When Dean Winchester is five years old, his brother is put up for adoption. Their dad has stopped working at the car shop and they travel around the country, meaning dad just doesn't have the money any more. He can't afford to look after two children, much less a baby. Plus, he needs to be able to leave the kid alone and it's much easier to leave a five year old than a baby.

So John puts Sam up for adoption.

Dean meets the family, once, when they take Sammy. They seem nice; a pair of bible-bashers from Illinois with a four year old son. The boy hides behind his father's leg, tentatively watching Dean as says goodbye to his brother and stepping forward as Dean passes Sammy over.

'I'm Jimmy.' He whispers as Dean shows him how to how the baby.

'I don't care.' Dean mutters back, planting one last kiss to Sammy's head before going to stand with his dad. Jimmy holds Sam a little tighter as his father picks him up, holding both his old and new sons close to his chest. Dad picks Dean up and carries him to Impala, neither of them looking back as tears swim in their eyes.

They both pretend they don't hear when Sammy begins to cry.

When Sam Novak is seven, he starts trying to find his birth family. Jimmy offers to help but Sam declines, knowing how bad his brother is with computers. Jimmy still does his best though, writing down everything he remembers about the people. A man in a leather jacket and a boy with short spiky hair. The boy was the same age as Jimmy, maybe a year older.

'They had a cool car.' Jimmy notes one day, while Sam is trying to hack the adoption database.

'What kind of car?' Sam says, putting in their parent's details. He knows he could have just asked mom and dad but he doesn't want them to feel upset.

'How should I know?' The two of them laugh slightly, before turning back to the computer, trying to guess the answers to the security questions.

'Sammy?'

'Yes, Jim?'

'You won't leave, will you?' Jimmy frowns. A small eyebrow raise makes him look five years younger, like Sam is the oldest of the two.

'Of course not.' Sam smiles back. 'I'll just have two families. No matter who my birth brother is, you'll still be my brother Jimmy.'

Jimmy smiles and the two of them turn back to the computer.

When Jimmy Novak is twelve, he meets his brother's brother. The family is coming back from church, their mother having done a sermon on angels, when they see the boy sitting on their front porch. He looks awkward, like he wants to be somewhere else, and is fiddling with an amulet wrapped around his neck.

Sam pretty much barrels out of the car, running toward the boy. Jimmy realises a few minutes to late who it is, watching from afar as Sam pulls the other boy- Dean he thinks- into a hug. He realises what the amulet is now; Sam had sent it to his brother last christmas. He had received some money in return and a card. Jimmy had gotten Sam his own gameboy and a Rubik's cube but the five bucks stashed into a folded bit of paper had made Sammy a lot happier.

Dean's dad- Sam's dad- arrives a few minutes later, apparently having been trying to find a good parking spot. Jimmy doesn't quite believe that, as their road seems quite empty. John Winchester wraps his son into a hug just as easily as Dean does, although seem to want to never let go of the boy they got rid off.

Jimmy doesn't even talk to Dean or John as the two of them begin to arrange meeting up with Sam over the next week, month, year.

Sam doesn't look at Jimmy once while Dean is there.

Dean Winchester is fourteen when Sammy spends his first week in nine years with his birth family. It's spring break- not that it means much to Dean- so Sam is spending the week with them before he has to go back to the Novak's. Dad is working a job, of course, but Dean spends the whole week with Sammy, teaching the kid how to wrestle, telling him about ghost stories- real ones that Sammy thinks are fake. It's quite funny.

What's not funny is the way Sam keeps glancing at the shotgun in the corner of the room. Dean knows how to use it, of course he does, but Sam can't understand why they need the thing, why they should need protecting. Dean tries to explain that it's just for precaution, that dad can't look after them if he's not there but Sam still doesn't get why they need a gun.

Things go to hell when Dad runs through the door, covered in scratches and bite marks. Sam looks scared for a few seconds, then the werewolf follows Dad inside and Dean has to grab the gun, firing two shots into the monster's chest. Sam is cowering behind Dad, watching as the creature dies, tears running down his face.

