- "You're my big brother and I love you Dean, there is nothing I wouldn't do for you. All you have ever done is been there for me.. Don't you ever think for one second that I wouldn't do whatever I could to save you. I need you.... I can't do this alone. You're not going to die. Okay? You cannot die. Please do not die... "
- —Sam Winchester to Dean[src]
Sam and Dean are brothers and the main protagonists of Supernatural. They are dedicated to one another, though there are many instances of strain throughout the series. Their relationship developed as one of the show's main plot lines.
Dean is four years older than Sam and was always told from a young age to "watch out for Sammy". When a demon killed their mother, it was Dean who carried baby Sam out of the house. Dean was tasked as Sam's protector and, as a result, views himself as such. Thus whenever their father John Winchester went out hunting, Dean would watch over Sam. He would cook and care for Sam as well as protect him while their father was out. One night in the motel room, when Dean got back, there was a Shtriga standing over Sam. Dean pulled a gun out, but didn't shoot. Their father showed up then and got rid of the creature.
As the boys got older, Sam started asking questions about what kind of work their father does and why they always have to move around. Dean tells Sam that their dad was a superhero. Sam continues on by asking if it was because of their mother. Dean gets angry and leaves. He comes back later and gives Sam "dinner." Sam reveals to Dean that he found Dad's journal and asks if it's true. Dean tells Sam it's all true (except for Santa) and how Dad fights these monsters. Dean is essentially the one who showed Sam the truth about the world and all the supernatural creatures. Realizing Dad is probably not coming home because of the job, Sam goes to bed upset. Dean feels sorry for his brother and tries to make it up to him by stealing presents from other houses. Much to his luck however, they are all girl presents. Sam thanks Dean anyway, and gives him the necklace he was going to give to their father. Dean continues wearing this necklace until Season 5.
Sam and Dean also went to high school together for a year (Dean in Gr.12, Sam in Gr.9). Dean displays his protective nature again when Sam gets picked on by a bully in Truman High. Dean threatens to tear the kid's lungs out, but Sam stops him. Dean wonders why Sam didn't take this guy down himself (due to their combat training). Sam doesn't want to be "the weird kid" again, which appears to confuse Dean.
A year later, Sam is left alone when Dean and John go after a kitsune together. Sam helps gather information for them, and often talks to Dean on the phone. Sam later asks Dean for advice on how to talk to girls, and tries it when he attempts to talk to Amy Pond. Sometime after that, they continue hunting until Sam wants to go to college. Sam leaves and doesn't talk to Dean for two years.
Sam: "I swore I was done hunting for good."
Dean: "Come on, it wasn't easy, but it wasn't that bad."
Sam: "Yeah? When I told Dad I was scared of the thing in my closet, he gave me a .45."
Dean: "Well, what was he supposed to do?"
Sam: "I was nine years old! He was supposed to say, 'Don't be afraid of the dark.'
Dean: "Don't be afraid of the dark? What, are you kidding me? Of course you should be afraid of the dark! You know what's out there!"
Sam is in bed with his girlfriend Jessica when Dean arrives to get Sam to join him in the search for their father. Sam is angry at Dean for even thinking of asking him to go on another hunt. Sam continues on about how messed up their childhoods were, which Dean appears not to have a problem with. Sam does give in though and joins Dean on the search for their father, on the condition they will be back by the following Monday. They head towards their father's last case, only to find he is no longer there. With that fact, they continue to work on the case, during which they have their first (on screen) run in with the cops. Sam gets angry when Dean doesn't show the cops any respect, and stomps on Dean's foot to get him to shut up. Dean follows up by hitting Sam's head. They finish the case and Sam heads home much to Dean's disappointment (Dean wants everything to go back to the way it was before Sam went to college).
Sam returns home, thinking that his hunting days can finally be over, when he discovers his girlfriend pinned to the ceiling with a slash across her chest. Her body then bursts into flames, which engulfs the entire place, the circumstances identical to the ones during his mother's death. Dean rushes in and sees Sam lying on the bed with a burning Jessica above him and drags Sam from the apartment, reminiscent of when he carried Sam out of his nursery when he was 6 months old. Now angry and wanting vengeance, Sam heads out with Dean, back on the job.Sam and Dean travel around looking around for their father, but the trail goes cold. Sam gets angry with this but Dean promises him that they will find their father, but in the meantime they should kill everything in their way and save people. Sam agrees, and helps Dean hunt. Dean also helps Sam deal with Jessica's death and his nightmares about it. He tries to get Sam to open up about it, but Sam refuses.
Sometime later, Sam gets a vision about their old home, and Dean gets upset with the idea of going back there. They go back anyway and find that the house is really haunted. They cleanse the house, and during this Sam gets attacked and Dean saves him (one of many occasions).
Dean is worried and slightly frightened by the increasing number of visions Sam gets, but he keeps it from him, and helps Sam stop them from coming true either way.
Sam is still annoyed by the fact that Dean does everything their Dad tells them to do. He expresses this harshly to Dean in Asylum when Sam's mind gets temporarily messed up by Doctor Ellicott's spirit. Dean attempts to reason with him, but was of no use and Dean knocks Sam out for his own good. Once the spirit is defeated, Sam wakes up, normal again, and the boys patch things up, though Dean knows deep down inside that Sam actually meant some of it.
They get a call from their father, and Sam wants to go after him, but he had given them a mission to carry out and Dean wants to follow through on that instead. The brothers separate, but not for long. Dean doesn't answer his phone for three hours, and Sam realizes that Dean's in danger. He thus returns and saves Dean.
Sam shows his protective side when Dean's life is in danger. Sam looked far and wide for a cure for Dean when he accidentally electrocuted himself in Faith while on a hunt and suffered a heart attack. Sam manages to find a faith healer who heals Dean. In The Benders, we see more of Dean's protective side when Sam gets kidnapped by a group of psychotic killers. Dean teams up with an officer to find Sam.
Dean also made it his mission to get Sam laid. Sam does not appreciate this but lives with it. Dean believes if Sam gets laid he would relax more and it would help him with Jessica's death. Dean tells Sam it's what Jessica would have wanted for Sam. They eventually team up with their father again, and Dean has to deal with Sam and John's arguing. Sam and Dean team up to defy their father's orders, and help him get the Colt, a special gun that can kill almost anything. They head out after the demon.
Dean: "I don't want you to leave the second this thing's over, Sam."
Sam: "Dude, what's your problem?"
Dean: "Why do you think I drag you everywhere, huh? I mean, why do you think I came and got you at Stanford in the first place?"
Sam: " 'Cause Dad was in trouble. 'Cause you wanted to find the thing that killed Mom."
Dean: "Yes, that, but it's more than that, man! You and me and Dad ... I mean, I want us to be together again. I want us to be a family again."
Sam: "Dean, we are a family. I'd do anything for you. But things will never be the way they were before."
Dean: "Could be."
Sam: "I don't want them to be. I'm not gonna live this live forever. Dean, when this is all over, you're gonna have to let me go my own way."
– Sam and Dean arguing about the future, Shadow
Sam gets a vision of the demon attacking another house, and they have to separate with their father. They go after the demon's next target. They arrive on scene, and the demon sets the place on fire, but Sam grabs the baby and manages to save the family. Seeing that the demon is still there, Sam tries to go back in, but Dean stops him. Sam is angry, but Dean believes being alive is better than revenge.
