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Dean Winchester is a fictional character and one of the two protagonists of The CW Television Network's Supernatural. He is portrayed by Jensen Ackles. Dean hunts demons, spirits and other supernatural creatures with his younger brother Sam.
Dean Winchester was born on January 24, 1979 to John and Mary Winchester in Lawrence, Kansas. He is the couple's first child, four years older than his younger brother Sam. He is named after his maternal grandmother, Deanna Campbell. When he was only four years old on November 2, 1983, his mother Mary was killed in Sam's nursery by the demon Azazel. Infant Sam is saved by the ensuing fire when his father takes him out of his crib and gives him to Dean, who then carries him outside while their father unsuccessfully tries to rescue their mother. After that night Dean felt responsible for Sam, and was always given the job to take care of him while they were growing up. Dean's father John raised him and Sam as hunters of the supernatural. During Dean's childhood John would be away "hunting" a week or two at a time. Growing up Dean's "job" was to look after/ protect Sam. John basically told him that his little brother's life was in his hands. So the term "Watch out for Sammy" became his life.
As the season begins, Dean, at the age of 26, is a hunter; he hunts and kills supernatural monsters. Usually, he is with his father John, but sometimes goes by himself. When his father goes missing, Dean asks for Sam's help to find him. They go in search of their father, saving people from the supernatural along the way, but at the end of the first episode, Sam's girlfriend Jessica Moore dies the same way as their mother did.
In the episode "Skin," Dean and Sam battle a shapeshifter responsible for a string of brutal murders in St. Louis, Missouri. During the course of the episode, the shapeshifter assumes Dean's form, causing police to believe that Dean is responsible for the murders. However, Dean kills the shapeshifter while it is still in his form; the authorities officially declare him dead and pin the murders on him.
John finally contacts the boys, revealing that he has been away from them because he is tracking the demon that killed their mother. His affection for his sons could be used against him, so he wants them away from him. However, the family unites as they come into possession of the Colt, a special revolver which John says can kill anything, including demons. The season finale concludes with Sam, Dean, and John escaping from their clash with Azazel, the yellow-eyed demon. While Sam is driving an injured Dean and John to a hospital, a demon-possessed driver drives his semi truck into the Impala, causing massive damage to the car and the Winchesters inside.
All three of the Winchesters survive the wreck, although Dean is more severely injured than his father or brother. In the season premiere "In My Time of Dying," Dean is in a coma. A reaper named Tessa tries to convince him to move on and accept his death as it is his time to die and warns him that, if he refuses, he will most likely become one of the vengeful spirits he and his family have so often fought. In order to save him, John makes a deal with Azazel, trading his life for Dean's. When Dean wakes from his coma, he has no memory of his time with Tessa; he does, however, comment later that, when he woke up, it felt wrong. When John asks Sam to get him quote "a cup of caffeine" he whispers something in Dean's ear which the audience cannot hear, then hands the gun to Azazel. His father dies immediately afterward, and is later revealed to be in in hell.
Throughout the first half of the second season, Dean struggles with the death of his father. He is also haunted by his father's last words to him. At the midpoint of the season, it is revealed that John told Dean that Azazel intends to turn Sam evil and, if Dean cannot save Sam, Dean must kill his brother.
During an investigation in Baltimore, Maryland in "The Usual Suspects," Dean is arrested in connection with another series of murders. It is revealed that Dean has a police record, with charges over the years including credit card fraud, breaking and entering, and grave desecration. Although Sam and Dean are able to prove that the murders were actually committed by one of the detectives on the case, whose partner lets the brothers escape. Since the authorities now know that Dean is not dead, he is again wanted for the murders committed by the shapeshifter. In "Nightshifter," a team of FBI agents, led by Special Agent Victor Henricksen, catches up with Dean and Sam in Milwaukee, Wisconsin, where an attempted bank robbery and several more murders are added to Dean's list of supposed crimes, thanks to another shapeshifter.
At the end of "All Hell Breaks Loose, Part 1," Sam is stabbed by Jake Talley, another of Azazel's "special children," and dies in Dean's arms. Crushed by Sam's death, Dean summons a Crossroads demon and trades his soul for Sam's life. The conditions Dean's deal are that Dean gets one year of life, at the end of which he dies and goes to Hell. If he tries to break the deal in any way, Sam dies. Dean wants to keep the knowledge of his deal from Sam, but Sam quickly figures it out and vows to get Dean out of the deal, no matter what. As the second season ends, Dean kills Azazel with the Colt, but not before Azazel has a gate to Hell opened, allowing hundreds of demons to escape from Hell as well as their father, with whom they share an emotional moment before he disappears in a glow of light.
