Crowley spent most of season 9 of Supernatural manipulating Dean to get him exactly where he wanted him: as Crowley’s ally. Clearly when Dean awoke as a demon Crowley likely had visions of the two being BFFs and raising some hell together (or does he have an even more sinister plan for Dean that he hasn’t revealed yet?)
In any event, it’s clear that Demon Dean isn’t turning out like Crowley had anticipated. We can see tension between the pair as early as episode 10.02 (see photos), when Crowley wants to give Dean advice about the Mark of Cain and how it’s affecting him as a demon and Dean disregards him. In episode 10.03, Crowley will realize that Dean is becoming even more of a liability that he had anticipated. When his antics start to cause problems for the King of Hell in Hell itself, Crowley approaches Castiel for help.
Meanwhile, Sam continues his efforts to save Dean from the Mark of Cain. During a sneak peek shown at Comic-Con (with some snippets in the preview for season 10), we see Dean hunting Sam in the bunker. Will Sam be able to re-capture and cure his brother?
Browse through photos above for the October 21 episode of Supernatural airing at 9:00 p.m. ET/PT on The CW.