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Dean has always known that his end will be all guns, guts and glory. Well, the actual thing only really had guts, but you get the idea. Ever since his mom died for the first time, Dean knew. It was something that his dad drilled into his head from the very start. When he was a teenager, he was always reckless. On each hunt he’d almost be begging to die, like his version of teenage angst, but then he’ll see Sammy’s doe eyes and Dean would realise that he shouldn’t be like this, he shouldn’t crave death by the hand of some monster. He should stay and fight for Sammy’s sake. He couldn’t leave Sammy alone. The kid might be smart, but he couldn’t take care of himself.
Then Sammy left. Sammy left to go to university and it crushed Dean. It’s not like Dean didn’t want Sammy to follow his dreams, far from it, but Dean didn’t want him to go. But he still did. Those four years Dean was alone, he became reckless. There was nothing that could convince Dean to fight for his life. Sam didn’t want him; his dad was off to who knows where without even a by your leave. Nobody needed Dean, and the world without Dean would still be the same as the world with Dean. A bleak place filled to the brim with evil sons of bitches with no one to actually spare a thought for Dean.
So, in those four years, Dean consumed more than he ever has and ever will in booze and drugs and sex and monster guts, and he had the mark of freaking Cain. Dean doesn’t even remember half of it, small blessings.
Then his dad went missing, Dean probably wouldn’t even have noticed if it wasn’t for John’s cryptic voicemail. That was the big surprise. That his dad had even called him. Dean probably called his dad thousands of times only to be greeted by automated beeps.
His dad went missing, Dean cared, but he didn’t really. Then he realised his dad’s last hunt was in California. Near Stanford. Near Sam. Then Dean did something really selfish: he dragged Sam back into the life. With Sam back, Dean calmed down again. He stopped being so reckless, because Sammy was there with him. Sammy needed him. So, the more frustrated Sam got about their ever-elusive father, the more Sam needed Dean.
Then their dad died, then Sam died, and Dean sold his soul. But hey, at least they killed the demon. Then Dean went to hell, and when he came back, he came back wrong. His skin was smooth and his body intact, but Dean hated it. And then Dean got reckless again. And this time it stayed that way through one apocalypse after the other.
And now?
Now Dean Winchester is in heaven. Even knowing that he has an in with the man (boy) upstairs, it still comes as a surprise to him. Dean wonders if Jack even knows he’s here, but then, why wouldn’t he? Jack cares too much for his own good, Dean treated Jack like shit, he had the honour of bestowing Jack’s first childhood trauma upon him. But even for all his doubts and scathing words, Jack is good. And it had nothing to do with Dean.
Dean is in heaven, and he doesn’t like it. Hell, he knew Jack made it better. He’s experienced it first-hand. But Dean doesn’t like it. Dean knew that he has been an exception all his life, he has died and come back too many times to count. He’s been to purgatory, a place no man should ever be. He’s been to hell, by the end of his life he could basically just stroll into hell and be welcomed with open arms and a proverbial homecooked meal. Knowing all that, Dean wished he could be an exception once more and leave this place.
It's almost sad. Paradise, perdition and purgatory. And Dean doesn’t belong in any of them. The only place he belongs is on earth, by Sam’s side. By Cas’s side. This place, the peace and quiet, it doesn’t suit Dean very well.
Because yeah, Dean knew he’d die bloody. He just wished that he had a legacy other than his brother’s pain.