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The Trickster had first seen the Winchesters by accident.
He had known who they were, of course. Even having cut himself off from his family, he had heard of them and their roles in the whole endgame. He was also pretty sure there wasn't a supernatural creature in creation that didn't know their names at this point. Still, he definitely hadn't been seeking them out, because where they were his brothers were sure to be close behind, and he wanted to stay under the radar. There was no way he was going to get involved in the family drama. Not again.
And so he had done what he did best, tricking the hunters into thinking they had killed him and then watching them go on their merry way. He had moved on to another set of assholes in need of a lesson, and that should have been the end of his dealings with the Winchesters
And yet...
He couldn't stop thinking about them. Well, the younger one in particular. In the end, Gabriel had given in to his curiosity and started to watch them. From a distance, of course. He still had no intention of allowing himself to get too close.
After Sam had died and Dean had sold his soul to bring his brother back, the Trickster had started watching a bit more closely, unable to help himself. It was like being unable to look away from a train wreck or a car accident.
Eventually he found himself wanting to help Sam. To make him understand that he had to walk away to save his own sanity. In the end, it would hurt a lot less if he just let go. It had worked for the Trickster after all, or so he told himself.
This is why he had killed Dean more than a hundred times, making Sam deal with the pain and letting it start to numb him to the loss. Well, that had been the intention, anyway. Yet even after months of leaving him without Dean, he still would not give up on his brother. Sam was easily the most stubborn human in creation. Which is why the Trickster had tried washed his hands of them completely, leaving them to their fates.
Except there were still whispers of the Winchesters among the supernatural community, and eventually he had to see what was going on. It was past time for them to have said yes and gotten things rolling. Not that he really wanted to see the end, but he was tired. Tired of hearing about his family and their war. It hurt, even after all this time, to think about them fighting each other. He just wanted it over, one way or another.
Somehow, he hadn't given the hunters enough credit though, and he found himself trapped and unable to escape. So he had told them his name. The one he hadn't thought about, let alone said, in longer than he could really remember.
Gabriel.
He tried to get them all to understand that it was pointless to fight. It was only prolonging the inevitable. He might have been a jackass about it, but he was just so damn tired of it all. Still, the disappointment in the eyes of Sam, in particular, had bothered him more than he would have thought.
Which is how he found himself standing up to Lucifer in a crappy hotel in the middle of nowhere. Not his brightest idea, but if there was anything that these Winchesters and their angel had taught him, it was that sometimes you just had to kick fate in the teeth despite the consequences. Besides, that look from Sam had tugged something in his Grace that Gabriel hadn't been able to ignore. He didn't want Sam to see him as a worthless coward who ran away when things got tough.
Still, Lucifer could kick Gabriel's ass and they both knew it, which is why he'd made the copy of himself and faked his death. It was a good distraction to let the Winchesters get away, regroup, and make use of the information he had given them.
So Gabriel ran again, and maybe it did make him a coward, but this time it wasn't really the family issues that made him run away. Instead, it was the growing feelings he had for a certain hunter, and the knowledge that he would only put Sam in more danger if he stayed.
Gabriel didn't know until that moment that running again could hurt far more than it had when he left Heaven.