be possessed by Azazel when the brothers come to his rescue in the first-season finale "Devil's Trap." However, he manages to resist the demon's control. Despite John's pleas for Sam to shoot him with the Colt, Sam cannot bring himself to do so and allows Azazel to escape. As the Winchesters flee in Dean's Impala, a demonically-possessed trucker crashes into them. In the second-season premiere, "In My Time of Dying," Sam and John awake in the hospital with only minor injuries, but a dying Dean is comatose. John secretly summons Azazel and seems to know what the demon's plans are. He then makes a deal to save Dean, giving up his life, soul, and the Colt. Before dying, John tells Dean, if he can't save Sam, he'll have to kill him, should he become evil. The fourth season episode "On the Head of a Pin" reveals that the demon Alastair tortured John in Hell for over a century, with John refusing the demon's offer to stop if he himself would torture someone else. His soul escapes from Hell in the second-season finale "All Hell Breaks Loose, Part 2" when a gateway to Hell is opened. He saves Dean from Azazel and distracts the demon by temporarily forcing him out of his host, long enough for Dean to kill Azazel with the Colt when he returns to his usual body. John then gives Sam and Dean a loving smile before becoming engulfed in a white light. However, the fifth-season episode "Dark Side of the Moon" suggests that he might not be in Heaven. In the show's 300th episode, "Lebanon", Sam and Dean accidentally draw John from 2003 into their timeline when they acquire a Chinese pearl that grants the owner's greatest wish. This 'trip' allows John to learn of his father's disappearance, confirm his knowledge of the Apocalypse, witness the Men of Letters bunker, and learn about Mary's resurrection, as well as allowing Sam and Dean a chance to apologise to him for their past fights and forgive him for his failings as a parent. However, John being drawn into the future begins to cause changes to history; Dean and Sam see 'Wanted' posters identifying Dean as a serial killer, Sam is now an internet celebrity who is also the head of his own law firm, and Castiel is still a loyal servant of Heaven and the living Zachariah who attack