Dean proves these beliefs further when they go rescue their dad and he brings the Colt despite Sam telling him not to. Dean uses the Colt to kill a demon that was trying to kill Sam. Sam is thankful, but is still angry that Dean brought the Colt. Now escaped, they hide in an empty house, and Dean realizes their Dad is not "Dad". When Dean tells Sam this, Sam believes him over "Dad". This proves Sam's trust in Dean. When their dad is found to be possessed by the yellow-eyed demon Azazel, he almost kills Dean, but Sam manages to shoot him in the leg. Dean begs Sam not to kill the demon, which will kill their father as well, and Sam doesn't, despite their father's pleas. After the demon leaves his father's body, Sam and John race against time to save Dean from his severe injuries but while driving to the hospital, they get hit by a possessed truck driver. The season ends with Sam, Dean and their dad all unconscious in the Impala.
- ""I don’t wanna hurt anyone else. I don’t wanna hurt you.""You won't. Whatever this is, you can fight it.""I can’t. Not forever.""
- —Dean and Sam[src]
After the accident, Dean falls into a deep coma, and Sam is only one who believes in him. Sam realizes that Dean's spirit is around and communicates with Dean which helps Dean realize he's being hunted by a reaper. Dean does not remember this after John made the deal with the yellow-eyed demon to save Dean. Before John died, he tells Dean one final thing about Sam, which Dean later reveals to him.
Following their father's passing, Sam and Dean are dealing with his death in different ways. Dean begins to fix up the Impala and refuses to actually deal with the grief. Sam shows him a message from one of John's old contacts, Ellen Harvelle. There they find a job and head out. Dean wonders why Sam is suddenly all for hunting now. Sam tells Dean that it's because it's what their father would have wanted. Dean is confused and angered by this because of the relationship Sam and John had. Sam tells Dean the reason is because John is dead, which is why Sam wants to do the job. Once they finish it, Dean asks Sam if Sam really meant it when he said he wasn't going to go to college anymore, and Sam replies yes. Back at Bobby's, Sam apologies to Dean, but points out that Dean's not handling John's death well. Sam leaves and Dean smashes the Impala with a crowbar in a fit of rage and grief.
Sam and Dean hit another speed bump when they meet Gordon Walker. Dean instantly bonds with him, because with Gordon he doesn't need a brave face (which he believes he needs with Sam). His beliefs get tested when Sam tries to convince Dean to leave the vampires alone because they weren't hurting people. In the end, Dean chooses Sam over Gordon.
Over the course of the first half of the season, Sam shows concern at Dean's apparent nonchalance over their father's death and makes several attempts to get him to open up, but Dean refuses. Eventually Dean's repressed emotions is unleashed when he hunts, scaring Sam with his recklessness and harshness. While doing a case over a zombie, Sam loses patience and confronts his brother over his behavior. Reluctantly Dean opens up and he admits he wishes he never came back because he knew it was why their father died.
Sam: "You're on edge, you're erratic. Except when you're hunting, because then you're downright scary. You're tailspinning, man. And you refuse to talk about it and you won't let me help you."
Dean: "I can take care of myself, thanks."
Sam: "No, you can't. And y'know what? You're the only one that thinks you should have to. You don't have to handle this on your own, Dean. No one can."
– Sam confronting Dean over their father's death, Children Shouldn't Play With Dead Things
Later on, they run into another special child, and Sam believes him to be a killer, but Dean believes otherwise. Andy, using his mind-control, makes Dean tell the truth about his feelings on Sam's powers. Dean gets more worried when Sam is immune to a violence-inducing virus that wipes a town in Croatoan. Prior to this knowledge as Sam is apparently infected, Dean defends his brother from the townspeople who want to execute him before he turns, and though Sam begs Dean to kill him, Dean refuses. Dean tells Sam he's tired, and wants it to end, knowing that he couldn't live without Sam. Their situation is resolved when it was revealed that Sam was not infected.
Once they leave town, Dean finally tells Sam what John told him - that Dean needed to look after Sam. Sam protests that this is nothing unusual, that Dean was always put in the role of Sam's protector, but Dean maintains that this was different. John told him that Dean needed to "save" Sam, because if he couldn't save him, then he'd have to kill him. Sam is furious that Dean kept this from him, but Dean begs him to stay with him so that he can protect him.
Gordon Walker begins to hunt Sam in Hunted, believing him to be a key player in the psychic children's army, and therefore, a monster and a threat. Dean, furiously protective of his brother, attempts to fight him off, but is captured in the process. With the help of a fellow psychic, Ava, Sam finds his brother and Gordon, who tries to kill Sam. Sam narrowly escapes, but Dean is still enraged at Gordon for threatening his little brother and wants to kill him, though Sam convinces him to let Gordon go, who gets arrested by the police anyway.
The brothers go back hunting together again, and Dean no longer carries his father's words as a burden. But now Sam does, he expresses this when he gets drunk and makes Dean promise to kill him if he turns into a monster, but Dean tells him he can't do it. In Born Under A Bad Sign, Sam goes missing and returns with memory loss and a murder on his hands. Dean refuses to kill him, and he later figures out that Sam was possessed by a demon. Sam is disturbed by the fact that Dean refused to kill him even though his behavior made him appear evil, but Dean reaffirms his faith in his brother and tells him that he couldn't kill him, and that he'd "rather die."
In Tall Tales, Sam and Dean get into their first (on screen) fight. Sam believed Dean took his laptop and Dean believed Sam messed with the Impala. Once they realize it was really a trickster doing this, the two apologize to each other, working together to kill the Trickster (albeit unsuccessfully).
Later on, Sam and Dean come across a werewolf case in Heart. Sam eventually forms a relationship with Madison, the victim Nate Mulligan's secretary, while he watches over her in her apartment, believing that she is in immediate danger of a werewolf attack. The brothers subsequently discover that Madison is the werewolf, with her unaware of this beforehand, and without a cure for her lycanthropy, Madison pleads Sam to kill her. Sam, who has fallen in love with her, is devastated but he kills her anyway.
The real trial comes when Sam gets kidnapped from the diner by a demon. Dean calls in Bobby to help him search for Sam, while Sam finds himself in an abandoned town with the other special children. Andy sends Dean a clue via long-distance mental projection informing him of Sam whereabouts. While waiting for Dean, Sam tells Jake, another special child, how Dean always tells him everything is going to be fine, like how Sam reassures the rest of the special children. Sam continues on how Dean can't always be there. Eventually, the special children get killed one by one, and Sam and Jake are the only two left.
Dean later arrives in town and finds Sam, only to witness Sam get stabbed in the back by Jake, after the yellow-eyed demon tells Jake that it was either one of them survives, or they both die, Jake not wanting the latter. Sam collapses into Dean's arms as Jake flees, Bobby after him, and Dean attempts to reassure his little brother that he will take care of him. However, Sam's spinal cord is fatally severed, and Sam dies in Dean's arms.
It's been a week since Sam died, and his body is laid in the bed in the next room. With Sam dead, Dean doesn't want to live without him. He doesn't eat, and only drinks. Bobby attempts to get Dean to work, but Dean yells at Bobby to leave. He also tells Bobby that he's given the world enough. With Bobby gone, Dean talks to Sam's body about its his responsibility to take care of Sam and his failure to protect him. With no other option, Dean makes a deal with the crossroads demon to bring Sam back in exchange for his soul, which will be reaped in one year's time, instead of the usual ten.
