Paul (99 Problems)

Paul was the owner of a tavern at a small town that was under siege by demons. Though he helped fight the demons, he was skeptical the commands that the Angels were supposedly giving the townspeople. He was outraged when the drinking was banned in the town - allegedly under the orders of the Angels - which put him out of business. Later on, the townspeople tried to kick him out of town for being a "sinner". When he refused to leave, a woman, Jane, shot him, killing him.

Dean witnessed Paul's murder and told Sam and Castiel about what happened. Castiel stated that Paul's death was only the beginning of the Whore of Babylon's plan to condemn the town to Hell.