Chapter Text
Dean could tell you exactly how he came to be an enforcer for a long standing prison gang called the Alphas. Each tick of the timeline was bold and distinct. His dad had been second in command for years until he took a shiv to his kidney for stealing hooch from some meth head. That's what happened to drunks on the inside.
Dean was practically born into prison life. With his mother dead and his dad locked up, he had spent all of his time trying to take care of his baby brother. Crime was the only method he'd been given.
So while Dean was cooling it off and on in juvie until 19, Sam had 4 years of tuition paid down at his fancy prep school that could fast track him to Ivy League. That's where Sammy belonged. Dean got his hands dirty so Sam could do something more, whatever he wanted really. He could be some broke ass hippie artist and Dean would be thrilled.
It was no shock that despite getting scholarships to college, Sam still struggled to make rent and like...survive. So it shocked absolutely no one when Dean started boosting cars and selling the parts. Thing was, sometimes he got paid to steal them & scrap them. Insurance paid out big for that. Those fancy fucks were always grateful and generous, as long as it meant they could squirrel away assets from their trophy wives.
Dean didn't care how he got the money. He did it. And now Sam was a big shot lawyer and doing his thing. Set up was pretty nice. Even if Dean ended up with 10 years. Even if surviving meant that he had another 5-10 tacked on to "make a statement." Truth was, Dean made more money on the inside than he ever did boosting cars. It all got put into an account set up for Sam. He jokingly called it a wedding fund, but the truth was a little more sinister.
It was there to help keep Sam safe in case anything ever happened to Dean.
48, 49, 50.
Dean dropped from the doorway, pacing the 6 x 8 room currently housing him.
"Back it up Winchester!"
Eagerly, he went to the back of his cell, holding his hands in plain view.
"Hey Vic!" he chirped, "How's the nephew?"
"Kicking ass and taking names. You ready to get outta here or what?"
"I'm your huckleberry, baby, tie me up."
Victor snorted at his ridiculousness, but Dean was so ready to get out of the hole and get some fresh air.
See, Dean was a fighter. He was a frequent flier in the hole, or Hell Block, as other inmates called it. For Dean, it was a pseudo-vacation. No fights, no fish trying to prove themselves, nobody barking orders at him. Not that Dean always listened . One of the benefits of nepotism, he supposed.
He chatted easily with Victor as they walked back to his block.
"You missed fish patrol."
"Bah. I hate fish patrol," he griped. "They're either hostile or about to wet themselves."
Victor tipped his head. "This one was interesting."
"What do you know that I don't?"
"Russians. Bratva, apparently. Transfers from the east coast. I hear there was some kind of turf war. One of em killed some COs. A warden too."
"And they sent em to Kansas ?"
Victor shrugged. "Maybe they need to lay low. Who's to say?"
Well shit.
*
Dean was loudly greeted by the other inmates. Especially the Alphas. His usual table was full; a mix of oldheads and younger guys that seemed to gel well enough. The older ones had done time with his dad, and so were more lenient with Dean than others. One, Luther, shoved a newer guy out of a seat so Dean could have it. Dean didn't bother apologizing or looking at the kid, it wouldn't do him any good. Everybody came up their own way.
"That was some fight," Chuck drawled from across the table, stretching out his hand for Dean to slap. "How was Hell Block?"
"Quiet. Boring. Got some good workouts in though."
"You all rehabilitated Baby Winchester?" one of the older guys, Dex, gruffed from the other end. Dex wasn't his actual name. Nobody knew Dex's actual name. Or how long he'd been locked up. Dex was Dex.
"Oh I'm peachy keen and headed for the straight and narrow, Dexisaur. I always see god down in the Hole." He tacked on a juicy wink just to get them all hoot and hollerin' about him being just like his dad. Dean tried not to let that stick too close to his bones.
"Winchester!" He twisted his head to see Ash coming over with his magical tablet. Most of the Alphas didn't have tech access. Just Ash, really. Because he was the Bank. For everyone involved in the fights. Didn't matter which gang, which ward, CO or convict, Ash did the book and made sure everyone got paid. So he got special privileges.
"Ash, light of my life, king of cell block D, tell me something good," he hammed up, slapping his hands together in solemn prayer to the only god who had ever responded.
"Three-K direct into your account," Ash shot him a cheeky grin. "X marks the spot, pretty boy."
Dean looked over the information and signed his name with a firm nod. Perfect. That would cover a chunk of the surgery upfront so Bobby could do a payment plan.