Dean has to stitch Dad's wounds up while trying to comfort Sam. When the wounds are dealt with, Dad wraps his good arm around Sam's shoulders. Sam looks up at John, glancing at Dean every so often.

It takes a while for them to explain every thing. It hard to talk about their job then it is to tell Sammy that all the ghost stories are true. Dean and Dad don't leave anything out, telling Sam all about monsters and hunting and mom. Dean has to explain mom because dad goes quiet then and grabs a beer from the fridge. Sam is silent for most of the talk but, after Dad has fallen asleep, he turns to his older brother.

'Do you hunt Dean?'

Dean grins wrapping a hand around Sam's shoulder. 'Of course, Sammy. I help Dad save people. It's the family business.'

'Do I have to?' Sam whispers, eyes widening.

'No, definitely not. Only if you want to, and only with training.'

Sam nods several times. 'I want to. Really I do.'

Dean grins, patting Sam's shoulder. 'Then we'll start training tomorrow.'

Sam Novak-Winchester is fifteen when his brother gets married. No ones really surprised, despite Jimmy only being eighteen. He and Amelia have been dating for about six years, having met at a Church week away in Vermont. When it turned out they both lived in Illinois, only a hour away no less, they began spending more and more time together, finally starting to date a week or so after Sam found his blood family. Sam invites Dean to the wedding but the older hunter just shrugs.

'I don't really know your brother, Sammy. I met him, what, twice? And he didn't really speak to me either time.'

Sam nods, scowling slightly at the nickname. He can't really expect his brothers to make an effort with each other, even if he wants them to. They don't exactly have anything in common.

Dean drops Sam off outside the Novak house two weeks before the wedding. There's a couple of hunts a few states over he needs to take care of but Dean says he'll be back after the wedding.

'I'll be gone three weeks, tops.'

Sam is quickly pulled into wedding preparations. He's fitted for a best man's suit and forced to learn a speech his Dad wrote for him. He changes the words overnight but checks them with Amelia before he uses them. She laughs, so he's sure Jimmy will too. Being the tallest in the family, he has to decorate the reception venue, hanging up bunting and fairy lights.

He sews a pocket into his jacket for his gun and tucks a knife down his pants. He doesn't expect anything to happen- its a church after all. But he's not going to risk a werewolf or a ghoul on hallowed ground. Dean would be proud.

The wedding goes by without any supernatural interferences. Sam stands beside his brother, handing him the rings when needed. He takes one look at Jimmy's face and knows that, one day, he wants to get married.

His best man speech hardly mentions that he's adopted and Jimmy seems happy for it. Sam's jokes are a bit lame but everyone still seems to laugh and that's all he can ask for. He dances with Amelia's best friend for tradition but the two of them spend the whole time laughing about it.

Six months later, when Claire is born, Sam can't help but laugh when he finally gets to visit. The baby sits comfortably in his arm as he rocks her back and forth.

'So this is why you got married so quickly.'

Jimmy punches his arm, the one not holding his niece.

Jimmy Novak is nineteen when his little brother stops coming to Illinois during the holidays. It's been years since Sam lived with his adopted family full time and months since he spent the majority of his time with the Novak's. In the six years Sam has been spending with the Winchesters, he's grown up and toughened up, always ready to take on a fight. Jimmy pretends he doesn't see the knife Sam always tucks into his trousers or the gun Dan, or whatever his name is, keeps on his dashboard. He doesn't like Dan so it's easy enough for the two of them to ignore each other whenever Sam is dropped off.

Of course, that doesn't matter now because Sam isn't being dropped off. Jimmy had gotten the call from his parents, saying they'd just gotten the call from Sam. He's not coming home this summer. Jimmy takes a second to wonder why Sam didn't call him but then Claire is crying and all thoughts of his brother are swept from his mind.

Sam calls Jimmy once a month, which is a small miracle. They never mention Dan or Jack or any of the other members of Sam's bio family that Jimmy can't be bothered to remember. They talk about Claire a lot because Sam can always hear her over the phone. He asks Sam about the road trip, since he knows the Winchesters don't actually have a home. Just a car from the sixties.