In the third season premiere "The Magnificent Seven," Dean decides to make the best of his final year, indulging in many pleasures and refusing to even think about saving himself, while Sam tries desperately to find a loophole in the Crossroads demon's deal. While searching for escaped demons to send back to Hell, Sam encounters Ruby, a mysterious blonde who assists him but who also informs him that, for some reason, demons are killing all of his mother's old acquaintances. Sam learns that Ruby is a demon, and she promises him help in freeing Dean from his contract. She fixes the Colt so that it can again kill anything and also shows them a knife in her possession that can kill demons. Later, Dean and Sam learn from Ruby that all demons used to be human, but had their humanity is eventually burned away during their time in hell.
During the course of the season, the brothers meet another woman, Bela Talbot. Bela acquires magical objects and sells them for a large profit, and is unscrupulous. In "Dream a Little Dream of Me," when Bobby falls into a coma, Sam and Dean investigate the murder of a scientist. In the course of viewing Dean's dreams, it becomes clear that Dean believes that Sam was their father's favorite, but only thought of Dean as a tool. Dean encounters a demonic version of himself in a nightmare, which shocks him into trying to break his deal. After waking up, Dean admits to Sam that he doesn't want to die. Meanwhile, Bela steals the Colt.
In "Mystery Spot," Sam is forced to relive the same day, repeatedly. On each new day, Dean dies a different way despite Sam's efforts to save him. Sam realizes that the culprit is the Trickster, a villain from Season 2. They finally escape the day, but 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 allows Sam to escape the alternate reality he has trapped him in. He is warned by Ruby that he might not make it back from hell.
In "Jus In Bello," the FBI and Agent Henricksen capture Sam and Dean, thanks to a tip from Bela. While Sam and Dean are in jail, a host of demons come to kill them. Ruby comes to help them, but is furious to learn that they have lost the Colt. She says that she knows of a spell that will destroy all the demons nearby, including herself. 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, but now Lilith is the leader of the demons.
Shortly before Dean's contract comes due, he learns from Bela that Lilith holds his contract; Bela had also made a deal with a demon, and she reveals this information before her contract expired. 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.
As Dean and Sam confront Lilith, Ruby appears and the three are chased into a room by a hellhound that has come for Dean. Dean quickly recognizes that Ruby's human host is now possessed by Lilith, not Ruby, but it is too late. A hell hound kills Dean and Lilith tries to kill Sam, only to discover that her demonic power has no effect on Sam. Lilith flees, leaving Sam alone with Dean's mutilated corpse. In the last scene of the season, Dean is shown in Hell, suspended in a void by seemingly chains and hooks through his flesh, crying out for help and for Sam.
The fourth season premiere, "Lazarus Rising," begins four months after the third season finale. Dean awakes to find himself buried and manages to dig himself out. Dean calls Sam, but finds his number disconnected. He calls Bobby, who hangs up on him, so he hot-wires a parked car and goes to Bobby's house. Dean and Bobby track down Sam in a town right near where Dean was buried in a hotel, but he claims he did nothing to bring Dean back and is in town because he is searching for a demon. Dean tells Sam he remembers nothing from Hell.
The Winchesters track down whatever force ripped Dean from Hell. 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. In the episode "Wishful Thinking," Dean confesses that he does remember every second of Hell.
In the "Are You There, God? It's Me, Dean Winchester," in the course of fighting off ghosts, Dean is told by Castiel of Lilith's plan to break the 66 seals and free Lucifer.
In "In the Beginning," Dean is transported back in time to Lawrence, Kansas in 1973. There, he meets younger versions of his father and mother, as well as his maternal grandfather Samuel and maternal grandmother Deanna (for whom he is named), and learns of a connection between Azazel and Mary. A causal loop is revealed in that the time-traveling Dean, by trying to stop Azazel in the past and change his future, actually made the demon aware of his family in the first place, setting in motion the events leading to the death of his parents, the corruption of his brother, and the life he tried to change, therefore setting up a predestination paradox. (However, it is implied by Castiel that the events would have happened anyway without him being there as they were already destined.) Upon returning to the present, Dean is informed by Castiel that Sam is "going down a very dark road" and that, if Dean doesn't stop him, the angels will.
