This morning, I watched “Mystery Spot”, which bore a strong resemblance to “Groundhog Day”. Sam has to relive tuesdays where Dean dies in a myriad of methods. He finally figures out that the trickster demon which he and Dean dealt with a while back was responsible. Sam is at his wit’s end, pleading with the demon to bring back Dean, but the demon refuses. At the end of the show, Sam wakes up, it’s Wednesday and Dean is hale and hearty. For someone who’s watched this episode, what made the trickster demon relent and bring Dean back? He got his jollies, finished teaching the boys a lesson, he’s not that bad a guy, what?
Spoilers below, obviously.
He isn’t a trickster, he’s the angel Gabriel. Yep, they retcon him and make him an Angel who has basically given up, but has a basic good nature.
Non-spoiler version: there’s more to the Trickster than meets the eye (duh, right?) and you’ll definitely see more of him in later seasons…but he does have some good reasons to bring Dean back.