Sam wakes up and Dean is thrilled to see his brother up and around. Dean tells Sam that it was Bobby who patched Sam up. Sam believes this and wants to get back to work. Dean isn't too thrilled, wanting Sam to rest and recover his strength, but goes with his brother anyway. At Bobby's, they figure out Yellow Eye's plan and head to Hell's Gate. There Dean watches his brother kill Jake, and later Azazel taunts him and tells him that the Sam he brought back might not be a 100% pure Sam, which worries Dean.
After Bobby and Ellen manage to close the gate, Sam confronts Dean about what happened as he learned that Jake severed his spinal cord when he stabbed him, and that he was probably not supposed to be alive. Sam figures out that Dean made a deal to bring him back from the dead, and asks how long he got, Dean replying that he got a year. Sam is upset that his brother made such a sacrifice for him, and when Dean claims that he had to protect Sam, Sam responds by saying that Dean saves his life over and over, and would do anything for him, but doesn't seem to realize that Sam would do the same for Dean. Sam swears that they will find a way out of the deal, and Dean, though less than convinced given the knowledge that breaking the deal risks losing Sam, nods in agreement.
Sam: "You shouldn't have done that. How could you do that?"
Dean: "Don't get mad at me. Don't you do that. I had to. I had to look out for you. That's my job."
Sam: "And what do you think my job is? You've saved my life over and over. I mean, you sacrifice everything for me. Don't you think I'd do the same for you? You're my big brother. There's nothing I wouldn't do for you. And I don't care what it takes, I'm gonna get you out of this. Guess I gotta save your ass for a change."
– Sam and Dean after Dean's deal, All Hell Breaks Loose - Part 2
- "Sam, I've got a year left to live. So what do you say we kill some evil sons of bitches and we raise a little hell?"
So now with only a year to live, Dean is living large. Sam goes along with it because he was trying to be nice to Dean. Sam is also trying to find a way out of Dean's deal. Bobby, later, calls in them in for a job, which they later find out is the Seven Deadly Sins. After it, Sam tells Dean he's had enough of playing mister nice guy and why doesn't Dean even try to get out of the deal? Dean tells Sam, because if he does, Sam drops dead. He continues on by saying that when John sold his soul for Dean, he already disrupted the natural order; at least now something good will come out of. Dean finishes by telling Sam he's tired and it's done. So Dean says "So what do you say we kill some evil sons of bitches and we raise a little hell?"
So they do that, then they run into some bad luck when they encountered a cursed rabbit foot stolen from John's storage. Sam touches it and gets good luck, which Dean is more than happy about. Then it gets stolen from Sam by Bela Talbot. So Dean now has to watch out for Sam and find Bela. Dean puts Sam in the room and goes after Bela. While he's gone Sam's luck gets him kidnapped by two hunters, but Dean comes in time to save him. As they are about to destroy the foot Bela comes in, but Dean tricks her into touching the foot. Once the foot is destroyed, Sam and Dean don't feel bad about Bela loosing her money.
Later on in Sin City, Dean gets trapped with a demon in a basement. He strongly believes Sam will find him. Dean also asks the demon about hell and eventually seems to get along with her. She tried to spare him the other demon, but before Dean can stop him, Sam uses the Colt and kills both without hesitation, startling Dean. Dean begins to wonder if Sam is still 100% Sam. Bobby tells Dean he's worrying about nothing.
Bobby: "Sam was saving your life."
Dean: "Yeah, but you didn't see it, Bobby. It was cold. [...] Back in Wynoming, there was this .. moment. Yellow eyes said something to me.[..] That when Sam came back from wherever ... that he came back different.[...] You think ... you think something's wrong with my brother?"
– Dean's fears Sam came back wrong, Sin City
Some time later, Sam confronts the crossroads demon about Dean's deal with the Colt in hand. The demon reveals she doesn't have Dean's contract and can't reverse it. In return, Sam shoots her in the face.
Sam also confronts Dean on his Kamikaze moves. On how Dean is valuing his life, and that Sam know how Dean really feels. Sam knows Dean is afraid, and wants his brother back. Realizing his action affects his brother, Dean agrees and sets up a defense against the now vampiric Gordon in Fresh Blood.
With his year ticking away, Dean wants to have Christmas. Due to unpleasant memories, Sam rather not. But after being almost eaten by Pagen Gods. Sam changes his mind and has the Christmas his brother wanted. They even get each other presents (Sam got shaving cream and Porn. Dean got oil and chocolate). With this in mind, Sam takes steps towards becoming more like Dean. This is seen when they encounter witches and Sam agrees with Dean that they need to be killed. Although Sam is not totally ready for Dean to die yet. When a hex bag is placed in their motel room, Dean starts coughing up blood and Sam goes after the witches with the Colt. Dean also finds out that demons were originally human souls, and in Dream A Little Dream Of Me, Dean finally agrees to help Sam in the search to find a way out of his deal.
While looking for Bela, Sam and Dean run into the Trickster in Mystery Spot. Here Sam watches Dean die over and over again. This makes Sam very on edge, upset and he tries to save Dean, but nothing works. While Dean has no clue what is going on, Sam is going insane watching his brother die. Sam eventually figures out the Trickster is behind the deaths and goes after him, eventually convincing him to stop. But when Dean dies yet again and it's not "Tuesday", Sam goes Rambo and hunts for the Trickster for months. When Sam finally catches him, Sam begs the Trickster to bring Dean back.
Sam and Dean continue to show they got each other's back. In Ghostfacers, Dean goes after the missing Sam. Their relationship also gets strained when Dean get a call from "dad", and Sam doesn't believe it's really him. Once Dean realizes it really wasn't "dad", he apologizes to Sam. In Time Is On My Side Sam finds a way to make Dean immortal, dispite the details of having to replace organs once and a while. Dean refuses to live like that.
During Dean's final hours, using Bela's intel, they discover Lilith holds Deans contract. They need to get close to her and Sam suggests they call Ruby. Dean refuses to ask for her help, but Sam summons her anyways. Ruby tells Sam there is another way to kill Lilith, which is to use his powers Azazel gave him. Dean walks in saying he knew Sam would summon Ruby and traps her in a Devil's Trap. Sam chooses Dean over Ruby and they takes her knife. Before leaving, Sam and Dean get into an argument and Dean points out how the bad things out there know how they sacrifice themselves for each other. That is their true weakness. On the way there, Sam attempts to say goodbye, but Dean stops him and turns on Bon Jovi's "Dead or Alive". Now it's a race against time and they arrive in the block Lilith is located in. They get into the house and Sam heads upstairs. When he's about to stab the little girl, Dean stops him. Lilith is no longer occupying her.
- "Sammy, you're my weak spot. You are. And I'm yours. [...] And those evil sons of bitches know it too. I mean, what we'll do for each other, y'know, how far we'll go? They're using it against us. [...] We take this knife and go after Lilith our own way. The way Dad taught us to. And if we go down, then... then we go down swingin'."
- —Dean to Sam[src]
Now it's a race against time and they arrive in the block Lilith is located in. They get into the house and Sam heads upstairs. When he's about to stab the little girl, Dean stops him. Lilith is no longer occupying her.Time is now up. Sam and Dean look at each other in despair. Then Dean hears the Hellhounds coming for him. Sam, Dean, and "Ruby" run into a room, and seal it off with Goofer Dust. Dean realizes that "Ruby" isn't Ruby anymore, and Lilith is actually inhabiting Ruby's body.
Lilith pins Sam and Dean. She lets her hellhounds into the room and Sam watches his brother die. Lilith tries to kill him too, but her power doesn't work on Sam. So she runs, leaving Sam with Dean's broken body. In Hell, Dean is calling for Sam.
