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Summary
My take on the idea that Chuck won and possessed Jack in 15x19.
"Dean should have known earlier. Everything about Jack had been wrong, somehow, but he’d attributed it to the various things that had gone wrong in the kid’s life plus the addition of the new powers.
It takes him a week to figure it out, a week after Chuck is powerless, two weeks after Cas is dead.
Then he knows, from something about the way he hasn’t heard from Jack, from how Eileen is still missing, from how Cas is still dead. It isn’t Jack, not the Jack they knew.
He tells Sam, of course, as soon as he realizes, not that it’ll matter. They’ve tried to fight Chuck enough times before. He knows them too well to let them win."