Dean follows Castiel's directions and witnesses Sam using his powers to exorcise a demon, also learning of Ruby's return. He conveys the warning of the angels to Sam. After he and Sam stop a rugaru in Missouri, Sam decides to stop using his powers.
In "Heaven and Hell," Dean reveals to Sam what happened to him in Hell: Time flows differently there, so four months on Earth was forty years in Hell. During that time, he was put on the rack and "cut, carved, and torn" apart until there was nothing left of him, only to be made whole again just so the demons could start over on him. Dean reveals that, at the end of every day, the demon Alastair would offer to take him off the rack if Dean would put souls on it and torture them. Dean resisted for thirty years, but eventually gave in and spent a 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.
The episode "After School Special" showed flashbacks of a teenage Dean and a pre-teen Sam while they are going to a high school. Dean was as promiscuous as ever when he was younger and the girl he was then dating told him that he acted cool when, in reality, he was a little boy who played with people's feelings to make himself feel better. Dean, clearly stung, from then on hated the school.
In the episode "On the Head of a Pin," Dean is pressed into service by Castiel and Uriel, who need him to torture Alastair for information on who is killing angels, since Dean was his "student" in Hell. Dean refuses at first, but eventually agrees. However, he only succeeds in getting Alastair to reveal that Dean himself was the first seal to break, by virtue of giving in and torturing souls in Hell. ("The first seal shall be broken when a righteous man sheds blood in Hell. As he breaks, so shall it break.") The distraction is enough for Alastair to free himself, the Devil's Trap set up by Castiel having been eroded by a leaking pipe. Alastair nearly kills Dean and then comes close to sending Castiel back to Heaven, but Sam arrives and kills Alastair shortly after. Later, as Dean recovers in the hospital, Castiel informs him about Uriel's betrayal; Uriel had been killing angels who did not join his cause to free Lucifer from Hell. Castiel also confirms Alastair's claim that Dean was the first seal, but adds that, because of this, Dean is the only man capable of averting the Apocalypse. However, Dean does not believe he is up to such a task and tells Castiel to find someone else as tears run down his face.
To put Dean back on the right path, Zachariah, Castiel's superior, re-writes Dean and Sam's memories to remove their knowledge of supernatural creatures, making them believe they are average people working regular jobs, and drops them in a haunted building. After the brothers proceed to defeat the ghost behind the hauntings, Zachariah restores Dean's memories to show him that hunting is in his blood. This renews Dean's resolve.
In "The Rapture," Dean witnesses Sam drink the blood of a demon he is about to kill. Later, Sam gets a request from Bobby to head to his house. Once there, Dean and Bobby trick Sam and lock him in the demon-proof panic room for his own safety as he detoxes from the demon blood.
While Sam is going through painful withdrawal symptoms from the demon blood, Dean asks Castiel for help. He takes an oath to serve God and the angels if it would mean that Sam wouldn't have to kill Lilith, to which Castiel says "If that gives you comfort." Sam escapes the panic room after Castiel releases him, and Dean tracks him down to a hotel, despite Sam's efforts to shake him. They argue over whether or not Ruby is corrupting Sam, if Dean is supposed to stop the Apocalypse, and if Sam is turning into a monster. Dean yells at Sam by saying, "If you walk out that door, don't you ever come back" -- the same ultimatum John gave Sam when he left for college years before, resulting in Sam's four-year estrangement from his father—after which Sam leaves the room.
In the fourth season finale "Lucifer Rising," the angels take Dean to a "safe" room, and Zachariah explains that they are preparing for the Apocalypse and will allow the final seal to be broken. They want Sam to kill Lilith as her death will break the final seal holding Lucifer, after which Dean will kill Lucifer and bring Paradise to Earth. Dean, shocked and horrified that the angels would allow the Apocalypse, asks Castiel for help; together they escape and meet the prophet Chuck Shirley to see where the final seal will be broken. As Castiel holds back the Archangels that start to descend, he sends Dean to Ilchester, Maryland to stop Sam from killing Lilith. Ruby prevents Dean from interfering and, after the final seal is broken, reveals that she has been working to free Lucifer the entire time. Dean manages to get to the two and then stabs Ruby to death with Sam's help. The season ends with a portal opening for Lucifer while Dean and Sam can only watch.
