Spades Slick was born into a fairly shitty house, his dad left for a pack of cigarettes when Slick was 6 and his mother was arrested for prostitution pretty shortly afterwards, and spent the rest of his childhood hopping from foster care to foster care until he finally got out of it. He is probably fairly agnostic/atheist/apathist from going from place to place and each family having a different doctrine to put upon him, sent to be an alter boy after he fucked up in one particularly religious household, got kicked out pretty fast for screwing a girl in the pews. His schooling was also really disjointed because of this, he moved from school to school. homeschooled no-schooled etc. When he was actually doing any sort of school work beyond the basics he did bare minimum to stay afloat. Really awkward puberty, poor hygiene didn't help much. Once he finally slipped free of that bullshit he was an errand boy for the mob when he entered and climbed through the ranks really fast but got bored of it quick, because whiel he was good he didnt have enough ties to actually get anywhere meaningful.

Droog was groomed for his position since childhood, born into a prestigious mob family, lived in a really lavish house with tall rooms and always smelled slightly of cigars. Maybe had an older sister? They weren't particularly close. His father was a high up and his mother was more like a bored arm ornament, always covered in really expensive furs and jewelry. Raised Roman Catholic but not really a believer, just went to church to keep up good appearances. Prim and proper since he was a kid, never was loud, seen and not heard, top of the class. Maybe lacrosse? Something to keep him fit and he'd be a yuppie like that. Blossomed into adulthood like a beautiful butterfly like some goddess had gifted him perfect aging. Probably got like one zit and got into a huge snit about it. Had a few very low key relationships through highschool before devoting himself completely to continuing his family's business.

Boxcars had a stereotypical Greek or Italian family. Baptist, also another mob family. Lots of brothers and sisters and close family. I'd say out of the lot he had the most normal upbringing?? Not really much to say on him, his grades were fine, probably did wrestling or something and had a few strong romances in highschool that didnt last because he went into them way too fast. His and Droog's families work together and are very close, but Boxcars's family is lower on the ladder, but theres a mutual trust agreement there. He and Droog became friends because they were similar in age and while Boxcars annoyed the SHIT out of Droog he was one of those friends that managed to force a smile out of Droog sometimes no matter how begrudgingly. And Droog if you tied him to a chair would say that he enjoyed when his family had to visit Boxcars's for business related reasons because while he enjoys things being very collected and calm he feels like he missed out on a family with all the detachment in his own. Also boxcars had a really scary puberty and just shot up like a tree, his voice dropped like 4 octaves.

Deuce grew up in a REALLY BAD household but not bad enough that he realized it until years later. He's not DUMB just a little slow on the uptake. His family was probably fake-some sort of christian where they celebrated christmas and deuce knows enough about jesus to not be baffled by a crucifix but hasn't touched a bible in his life. His dad was abusive to his mother and his mother was a bit of an alcoholic, his dad also brought home a lot of floozies and left for long periods of time. Deuce was an only child, and usually stayed out of their way, coming home pretty late and spending most of his time with his friends. He was never really a big player in his groups of friends, but like that kid who is always there that no one minds but they dont remember how they became friends with him. Sometimes he would come home to his mom drunk out of her mind and she would rant for a while like he was tumblr and she had all the vagueposts and readmores in the world to get off her chest. They weren't involved with mobster bullshit, but deuce sort of accidentally got into the business? Worked a construction site or something, and sometimes had to bury bodies or blow up buildings and Deuce knew it was illegal, he just didn't really care and decided that turning a blind eye was the best way to do it. Really really really average in school, no extra circulars (did i spell that right???) Puberty was basically nonexistant for him, pudgy baby face forever. Hasn't really had a girlfriend, but a one night stand with a nice girl or two. He sort of figures out that his childhood sucks mid sentence, and accidently slips things in conversation like, "Aw gee Droog thats a real bad shiner, my mom knew some great ways to cover that up when she ran into doorkn-" and then he just stops and stares off like oh..... or stuffs whatever he's eating into his mouth to stop him from talking and Droog stands around awkwardly.

They got together by Slick working closely with Droog's family, and Droog being the only person who really saw what sort of potential this back-alley guy and made a deal with slick that theyd break off and be their own thing- Droog was bored of the huge business anyways and felt that too many people made it too hard to get anything done. Suggested Boxcars to join them because of their friendship back when they were teens and early 20s, and the crew was just that three. Then they needed Deuces expertise in demolitions a few times and kept going to him for help- and he turned out to be a really good asset to the team and sort of accidentally joined the crew.

I cant really decide their ages in relation to eachother but i feel like Deuce is the youngest (not a baby) and maybe boxcars or droog the oldest???? slick is probably second youngest but age doesnt really mean much to them.