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Summary
Alt 2014 - Cas had known of course, going in... There had been no doubt in his mind that things were not going to end well, for any of them, and he had walked to his death with a sense of finality, of peace. But of course, he should have known his father would be a cruel bastard, even at the end.
2020 - Jack was struggling. He might have been God now, but at the end of the day he was still a kid- still half human, and he missed Castiel. Try as he might to convince the empty to set him free, he had yet to be successful, and while he was mourning, it seemed like his struggles were nothing compared to Dean's. He hadn't wanted to lose him too... but after he had swooped in last second to pour life back into the man, healing the damage from the rogue piece of rebar, Dean had stopped trying to fake it... and that was almost worse.
Sam was tired. Roles were reversed, trying to essentially parent his shut-down brother all while trying to live for himself for a change was painfully smothering. He was terrified to let Dean tag along on any hunts, for fear of a repeat performance. But he was equally worried about leaving him alone in the bunker for any significant amount of time. But someone had to keep on fighting.