The fifth season begins right where Season 4 ends with the portal for Lucifer opening. As Lucifer escapes, the brothers are teleported into an airplane by an unknown force (later revealed to be God). Later, Dean is told by Zachariah that he is "Michael's Sword," meaning the Archangel Michael will use his body as a vessel to lead the forces of Heaven against Lucifer, 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.
In "Good God, Y'All!," Dean and Sam fight War, one of the Four Horsemen of the Apocalypse, in a town where the people think that their neighbors are demons. Once the brothers cut the ring finger off of War, restoring the town to normal, Dean worries that Sam cannot control his urge to drink demon blood, and the brothers agree to go their separate ways because Sam is a liability with his demon bloodlust.
In "The End," Dean is transported forward in time by Zachariah, who wants Dean to see what the future will be like if continues to refuse giving his consent to Michael. He finds himself in the year 2014, eventually meeting up with his future self, as well as the survivors and victims of the Croatoan virus from Season 2. Dean finds out that Sam let Lucifer into his body, and this was the reason the world was in such disarray. Later, the future Dean is killed by Lucifer in Sam's body. After being told by his future self to accept Michael into his body, Dean is transported back to his own time, where he comes face-to-face with Zachariah; he again refuses to become Michael's vessel. In the end of the episode, the brothers meet back up again and decide that they should stay together, to "keep each other human."
In the episode "Changing Channels," it is revealed to Dean and Sam by The Trickster (who reveals that he is the Archangel Gabriel) that their relationship (Dean the older brother loyal to an absent father and Sam the younger brother who is rebellious of the father's plan) mirrors the relationship between Michael and Lucifer, and has been told to the angels since the beginning to bring about Judgment Day.
In "Abandon All Hope," Sam and Dean plan 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. The Winchesters then find out that Lucifer is one of five things in the universe that the Colt cannot kill when Dean tries shooting Lucifer in the head with no effect. Having lost another plan, Dean becomes more disillusioned and hopeless, and in "Dark Side of the Moon" where, after spending time in Heaven and finding out God doesn't see the battle with Lucifer to be his problem, 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 "99 Problems". Before doing so, though, he visits former girlfriend Lisa Braeden (Season 3 "The Kids Are Alright"), confessing that when he dreams of being happy its with her and her son Ben, and promising to get them protection for what's to come.
During the series' 100th episode "Point of No Return," Dean was preparing for his possession by Michael before being discovered by Sam and Castiel, who take him to Bobby's house. They convince him to allow them some more time in order to research another method of stopping Lucifer; however, the unexpected resurrection of their half-brother Adam, planned to be Michael's vessel, forces Sam, Bobby and Castiel to keep 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 taken by angels. Despite Bobby and Castiel's insistence in keeping Dean from Zachariah, Sam allows him to try to rescue Adam. With Castiel removed, along with angel guards, 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 kills him and rushes out, unfortunately leaving Adam 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."
After being trapped in "Hammer of the Gods" by a group of gods bent on using them as bargaining chips in the upcoming Apocalypse, Dean and Sam learn from Gabriel that the cage Lucifer was sprung from was still open and, if they could get all four Horsemen's rings, they could put him back in and trap him again. He also claims that Lucifer has no knowledge that he can be trapped again. In "The Devil You Know", the demon Crowley returns and leads Dean to a confrontation with Brady, one of Sam's college friends who in fact was a demon "Handler" for Pestilence. Despite being beaten badly, Dean and Crowley trap Brady and are eventually able to get the location of Pestilence.
In "Two Minutes to Midnight" the brothers go after Pestilence and, with help of a nearly-human Castiel, take his ring. During the trip, Sam tells Dean that he believes the only way to trap Lucifer is to say yes and allow him to be possessed, believing that he can overcome Lucifer long enough to throw himself into the trap. Crowley then takes Dean to Chicago where they have located the final Horseman. In the midst of a massive storm, Dean confronts Death in a pizza parlor. Revealing that Lucifer controls him due to a spell, Death agrees to give Dean his ring with the explicit condition that Sam say yes so he can lure Lucifer into the trap, and that Dean allow his brother to jump into the pit. Dean reluctantly agrees and gets the ring and instructions from Death on how to use the four rings. Upon returning, Dean claims he lied to Death, but upon talking to Bobby it becomes clear that their last best chance may be to let Sam say yes, with Bobby asking Dean if he was more afraid to lose, or to lose his brother.
