The Devil You Know

The demon Crowley tells Sam and Dean he can help them find the remaining Horsemen rings so they can trap Lucifer. The brothers are doubtful until Crowley leads them to Brady, the Handler for Pestilence, and Death. However, Brady refuses to give up their locations and sets Pestilence after the Winchesters....

Summary
Dean and Sam encounter Crowley while on the trail of Pestilence. Both brothers are angry at Crowley for giving them the Colt which did not work on Lucifer. Crowley mentions that he's being hunted down by his fellow demons and tells the brothers that he knows where the last two rings can be found. He directs them to Brady, the demon handler for the Four Horsemen of the Apocalypse. However, Crowley will only show the way if Sam does not go with them.

Later, Sam and Bobby have an argument over Sam intending to trick Lucifer back into Hell by letting the Devil possess him. Dean meets Brady, the demon-possessed CEO of a pharmaceutical company, who is under Pestilence's orders. Dean tries to trick Brady with a proposition but the demon does not buy it, intending to just kill Dean. However, Crowley gets the drop on Brady and knocks him unconscious. Dean is warned by Crowley that Sam and Brady have a history; Brady is in fact Sam's classmate from college. The Handler possessed Brady since sophomore year, and deliberately introduced Jessica to Sam and then killed her to put Azazel's plans into motion. Sam is furious and wants to kill Brady but Dean stops him. While Crowley is away, Sam traps Dean in the bathroom as he plans to kill Brady. Brady goads Sam into killing him but Sam manages to calm himself and leave. Crowley returns after killing a nest of demons and making it look as though Brady joined his side.

However, Crowley is tracked down by a hellhound. Crowley escapes, leaving Dean, Sam and Brady in the hideout. While Dean attempts to fight off the hellhound, Crowley returns with his own hound against the other hound. After the four of them escape, Brady gives up the location for Pestilence. Dean then allows Sam to finish Brady off. Later, Crowley appears to Bobby and tells him he will reveal Death's location in exchange for his soul.

Major Characters

 * Dean Winchester
 * Sam Winchester
 * Crowley

Minor Characters

 * Bobby Singer
 * Brady
 * Pestilence (Unseen)

Featured Supernatural Being
Demon

Trivia

 * Pestilence only appears in a flashback at the beginning of the show and Brady communicates with him in a bowl of blood similar to the one the demon that possessed Meg Masters used to communicate with Azazel.
 * The title is a reference to the rock song "The Devil You Know" by Heaven & Hell.