(A/N Um, so, this. This is me sticking my toe into writing Supernatural. It's... kind of terrifying. I'm so worried about OOC-ness in this fandom. This, despite it's shortness took like a month to write. This is basically the theory I came up with at 3 am one night and have stuck loyally by since. No beta, feel free to point out any and all mistakes, would love some constructive criticism. Enjoy!)

In the end Sam never really gets it. Gabriel is kind of disappointed and a little irritated, but he can't quite bring himself to give in and tell Sam what he meant by the whole episode.

When Dean had first died it had been the first initial shock, something that should scare, warn, and motivate Sam in equal parts. It pretty much worked. So Gabriel, satisfied with his results, had set the clock back to zero. Sam now should get the gist of this idea, he had unlimited time, resources, and the idea of his brother's death fresh on his mind.

Sam didn't get it became soon apparent. There was relief and confusion on the second day. Understandable, Gabriel supposed. Most of his brothers were giant dick-bags so he wouldn't be all that torn up about some of their deaths, but others. Well. It was reasonable.

At the end of the day Gabriel decided to kill Dean again. It was one part boredom and two parts reminder for Sam. This wasn't a dream, wasn't a premonition, wasn't some monster-of-the-week. He needed to get a move-on.

Sam still doesn't get it. He was baffled and perturbed and really, really relieved but he still didn't get it.

After the first almost month of not getting Gabriel felt his patience flickering like the light of a candle. Wasn't Sam supposed to be the smart one? How was Sam missing this? He was stuck in Gabriel's world with a dying brother, unlimited resources and zero repercussions. He could do what he had to do, he needed to do this.

Even though Gabriel was beyond frustrated with Sam's apparent obliviousness to the obvious, Gabriel never told him.

He just- he couldn't bring himself to outright state that he was trying to help Sam. It made him feel like he was breaking his long standing neutrality, as if as soon as he told Sam, he would be exposed and forced to take a side. So he kept his silence, gets less and less subtle, and wished desperately that Sam would get a clue.

This is perhaps his biggest regret.

At first Gabriel lets Sam stay the same. When Sam punched that wall in frustration toward the second week, well, Gabriel set back the clock, repaired the cheap plaster, and let him keep his bruised hand and have it heal on its own. He felt like he owed Sam that much- something to tell reassure him that Sam was still changing, that he could still change.

By the 12th day of the second month Gabriel can no long give Sam this luxury. Because Sam, well, Sam stopped eating. He stopped eating and stopped showering and stopped taking care of himself, so Gabriel figures he going to have to do it for him. He'll take care of Sam for the time being until Sam snaps out of it and takes of himself and his brother.

So Sam stops getting thinner, but he doesn't seem to be getting any smarter.

After months and months and months of this game Gabriel feels like sadist as watches Sam. When Sam finally figures out it's him, and corners Gabriel, begging for his brother back, Gabriel can't say no, and perhaps this is his greatest regret. That he led Sam into this false sense of security, brutally ripped out the rug from under him, and Sam still never got it.

Gabriel find himself pondering when this little stunt crossed over from helping the greater good to the relentless torture of the Winchesters.

When he finally gives Dean back, seeing the look on Sam's face, Gabriel thinks that maybe he won't have to keep this up, that maybe they're enough.

He wants to leave Sam, God-fucking-dammit, does he want to, but he just- can't risk it.

So he doesn't.

The game plan changes and he kills Dean and Gabriel thinks that if he can't make Sam figure out how to save Dean from going, he figures he can make Sam figure out how to get him out right away.

Only Sam doesn't quite get this one either. He's just- he's too focused on the trickster. On the revenge aspect. Gabriel thinks that if Sam was one of the stupid new-age classical composition that liked so much, then mourning and longing would be the back-up while revenge- revenge would be the melody.

So Sam looks and curses and hunts, and eventually Gabriel tires of this game as well. He stops Sam from killing Bobby (that's one moral even horizon he doesn't even want to begin to ponder) and turns back the clock, and Dean's alive, and Sam is none-the-wiser.

Gabriel leaves feeling useless and inadequate, but not enough to break his oath of silence, never enough for that. Dean went to Hell, and he thought about Sam his lonesomeness and his near consuming need for revenge, and decided maybe next time, Dean would get it.

So Gabriel watches and plans and doesn't stop his brothers from getting involved, but along the way decides Dean would definitely get it.

Those boys always did watch way to much TV.