's presence. When Castiel is unsuccessful, he declares the amulet "useless," and Dean throws it away.
Dean mentions to Haley Collins in Season 1 that he doesn't wear shorts.
Dean has recently received the Mark of Cain, manifesting just below his elbow. Since separating from Sam his appearance has become more scruffy and unshaven.
Dean briefly possessed a pair of black eyes while he was a demon but they are gone now that he's human again.
Dean is shown to be by turns understanding, kind, funny, mischievous, and, in contrast to his younger brother, a little immature. At an early age, Dean was trained by his father, John Winchester, to hunt and kill creatures of the supernatural. However, unlike his brother Sam, he did not resent his father for having him "raised like a warrior". He seemed to prefer hunting the supernatural over any normal "apple pie" life, though it was revealed that when he was Sixteen, he did in fact desire (or at least hope for) a normal life: He just couldn't leave Sam. This however did not last long, as later on while still Sixteen, following a Werewolf hunt he realized just how unique his life was. However, by Season 7, following all that he has seen and done, Dean admits to Eliot Ness that he no longer wants to be a hunter and would give it up if he could.
Dean is an avid fan of classic rock music. Many of his aliases have included the names of famous rock musicians. He is known to use crude humor, make sexual innuendos and indulge in pornography (especially for Busty Asian Beauties).
Dean typically avoids emotional intimacy, preferring to engage with women only as sexual partners. However, he has had a few long term relationships over the years, with Cassie Robinson, pre-series, and Lisa Braeden, in Season 6. After the tragic events that led Dean to ask Castiel to make it as if Lisa and her son Ben had never met him, Dean seemed to give up on ever having a family other than his brother. After his break up with Lisa, Dean was reluctant to get back into his old routine of "New Town, New Girl". However, the one time he was shown to indulge in a one night stand in The Slice Girls he ended up fathering an Amazon that tried to kill him. He was reluctant to defend himself against his Amazonian daughter and Sam ended up making the kill. After these events he became even more reluctant to get in a physical relationship let alone an emotional one.
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 keeps himself in excellent physical shape, he is known to have very bad eating habits. He is often shown enjoying greasy, fattening or otherwise unhealthy food, especially cheeseburgers and pie, and dismisses salads as "rabbit food".
Dean is terrified of flying and claims that is the reason why he drives everywhere.
Despite his working knowledge of the supernatural, Dean is skeptical with regard to the "good aspects of religion." However, he becomes somewhat more open-minded after meeting the angel Castiel.
Dean has also shown on several occasions that he is a great fan of movies, particularly westerns, and was thrilled to be given a chance to go to the old west. He was also overjoyed when he met and was able to work with Eliot Ness, frequently referencing The Untouchables during the episode.
Dean is typically ruthless and aggressive when he is hunting, a task which he approaches enthusiastically, making him the more merciless of the Winchester siblings. But in spite of that, he is capable of acknowledging whenever he's going too far, as seen with his interaction with Lenore and Gordon (Bloodlust). Whereas Sam is at least willing to sympathize with what they hunt, provided that their motives can be counted as morally gray, Dean mostly sees the world as black and white. He passionately despises what he hunts, especially demons, and is prepared to kill without question more often than not, unlike his brother. This has caused him to develop a bigotry against most supernatural creatures and beings.
He dislikes showing his emotions to monsters, and when facing beings like Abaddon or Azazel he acts threatening and determined. When facing the angels, even knowing what they could do to him, Dean is sarcastic, rude, and insulting. The only being he is openly afraid of is Death; on the rare occasions that they meet, Dean is nervous and cautious, and when Dean is angry or frustrated enough to talk back, he becomes visibly scared and backs off the moment Death appears annoyed.
Despite these traits, Dean is very laid-back and well-disposed when not on the hunt, and he values the safety of his family and innocent civilians above all else, even his own life. Though on occasion he can be somewhat impulsive as well as arrogant, Dean is both extremely intelligent and competent. He is more likely to exhibit irrational behavior when his family is threatened.
Underneath his seeming arrogance and self-righteousness, Dean shows many signs of self-loathing and insecurity. He always blames himself when things go seriously wrong, regardless of whether he's to blame or not. He constantly downplays himself and his achievements. He puts up with abuse from others, simply because he believes he deserves it. Despite being the better hunter, Dean admits he doesn't see himself as anything other than a "grunt". Likewise he constantly is willing to throw his life away, at least in part because he doesn't value it as worth much. He is constantly called out for feeling this way by Bobby and Sam. But regardless his feelings always return. These feelings can be traced back to his relationship with his father John, who at times treated him as a tool rather than as a son and who held him to unrealistic or unfair standards.