Jimmy wants to speak to his brother more but every time he tries to ring, Sam is busy and can't talk at that moment. This happens every time Jimmy calls, no matter what time of day. Which means he'll have to drop everything when Sam calls, or he won't be able to speak to his brother for another month.

'You shouldn't put up with this.' Amelia says, watching as Jimmy hangs up the phone. Sam had cut off quickly, shouting a hurried goodbye and love for Claire.

'He's my little brother. I can't just stop caring about him.' Jimmy frowns, taking his daughter from his wife.

'But he's with his family.' She smiles, sitting down next to him and looking through the notes he discarded when Sam called. 'And you have an interview on Monday. One you can't afford to miss.'

He nods, sighing. 'I know.'

Dean Winchester is twenty three when his brother leaves for college. It's the biggest fight he's seen in the nine years Sam had been spending time with him and Dad. There seems to be no let up on either side as they scream at each other.

'If you wanted to leave, why didn't you just say?!' John is yelling, the argument gone from angry to petty.

'Maybe Dad, because whenever I try to bring up my other family, you go off the head!' Sam shouts back, eyes flashing.

'They're not your family!' John practically screams, fists clenching.

'You didn't seem to care that much when you left me with them! When you abandoned me!' Sam takes another step towards the door, waiting for John to say something. When he can't, when the words just stick in the oldest Winchester's throat. Sam throws open the door, ready to step out.

'You leave boy, you don't come back. You understand me, Samuel Winchester.'

Sam doesn't even look at Dean as he bites back. 'It's Sam Novak.'

The door slams and Dean flinches, not even looking at his Dad. John swears once, twice, three times before throwing the bottle of beer in his hand across the room. Dean looks up at the smash, eyes wide. John sighs, grabbing two more bottles out of the fridge and passing one to Dean.

'To Sam. And Stanford.'

Dean laughs slightly because why couldn't Dad say that ten minutes ago. 'To Sam.'

They sit in silence, wondering how far away Sam is by now, if he's contacted his adopted family yet. The Winchesters are currently in Maine, so Sam will likely pass through Illinois to get to California.

'Did he tell you?' Dad mutters after ten, twenty minutes.

'No. I saw the papers but...' He shrugs, not sure himself why he didn't say anything to his brother.

Dean sighs, looking down at his hands. He's lost his little brother, again.

Sam Novak is twenty two when he watches his would-be fiancée burn up on the ceiling. He is still screaming, trying to help in someway when Dean runs in, barrelling him out of the house. He doesn't stick around for long afterwards, which he knows will seem suspect but he just wants to get moving, to find the thing that got Jess, that got Mom.

He still calls Jimmy once a month and their parents every other month. He sends an email every time he and Dean visit somewhere special and borrows the Impala whenever they are near Pontiac. He invites Dean to come with him, to meet Claire and get to know Jimmy.

'Someone's gotta stay here and do research.' His oldest brother always says. 'Besides, I hardly know the guy.'

Sam nods, accepting the excuse.

His niece is seven by now and just as adorable as the day she was born. Claire no longer has to be reminded of Sam's name when he visits and doesn't hide behind her father when he walks into the house.

Sam still prays, every night, even if he's not going to church anymore. He talks to Jimmy about it, on the phone. His brother assures him that going to church is more of a social thing. Prayer's the most important part of being a Christian so Sam continues praying.

Dean scoffs when he finds out about Sam's faith but, as Sam constantly points out, there has to be good in the world, somewhere. Dean just shakes his head.

When Dean's deal runs out and Sam is cradling his brother's body, he prays for the last time. It's not really a prayer, more like screaming at the sky, damning every angel in heaven.

He doesn't pray for four months.

He doesn't contact Jimmy either.

Jimmy Novak is twenty eight when the angels start talking to him. Well, one angel. He likes talking to Castiel, it's a lot easier than talking to most people. Castiel doesn't judge his faith, or his lost brother, or the fact he had his daughter when he was eighteen. The angel just talks to him, asking his for small favours to prove his faith, telling him he's been chosen by God.