"That was some fight, cher," said a smooth twangy voice that made Dean smile. He looked over to shake hands with Benny LaFitte. A Louisiana smartass with a rap sheet longer than a caf table, who'd run with his dad for a bit at the end. He was Dean's first celly when he landed in prison. Benny tugged him in for a quick hug, smacking his back even though the COs snapped irritably at them both.
"Fuck 'em, good to see you out."
"Thanks Ben," he said sitting down. "Honestly needed the break though. Every time Gordon loses money, he guns for me."
"Ha!" Dex snorted. "Gordon always loses money."
" Exactly . Not my fault he's stupid. And too slow."
Benny grinned and opened his mouth to say something before he was interrupted by movement and chatter. Guys started moving quick, making a path.
"Aaron's on one today, cher."
Dean rolled his eyes and leaned back, elbows on the table behind him.
"Isn't he always?"
Benny kicked at his foot and hissed a warning. Dean pretended to ignore it, of course, but took it to heart. Benny was like the older brother he'd never had.
And if that was the case, then Aaron was the dickhead friend he'd never wanted.
People had expected that Dean would try to take over the Alphas, to run things like his dad had always done. But that wasn't his thing. Dean didn't want to make a life in prison. He was trying to get out, to move on. The gang bullshit meant nothing to him. It was a means to an end. He got protection and he got paid. Easy. Clean. He didn't get the stupid tattoo and he definitely did not give a shit who was in charge.
Aaron Hesson did not like that. At all. But he had to put up with Dean or half of his crew would riot for sheer principle. So Aaron bossed Dean around like he had some kind of say and Dean let him. Sometimes. Mostly he chose what he would and would not do, and fuck Aaron's bitching. Benny frequently reminded him to be a little more diplomatic, but again, prison gang politics were not his fucking forte.
"Winchester!" Aaron snapped. "Good you're out. Come with us." He was leading a group of twelve to the door. Dean scowled.
"I just–!"
"Now Winchester! Russians. Five minutes."
He hung his head. "Fuck me." And then immediately popped onto his feet and clapped Benny's shoulder. "They're singing my song, Benjamin. See ya on the flip side."
Benny stopped him for a second, grabbing him by the arm. Dean pretended to be jerked back and spun on his heel to face him.
"It's just a meeting, Ben."
"It's Russians, cher. Be careful. To konmprann?" (Understand me?)
"Hey, mo konmprann, latét prop." (I understand, baldie). He rubbed Benny's bald head for emphasis.
"W ap kon jòj ," he shot back, swiping at Dean to get him off. (You'll learn the hard way.) Dean just chuckled, tongue behind his teeth as he danced away.
"You worry too much, oldhead!"
If Benny responded, Dean didn't hear him because he was already through the door, jogging to catch up with the Alphas. The dude really did worry too much.
When he got to Aaron, the gang leader tugged him closer so they walked in step. He lowered his voice but filled Dean in on what he'd missed. Some kind of scuffle with the Russians is what it boiled down. A territory dispute, a miscommunication, some kind of disrespect. Gang politics made even less sense than prison politics, honestly. Any and everything could be seen as disrespect and there was some kind of intuitive system of tiers that Dean had never bothered to figure out. Talk shit, get hit. That was Dean's policy. It addressed every direction of talking shit and in the end he would get punished no matter who he hit. For the sake of the warden's reputation, of course.
"I just need you to get a read on the new guys, size up if they're going to be a problem, and let me know what they're saying."
"They talk too fast, dude, I can't always–"
"Just fucking try, Winchester!" he snapped, tossing his hands up like he'd been fighting a tantrum all day. "Do your fucking job!"
Dean rolled his eyes at Aaron's back and tapped Shep's arm.
"Who the fuck pissed in his Lucky Charms today?"
Shep snorted. "Hanley."
" Again ? Are you fucking serious?"
"Can't fight if you're in detox."
"How much?"
Shep shrugged. "Nothing like your numbers. But enough that the ABs cried foul and want a double."
Dean stopped short, pulling the attention of a few guys.
"So I get sent to Hell Block because Hanley fucked up a deal and Hewie raged out, I have to listen to boring Russians bitching about boring shit, and I have to fight a double because Hanley OD'd? Again!"
They shared an amused glance amongst each other and nodded.
"That's about the whole of it, yeah."
"Fucking christ," he snarled, shoving past to push the door open. "Anything else I need to know? Did he sign me up to donate a kidney? Part of my liver? Someone plotting a jailbreak and I'm the patsy?"
For whatever reason, his audience's appreciative chuckles didn't soothe his frustration like it usually did. Aaron's decision making and choice of friends was questionable on a good day. On a bad day, Dean wished like hell he had a shiv.
*