Undying thanks to Gem and TraSan for the amazing feedback and betas! I'd be lost without them!!

You know, I always liked those Winchester boys. Sam and Dean. They've been a lot of fun to mess with – a great challenge. I know they think that what I do is cruel and unusual, but…well, yeah, I guess it is, but I'm only trying to stick it to the dicks of the world. I mean that sorority kid? That was one my best ones yet. Anal probe, baby! Slow dancing to Lady in Red? That was freaking awesome! I'm like the anti-bully, so what's wrong with that? I guess they didn't see it that way.

But despite their innate instincts towards all that is "right," they're not the typical kind that I deal with. They're smart, they're funny and even though they're good looking, they're mostly down to Earth. Well, at least Sam is, or was. That Dean? What a character. Comedian through and through. Gotta love the guy though – thinks he's God's gift.

Oh wait; I guess he kinda is.

As things started to unravel in the universe and I saw where this whole parade was parking, I knew I wanted to try and "help" them. Maybe my kind of help isn't generally wanted but I felt like I owed these kids on some level. They entertained me, made me work for my end results. Sure, they tried to kill me, but honestly? I wasn't too worried. I like that quality in prey.

That last time I was messing with Sam, you know, killing Dean every day, I wanted to teach him a lesson. I knew all about the deal and I'd heard rumblings about what was cooking downstairs; wanting to break Dean so he would be the first seal once he got there. I wanted to help Sam; make him understand what life was going to be like without the overshadowing presence of his older brother and how to be stronger. Thought it might be exciting to keep him around to toy with if I gave him a little more insight into life sans Dean. I guess I didn't quite realize Sam would turn into his Dad, Hell-bent on revenge! Especially towards me. Not as fun as I'd imagined.

And Dean? He never knew about those six months that Sam had without him; how he'd turned into Rambo. Man, talk about scary! I think if Dean would have pushed Sam to talk about it, things may have turned out different, you know? Maybe not put them on the same page, but at least hit the same book. You think it would kill these boys to talk to each other! Geez! Talk about hard heads!

So, I felt a little guilty when Sam's whole personality changed. Actually, it was more like he'd turned into a crazed psychopath! After Dean really died, the kid went suicidal, which I'd expected. I mean, he did see his brother ripped apart by Hell hounds. It's a little different than a piano dropping on his head or eating a bad taco. But that demon, she found the right way to niggle in, channeling her own inner Dean to get through to Sam. I had no idea that she was the key player to this whole damn thing and that my lesson pushed him right towards her.

By then, the kid felt like he had nobody; that he was a burden. Watching him with Bobby Singer for those first few weeks? Chick flick vs. horror movie! It's no wonder he ran off – the two of them drank enough to put a distillery on notice.

I thought he'd be more fun, but I may have been the one that pushed him to the dark side.

My bad.

Then I heard that the angels were part of this Apocalypse babble as well as the demons and that Sam was the only one who could kill Lilith – the last seal - I knew that things were not going to go down well. I'd watched Dean after he came back from the Pit a broken man, afraid of his own shadow at times. This was the angel's savior? The kid was a mess, and understandably so. Hell is not sunshine and roses, man. It became pretty clear that Sam was the one who could kill Lilith, not Dean, no matter what BS the angels were feeding them.

Let me be clear: I don't really have a stake in this whole Armageddon thing one way or another but I can tell you that I do enjoy teaching lessons, an old-fashioned schooling if you will - especially if you're an indignant prick. If humans were wiped off the face of the earth, what would I do? Pull the feathers from angels? Throw holy water on demons? That gets old really fast. Been there, done that.

But humans? They are unpredictable, always evolving. Fascinating to observe and manipulate. Way more fun to fool around with. So I guess I'd like them to stick around a little longer. That's just me being selfish, I guess.

And now it seemed that the fate of the world was riding on these two brothers.