Jimmy hasn't spoken to his brother in four months when Castiel asks for his last favour. A man needs saving from Hell and the Seraph needs a human vessel to be able to do it. Amelia thinks he's insane and threatens to take Claire away so Jimmy needs more information.

'Who is this guy?' He asks as he dons a suit and trench coat. He's going to say yes, how could he not but he doesn't want to go in blind.

'His name is Dean Winchester. He needs saving so he can stop his brother Sam going down the wrong path.'

Jimmy almost falls over at those words. Sam? Go down the wrong path? He'd ask why he can't help but Sam hasn't spoken to him in months, why would he listen to him. So Jimmy steps outside and says 'yes'.

He spends the next year screaming inside his own mind.

Dean Winchester is twenty nine when he meets the angel that saved him from Hell. He instantly doesn't like the guy because, even if the meat suit prayed for it, it's still possession and it's not right.

Plus Dean can't shake the feeling he recognises the meat suit.

Sam Winchester-Novak is twenty five when he comes across the Samhain case. Witches are difficult enough to deal with but with a apocalyptic demon about to be sprung, Sam's even more on edge. So when he walks into his motel room to see two stranger's standing there, he instantly pulls his gun.

Dean comes running into stop him when the guy in the trench coat turns around. A smile stretches across Sam's face as he realises it's Jimmy. His brother.

He throws the gun aside as he pulls Jimmy into a hug, surprised when his brother just stands there, not moving to return the hug.

'Please get off me.' Jimmy mutters, his voice a lot gruffer than normal. Sam steps back, holding the older Novak at arms length.

'Jimmy? What's wrong?'

Jimmy's head tilts as Dean steps in, standing between them and frowning at Sam. 'Dude, that's Cas. The angel.'

Sam raises an eyebrow, shaking his head. 'Dean, this is my brother. Jimmy.'

Dean has the decency to look guilt as Jimmy, no Castiel, narrows his eyes confused. Sam looks between the two of them and is ready to say something when the other stranger speaks up.

They defeat Samhain but break the seal anyway. Cas goes to speak to Dean while Sam is stuck with Uriel. He doesn't really care what the angel has to say.

He doesn't really like angels anymore.

Jimmy Novak is twenty nine when he gets his body back. He blinking awake when Dean runs up to him, shouting the angel's name. He's pulled to his feet, Dean looking at him with such fear and concern it almost makes him sick. Dean doesn't care about him, just the bloody angel that stole his body for a year. Sam doesn't even look at him, doesn't look at Cas.

'Castiel, I'm not Castiel.' He says, his eyes on his brother. 'It's me, Sam, it's Jimmy.'

Sam turns instantly, pulling Jimmy into a hug. The older brother laughs, hugging back while Dean looks on, eyes narrowed.

'Where the hell is Castiel?'

Jimmy stops himself from smirking. 'Gone.'

Jimmy eats through about a hundred burgers, quicker than he's ever eaten before. He never thought he could be so hungry. Dean makes some comment about slowing down but Jimmy just scoffs, explaining how he hasn't eaten in months.

'What was it like?' Sam mutters, watching Jimmy eat, as if he expects him to suddenly change back into an angel. 'Being possessed?'

'Like being chained to a comet. I remember bits and pieces. Which reminds me.'

He leaned over and smacked Sam around the head.

The younger Novak yelled, glaring at his brother. 'Ow, Jim. What was that for?'

'Ghosts, Sam? Vampires, werewolves, demons? You couldn't have told me about any of this? I had to get possessed to find out.'

Sam flinched, looking embarrassed. 'How was I supposed to tell you? It's not like it's perfectly reasonable.'

Jimmy smacked his brother again, getting a laugh out of Dean. 'I don't care. I'm your goddamn brother.'

Sam glanced at Dean who shrugged. 'He is your brother.'

Jimmy grinned and Sam's older brother both smirked at him in unison. The youngest rolled his eyes. 'This is why you two never met.'

Jimmy laughed, winking at Dean. The other man winked back. Jimmy smiled, wondering why he had never met his brother's brother before.

'Now, when can I go back to my family?'

