Dean Winchester is born in the coldest, cloudiest month in 1979. But Dean Winchester is warm and chubby, and smiling before they know it. He's a good, quiet kid. He listens to his father and takes care of his mother. He's not shy, but he's not disruptive or wild.
When Mary gets pregnant with Sam, Dean puts his hand on her belly and says he's talking to Sam. He laughs sometimes, especially when he feels him kick. He tells John and Mary that he can't wait until Sammy is born, can't wait until he has a brother to play with.
Dean's little brother isn't all that he expected. He cries a lot and can't be left alone. Dean feels a little bit abandoned. John works all the time, maybe to get away from the crying, maybe because there's another kid in the picture and he needs to work more hours to support his family, but when John comes home, Mary gives Sam to John, gives John a kiss and whispers into his ear, "Your turn."
John grumbles that he doesn't remember Dean being this hard but he's not unhappy. Nobody's unhappy except for Dean. He just wishes that Sammy could hold his head up by himself so he could carry Sam without Mary hovering anxiously over his shoulder. He wishes Sammy could stand up and play like he could.
And then there's a fire and Mary is dead, and Dean, just four years old, doesn't understand why, no matter how John explains it to him. "Is Mommy coming home today?" he asks. "Where's Mommy?" He asks every single day until John is exhausted with the questions and stops answering. When John runs out of answers to give, Dean stops asking, and then he stops talking. John doesn't send him back to preschool. He doesn't know if he should send him to kindergarten the next year. He asks his mother and his step-father and his brother and some of the guys at the garage, and then he moves. They all said the same thing: you'll have to wait and see what's right for Dean.
He sends Dean to kindergarten in September, but he doesn't know if he should. Dean's talking a little again. But not to strangers.
Dean's scared about kindergarten too. He doesn't want to go. He decides the morning that John tries to take him. Dad's not being nice. Dad is making him go to school, but Dean is so scared his mouth won't work the way it's supposed to, and he can't remember the words he's relearning, can't figure out how to tell his dad that he doesn't want to go. John crouches down next to him, tells him Mommy would want him to go to school. John tells Dean he knows he can do it. He's brave.
Dean goes to school reluctantly, but he goes. And he comes home, a little quiet, but mostly okay and a little excited about going to school again tomorrow.
He's a good kid, no matter what town they drive through. He looks after Sammy when John is working; he looks after John when he comes home. He goes on his first hunt when he's ten, and when he's twelve he's embraced the life. John takes him out shooting. Dean gets a wild grin when he does, and he smiles and laughs when he's on a hunt. John knows that Dean's made to be a hunter. No matter how much he cares about his family, and everyone they save, Dean is made for this life.
Sam moves out when Dean is twenty-two and Dean takes it hard Eventually, he gets over it, right around the time he realizes that John's keeping an eye on Sam at school.
When he's twenty-six John leaves. He's preparing to die and he leaves while Dean's on a hunt and he knows that Dean won't like it; he might even go find Sam. He'll go find Sam at college, and he'll pull Sam back into his life, and Sam will follow because Sam always followed Dean's lead.
Sam and Dean Winchester become the dream team. Nothing stands in their way. John is proud of his boys.
When John dies and leaves Dean with a message that destroys him, he keeps Sam at arms' length and Sam pushes to get close. They struggle and push each other until Sam dies.
Sam dies, kneeling in the mud, on April 30, 2007, two days before his twenty-fourth birthday, and it takes Dean two days before he realizes that Sam is gone. He drives out to the nearest crossroads, pawns off his soul to the nearest demon, and Sam wakes up on his twenty-fourth birthday like nothing ever happened and Dean is thankful, until he does find out, and Dean gives in and tells him with the biggest smile on his face that he's going to Hell for him. His heart sinks guiltily when he sees Sammy chase his tail to save him. Dean's going to Hell but Sammy's going to run himself into the ground first, and then his sacrifice won't mean anything.
It will mean something. It means that Dean gets a couple more months with his brother, gets to see him smile a couple more times. And then, it's May 2, 2008, and Sam is twenty-five, and the last thing Dean will ever see is Sam crying. He holds onto that in Hell, holds onto Sam's face, missing him. He tortures for Sam. He stays human for Sam, and when he sees Sam again, he's so happy that Sam's okay that he can't think about the girl in her underwear or Dean's amulet around Sam's neck leaving bruises bigger than any Dean ever got.
