Actually fuck it I'll say it with my whole chest. If this season ONE finale did nothing else, it absolutely spit in the face of SPN's ending, and of the idea that it was a good or happy ending for Dean, or his "success story." Or it being all about Sam, for that matter!
Dean looked two seconds away from crying every single time we saw him. He literally broke out of Heaven first chance he got, in search of a world where his family got a happy ending. Why? Because he doesn't consider dying young after a life of suffering and going to Heaven a happy ending!!! He wasn't happy. He wasn't at peace. He couldn't rest. He wasn't content to just sit back and wait for Sam, either!
So no, if it gave us nothing else (and I'd argue it gave us plenty actually, with the door wide open for more), season one of The Winchesters solidified as canon that no, Dean's story is NOT all about Sam, Dean himself is not all about Sam, and Sam getting to live a life isn't enough for Dean on its own. He wanted something for himself, goddammit.
And tbh? I don't think he's done looking for it. I don't think for a second he's going to go back to Heaven and be a good little boy after this. Because he STILL didn't look happy, fulfilled, or at peace.
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