Sam: "You were gone. I was here. I had to keep on fighting without you. And what I'm doing, it works."
Dean: "Tell me, if it's so terrific, then why'd you lie about it to me? Why did an angel tell me to stop you?"
Dean: "Cas said if I don't stop you, he will. See what that means, Sam? That means that God doesn't want you doing this. So, are you just gonna stand there and tell me that everything is all good?
– Sam and Dean, Metamorphosis
This season we see Sam and Dean's relationship beginning to become even more strained. Sam and Dean are reunited 4 months after Dean's death in a hotel room. When Sam first sees Dean, he attacks right away, believing it to be an impersonation of some sort. Bobby stops him, saying it's really Dean. Sam and Dean hug. Dean initially believes it was Sam who brought him back, but Sam denies this. He tells Dean he hadn't been able to find a way, although he tried everything he could think of. They begin to investigate who would have had the power to raise a soul from hell, as well as reconstruct Dean's body. During the investigation, Dean asks Sam if he's continued using his psychic powers. Sam assures him that he hasn't, as it was Dean's dying wish that he stop. This is proved false shortly after, when Sam goes after some demons the brothers encountered. Pamela, a friend of Bobby's, is able to use Dean's body to contact the being who raised him. They get a name, "Castiel," before Pamela's eyes burn out from seeing the true form of the creature.
After meeting Castiel, who reveals himself to be an Angel of the Lord, Castiel cautions Dean to stop Sam, or they (being the angels) will. Although initially confused by this ominous warning, Dean discovers Sam using his powers, and realizes Sam has been lying to him all along. Dean confronts Sam, asking sarcastically if there's anything Sam wants to tell him. Sam tries to explain and Dean notices Ruby. Dean attacks Ruby, but Sam saves her. Despite all the evidence to the contrary, Dean still wants to believe the best of his brother. Dean thinks Ruby must have tricked Sam into using his power, but that is not the case. Distraught, Dean tells Sam, "If I didn't know you, I'd want to hunt you". Then Sam gets a call, and they head out. While driving Sam reveals that he knew about Azazel bleeding in his mouth to Dean, and Dean gets angry. Sam tries to apologize, but Dean is too angry to hear.While talking about the case, Sam believes this guy can fight off his blood, but Dean doesn't think so. Dean says "Something in his blood, maybe you can relate". This makes Sam angry and tells Dean to stop the car When the car is stopped, Sam gets out and yells at Dean. He tells Dean this is why he didn't tell Dean about his powers because of how Dean's reacting. He continues on by telling Dean that he has demon blood in him and "this disease pumping through my veins, and I can’t ever rip it out, or scrub it clean! I’m a whole new level of freak! And I’m just trying to take this… curse, and make something good out of it! Because I have to." Dean thinks about what Sam has said and agrees to talk to Jack.
So they talk to Jack, but he kicks them off his property. So they follow him and come back only to find that Jack took the bait. Jack knocks Sam and Dean out; Sam is locked in a closet. Sam tries to talk Jack out of it, but it's too late for Jack. As they are leaving Sam tells Dean he's not going to use his powers anymore, but not for Dean or anyone else. Though Sam does use his power again, much to Dean's displeasure in It's the Great Pumpkin, Sam Winchester. Also in that episode, Uriel reveals to Sam that Dean actually does remember Hell.
In Wishful Thinking, Sam confronts Dean about his memories of Hell, but Dean denies that he recalls any of it. But in the end Dean tells Sam he does remember Hell, and doesn't want to talk about it. This makes Sam upset due to his brother's pain and gets drunk at a bar. Dean comes in seeing his brother drunk and then see Sam go towards Ruby. Ruby gives them a job to find a girl the demons are after. Sam and Dean track Anna Milton down, but demons followed them there. After their escape Dean asks Sam why he trusts Ruby so much. Sam tells Dean his story about how Ruby saved him and taught Sam to use his powers. Then Ruby contacts them and they head towards the cabin. They find out the angels want Anna.
They find out Anna is actually an angel, and both Heaven and Hell want her. So they hide her in a building but Dean gives away their location due to Uriel threatening to kill Sam. But the Winchesters have another plan, to let heaven and hell battle it out. Once the battle is over, Dean tells Sam what Alastair meant by he had such promise. Dean reveals that 4 month is like 40 years in hell. 30 years Dean was tortured, but he couldn't take it anymore more and tortured others for the other 10. Dean tells Sam he wishes he couldn't feel a thing.
Their relationship hits another road when a siren comes between the two of them. It doesn't help that earlier that morning Sam lied to Dean about taking a phone call from Ruby. In Sex and Violence the siren uses his power to make Sam and Dean fight each other. During the fight Sam and Dean reveal their true feelings (Dean knowing about Sam's phone calls with Ruby, and Sam about Dean being weak). Just as Dean is about to kill Sam, Bobby comes in and saves them.
In On the Head of a Pin, Castiel takes Dean away to torture Alastair. Sam begins to look desperately for him because Sam believes Dean is not strong enough because of what happened in Hell. Just as Alastair is about to kill Castiel, Sam comes and kills (not right away) him. As Dean recovers, Sam stays near Dean's bedside in the hospital.
Later, Sam and Dean discover there is a book series about them about there called "Supernatural". Not only that, but Sam/Dean fan-fictions, which Dean expresses his disgust at. They meet the author and he later tells them Lilith is coming for Sam. Dean is shocked at this and tries everything to make sure it doesn't happen. Sam on the other hand, wants Lilith to come so he can kill her.
Everything changes when Dean finds out that Sam has been drinking demon blood. Dean locks Sam away so he can detox. Sam begs Dean to let him out and tries to explain why he was drinking the blood. Dean won't hear it and leaves. This action though, does kill Dean inside and he asks Castiel for help. Later Sam escapes and Dean follows him. At the hotel, Dean and Sam fight, but Sam comes out the winner. Dean tells Sam if he leaves, don't ever come back. Sam looks at Dean and leaves.After the fight, both sides are hurting. Dean wants to have nothing to do with Sam anymore, but it's Bobby who convinces him that Dean needs to reach out to Sam. Dean attempts to call Sam though from the angel's room, but gets voice mail. The angel play the brother's relationship beautifully, by using Dean's voice to send Sam a fake hate message. This causes Sam to go over the edge and head full speed towards Lilith. Dean, with Castiel's help escapes the room and heads towards Sam. Dean arrives just as Sam is killing Lilith. Once Lilith is dead and Ruby's betrayal is known, Sam helps Dean kill Ruby. Sam apologizes to Dean for everything and they watch Lucifer's cage open.
Dean: I tried, Sammy. I mean, I really tried. But I can't just keep pretending everything's alright. Because it's not. And it's never going to be. You chose a demon over your own brother and look what happened."
Sam: "I would give anything, anything, to take it all back."
Dean: "I know you would. And I know how sorry you are, I do. But man, you were the one I depended on the most. And you let me down in ways that can't even ... [...] I just don't ... I don't think we can ever be what we were. You know? I just don't think I can trust you.
– Dean's broken trust, Sympathy for the Devil
Sam and Dean are mysteriously placed on a plane. They start off by trying to find Lucifer. Sam tries to talk about what happened, but Dean refuses. Later on Chuck sends them the location of the Michael sword, a weapon that could kill the devil. Once there they discover Zachariah waiting for them and he tells them that Dean, in fact, is the Michael sword. Michael's true vessel. Dean realizes Michael need permission to enter his body. So to persuade Dean, Zachariah breaks Sam legs. Then takes away Sam's lungs. Despite seeing Sam in pain, Dean still refuses. To Dean's luck, Castiel arrives and save them both. As they are leaving, Dean tells Sam how hurt he is that Sam chose a demon over him and started the Apocalypse, and that he doesn't know is he can trust Sam again.
