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It was the wings that broke him.
Every time he had thought Castiel was gone in the past, the angel had made an unexpected return. He had been destroyed by Raphael, blown up by Lucifer, taken over by Leviathan, left behind in Purgatory, stabbed by some bitch while he was human, and then there was that whole staff thing. Yet every single time Cas had come back.
Every. Single. Time.
Now Dean remembered the few times he had seen the shadows of the angel’s wings flare to life behind him. The sheer awesome power that they had represented. Even as shadows they had been more than a little impressive.
Now he was seeing them one more time, but the power behind them was gone. They were just a blackened shape on the ground behind the angel he had lost, yet again.
Those charred remains told him just one thing.
This time, there would be no coming back.