|“||You sure you wouldn't be more comfortable in a bedroom, or my motel room? I mean, not for nothing, but you know... I got oils.||”|
— Richie to Casey
in Sin City
Sam and Dean Winchester bump into Richie in Elizabethville, Ohio, while investigating strange happenings seemingly caused by demon activity. Dean recognizes Richie, having saved him from a succubus in Canarsie. Dean says this was while Sam was at Stanford. Apparently after this experience, Richie decided to become a hunter, but Dean doubts his capabilities and urges him to step down.
Richie is killed by a demon when she lures him into her basement with the promise of sex, knowing he is a hunter. Dean eventually becomes suspicious and tracks the GPS in Richie's cell phone, leading Dean to his body. As Dean later tells the demon, after trapping her, he gave Richie a proper burial so he wouldn't have to rot in the basement.