Dean enjoys the uncomplicated things in life, such as good food and television. He almost constantly displays some level of humorous behavior, and frequently makes light of tense situations. He sometimes appears foolish due to this habit, but this seems to be merely his means of dealing with the stress of hunting.
Dean shows on multiple occasions a soft spot for children. He is very good with them, able to talk to them with ease, and he is always very sympathetic; this most likely stems from the fact he practically raised Sam when he was a child. Dean's affection extends to nearly all children, particularly young ones, although he also cares about teenagers. Dean is more willing to put his life in danger for children than he is for nearly any others. Dean's affection even extends to monster children, and despite his ruthless approach to hunting he's usually unwilling to kill monster children unless he has a crucial need.
After his extraction from Hell by Castiel, Dean begins to exhibit noticeable anxiety and experience chronic, abominable nightmares of his experience there. He also seems to have some form of flashback after seeing a collection of masks in the episode It's the Great Pumpkin, Sam Winchester, when blood is seen around eyes, such as Alistair's first appearance, when a statue's eyes bled. Initially, Dean denies remembering anything of his time in Hell, but eventually confesses to Sam that he remembers every detail. He rejects any discussion about it, either not wishing to burden his brother with his pain or not wanting to relive the details of the "indescribable things" he saw. He later reveals that he not only saw terrible things, but (in Hell time) was in Hell for around forty years. He confesses that he lasted thirty years without torturing other souls so as to escape the torment himself, but that he finally broke down and tortured for the last ten years. Dean's experience in Hell left a profound mark on him. He exhibits extreme grief and guilt, both for his own torment and for the fact that he eventually gave in and tormented others. Due to this, he believes he was unworthy of rescue. He has also explained to his brother that he wishes he couldn't feel anything, as the sorrow he feels is so overwhelming. He has become obsessed with saving people, often going without sleep in order to save as many as he can. In the episode Family Remains, however, Dean states it is not just the fact he tortured souls, but the fact he enjoyed it which causes his guilt and shame. Taking up the instruments of torture himself gave him the opportunity to put his pain on other unfortunate souls. It was this act, of a righteous man turning on others, that broke the first seal.
Another side of Dean shown recently is his utter disgust at Sam for many of his dangerous or foolish actions, such as drinking demon blood, and having a sexual relationship with a demon, possibly because he is scared of Sam becoming a demon like the ones he saw in Hell. While he remains angry at Sam, he vows to save his brother and still loves him. Dean also realizes family isn't perfect and there will always be times when they hurt him. In the final episode of season 4 after the argument with Bobby when he was in the "safe house", he forgave his brother during the final few moments when Lucifer was rising.
As of Season 5 Dean does not trust Sam, and feels as if he is holding himself back and putting the world in jeopardy just to keep Sam safe. He tells Sam that Lucifer will use the fact that they are family and have love for each other against them until he was sent to the future by Zachariah. Once there, he realized that he and Sam kept each other grounded, and when he got back, he immediately called his brother. They were a team again, even though it was difficult for Dean to trust his brother again, as Sam continued to lie to him.
After his time in Hell, Dean slowly started to use alcohol as a crutch. He cut back on his drinking while he was living with the Braedons between Seasons 5 and 6 but after being kicked out of the Braedon Household after the events of Live Free or Twihard and You Can't Handle the Truth his long term depression worsened and he dove back into the bottle. In Season 7 both Bobby and Sam stated that his drinking was becoming a problem that could potentially cost him his life during a hunt.
Following Bobby's death at the hands of Dick Roman, Dean developed a very strong, obsessive revenge streak in him and spent the entirety of Season 7 hunting Dick down to kill him. As part of Bobby's last wishes he tried to let go of his anger and vengeance, and while in the end he succeeded in killing Dick, it was as part of the job and not for vengeance. However, this caused to him be sent to Purgatory in the process, where he resided for a year (possibly much longer, as time moves differently between dimensions).