In "Swan Song" Dean relents and agrees to let Sam say yes. As Sam prepares to drink demon blood to become strong enough to take in Lucifer, he makes Dean promise that he won't attempt to come after him once he has jumped into the pit. Dean objects, but Sam insists, begging that he instead go to Lisa and try to live a normal, happy life. Dean promises he will do so, and after drinking the demon blood, the brothers go to confront Lucifer in Detroit. Despite Lucifer revealing that he did indeed know about the brothers' plan to trap him again, Sam says yes believing he can overcome him nonetheless. After taking over and briefly knocking Sam unconscious, Dean opens the portal to Lucifer's prison, and Sam wakes up and prepares to jump in. At the last moment, though, Lucifer reveals himself, claiming that "Sammy is long gone". After closing the trap, taking the rings, and briefly taunting Dean, Lucifer disappears.
As omens begin to signal the final battle, Dean calls Chuck to try to pin down the location of the final battle, which will occur in Stull Cemetery back in the brothers' hometown of Lawrence. While Castiel and Bobby seem despondent, believing the battle to be lost and further confrontation pointless, Dean vows to go to the fight between Lucifer and Michael (now possessing his half-brother Adam), claiming at the very least he "won't let his brother die alone". As Lucifer and Michael prepare to fight, Dean interrupts and drives the Impala into the graveyard. He attempts to reach out to both Sam and Adam, asking for five minutes with Sam, but is dismissed by both. Bobby and Castiel suddenly appear, and Castiel throws a molotov cocktail with holy fire at Michael, burning him out and buying Dean five minutes. It comes at a high price: an enraged Lucifer snaps his fingers, making Castiel explode for interrupting the fight. Lucifer and Dean begin to fight, with Dean taking a beating. He continues beating Dean and, with Dean backed against the door of the Impala, prepares for a kill shot. However, at that moment, he catches a glimpse of a toy soldier that a young Sam had stuck in the Impala's ashtray, and the memories of his brotherhood with Dean help Sam to overpower Lucifer and take control of his body. Sam reopens the pit, and though Michael returns and attempts to stop him, Dean watches as Sam pulls Michael into the pit, which closes as they both fall in, trapping both in Hell.
A fully restored Castiel suddenly appears, claiming to have been resurrected by God. He heals Dean and plans on returning to Heaven and bringing new order now that Michael is gone. Dean claims that he will go after God next, but Castiel claims, before disappearing, that Dean only got what he wanted in the end: no Paradise, no Hell, more of the same-freedom over peace. After an emotional goodbye with Bobby (it is said in Chuck's epilogue that the two will not see each other for some time), Dean returns to Lisa Braeden as Sam had suggested. Dean is last seen sitting down to dinner with Lisa and her son Ben. Unknown to Dean, a streetlight just outside the home goes out, and Sam is inexplicably standing beneath, watching the home with a blank look on his face.
The sixth season picks up a year later. Keeping the promise he made to Sam, Dean gives up the life of hunting and now lives with Lisa and her son Ben. After Dean became poisoned by a Djinn, begins hallucinating his worst fears. Sam saves Dean by injecting him with an antidote and later wakes up seeing Sam alive and well. Sam reluctantly tells Dean that he has been back for nearly a year while hunting with their grandfather, Samuel. After helping kill the Djinns, Dean declines returning to the life of hunting and decides to continue living with Lisa and Ben in order to keep them safe. Lisa tells Dean to return to the life of hunting and she and Ben will be there when he gets back.
In "Live Free or Twi-Hard" Sam and Dean investigate cases of missing girls that are obsessed with vampires. They stake out a bar that eventually leads them to the cause. Dean later crosses paths with a vampire that turns him into one. Expecting to have to be "put down", he goes to visit Lisa, but almost loses control while talking to her and flees. After being cured, he realises that Sam may possibly have let him be turned; but to an unknown end.
