All three of the Winchesters survive the wreck, although Dean is 더 많이 severely injured than his father 또는 brother. In the season premiere "In My Time of Dying," Dean is in a coma. A reaper named Tessa tries to convince him to 옮기기 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, 코멘트 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 초 season, Dean struggles with the death of his father. He is also haunted 의해 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 의해 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 의해 the shapeshifter. In "Nightshifter," a team of FBI agents, led 의해 Special Agent Victor Henricksen, catches up with Dean and Sam in Milwaukee, Wisconsin, where an attempted bank robbery and several 더 많이 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 의해 Jake Talley, another of Azazel's "special children," and dies in Dean's arms. Crushed 의해 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 년 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 초 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.