The Journal mentions that prior to Mary's death, Dean played t-ball. November 2, Mary Winchester is killed by Azazel when she interrupts him feeding demon blood to Sam. John hands the infant Sam to Dean as the nursery burns and tells him to "Take your brother outside as fast as you can! Dean faces off with a shtriga. When Dean is "6 or 7," John takes Dean out shooting for the first time, using bottles as target practice.
According to Dean, he "bullseyed every one of them. Dean cites this story as one of the fonder memories of his father. Dean gets bored and goes out, and comes back to find the shtriga attacking Sammy. John returns in time to scare the shtriga off.
Dean is haunted by his failure to defend his brother. Ten-year-old Dean tells him, "Dad says I'm supposed to practice with the double-barrel," but Bobby insists that he gets to throw a ball around "like a regular snot-nosed little jerk.
When Dean is in sixth grade he makes his first sawed-off shotgun. Dean is left to babysit Sam 8 years old while John is on a hunt, and Sam begins to interrogate Dean about what it is that their dad actually does. Dean responds "You know that. Don't you ever talk about mom! Upon his return, Sam reveals to Dean that he found and read their dad's journal, and demands to know if monsters are real.
Dean finally resigns himself to telling Sam the truth. I swear, if you ever tell dad I told you any of this, I will end you. First thing you have to know is He's fighting them right now. It is hinted at that Dean still believes that his father is a "superhero" at this point, and continually excuses his flaws, while the tension between Sam and John is clearly starting to take root.
Disappointed with John 's lying and absence, Sam gives Dean the present intended for his father: As told by Dean to fellow hunter Gordon in 2. So, I picked up this crossbow, and I hit that ugly sucker with a silver-tipped arrow, right in his heart. Sammy's waiting in the car and, uh, me and my Dad take the thing into the woods, burn it to a crisp. I'm sitting there and I'm looking into the fire, I'm thinking to myself I'm sixteen years old. Kids my age are worried about pimples, prom dates I'm seeing things they'll never even know.
Never even dream of. So right then I just sort of Dean spends two months in at a boys home after getting caught stealing food, prior to being arrested he mentions to Sonny that he got his injuries during a werewolf hunt.
In summer John , Dean and Sam are hunting a werewolf. While Sam is having trouble with a bully named Dirk McGregor , Dean gets a girlfriend, Amanda Heckerling ; although he becomes uncomfortable when she wants him to meet her parents. When she catches him cheating on her with another girl, she challenges him, charging that his "cool" persona is a cover for his loneliness. Dean goes on a road trip that was supposed to be "5 states, 5 days" while Sam 15 or 16 was "in Orlando with dad, wrapping up that banshee thing.
It was the bendiest weekend of my life. While there he becomes estranged from Dean and his father, and doesn't speak to them for at least a couple of years. During this time, as Dean tells Sam in 1.
She was "finishing up college" she was therefore approximately 21 or 22 and they "went out for a couple of weeks. When he found out he was leaving, he told Cassie the 'big family secret' about hunting because, as Dean says in the episode, he "just couldn't lie to [her].
This, as Dean also revealed in the episode, really hurt him, and he decided at that point that it was "stupid to get so close" and that he didn't need to open up to anyone. It is likely that it was around or , during the "almost two years" that Dean did not speak to Sam, because Sam claimed that Dean hadn't told him anything about it.
That means Dean was approximately 24 or October Dean is Dean explains that before he showed up in Palo Alto to get Sam from Stanford, Dean was "working [his] own gig How long did Sam spend at Stanford? Considering the two men had not spoken in "almost two years," as Dean points out in 1. Episodes Season 1 When John Winchester goes missing, Dean goes to Stanford to enlist the help of the brother he hasn't spoken to for a couple of years.
After spending an unsuccessful weekend trying to track down John, Sam returns to Stanford, despite Dean's obvious desire for him to stay. Sam's commitment to returning to shaken when his girlfriend, Jessica Moore is killed in the same manner as their mother.
Sam joins Dean, and they go on the road with the aim of finding their father and killing monsters along the way. In particular, they are after the demon that killed Jess and Mary Winchester. In season one, it is obvious that Dean is happy with his life as a hunter, and he tries to draw Sam back into the life: Gradually, Sam and Dean become reacquainted with each other after their long separation — and often clash. He states that he knows eventually everyone will leave him. They clash over Dean's loyalty and obedience to John.
Ellicott , Sam tries to shoot Dean in a spirit-induced rage over Dean's insistence in obeying John's orders rather than going to California to find their father. In the following episode Sam actually does leave Dean, who insists he and John are both selfish because all they care about is revenge then later who tells Sam he was always proud of how he pursued what he wanted.
Sam eventually goes looking for Dean when he can't reach his brother on his cell phone. When Dean asks why he was saved, Roy Le Grange says he looked into Dean's heart and saw "A young man with an important purpose. A job to do. And it isn't finished. They come closer to this possibility in 1. The Winchesters manage to acquire it from a group of vampires. The Yellow-Eyed Demon and his "children" Meg and Tom are quick to act, and begin killing John's friends and threatening to kill more until John gives them the Colt.
John tries to trick them and is captured. In the season finale, the two Winchester brothers must rescue their father and face the Yellow-Eyed Demon, who possesses John. It is Dean who senses that something is wrong, when his father, uncharacteristically, praises him. Azazel is able to hold the brothers in check with his powers, and begins to torture Dean.
The demon taunts him: Not like you need them. John pleads with Sam to shoot him with the Colt, but Dean begs him not to. The demon leaves John's body after Sam shoots him in the leg, and the three Winchester men drive towards the hospital. Suddenly the Impala is totaled by a demon driving a big semi-truck. Season 2 The season opens with Dean comatose from his injuries. Just as Dean is about to choose, he is returned to his body and healed because John has made a deal with the Yellow-Eyed Demon , trading his life for Dean's.
Before he dies, John gives Dean a last, secret command — that he should save Sam , and if he can't save him, he should kill him. Throughout this season Dean struggles with this secret and his grief and guilt over his father's death.
As much as he wants to, he has trouble admitting the secret to Sam. He becomes increasingly concerned about Sam's powers as the season progresses, but attempts to be supportive. During Sam's possession later in the season, Dean insists that Sam could not be responsible for the actions attributed to him, because in spite of Dean's own fears he believes in Sam.
Dean makes a deal with a crossroads demon to resurrect Sam. Dean's police record begins to be a problem for the brothers this season.
Dean is picked up in Baltimore on suspicion of murder, and the national authorities become aware that he is alive. They associate the crimes of the dead shapeshifter who took Dean's form in 1. Matters become even more convoluted when Sam and Dean deal with another shapeshifter in 2.
Their notoriety does allow the brothers access to a prison they are investigating in 2. Some of Dean's inner desires are revealed in 2. It uses a strong desire from Dean's subconscious that his mother never died to hold Dean captive in a dream world. There, Mary is indeed alive, Dean has a girlfriend and a job as a mechanic, but Dean and Sam are not close, and rarely speak. However, when Dean finds out that it is a fantasy and that all the people he has saved are dead in this reality, he struggles to escape it.
He decides in favor of his life as a hunter, but he later admits to Sam that "I liked it there. I didn't want to leave. Dean and Bobby arrive as Sam is battling Jake. Jake comes up behind Sam and stabs him in the back with a knife.
Sam dies in Dean's arms. Grief stricken, Dean makes a deal with a crossroads demon that echoes what his father did for him - Sam's life for Dean's, and Dean is given one year to live. Dean also agrees not to fight the deal, on pain of Sam's death.