The constant life-or-death situations Dean was forced into in Purgatory created an extreme change in him. While he was stuck there, he became emotionless and paranoid of the fear of getting attacked. He killed monsters of Purgatory with ease and was always fighting for his survival. When returned back to Earth, his new outlook on life was clear. He became hardened, emotionless, and at times ruthless; his humor and puns were nonexistent when hunting unlike in Season 7. That has changed with Castiel's return from Purgatory after which he started to show his lighthearted side again.
Having a now haunted sense of self created in him during that year, he became firmer in his belief of hunting. He had personally seen all the monsters they hunted in Purgatory and in doing so, developed a strong sense of responsibility to the people they saved. Dean now believes that it is their duty to save people and quitting out of the hunting business is permanently out of the question. Despite becoming more ruthless, Dean has developed more faith in monsters managing to recover their humanity, as shown with him willing to let Kate go, presumably developed from his time with Benny. However following Castiel's return, Dean began to slowly return back to his previous more laid back personality.
Following Kevin's death, and Gadreel taking complete control of Sam, Dean became desperate to save him. When Sam was freed, Dean's self loathing seems to have reached a new height: He claims he's poison, and that anyone near him dies.
Since acquiring the Mark of Cain, Dean's personality began to alter, turning darker. He has since shown extreme levels of aggression and wrath, an example of this is when he fully attacked a good angel and putting an Angel Blade to her throat in Stairway To Heaven. As well as being openly more hostile, even towards his friends and brother. He's also got more distrusting and suspicious, and more hate-filled toward the supernatural.
From what has been seen so far, Dean's transformation into a demon has darkened his personality. As his soul is twisted, he no longer empathizes for others, and only cares for his own needs and wants. He is so far from his former self, that at one point, he stalked Sam through the bunker and attempted to kill him with a hammer, missing only by inches. He also seems to like taking his time with his tasks. While stalking Sam, he talked in a taunting manner, as though he was enjoying himself. This is furthered by the fact that instead of an axe, he decides to use a hammer to break through a door and kill Sam, despite both tasks requiring much more force with a hammer than with an axe. Dean as a demon apparently cares about the natural order, something old Dean despised. He even considered himself, as a demon, a part of the natural order, and that it was all set up in this certain way.
Sure enough, the transformation has turned Dean more selfish and arrogant, acting like a hedonist and only caring about himself, completely in opposition to his former personality. He has kept some familiar traits, such as a love of drinking, roadhouses and games such as pool, darts and foosball. Dean is now noticeably more brutal, happily beating people and demons beyond a reasonable point, with limited provocation. He is also colder, and while initially coming across down-to-earth and charismatic, he quickly turned cold and ruthless when others proved to be uncooperative, as shown by him outright shaming and humiliating Ann Marie for sleeping with him the moment she rejected his advances, not caring that he had left her near tears.
Dean's transformation has also caused him to no longer care for Sam, shown by how he told Cole that he didn't care what he did to Sam, and even threatening Sam himself. He has also shown to no longer care about innocent people, willing to kill a cheating housewife just to sate the Mark's need for a kill and instead killing her husband, as well as calling his beloved Impala 'Just a car' and not bothering to tend to it's condition.
Dean 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 brushed stainless steel Colt 1911 with ivory grips, which John is seen using in a flashback, and also uses a Baikal sawed-off double barrel shotgun when he needs extra firepower. However lately he has used a lever action Winchester 1887 shotgun (given to him by Jo before she died) on a more regular basis than his usual shotgun.
He has also been seen with an G3 SG1 marksman rifle in Simon Said and All Dogs Go To Heaven and was proficient enough with the weapon to act as a sniper and kill several skinwalkers. Dean is shown to possess a large machete in Dead Man's Blood, and among other regular hunting items. Also, both Dean and Sam have acquired angelic blades which Dean has successfully used. Dean uses one to kill Zachariah, becoming the first known non-angel to kill an angel in the series. After emerging from Purgatory, Dean started using a large, machete-like blade from the monster realm. The blade is crude in design, featuring a large bone hilt and a stone-like blade. The blade is powerful as Dean used it to behead a Leviathan and later a group of vampires.
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.
Since moving in to the Men of Letters Bunker, Dean has kept many of his weapons hanging up on his wall.
The First Blade is another one of Dean's weapons that can kill any demon no matter their age or power. Because it draws its power from the mark, which has the power of Lucifer, it can kill any supernatural being Lucifer could kill. The First Blade can only be used if the user has the Mark of Cain which means only Dean could use it and make it powerful to kill anyone. The Mark of Cain gives him incredible strength, telekinesis (only in the presence of the blade) and immunity to all demonic powers, as seen in King of the Damned.