There were so many secrets and lies between the both of them—and who'd've thought anything could come between the Winchesters?—but I think the biggest problem was not really diving into what happened while Dean was in Hell. I watched what Sam was doing, how he was getting stronger but I knew I couldn't interfere. I saw how desperate he was at getting for revenge on Lilith for taking his brother. Blinded by it. It was already bad enough that Dean sold his soul for Sam. Sam never wanted that. But then Dean came back and Sam started to question himself and his actions, but not enough to stop his hunt. Not enough to stop the sneaking around. Not enough to shut out Ruby and stop drinking the blood. Sam was a man driven on revenge and that demon bitch had the keys to the Caddy.

That final fight they had when Sam left Dean gasping on the floor in the wedding suite of the hotel? Heartbreaking. No, really. I know you think I'm heartless, but like I said, I like these boys. But I understood why Sam did it. He thought he was protecting Dean – his own warped version of loving him - and Sam knew that his brother could never kill Lilith. I mean, the angels tried to get Dean to take on Alastair and look how well that turned out. Sam wanted Dean with him to go after Lilith, but there was no way in Hell that Dean was going anywhere near Ruby. He's obviously never heard the saying about keeping your enemies closer.

Once Sam got it in his head, there was no stopping him. It didn't help that Dean threw the same words his dad threw out at him when he left for "normal." This was a recipe for disaster – literally.

And those stupid angels were sitting back on their haunches doing nothing watching, letting this all unfold. Zach? There's a guy I'd like to take out. And the way he played both those boys? Geez! They think I'm bad! Then Castiel finally realized how f'ed up this whole thing was and sent Dean to try and stop Sam.

But Sam didn't need any help, just a little push here and there from Ruby. And he actually did it – killed Lilith and started the Apocalypse. The surprised look on Sam's face when Ruby told him he'd pulled out the red carpet for the Devil, opening the door to Hell? Oh man, that was just killer. He'd never expected to come back from that fight alive, hoping to die a hero in his brother's eyes. Some kind of redemption for how badly he'd screwed up. I don't think he wanted to live past that day; not without Dean. I mean, I'd already watched him self-destruct twice, and there was no way he was coming back from this one. And then, everything that Dean had warned him about came true. He'd trusted the wrong people.

So, then I felt a little guilty. Yeah, I'm a sucker.

It was all too late to stop the gate opening – really, nothing I could do - and that beam of light came shooting out of that nunnery like a rocket as Lucifer made his grand entrance. So, I figured I'd jump in and make things…interesting. I do like to be mischievous – screw around with both sides of the G vs. E coin. I really don't really care one way or another who wins this apocalyptic battle but I want to still be able to have fun through it all, so I have to place my bets on who will bring me the most pleasure.

There was a plane passing by that seemed the perfect refuge (plus I know how much Dean loves to fly; I'm always messin'), so I decided to beam them up there, Star Trek style. I'd remembered that Yosemite Sam cartoon where he bargains with Satan (like the irony there?) and threw that on the screen as a hint that I'd saved them, but we'll see if they figure it out. Probably not, but that's okay. But I guess the plane was a little too close to the epicenter, so I had to try again, sending them to the car. Their faces were priceless, like those commercials for MasterCard, and they could concentrate on being confused about what was going on rather than being mad at each other.

Baby steps.

Also, figured I'd kinda owed Sam for screwing with his head so bad that I cleaned him up from that nasty demon blood withdrawal. That stuff is a bitch! I saw what happened to him last time and even if I was playing a trick on someone, I don't know that I'd put them through something like that. Well, maybe I would…

Like I said, I like the Winchesters.

I don't know how the Hell they're going to stop Lucifer and I don't know how much I can help them, especially when they can't help themselves. Should I help them? Where will it put me? Maybe that's part of what makes this so interesting. Hopefully, they'll finally do some talking and start being the same pains in my persqueeter that I love to harass.

In the meantime, I'll just sit back and watch.

The End


A/N - To be fair, the idea of the Trickster saving the boys actually came from discussions about the episode on Tvguide. The more I thought about it, the more I liked it since God has seemingly left the building. Cas never answers the boys, and it's implied that God is behind it, but I actually like the idea of the Trickster stepping in better.

Take my $.02 for whatever it's worth. Thanks for reading!