The first thing they learn is that it's hard to con a conman, and they learn it the hard way. Their mark is smart, slick, and French, and he kicks their asses all the way back home. John grumbles that they should've known better, and Bobby whacks him with a folded newspaper.
The second thing they learn is that nobody gets left behind, and they learn that the easy way. Their father takes them out into the woods, tells them to stick together, and then sends a dirty cop friend of his after them with a double barrel. They split up and get caught almost immediately. "Again," John says, and this time they stick together and make it back before the cop friend. That's the easy way in their family.
And then their father dies in action. It's a tough blow, to both of them, losing John. He'd taught them everything, and even if they'd moved slightly beyond petty fraud – a murder here and there, they all deserved it anyway – they still stuck to his training and basic strategy. They cremate him in a field and crash their car just for the hell of it.
People think they're together. They're not, they're brothers, but they play it up because for some reason people trust a couple acting suspicious more than brothers doing the same. Bobby still gets them jobs, puts them in contact with fellow conmen, and doesn't mention the trail of bodies they're leaving. Dean's worse than Sam; every time he gets remotely upset, at least two more people die in the city, and he shrugs it off with a "had it comin'". But where Dean's precise and cleans up well, Sam's more violent, takes out all his anger on the people he kills, until they're barely recognizable. They both take the hands and feet and teeth of the bodies; burn them in a different place. Dean fucks his way through every town they stumble upon, and Sam stays home and reads books about God and damnation and decides he's going all the way down.
They get tripped up on a motion sensor, because Dean's an idiot who wouldn't know technological progress if it punched him in the face, which incidentally is what the Fed who's been tracking their fraud trail does when they get caught. Sam thinks that's probably illegal, and then he gets clocked too and wakes up in a cell. Thankfully, nobody knows about the dead bodies following them across the country except Bobby and they're pretty sure the law enforcements don't know that Bobby Singer exists. The Fed calls himself Henrickson and grins like the Cheshire fucking Cat at them when he tells them their charges. Their lawyer looks at them like she doesn't have a hope in the world for them.
So they go to prison. Hell might be better, actually, than prison. They're shoved into a system that doesn't like them, doesn't want them, and is willing to crush them to sustain itself. Dean has a run-in with a goddamn Golem or something that Sam accidentally pisses off on their second day, and the guards haul him off to the infirmary and then solitary confinement. They leave Sam alone, surrounded by the Golem's friends, every single one of whom is glowering at him.
The shit hits the fan as soon as the guards get out of earshot, and one of Golem's friends, who looks like a failed high school teacher who's lost way too much or maybe that one guy from Lost, and actually inspires deadly silence when he sits down across from Sam, grins slowly. "Sammy, right?" he says cheerfully, and Sam scowls blackly. "It's Sam," he insists and the guy just grins bigger before lashing his fist out and punching Sam square in the face. He's surprisingly strong for someone so…suburban, and out of the corner of his eye, Sam catches a wiry dark-haired man restraining a shorter gold-haired guy at their own table. Dark Hair lets go of Short Guy when the asshole standing above Sam raises a foot above his head, making to stomp down hard.
Sam's not really sure what happens, but there's a blur and the asshole's foot is gone and there's a loud crash and someone hauling him to his feet. And then the guards make it back and everyone scatters except for the asshole and Short Guy, who are still fighting tooth and nail and wow, elbow and knee and foot too, right up until the guards pull them off each other. Dark Hair's got Sam by the jumpsuit, but lets go quickly when the guards glare at him. "I was helping him to his feet," he explains calmly, and the guards seem to believe him.
"Milton! Novak!" one guard barks, "Solitary!"
Short Guy rolls his eyes like this is nothing new, and The Asshole growls low in his throat at the guard. The guard backhands him, and then he goes quietly.
Sam stares after them, slackjawed, and then Short Guy – Milton? He'd perked up when the guard said that name – twists around and winks at him over his shoulder. The only thing that worries Sam about it is how not worried he is.
Dark Hair steps back even further, and scrutinizes Sam's face. "You will not need the infirmary," he proclaims sombrely. "I am Jim Novak. Credit card scams."
Introductions in this prison go as such: Name, Crime. It seems to Sam like Jim Novak's not really the criminal type, but then he says, even quieter, "At least that is what I was convicted of," and yeah, okay, maybe it really is always the quiet ones. Sam eyes Jim Novak and his extended hand.
"Sam Winchester," he says, taking the hand and shaking it, "armed robbery." Jim nods solemnly, like it's a noble thing to be caught doing.
"The man who punched you is my elder brother, Dante," he explains. "Break and Entry. He does not take well to new people. Or authority. Or family," he adds, looking somewhat sheepish at the fact that he's related to this Dante guy. Sam shrugs. He gets that, he's got cousins who have called the cops on he and Dean on numerous occasions.
"And the other guy?" he asks warily. Jim sighs deeply. "That," he says, world-weary, "is Gabriel Milton. He and I worked together. Dante dislikes him strongly and was quite upset when Gabriel ended up here."
Sam's staring, his mouth hanging open at this sudden information sharing.
"So…what do I owe you and your friend for saving my ass?" he asks, because he's not stupid, and how things work have been made pretty obvious to him.
"You owe me nothing except perhaps conversation. Talking with only Gabriel can be tiring," Jim says. "As for Gabriel himself, I am not sure. You'll have to ask him when he returns from solitary confinement. I believe he has his name on a cell at this point."
Sam grins, suddenly. Dean is going to hate Gabriel, he can tell.
"Well, solitary's gonna be damn crowded today," he replies and Jim smiles almost imperceptibly and moves his tray to Sam's table.