Season 8:14 Trial and Error
"I'm a grunt, Sam. You're not; you've always been the brains of this operation. And you told me yourself that you see a way out. You see a light at the end of this ugly ass tunnel. I don't. But I tell you what I do know- is that I'm gonna die with a gun in my hand."
Dean dies with a gun in his hand. He doesn't die like how he always wanted to, though; He doesn't die fighting. He dies slowly, piece by piece, begging for it all to stop.
Because the world ends not with a bang, but with a whimper.
Sam leaves him, and finds a girl, Cindy. He stops all contact with his brother when their first child is born, a baby girl named Kathy.
Dean starts drinking again, and taking risks on hunts. Gets taken by an angry nest of vamps, the remains of several the Winchesters had torn apart. It looked like they had banded together to take down the man. It had almost worked, too. So in pain, and pissed off he went to the bar and drank.
He thought about Sam, and Cindy and Kathy. If Dean ever has a baby girl, he thinks he'll name her Mary, after Mom. She was a great woman, and their dad hadn't deserved her. If he ever finds a girl, he'll make sure she knows he loves her, always. Because that's all he's ever really wanted, is to be loved unconditionally. To find a pretty girl and fall in love slowly, and have someone who will always have his back.
Mom is the only one who hasn't ever left him, not willingly. Dad did, dad always did, since the day he started hunting the demon. There's a lead on the demon I have to check out. Take care of Sammy, Dean. I'll be back in a few days, week tops. There's food in the pantry. He had been leaving ever since Dean could remember.
Sam had always left, too. Since he ran away in Flagstaff all those years ago, decades ago. He had just left Dean there in that hotel to face John alone. That was not one of Dean's best moments. His brother left again for college. And then he had ran off with Meg, and then ruby, and then hit a dog and found that Amelia girl.
Dean was the only one Dean could count on. He doesn't even try to hit on any of these girls, they're giving him funny looks anyways. So he stumbles home, limping and angry and feeling lonely. He drives his baby to the cheap hotel, and limps in. He's hurt from the vampires, but he doesn't want to take care of it. He thinks maybe he would enjoy letting himself bleed out, he would enjoy the weightlessness.
He calls his brother, but Sam doesn't answer. He tries it again, scowling. The third time, he's feeling hurt. The fourth time, he lets it ring and ring. There's a gun poking into Dean's back as he slides down the wall. He takes it out of his waste band, and can't seem to put it down once it's in his hand. It's black and plain, and he keeps it in his hand as he calls Sam. Sixth calls, and no answer. There's an answering machine that says 'Sam and Cindy Winchester. We can't get to the phone, but please leave a message and we'll call you back'
Beep.
"Sam. It's me. I'm done hunting…" I'm done with everything "I just wanted you to know." He hands up.
He's been staring at the pistol the whole time. It's empty, so he stumbles to the bag and loads it.
Dad's voice is going through his head. Keep your gun loaded, Dean. You never know when some monster's going to jump at your ass.
So he loads it, Sam's voice haunting him and Dad's goading him on. He leans against the wall again, it's the only thing keeping him up right now.
He calls Sam one last time, praying.
It rings and it rings, and Dean has the gun pointed at his temple. If Sam answers, he can put it down, but he doesn't even really realize it's there. He can't feel it there, though he knows that he's pressing hard. He can't really feel the stinging in his eyes, either. The hopeless, lonely feeling that's making tears streak down his cheeks. He feels so useless, not good enough to keep anyone around.
He pushes the end button, and then he throws the fucking phone so it busts against the wall. He stares.
And then he pulls the trigger.
Dean helped start the apocalypse, and he fought to end it.
He has lost everything his life he has ever loved.
He has died and gone to heaven.
He's fought along side Angels. And Demons.
He's met Lucifer.
He's been the worst demon the world's ever seen. He's bore the mark of Cain.
Dean Winchester dies with a gun in his hand. And a bullet in his brain.
Sam hears the phone ring, again and again. He hears the message Dean croaks into the phone, and is glad to know he's alive, and he's quitting.
But it's days later, when he gets the call from Lawrence, Kansas police. Dean killed himself in a cheap motel, after he had called.
Sam's heart breaks, blaming himself. If he had just picked up the phone, he could have helped.
But 'Dean was right ,"he thought. "He did die with a gun in his hand."