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,
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, virtually injury-free, he has no memory of
his time with the reaper; he does, however, comment later that, when he
woke up, it felt wrong. John whispers something in Dean's ear which the
audience cannot hear, then walks into another room and dies.
Throughout the first half of the second season, Dean struggles with the
death of his father, as well as with the knowledge that he was the one
who was supposed to have died, and the belief that his father is now in
Hell. Furthermore, he is 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 rather impressive 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, it is unclear whether
or not the charges against Dean are ever officially dropped. However,
since the authorities now know that Dean is not dead, as they had previously
believed, he is again wanted for the murders committed by the shapeshifter
in "Skin". In "Nightshifter", a team of FBI agents,
led by Special Agent Victor Hendrickson, catches up with Dean and Sam
in Milwaukee, Wisconsin, where 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", just as Dean
arrives to rescue his brother, Sam is stabbed by Jake (another of Azazel's
'psychic 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 bill
to come due in one year. Bobby Singer berates Dean for making the deal,
and Dean's utter lack of a sense of self-worth comes out in the conversation.
Shortly thereafter, in a confrontation with Azazel, the demon implies
that what Dean had brought back from the dead might not be "pure
Sammy," since Sam unhesitatingly kills Jake without any sign of remorse.
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 Hell's gate opened, allowing hundreds of demons to escape
from Hell as well as a number of non-demonic souls, including that of
their father, with whom they share an emotional moment before he disappears
in a glow of light. Dean and Sam must now hunt down all of the escaped
demons, as well as find a way to save Dean from dying in a year's time.
Source: wikipedia.org
