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Both Castiel and Chuck were too late in doing anything to save anyone. Castiel loses all hope, but Chuck is desperate for everyone (mostly) to have a happy ending, so he gives Castiel a choice; a chance to do everything all over again with no guarantees or to accept what has happened and live his days out on the soon to be ruins of earth and in hiding from many. Of course, Chuck mentioning changing Sam and Deans fate, Castiel immediately knew what he had to do, or in this case RE-do.
- Part 1 of Castiel Winchester, Saving one at a Time