The first time Gabriel saw Sam Winchester he just sighed.

And no, the first time was not at the college where he posed as (and enjoying being) a janitor. The first time was in Montana when Sam was 16 and John was on Gabriel's tail, though he thought it was a ghoul (the victim in question had been torn apart by a 'dead ex-girlfriend' who he had gotten pregnant. Apparently, that fit somehow. Hunters were idiots). Gabriel, then posing as a bored librarian (he had a thing for working in buildings where he could stay low and not do much), watched Sam curiously for days as he came to do research neither of the other Winchesters wanted to do. At that time Gabriel couldn't quite place why the kid seemed so important. It was when Dean came by to pick him up one day that he finally got it.

"Sam! Come on and get your ass in the car." Dean had yelled from the front door of the library, as if he was afraid to enter. Gabriel kept up his charade and glared at Dean. He also made sure that Dean slipped and fell more times during that day than he had done so far in his life.

Sam and Dean Winchester; the vessels for his brothers.

So, it had started then. Well, not then obviously, it started as soon as dear ol' Dad imagined this world, hoping to get the recipe for humans right this time (the Universe was filled with His other attempts. He considered them failures for the obliviousness that those humans possessed).

Gabriel figured he had about 10 years, give or take, before the real battle began. He would try to enjoy those years as much as he possibly could. The next day, when Sam came in, Gabriel decided to take the next few years off when he finally thought to look at the kid's Soul.

It was tarnished and nicked and covered with annoyance and grief and hatred. That was only on the surface though; they were things that could heal. The actual goodness of the Soul … it was blinding. Only one thing marred that perfect Soul and it was a gelatinous blob of black just hiding in the very depths of Sam's soul, waiting for the time when it needed to come forward.

Gabriel wouldn't have been too worried, not with a Soul that pure, curious, excited about life, hopeful, and faithful. If it hadn't been for the life Sam led and the Destiny laid out for him.

Sam was a curious, excitable, stubborn being that believed in a God that didn't exactly visit his world anymore. He wanted normal, he wanted kind, he wanted acceptance and fond memories. The life his dad dragged him around on was anything but that. It was unstable and it tied Sam down. Not to a town or even a state but it kept him tied to a family that didn't understand him, that didn't understand his curiosity and thirst for knowledge. And within just three years Sam's Soul wouldn't be so completely pure anymore, there would be a deeper anger and hurt lingering just under the surface, one that would fester and grow for years until Lucifer was freed. And then that would feed him during the possession.

In the first time in a few millennia Gabriel wanted to actually help. But there wasn't much he could do without the God Squad coming to look or make them wonder, just a few years down the road, where the main piece of their chess board went.

So, Gabriel created the ghoul that John wanted, let him kill it like he wanted to, and he watched them leave town. He left only a few hours after that, needing something to forget his revelation in. Though he still wasn't worried, not really. He hadn't gotten Word from Dad in thousands of years, especially nothing about blowing his Horn to signal the Start of the Apocalypse. And it wouldn't start without Gabriel; it couldn't.

Or at least that was the idea.

When Gabriel sneaked back into Heaven to get his Horn he found it gone, along with one or two other precious items no ordinary Angel could take, and ones that definitely should not have been gone from the Armory at the time. Gabriel narrowed his eyes. And then rolled them. Gosh dang that Brother of Gabriel's; always testing his hand while on duty. One day it was going to get him killed; his dalliances.

When Gabriel ran into the Winchesters the next time he saw that the chess pieces were already advancing forward, prepared to strike. Don't do it Dean, he mentally pleaded with the elder Winchester as he offered his favorite girls to him, don't hang on too strongly to your brother when the time comes, you don't need him to survive.

Why Dean couldn't have listened, have realized how strong his own Soul was? But then, if these two were mentally stable and not strangely, emotionally co-dependent then they wouldn't be Winchesters or the ones meant for this. For that was the key to their survival: their unwavering loyalty to family.

And dammit, he was not going to do anything, he was not going to intervene. He had not built up this life and hidden himself for all these years just to be outed by (very good) puppy-dog eyes and a gun-wielding maniac. He fought his own Destiny until he couldn't do it anymore.

He was to face down his brother for those two gosh-damned idiots. And that's where his scripted Destiny stopped. Dang it Dad, I know you're not the best writer but really? Help me out here a bit!

And that was the first time in a very, very long time that he got even a whisper from Dad.

~Free Will, Gabriel, is not meant just for humans.~

And Gabriel, an Arch Angel and the Messanger of God, finally got it. Got what Castiel, the simple Angel of Thursday, had already understood for a year and a half.

And so, that's what he did. He prepared for a few weeks and when the time came, he faced his brother. No hesitations, no take-backs, no regrets. He followed his own script well, believed Dad would be proud (of his writing more than his actual decision), and just barely held onto the illusion as his Grace shattered apart and scattered across the Universe.

He passed out for the first time on an actual-honest-to-Dad bed, in an actual-honest-to-Dad hotel that he paid with actual-honest-to-Dad money (okay, fine, that he took from Switzerland – they had enough) on Sunday, April the 22nd of 2010. (One usually remembers their almost-death (unless you were the Winchesters, in which case, what's the point when you have so many?).)

Still, Gabriel would never regret the day he first saw Sam Winchester.
Or the second or the third or the even the tenth time. Because it lead him to his almost-death and he would definitely almost-die for that smile, those dimples, a single kiss … for that Soul over and over again.