Sam and Dean head to a town that is apparently infested with demons. There Dean is watching Sam's every move. First when they head out to get guns and salt. Dean wants Sam to stay behind, but Sam refuses. The next time when Ellen wants to go to look for Jo. Dean tries to get Sam to stay behind, but Sam refuses. Sam asks Dean if Dean thinks he is going to loose control the moment he see demon blood? Dean asks are you? Sam pushes Dean in anger and yells. Sam leaves with Ellen for the search party, but end up getting captured. Despite knowing Sam is captured, Dean manages to keep his cool and figures out it's the horseman war doing this. So once Dean gets Sam, they go after War and cut off his finger. After is over, Sam and Dean have a talk. They realize they need to separate, due to individual problems (Sam knowing he's weak and Dean tired of looking after Sam). Sam also says they could never go back to they way they were. In fact that was the problem. So Dean continues hunting and Sam works in a bar.
They don't stay separated for long though. Dean realizes even though they are weak together, they keep each other human. So in Fallen Idols Sam and Dean put the training wheels on and try to fix their relationship. Sam walks in on Dean talking to Bobby and stating the fact that Sam started the apocalypse. Sam asks when will he be off double secret probation, and Dean asks when I say so. Sam argues this was supposed to be a fresh start. After the job, Dean tells Sam he needs to let Sam grow up and they reconcile.
So now Sam and Dean revert to a new state of normal. It's different then before, but yet similar. They continue hunting and they manage to find the Colt and Lucifer. So in Abandon All Hope.... they go after Lucifer but only to find that the Colt does not work on him.
After Ellen's and Jo's death, Sam and Dean investigate an incident in an insane asylum. Slowly the two go insane and don't know whats real and whats not. Due to an incident, Sam gets locked up and drugged. During this time, Dean comes to visit Sam. Sam tells Dean, that Dean has always been a little crazy. Sam also mentions something about Jo and Ellen's death. Then goes on about how Dean is his brother and how Sam loves him. Later in the episode Dean saves Sam from the Wraith, and the go back to normal.
In Swap Meat it takes Dean a while to realize that "Sam" isn't Sam. They two realize the truths about each when Sam and Dean enter heaven in Dark Side of the Moon. Dean's heaven is composed of his family. Like when him and Sam lit fireworks in a field. Or even when his mother made him a sandwich when he was young. On the other hand, Sam's is composed of the moments when he was able to be on his own. This surprises Dean at what Sam considered happy moments. Sam's happy moments were not so great for Dean. They put this behind them when Zachariah finds and chases them. After returning home, Castiel returns Dean's necklace. As Dean walks to the door, he drops the necklace in the trash in front of Sam.
Dean starts to lose faith and begins leaning towards saying yes. Sam notices this beginning in 99 Problems. At the end of the episode Dean runs away and goes to Lisa's before heading to a motel. In Point of No Return, Dean has his mind up to say yes to Michael. Sam comes to his motel to try to talk Dean out of saying yes to Michael, but it doesn't work. Sam tells Dean he has to stop him, and Dean tells Sam he can try. Sam had come prepared though, and brought Castiel. They put Dean under watch in Bobby's house. Dean manages to escape though and attempts to contact Zachariah. Castiel brings Dean back though and Dean awakens in the panic room. He tells Sam that he doesn't believe in Sam. Sam looks sad and tells Dean that he believe Dean will do the right thing. He unlocks Dean's handcuff and takes him along on Adam's recuse. Zachariah manages to corner Dean with his brothers' pain. Dean is about to say yes, when looks at Sam and sees Sam's disappointment. Unwilling to disappoint Sam, Dean kills Zachariah and escapes the room with Sam, but Adam is left behind. As they drive away, Dean apologizes to Sam and still can't believe how much trust Sam has in him.
Dean later returns this trust in The Devil You Know when he and Crowley bring Brady back to the house despite Crowley's warning not to. Dean tells Sam he trusts him and to keep calm. Sam sees Brady and gets angry, but Dean holds him back. Sam manages to lock Dean in the washroom and confronts Brady. Sam realizes Brady isn't worth it and lets Dean out. The real trouble comes when Sam suggest that he says yes to Lucifer and jumps in the hole in Two Minutes to Midnight. Dean doesn't like this idea one bit, but Sam believes this to be the only way to defeat the devil.
As Dean promised to Death, he agrees to let Sam jump in the hole. On the way there, Sam makes Dean promise not to bring him back and to go to Lisa once this is done. Basically live an "apple pie" life. Dean doesn't agree at first, but in the end, he does. When Sam has to drink the Demon blood, he asks Dean to turn away, because he doesn't want Dean to see this. Then they go confront Lucifer, and Sam says Yes. Unfortunately, Lucifer wins and Sam is gone. Dean sinks in defeat and mourns for his brother. But he doesn't give up.
Dean heads towards the showdown area for Michael and Lucifer. Dean keeps trying to reach for Sam and help Sam beat Lucifer, but his efforts appear to have no effect. Lucifer begins to beat Dean into a bloody pulp. Dean reaches up and says "I'm here Sammy". Just as Lucifer pulls for the final punch, Sam notices all the memories in the Impala. Like the army man he stuffed in the ash tray when he was a kid. With the power of his memories and his relationship with Dean, Sam overpowers Lucifer and tells Dean "its going to be okay. I got him". With this, Sam jumps in the hole, leaving Dean there. Dean keeps his promise to Sam and goes to live a life with Lisa. That same night, Sam mysteriously re-appears back from Hell in front of Lisa's house.
- "You just went. You didn't hesitate, because you care and that's who you are. Me, I wouldn't even think to try."Yes you would.""No Dean. I'm telling you. It's just better with you around."
- —Sam and Dean[src]
Sam saves Dean after a Djinn attacked Dean. Dean is surprised to see Sam again and gives Sam a big hug. Dean ask Sam how he's back. Sam tells Dean he's been trying to figure out who (or what) brought him back for about three weeks but gave up. Dean gets angry that Sam been back for a year now and didn't tell him. Sam replies that Dean had a good life going and didn't want to ruin it. After they face the Djinn, Sam ask Dean to join him in hunting again, but Dean refuses and goes to pick up Lisa and Ben.
Sam calls Dean in on case in Two and a Half Men. With Dean on the scene, he suggests they go to pick up supplies where Dean surprises Sam with his knowledge of baby stuff. They notice though that the baby is a shapeshifter and they bring it to Samuel's place. The alpha comes and takes the baby. At the end of the episode, Lisa tells Dean to go back hunting with Sam, but come back when he can.
Though Dean begins to notice changes in Sam. Like when Sam held him back when Castiel soul probed a young kid. Dean expresses this concern to Bobby in Weekend At Bobby's. This confusion deepens further when Sam appears to let Dean get turned into a Vampire. As a vampire, Dean notices Sam unusually calm, but Sam tells Dean is trying to keep calm in this situation. Once cleaning out the nest and getting cured, Dean gets a flashback where he noticed Sam watching him getting turned.