Dean was transformed into a Knight of Hell by the Mark of Cain and possessed powers that far surpass that of low and mid-tier demons. Since then he has been cured and possesses no supernatural powers. However, with the Mark of Cain still attached to him, Dean will revert back into a Knight of Hell and hence a demon if he dies again in his human form, thus giving him some degree of immortality, even as a human.
Below are powers Dean has demonstrated as a demon. For all the abilities that Dean possessed, yet never demonstrated, see Knights of Hell.
Dean, trained by his father from early childhood as a hunter of the supernatural, possesses excellent combat and hunting abilities; 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 has also bested his younger brother Sam on two separate occasions, despite Sam's equal status as a hunter. Due to his year-long stay in Purgatory and the realms animal-like survival of the fittest environment, Dean greatly honed his hunting skills and instincts. This is shown on a few occasions such when Dean managed to get the jump on a Leviathan and behead him before the latter could even react and effortlessly killed five vampires singlehandedly when helping Benny track down and kill the nest he lived on. When confronted with three demons, despite a hard fight and all three being more powerful than him, Dean was able to take them down single-handedly using only his hand-to-hand experience and the demon killing knife, something which impressed the powerful demon, and his ancestor, Cain greatly.
Dean is well-versed with multiple types of firearms and is an expert marksman, he seldom misses his intended target and can efficiently put down anything vulnerable to bullets. During an old-fashioned duel with Elias Finch, Dean won, killing Finch without being harmed in the process despite Finch getting a shot off. The same also happened in an impromptu duel with werewolf Joy. 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 supernatural mythology. He is well-versed in how police, fire departments and various government agencies (FBI, CDC) typically operate and conduct investigations. He also knows how to both impersonate and evade them effectively. Dean is a virtuoso of escape, evasion, silent movement, and 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 on Sam), car jacking and gaining an 'advantageous purchase' comes naturally to him.
Dean has shown on several occasions to be a natural leader, when operating in groups, he commonly takes command, unless the group includes someone who he himself sees as a leader, such as his father or Bobby. Between him and Sam (and Castiel), he nearly always calls the shots, and acts as de facto leader. Dean also has a skill for motivation, and is a capable orator, being able to motivate others to remain strong and carry on, even in darkest moments, with mere words. This skill also allows him to inspire trust in others, something which comes in handy, when he has to explain the existence of the supernatural to non-believers.
An accomplished mechanic, he maintains his Impala in tip-top condition (and once rebuilt the vehicle entirely from being completely destroyed) and has maintained an intimate knowledge of automobiles and engines since childhood. He is also very talented at making electronic devices, most notably his EMF meter which he made using an old Walkman and an electromagnet powerful to wipe out an entire room full of computers in Ghostfacers.
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.
Dean is also shown to be quite a capable strategist, able to come up with many quite clever, and unorthodox methods of defeating his more powerful opponents, for example he defeated the mother of all, by swallowing Phoenix Ashes (her only weakness) and tricking her in to biting him, causing her to swallow the ashes. He also devised a way to trick Dick Roman so he, Sam and Castiel could not only sneak in, but so that he could catch Dick off-guard and kill him. This was quite a feat as Dick was a master strategist capable of developing very complex and long-term plans. Another show of his strategic abilities is when he manages to capture Crowley by luring him in with a deal and then slapping handcuffs on him when he least expects it painted with a Devil's Trap. Crowley, who is shown to be a cunning strategist himself, is caught completely off-guard by this and doesn't even realize what Dean has fully done until he tells him. However he will also rush into situations, particularly if he doesn't believe there's time to stop and plan. Dean is also a capable survivalist, as he was able to survive a year in Purgatory with limited resources.
Despite all of this, he believes himself to be only a "grunt," but according to Sam, Dean is actually the best at lore (Sam refers to him as a "genius") and is a better hunter than anyone Sam has ever encountered including Sam himself and John Winchester.
Dean was a spirit briefly in In My Time of Dying.
In Dream A Little Dream Of Me, Dean temporarily gained the ability of Dream Walking through African Dream Root. This allowed him to enter Bobby Singer's nightmare and help wake him up. He later used this ability in conjunction with dream root again in Pac-Man Fever to enter Charlie Bradbury's djinn-induced nightmare and wake her up.