In "You Cant Handle the Truth" Dean and Sam investigate a town in Illinois, where everyone who wishes for truth, not only receive their wish, but to the extent that everyone who has done so has become insane, and commits suicide. While initially believing that the Horn of Truth, an angelic weapon, is the culprit, Sam discovers the summoning ritual to Veritas, the pagan goddess of Truth. However, Dean unknowningly invokes her and is forced to deal with harsh truths from everybody; including Lisa, who calls about the events of last episode and ends up telling him not to ever come back. Questioning Sam, he believes he gets the truth from him about why he didn't help him from being turned, but when Veritas captures them on their raid of her property, she declares that Sam is inhuman, as no human is immune to her aura of truth. The brothers manage to dispatch her, but Dean holds Sam at knifepoint, demanding the truth. Sam admits his lack of emotion and fear, but Dean doesn't accept it and beats him unconscious. Dean learns from Castiel that Sam has no soul, also that Crowley was the one who brought Sam back from Hell. Crowley also says that the only way to get Sam's soul back is to help him find Purgatory. Dean and Sam attempt to capture Crowley to force him to give back Sam's soul. Crowley tells them that not only can't he get Sam's soul but also that Sam's soul has been tortured endlessly by Lucifer and giving Sam back his soul would leave him useless. Once learning this Castiel kills Crowley, so Dean goes to see Death to have him bring back Sam's soul. Death agrees but only if Dean can becomes Death for one day and never take off his ring. Dean fails, but Death still agrees to return Sam's soul since Dean learned about messing with the natural order.
Dean is well-versed with multiple types of firearms; he prefers his Colt 1911 and sawed-off shotgun, but is proficient with most other weapons he might acquire. An expert marksman, he seldom misses his intended target and can efficiently put down anything vulnerable to bullets. As shown in the episode "Frontierland" where he shoots down a phoenix with one shot.
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. In "Nightshifter", he killed a shapeshifter armed with a simple silver letter opener. In "Fresh Blood," he managed to subdue a vampire long enough to inject her with a shot of "dead man's blood." In "The Magnificent Seven," he fought and held off several demons by himself, armed only with a flask of holy water.
Highly resourceful, he frequently utilizes improvised weapons and explosive devices; in "Croatoan," he demonstrated knowledge in chemistry constructing Molotov cocktails and improvised explosive devices, and in "Phantom Traveler," he revealed knowledge of electronics and reverse engineering, having built an electromagnetic field detector from an old Walkman radio.
Dean also possesses extensive knowledge of the supernatural and mythology. He is versed with how police, fire departments and various government agencies (FBI, CDC) typically operate and conduct investigations, and knows how to both impersonate and evade them effectively. An accomplished mechanic, he maintains his Impala in tip-top condition and has maintained an intimate knowledge of automobiles and engines since childhood.
Dean is a virtuoso of escape, evasion and silent movement, when the situation requires subtlety and stealth. Lastly, he is skillful in: lock picking, breaking into security systems (not so much computers, which often falls to Sam), carjacking and gaining an 'advantageous purchase' comes naturally to him.
Due to his time spent in Hell as Alistair's "student," Dean has an in-depth knowledge of torture.
During Season 4 Dean gains magic effective against angels, he learns a banishing spell that sends angels back to Heaven from Castiel. He is also untraceable to angels after the season 5 because he has Enochian symbols carved into his ribs by Castiel to hide him and Sam from all angels in existence.
Throughout the series, Dean is shown to possess a large amount of weaponry. He tends to use a Colt 1911. In addition to which, he also uses a sawed-off shotgun on occasions where greater firepower is required. He has also been seen with an MSG3 sniper rifle in "Simon Said."
Dean is shown to possess a large machete in "Dead Man's Blood," and has used a knife in several episodes. He is shown to possess a Desert Eagle loaded with wrought iron in the episode "Something Wicked" and tasers which he and Sam used in the start of "Faith". Throughout Season 5, he uses a Model 1887 shotgun against hellhounds and zombies. When weapons are scarce and Dean is in a dangerous situation, he uses hand-to-hand combat or whatever is available as a weapon.
During the fourth season episode "On the Head of a Pin," Dean is shown with a number of torture implements, including syringes of holy water.
The trunk of the Impala contains numerous weapons which are implied as having been needed in the past, notable examples include sheath knives and, perhaps the most alarming, an DefTech 37mm grenade launcher.