In You Can't Handle The Truth Dean gets a truth curse cast upon him and he attempts to use it on Sam about what happened when he was turned into a vampire. Sam tells Dean that what he thinks happened didn't. But the encounter with Veritas confirms Dean suspicions. Sam tells Dean he did let Dean get turned because he knew they had a cure and so they could find the alpha vampire. Sam tells Dean there is something wrong with him. Dean is silent and then breaks out with a punch. Dean beats Sam unconscious.
Dean enlists Castiel to help figure out what's wrong with Sam. Castiel asks Sam a bunch of questions and Sam answers. Sam can't believe Dean is having Castiel treat him. Castiel soul probes Sam and finds that Sam is missing his soul. This explains Sam's actions to Dean, and Dean asks when Sam is still even "Sam". In the end though, Sam still chooses Dean over Samuel. So they follow Samuel to a compound where they take all the captured creatures. There they meet Crowley who claims to be the one who brought Sam back, and forces the boys to work for him. Dean doesn't like the idea, but Sam promises Crowley will get what's coming to him.
Dean now knows Sam is soulless, and tries to deal with this fact. In All Dogs Go To Heaven, Dean tells Sam to stop trying to be "Sam." Mostly because this soulless version could never be the real one. In the end of the episode, Sam tells Dean the truth about how he really feels. He tells Dean he doesn't care about anything, including Dean, but he needs Dean's help. Dean later acts as Sam's conscience in Clap Your Hands If You Believe due to the fact that Sam doesn't feel anything. Like when Dean gets kidnapped, Sam goes has sex with the hippie girl. Later though, Sam begins to wonder if he really wants his soul back, meanwhile Dean still wants Sam to have his soul.
They attempt to get Sam's soul back when Sam makes a deal with Meg Masters for help on making Crowley give Sam his soul. Dean is shocked and not too happy with the fact that he's working with demons. After Crowley reveals he can't get Sam's soul and is "killed" by Castiel, Sam tells Dean he doesn't want his soul back. Dean can't believe this and Sam walks away.
But Dean doesn't give up. In Appointment In Samarra Dean makes a deal with Death for Sam's soul. Sam who still doesn't want his soul, tries to look for the rings, but Dean already has them. Sam lies to Dean saying he's fine with getting his soul back, when in reality, Sam doesn't want it back. Dean becomes Death for Sam, but loses the wager. Even though he lost, Death gets Sam's soul and places it back in Sam. Dean is troubled though by Sam's screams of agony.
While waiting Dean is worried Sam will never wake up, but as Bobby and Dean are talking about a hunt, Sam appears and hugs Dean. At last, the real Sam is back. Which Dean is more than grateful for. He expresses this when he and Sam are on a hunt for Dragons in Like A Virgin. Sam though is made aware of what happened when he was soulless (thanks to Castiel) and he apologizes to Dean. Dean tells Sam it not his fault, but Sam disagrees.
Sam continues to investigate what happened during the time he was soulless and Dean does not want Sam to dig any deeper. He is afraid the wall in Sam's mind will break. In Unforgiven Sam passes out and sees a moment of hell. Sam's passing out frightens Dean and he has no idea of what to do. Sam does wake up and Dean takes him out. Dean later asks if Sam wants to talk about it and believes what Sam saw was hell. Dean tells Sam to just forget about it and don't kick the wall. Sam doesn't want to forget about it but leaves it alone. Sam and Dean continue to hunt without Sam kicking the "wall". Although Sam does thank Dean for getting his soul back, which Dean is thankful to hear.
Then in the final hours, Sam and Dean's relationship is tested. In Let It Bleed, Sam stayed with Dean in the hunt for Lisa and Ben. He is also concerned when Dean starts torturing again. When they do find Lisa and Ben, Sam comes with Dean. With them rescued and memories erased, Sam is concerned for Dean, but Dean threatens Sam to never talk about Lisa and Ben again.
Then it gets switched when Castiel destroys Sam's wall inside his head (The Man Who Knew Too Much). This puts Sam into a comatose state and Dean gets worried. Dean stays beside Sam's bedside while waiting for him to wake up. Sam begins to move, Dean gets really concerned. When Bobby makes Dean go back to work, Dean stays by Sam's side until he can't. While leaving Dean leaves Sam the address of where they'll be. Meanwhile in Sam's head, he has to choose between not remembering everything and forever stay in a coma or remember everything and help Dean. When Sam does wake up, he heads to Dean's location while he still is messed up. In order to save Dean from Castiel, Sam stabs Cas only to find out it doesn't work, because the latter was no longer an angel.
- "Sam, I am so very, very, very, very, very, very tired." "Dean, like it or not, the stuff you don't talk about doesn't just go away. It builds up. Like whatever's eating at you right now..." "There's always something eating at me. That's who I am. Something happens, I feel responsible. All right, uh, the Lindbergh Baby — that's on me. Unemployment — my bad."
- —Dean and Sam[src]
Dean has to deal with Sam remembering hell and not being able to stop it. Sam begins showing signs of his wall breaking already in Meet The New Boss. Sam collapses on the ground and passes out. When Dean sees Sam walking around, he is surprised, but Sam reassures Dean that he's fine. Since they can't stop Cas, Dean and Sam work on fixing the Impala together. When Sam realizes that he may not be alright, he goes to tell Dean, but overhears Dean saying how he can't take anymore 'hits'. In order to not worry his brother, Sam decides not to tell Dean. When Dean does find out, he is angry that Sam is lying to him. Sam tells Dean he didn't want to add to his problems.
In Hello, Cruel World, Dean finds Sam, and brings him back to Bobby's. Sam tells Dean on how he has been having trouble differing between real and fake. In addition to hallucinating Lucifer. This worries Dean, and Sam tells Dean he knows he's not alright. While Sam is working on his gun, Dean goes to Sam's cell phone and turns on the GPS in case Sam goes AWOL. This way Dean can find Sam if Sam goes crazy. When they hear rumors of the Leviathans, Sam insists that Dean goes, and he stays. So Dean goes, but when he comes back, Sam's gone. This is because Lucifer turned into Dean and tricked Sam somewhere. Dean is able to get through to Sam though, when he finds Sam. Knowing the same pain Sam is experiencing, Dean is able to convince Sam this is reality by using pain.
They return together to Bobby's house, but find it burned, and no sign of Bobby. They are soon attacked by Edgar, and they manage to crush him. Although Sam is knocked out, and Dean's leg is broken in the process. Dean tries to wake Sam, but to no success.
In The Girl Next Door Sam and Dean managed to get away from the hospital. Sam is still seeing things, but is using the scar he has to keep him balanced. Dean is still concerned about Sam's mental health. Then Sam sees a familiar case and takes off. An angered Dean quickly chases after Sam, and when he catches up with Sam, punches Sam. In the motel room, Sam asks Dean to trust him, which Dean seemly agrees to, but is lying, and he goes to kill Amy behind Sam's back.
When Dean is put on trial by Osiris, Sam desperately tries to save him, but Dean lets Osiris sentence him before bringing out the third witness (possible Amy Pond). Dean doesn't want Sam to know that he went behind Sam's back and killed her. Sam believes that Dean trusts him because of Dean's lie.
Although in Shut Up, Dr. Phil Sam notices Dean's drinking and later asks Dean what going on with him. Dean points out to Sam that he always feels guilty. Sam does find out later in Slash Fiction when the Leviathan Dean tells Sam that Dean killed Amy. Sam is shocked and angered by this. Later on Sam reveals he knows to Dean, and Dean tries to explain himself. Sam stops Dean, so angered, Sam tells Dean he can't talk or face Dean and leaves. Feeling guilty, Dean lets Sam leave.