In Death Takes A Holiday, Dean temporarily becomes a ghost through astral projection and displays all the normal ghostly powers such as intangibility, invisibility and telekinesis, though it took the help of the ghost of Cole Griffith for him to master it and a lot of concentration compared to more experienced ghosts like Cole who could easily do it. However, combined with Sam, he had enough strength to drop a chandelier on a wooden floor from the ceiling with telekinesis.
In Live Free or Twihard, Dean was turned into a vampire and possessed all their basic abilities, notably enhanced hearing, sensitivity to light, and increased strength, as well as the ability to smell vampires from miles away. He also displayed the ability to jump from a balcony to a lower floor and land on his feet. Using his abilities, Dean was able to take out an entire nest of vampires, including his boss, Boris who was stronger than an ordinary vampire due to his 600 years of age. However, when Dean took the cure that reversed the transformation, his enhanced abilities and vulnerabilities were lost and back to normal human status.
In Appointment In Samarra, Dean became Death for a day, however it was a bet made by Death in order to bring Sam's soul back from Lucifer's Cage. Dean was required to put on Death's ring and do his work for 24 hours without taking it off, Dean became invisible had the ability to teleport anywhere and kill with a simple touch. He was also likely intangible as he had to take off the ring to interact with the physical world. However Dean lost the bet but Death still retrieved Sam's soul. Dean lost all the abilities after taking off the ring which is now back in Death's possession.
In Dog Dean Afternoon, as the result of a spell, Dean takes on the personality traits of a dog and the ability to communicate with all animals telepathically. Among the traits he takes on is an ability to sense when people are sick such as with cancer. These abilities disappeared when the spell wore off.
In First Born, Dean received the Mark of Cain, something that will allow him to wield the First Blade once it is found and kill the Knight of Hell, Abaddon. Any further abilities that come with it are so far unknown. There is also some sort of terrible price, but Dean didn't care and took the Mark without learning what it is. Later, when he used the First Blade for the first time, the murderous rage that he felt did not dissipate after killing.
In King of the Damned, in the presence of the First Blade, the Mark grants Dean immunity to Abaddon's powers at first with great concentration and then no effort. He also displays telekinesis and strength great enough to lift Abadddon off her feet effortlessly. However, the Mark and Blade's effects cause him to go overboard and repeatedly stab the dead Abaddon after he kills her.
In The Things We Left Behind, Dean, under the Mark's power, has a precognitive nightmare about a group of murders he commits under its influence.
Having been abducted to Avalon, Dean can since perceive fairies that may appear invisible or just like normal humans on Earth.
After becoming a Knight of Hell, Dean possessed these weaknesses.
Throughout the course of the series, Dean has died many times.
Sam Winchester and Dean are brothers, with Dean being older by 4 years. When Sam was a baby, John told Dean to take care of Sammy and Dean spends his life doing so. Nothing takes precedence over Sam, even to the extent of selling his own soul or killing Death for Sam. Like all siblings, there are squabbles, joking, and teasing. Dean taught Sam everything growing up - how to connect with girls, working on the car engine, even walking and talking. Dean loves his brother fiercely, and cannot imagine living without him, although he has been forced to do so on occasion, most notably when Sam jumped into the Cage. Other times Dean and Sam fight. Dean has walked away from Sam three times; once thinking they were better off apart during the Apocalypse, once after Gadreel was expelled from Sam, and once when the Mark of Cain held sway over him.Sam has done everything in his power to save Dean - drank demon blood to stop the Apocalypse in Dean's place, did the Trial to close Hell, made demon Dean human again, and set free the Darkness to save Dean from the Mark of Cain.
Mary Winchester is Dean's mother. She loved him fiercely, as only a mother could, even cutting of the crusts of his sandwiches and "baking" pies. It could be argued that Dean loves pie because of his mother. She died when he was 4. Dean's life was shaped around Dad turning to hunt to get revenge on Mary's killer, and making Dean into a perfect soldier to hunt in Mary's memory. Dean saw Mary's ghost when he went back to Lawrence on a hunt. Dean visited Mary's gravestone with Sam and others, to say goodbye to his mom before embarking on a suicide mission to blow himself up to kill Amara. However Amara, upon departure, gave Dean what he most wanted since he gave her what she wanted. Mary Winchester was brought back to life. In trying to acclimatize to being alive again, she tried to hunt but eventually left Dean to have some space. This has hurt Dean badly.