Dean Winchester watched as Sam said goodbye to his sister-in-law and niece. Jimmy Novak sat in the back of the car, watching his family. They were leaving and Jimmy wouldn't see them again.

'Yeah, right.'

Dean turned. 'What?'

'You think they'll give up, the demons. You forget, I was in an angels head. I know demons, they don't give up. They'll use my family to get me back and I'll end up being worn by an angel.'

Dean raised an eyebrow. 'Is there a reason for this little pity party?'

Jimmy shook his head. 'I can ask the angels to protect my wife, my daughter. Hell, they might even do it. But no angel worth their wings will agree to protect the boy king.'

'The what?' Dean had heard demons call Sam that before but never asked what it meant. 'Boy king, what does that mean?'

'Boy with demon blood, Azazel's favourite, something about a seal, something about a vessel. I don't know, Dean, I just know Heaven isn't a fan of Sam. So they won't protect him.'

'Okay. Again, any reason for this?'

Jimmy leaned forward, his face coming next to Dean's. The hunter turned to face him, having long since gotten used to no personal space with Cas- even if he currently wasn't Cas.

'I don't want anything to happen to my brother. But something is going to happen to him, if Heaven is right, I just don't know what.'

'So you want me to stop it. You want me to protect Sam, because I already do that.'

Jimmy looked out the window watching Sam walk back towards the car. 'I know but it's not that. Sam can look after himself. I just want you to be there for him, don't abandon him.' He leant back in his seat, eyes sad. 'Look after our brother, my brother. Promise me that.'

Dean took one look at Jimmy, who's face he was so used to associating with a good friend of his, perhaps his best friend. Jimmy was looking at him, ready for rejecting but hoping for acceptance. Dean nodded at the man he wished he couldn't gotten to know, who he was sure he would have been friends with.

'I promise. I won't leave our brother.'

Sam Winchester watched the light fill his dying brother's eyes as Jimmy agrees to be a vessel again. He wants to protest, to ask for some other guy to get the angel possession but it would be pointless. One, because Jimmy would die anyway. Two, angel's need specific vessels, he knows that. And three, why would Castiel listen to him with blood around his mouth.

His brother stands up, no longer his brother. Castiel walks past the two Winchesters, explaining to Dean how he no longer serves humans. No longer serves Dean. The two hold each other's gaze for a few seconds before Dean shrugs.

'Just tell Jimmy I remember my promise.'

Sam raises an eyebrow, looking at Dean in shock. What did he promise Jimmy? What did Sam's middle brother ask for?

Sam looks back at Castiel in time to see him glance at the younger hunter. There's a look in his eyes that isn't Castiel. Isn't angelic or emotionless. It's caring and brotherly and Jimmy.

Sam allows himself a sad smile when the look is gone and Cas goes with it.

Jimmy watches as the Grace, the great bright light that shines next to his soul moves. It's not a comet anymore, not simply using his body and forgetting him. The Grace cradles his soul now, protecting him from the worst of the pain Castiel goes through. He is closer to the surface now, can see everything that happens.

When Raphael kills them, he still feels Castiel's Grace trying to keep him safe and he holds onto the angel, trying to stay close to the angel. They are brought back in a body soon afterwards but, for a few moments, they are without a body but keeping together, a soul and a Grace. They cling together, neither wanting to let go.

'Why are you doing this?' He wonders once, not expecting an answer.

'Dean Winchester made you a promise and it's one that I will keep to.'

'Dean promised to look after Sam.'

'And Sam is looked after best if he has both his brothers with him.'

Later, talking to Anna, Jimmy is right at the forefront of their mind. He has no control but he is seeing Anna clearing, his vision not obscured by Castiel's Grace. No stupid angel gets to threaten his brother.

'If you want to stop the devil, this is how.'

'The answer is still no because Sam Winchester is my friend.'

Anna scoffed, ready to reply with some biting retort.

'And.' Castiel said, smirking. 'Sam Winchester is my brother.'

A/N: Possibly the longest one-shot I've ever written. There just didn't seem to be enough Jimmy fics around.