|Dates||????-April 2010 (killed by Sam)|
|Episode(s)||5.20 The Devil You Know|
Tyson BradyS5Com was a close college friend of Sam's from Stanford. During his sophomore year, at the Thanksgiving break, he was possessed by a demon. When he came back to school he "went off the rails," partying and dropping out of pre-med. Sam tried to help him. Brady introduced Sam to Jess. Azazel was concerned that Sam was losing his potential, and so Brady orchestrated the introduction with the plan that her death would drive Sam back to hunting. It was Brady who killed Jess, on Azazel's instructions.
Crowley describes Brady as "the Horsemen's stable boy." He is now working as an executive for the Niveus Pharmaceuticals, the drug company which is part of a scheme by Pestilence to spread the Croatoan virus. Crowley later reveals that he was vice president of distribution. He communicates with Pestilence through a Goblet of blood. He is captured by Crowley and Dean, and is transported unconscious with a bag, marked with a devil's trap, over his head. Crowley also carves a binding link into his chest so he can't vacate the body. They tie Brady to a chair placed over a devil's trap to interrogate him.
Sam is enraged when he finds out that the man he thought was a friend was really a demon who killed Jess. However, he doesn't kill Brady, as they need him to find Pestilence. Crowley's argument that Lucifer will kill all demons doesn't persuade Brady to betray his masters, so Crowley massacres a 'nest' of demons. He allows one to live to spreading the rumor that he and Brady are "lovers in league against Satan". Faced with eternal torment over this suspected betrayal, and fearing hellhounds, Brady finally reveals Pestilence's whereabouts. Sam then kills him using Ruby's Knife.