A week and a half later (The Mentalists), the two bump into each other again, and Sam is still mad at Dean. Dean manages to convince Sam to work with him though. Finally had it with Sam's attitude, Dean confronts Sam on it, and tells Sam he killed Amy because it felt right due to Amy killing four people. In addition to that, Sam would have done it too had Sam not known Amy. When the case is done, Sam and Dean reconcile and begin working together again. Sam even gets Dean to admit what is eating him. Dean admits that he didn't feel guilt for killing Amy, but about lying to him about his actions. Sam realizes that if he didn't know Amy, he might have done the same thing too and the brothers begin working together again.
A few weeks later the brothers split up for separate down time and Dean gets a mysterious text message from Sam telling him to come in his FBI suit. Dean arrives and discover Sam is getting married to no other than Becky Rosen. Under the influence of the spell Sam tells Dean that he doesn't need him anymore. When Sam finally snaps out of it, Dean pokes fun at what happened, and Sam mentions that Dean did fine on his own. Dean although isn't happy with that idea.
When Bobby is shot in the head by Dick Roman, Sam tries to brace Dean and himself should Bobby die, but Dean refuses to consider the possibility, saying that they've been through enough. Then Bobby passes and Sam and Dean are alone again. In Adventures in Babysitting when Frank suggests Dean should quit, Dean refuses saying he can't leave his brother by himself.
Sam begins to worry about Dean when Dean begins to believe that Bobby's spirit is around. Sam quickly turns this idea down. In The Slice Girls, Sam gets angry with Dean for not shooting Emma and the fact the he had to. Sam gets even more insight on Dean's mentality when he asks Dean to stay alive and Dean says he'll do his best. In Plucky Pennywhistle's Magical Menagerie they investigate strange murders at the place, and Sam complains to Dean how in the past Dean used to dump him there. Later on Dean apologizes to Sam for doing that, but not after laughing at the sight of his brother covered in sparkles.
Dean becomes concerned for Sam when Sam lands in a mental ward in The Born-Again Identity. Dean becomes angry at Sam's defeated attitude about his condition. Sam tells Dean that he's too tired to do anything, which makes Dean sad. Unable to sit by and do nothing, Dean begins calling up hunter contact and finds a healer for Sam. This healer just happens to be Castiel, but for the sake of his brother, Dean puts his anger aside. Dean manages to get Castiel to help, but it's too late since Sam's mental state is too crumbled. Castiel manages to shift Sam's hell and Dean is glad to see his brother on his feet again. In Party On, Garth, Dean asks Sam if he alright, and Sam tells Dean that he's fine now.
In Survival of the Fittest, Sam takes care of Bobby due to that Dean is too close to Bobby to do it. So in order to spare his brother heartache, Sam takes care of Bobby. When Dean finally takes care of Dick Roman, and an explosion occurs, sending Dean to Purgatory, separating Sam and Dean on different worlds.
- "I mean, maybe at you're best hacking and slicing your way through all the world's crap alone, not having to explain yourself to anybody." "Yeah, that makes sense, seeing as I have so many other brothers I can talk to this stuff about."
- —Sam and Dean[src]
In Heartache, Dean drags Sam along on a hunt hoping Sam's hunting passion would kick in again. In Blood Brother, Dean drops everything and leaves Sam. Sam is shocked and angered by this, but Dean rebuts that he needs a day and that Sam took a year off. Dean later calls Sam and after some ranting on Sam's part about taking down a Vamp nest by himself, Dean tells Sam his location. Thus Sam and Benny meet.
In Southern Comfort, there is tension between Sam and Dean since Sam figured out Benny was a Vampire. When possessed by the Spectre, all Dean's fury at Sam for once again letting him down is brought out and he tries to kill Sam. When free, Sam criticizes him for holding in all that, and tells him to let it go or he would leave. Following the return of Castiel, their relationship returns back to normal, and greatly improves, the tension seeming to disappear.
However in Citizen Fang, after learning that Sam had been keeping tracks on Benny, Dean was shocked. Likewise strain was once again put on their relationship, with no help from Martin who had been keeping an eye on Benny. When defending Benny, Dean once again remarked that he was the only one who had never let him down, hurting Sam. Martin again lights this by remarking he agreed with Sam, about Dean picking a vamp over his own Brother. Later, to save Benny, Dean tricked Sam into thinking Amelia needed him. Upon learning of his trick, and Martin's Death at Benny's hand, Sam was deeply hurt, and simply hung up on Dean not wanting to talk.
In Trial and Error, Dean states that he should be the one to take on the trials as he doesn't have a future, but Sam ends up taking them instead.
In Taxi Driver, Dean shows great concern while Sam is trapped in Purgatory. So much so that he kills Benny to go and save him. In Purgatory, Benny stays to fend off some vampires so Sam and Bobby can escape. When Sam returns to Earth, Dean greets him with a hug and gets worried when he sees Sam's condition get worse after fulfilling the second trial.
In Season eight's finale, Sacrifice, Dean deeply emphasized that he cares about Sam, to the extent of putting him above all of his other relationships - like Benny and Castiel.
- "I made you a promise in that church. You and me, come whatever. Well, hell, if this ain’t whatever. But you gotta let me in, man, you gotta let me help. There ain’t no me if there ain’t no you."
- —Dean to Sam[src]
With Sam dying from the damage the Trials did to him, Dean goes to desperate measures to save him, tricking him into allowing Gadreel to possess him to heal him from the inside. Dean keeps Gadreel's actions from Sam, coming up with various cover stories but growing less sure of the angel as time goes on due to his continuing insistence on hiding the truth. Dean also hides his concern over Sam's physical state as he slowly heals. Dean is forced to choose between Sam and Castiel due to Gadreel threatening to leave Sam if he doesn't send Castiel away and as this would result in Sam's death, Dean has to send his best friend away to protect his brother.
Finally, after learning that Ezekiel, the angel Gadreel claims to be is dead, Dean tries to tell Sam the truth, but Gadreel only pretends to be Sam and takes permanent control, murdering Kevin and leaving Dean to mourn the loss of both Sam and Kevin. Believing there is no way to save Sam, Dean decides to kill Gadreel at Sam's expense to get revenge for his loss, but dedicates himself to saving him even at the cost of releasing Crowley after Castiel reveals there is hope. Dean goes so far as to allow Crowley to torture Gadreel and thus Sam, though he is unaware of it to try to free him and goes as far as allowing Crowley to possess Sam to save him on the condition Crowley leave Sam afterwards. Dean's efforts ultimately succeed and Sam expels Gadreel, mostly healed by the angel's possession of him to the point that Castiel can finish the job over time. However, Sam is furious about Dean tricking him as he wanted to die and does nothing to stop Dean from going off on his own, telling him to go if he wants and that Gadreel is not the problem as Dean thinks.
Dean goes off alone to find a way to kill Gadreel. However, he finds Crowley on the way who insists on helping find a way. They go to Cain's house and after proving to Cain that he is worth it, Dean gets the mark of Cain. Meanwhile Sam and Castiel are working together to collect Gadreel's grace from inside Sam so that they can kill him once and for all. This however fails because doing so could kill Sam and even though Sam accepts this, Cas does not and stops the procedure.
