Sam and Gordon

Season Two
When Sam and his brother Dean Winchester meets Gordon. He refuses to listen when Sam explains that the vampires are not evil they are not feeding on humans but on animals. Gordon captures and tortures Lenore, even cutting Sam in order to tempt Lenore with human blood. Dean overpowers him and after the vampires escape, Gordon is left bound to a chair in an old farmhouse. We find out in Hunted that Dean left him there for three days before alerting anyone.

Gordon is on Sam's trail, trying to kill him. He has found out from someone at the Roadhouse that Sam has psychic abilities, and knows from a demon he tortured that people like Sam are going to be soldiers on the side of evil in a coming war. Gordon uses Dean as bait, but Sam foils him, calling the police who arrest Gordon.

Season Three
Gordon, still in prison, is visited by Kubrick. He explains that contrary to Gordon's beliefs, he has found out that Sam was trying to keep the Devil's Gate in Wyoming from opening. Gordon states that he doesn't believe Sam is even human, and must be killed. A series of coincidences help Kubrick and Creedy track Sam down and they capture him but are foiled by Dean. Returning to Gordon, Kubrick now believes that he is on a mission from God to kill Sam. While Gordon obviously disbelieves this, he enlists Kubrick's help in planning his escape.

Gordon has escaped from prison, and tracks down Bela after he finds out she had been working with the Winchesters, convinced Sam is the Antichrist. Although he threatens to shoot her, she only reveals their whereabouts when Gordon gives her a priceless Mojo Bag. Along with Kubrick, Gordon interviews one of the victims of a vampire Sam and Dean are hunting, and tracks them down. The boys escape, but Gordon is captured by Dixon, who turns Gordon into a vampire. Gordon is determined to kill Sam as his last good act, before killing himself. He returns to see Kubrick but when Kubrick attacks him, Gordon kills him. Using a girl as bait, Gordon lures the boys to a warehouse, where Sam eventually kills him by garroting him with razorwire until he is beheaded.