Supernatural’s penultimate episode of Season 10, “The Prisoner,” finds the Winchesters saying goodbye to another family member—Charlie Bradbury. Sam Winchester’s desperation to keep the Mark of Cain from turning his brother Dean back into a demon has backfired in more ways than one. Not only is Charlie gone, her death has only pushed Dean further towards an angry, dark, violent, cruel, and vengeful version of himself. Dean has yet to revert to Demon Dean, but it feels like he’s well on his way. All hope is not lost in the world of Supernatural, but it’s hard to imagine how things can get better.