When the brothers meet up again Sam tells Dean that they can work together but they have to accept that the brother bond was broken. Dean agrees to this but is heartbroken. Later Dean confronts Sam and says "if the situation was reversed and I was dying you would do the same" to which Sam says "Same circumstances I wouldn't". This leaves Dean in shock and he eventually comes to terms that Sam would not save him if he was dying. Through the next part of Season 9 we see Dean and Sam's relationship getting worse as Dean is obviously hurt and Sam is mad. We get to see a more concerned side of Sam when the mark of Cain starts showing its affects on Dean. Dean, Crowley and Sam locate the first blade and after that they go on search for Abaddon. After a little help from Crowley, Dean kills Abaddon with the first blade but when the rage from the mark takes over he starts to mutilate her corpse using the blade until Sam snaps him out of it.
After this Dean is keen on keeping the blade with him at all times. When Castiel calls them to and tells them to meet him, Sam insists that Dean leaves the blade at the bunker. They bicker about it but Dean eventually says yes and leaves the blade there but we later find out that Dean in fact did take the blade with him. He kills the reaper Tessa making everybody else furious.They other angels tells Cas to kill Dean in order to prove his loyalty but Cas refuses causing the angels to leave him and join Metatron. When they along with Cas get back to the bunker, Dean tells Sam that they are not partners and that it is a dictatorship since Deans the only one who can kill Metatron. Later Gadreel shows up asking for forgiveness and insists on helping them defeat Metatron. Dean goes to shake his hand and then later whips out the first blade and slashes him with it. Sam and Cas try to hold him back.
In the finale, Cas and Sam lock up Dean because he is out of control. They try to find Gadreel while Dean summons Crowley and asks him for help in escaping. When Sam and Cas come back Deans gone, along with the first blade. Sam eventually finds Dean and they have a plan to find Metatron together. However when they get to the place Metatron is living, Dean knocks Sam out and says it not his fight. Dean fights Metatron but fails because Metatron has taped into the power of the angel tablet. Dean is beaten up and he "calls" the First blade over to him but as soon as gets it, Metatron stabs Dean in the heart. Sam sees this and yells "NO!" and then runs over to Dean. Metatron flees and Dean is about to die. Sam tells him to hold on as he gets him up and starts walking. Dean then questions Sam saying how he said he would be okay with Dean killing Metatron no matter the consequences to which Sam said "I lied". Later Dean tells sam to stop and tells him he has to say something To say Sam says "what" and Dean says "I'm proud of us" and then dies in Sam's arms. Sam breaks down in tears, and gets him back to the bunker. It is shown that he is drinking alone and he tries to summon Crowley so that he can save him. Now that Dean's actually dead, Sam is trying to make a deal with Crowley. What he doesn't know is that Crowley is already in the bunker, talking to Dean's corpse.
Crowley: "Your brother, bless his soul, is summoning me as I speak, make a deal, bring you back. It's exactly what I was talking about isn't it? It's all become so... expected. You have to believe me, when I suggested you take on the Mark of Cain. I didn't know this was going to happen. Not really. I mean I might not have told you the entire truth but I never lied. I never lied Dean, it's important. It's fundamental. But there is one story about Cain that I forgot to tell you. Apparently he too was willing to accept death rather than become the killer the mark wanted him to be. So he took his own life with the blade. He died. Except, as rumor, the mark never quite let go. You understand why I never spoke of this. Why set hearts a flutter at mere speculation? It wasn't until you summoned me, no, It wasn't truly until you left that cheeseburger uneate , that I began to let myself believe maybe miracles do come true. Listen to me Dean Winchester, what you're feeling right now it's not death, it's life. A new kind of life. Open your eyes Dean, See what I see, Feel what I feel. Let's take a howl at that moon."
After this speech the camera zooms into Dean's face and Dean opens his eyes, which are now demon black. Season 9 finishes off there and whether he is a normal demon or a Knight of Hell is not clarified. As of now Sam does not know of his brother being alive or of him turning into a demon.
In Season 2's What Is And What Should Never Be, Dean is in a world created by the Djinn. A world where his mother never died, and they never become hunters. Sam even turns out normal and is engaged to Jessica (which Dean is happy about). Dean finds out that not everything is as perfect as he thought. He and Sam don't have a good relationship. In fact, they have nothing in common with each other. This contributes to Dean's drive to return to his own world.
In Season 4's It's A Terrible Life, Sam and Dean lose their memories about each other and hunting, and instead live normal lives working in a corporate building. Sam, despite his normal exterior, still has dreams about being a hunter. Sam tries to confront Dean in the elevator and ask him about the dreams, but Dean tells Sam to keep to himself. There is a string of weird murders in the building, and Sam and Dean team up to solve it. Even though they don't remember each other, their previous relationship comes out. Along with Sam's dreams, this speaks to the boys subconscious still retaining memories of their real lives. Dean and Sam banter back and forth and tease each other like normal. Eventually Dean discovers that this life is an elaborate illusion.
Skills & AbilitiesEdit
While they're quite formidable separately, they are a force to be reckoned with together, as they have actively stopped many high-level demons and world-threatening entities together. Crowley, a high-level demon himself and current King of hell, noted them as "denim-wrapped nightmares" and shouldn't be underestimated by anyone. The Leviathans even claimed the brothers ranked high enough to be considered a threat and immediately targeted them after their release.
Both brothers are extremely proficient in hand-to-hand combat, with Dean being better at hand-to-hand combat and Sam physically being the stronger of the two, although at times, because of Dean's feelings, Sam beats him.
Sam, on the other hand, tends to act smarter and solves problems more economically than Dean does, in the beginning, especially considering the feelings and wants of others. However, Dean is smart though he tends not to show it. Sam refers to Dean as the best hunter in existence, better than himself and other great hunters such as their father and a "genius" at lore.
Their true strength lies in their teamwork, as they are able to make coordinated plans from non-verbal cues. Their teamwork built from years of trust and their joint belief in "Family Is Everything". While this is belief and trust has been strained and broken over the years, it has always come back better and stronger than ever.
In fandom, a popular pairing involves Sam and Dean. Wincest is the term used to refer to slash pairing between the Winchesters.
"Wincest" is a very popular style of writing and can mostly be found on Fanfiction.net or at other created websites, such as livejournal. With the first Wincest fanfiction, being published shortly after the airing of the first episode Pilot, although the term Wincest was not dubbed until a few weeks later.
Although normally focusing on the brothers, some Wincest stories also feature their father, John Winchester, involved with either, or sometimes both, of the brothers. In addition, after his introduction, some fanfiction began to feature Sam and Dean's half brother, Adam Milligan, as he is also technically a Winchester.
Wincest Referenced in Supernatural:
Example from Bugs:
- Real Estate Agent: We accept home owners of any race, religion, color, or... sexual orientation.
- Dean: Right. Um, I'm gonna go talk to Larry. Okay, Honey? (smacks Sam on the butt)
Example from from Playthings:
- Dean: Of course, but the most troubling question is, why do these people assume we're gay?
- Sam: Well, you are kind of butch. They probably think you're overcompensating.
Wincest fanfiction was mentioned in The Monster at the End of This Book by Sam and Dean.
- Dean: (Reading on the computer) There's Sam Girls and Dean Girls and - What's a slash fan?
- Sam: As in Sam-slash-Dean... together...
- Dean: Like "together" together?
- Sam: Yeah.
- Dean: They do know we are brothers, right?
- Sam: Doesn't seem to matter.
- Dean: Aw, come on. That's just plain sick!
→ see also Sam and Dean/Gallery
- Elias Finch says that God judges and in "Swan Song," Sam and Dean were judged by the Creator to have "done alright."