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John Winchester would not recommend being possessed by a demon to anyone. It was an experience he would not wish on his worst enemy. The feeling of being helpless in his own body was devastating. As an alpha being helpless was not something he was used to feeling.
All that said, it was when he was being possessed that he finally learned some hard truths. The first one being that apparently he was such a bastard to his kids that when the yellow-eyed demon pretended to be him, it was too nice. They were immediately suspicious and that kept them from being taken in by the demon.
The second thing he learned was that Sam was more like him than he had thought. They had both been willing to let John die if it meant that the yellow-eyed demon died as well. It was Dean who had protested, citing family above all else. It was ironic hearing the values he had imparted on his oldest son work against him. In the end Sam had chosen to listen to Dean over him and the demon had gotten away.
The last thing John had learned before the demon had fled was the secret his oldest son had been hiding from him for years; Dean was an omega. Suddenly a lot of things over the last decade had made sense. The subtle scent of omega that John had always dismissed as residual from the women Dean slept with, the way he had with children and witnesses, the way he was almost always able to de-escalate fights between Sam and John. It made sense, omegas had special pheromones that caused others to want to take care of them. Given that John himself hadn’t known his son was an omega, it was likely that no one else was figuring it out. They all just catered to him.
He didn’t have to wonder long why Dean hadn’t told him. As the demon used John’s body and its powers to hurt Dean it whispered all the things it could make John do to Dean. It told John how Dean’s scent attracted the supernatural and how every heat would be a battle for his life. It made John think of those mystery hunts of Bobby’s he had heard about. He’d never been invited to one but had enough hunts of his own that he never really thought about it. Now he realized that those hunts must have been Bobby protecting Dean during his heats, acting more like a father than John had.
John didn’t have time to talk to Dean about what he’d learned after the demon fled. First they were fleeing themselves and trying to get somewhere that Dean could have medical attention, then they were hit by a large truck. When John had come to, Sam was fine but Dean was in a coma and dying.
John knew he hadn’t been the best dad, but when he was possessed he was exposed to how shitty a dad he’d been. Even demons acted nicer than him! Now he had a choice: he could let his son die and continue on his mission to kill the yellow eyed demon or he could make a deal, save his son, and let his two boys continue the mission. It wasn’t a hard choice.
The demon gave him just enough time to make sure that the he kept up his end of the deal. John was able to see both his sons alive and well and tell Dean how proud he was of him. Then with no regrets, John died.
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When the gates of hell opened up, demons started rushing out. John wasn’t sure what was going on but no one was watching him so he crawled and fought his way until he got through. He could see Bobby and Ellen fighting to get the gate closed. Further away his boys were fighting the yellow eyed demon. The demon was standing over Dean about to kill him when John made his move. The demon wasn’t going to take any more of his family from him. He was able to distract the demon long enough for Dean to get the Colt. Then he watched as Dean finally killed the demon that had killed Mary.
As his boys stood in front of him John smiled, hoping they knew how proud he was of them. He felt a pull and knew he couldn’t stay. He regretted that he hadn’t been a better dad, the kind that his boys would have felt safe to share their secrets with. But maybe it all worked out. They were alive and they had each other.