Dean's Crossroad Demon

This was the crossroad demon who Dean made a deal to resurrect Sam.

Season 2
In Crossroad Blues, the background to the episode is the legend of blues player Robert Johnson who is reputed to have sold his soul for his talent.

Ten years before the episode begins an artist, George Darrow, summoned a Crossroads Demon in order to make a deal for greater talent. Instead of leaving after their deal was arranged, the demon hung around at a bar called Lloyd's and made deals with Sean Boyden (architectural talent and success), Silvia Pearlman (success as a surgeon) and Evan Hudson (his wife's life) as well.

Dean traps the demon beneath a Devil's Trap, and threatens to exorcise her unless she breaks the deal with the sole survivor, Evan Hudson. The demon admits to knowing about the Winchesters, and taunts Dean with mention of how his father is suffering in Hell. She offers to return John Winchester to life in exchange for claiming Dean's soul in ten years time. He refuses and she finally makes the deal to save Evan, only for Dean to finish the exorcism. The demon is banished from the body it is possessing, leaving a confused young woman behind.

Dean summons the Crossroads Demon in All Hell Breaks Loose - Part 2 after Sam was killed by Jake Talley. In return for bringing Sam back to life, Dean exchanges his soul, which the demon will claim in one year's time. She states that if Dean tries to get out of the deal, Sam will die.

Season 3
In Bedtime Stories, Sam summons the Crossroads Demon and demands she release Dean from his deal. When he threatens her with The Colt, she deduces that Ruby must have been involved in re-building it. She tells Sam that killing her won't break the deal either, she is 'just a saleswoman' and that someone higher up holds the contract. After she suggests that Sam would actually be relieved when Dean dies, Sam kills her with The Colt.

As a result of the deal, Dean went to Hell in No Rest For The Wicked after his time was due.

Appearances
Season 2 Season 3
 * Crossroad Blues
 * All Hell Breaks Loose - Part 2
 * Bedtime Stories