The way Dean sees it, you got to be some kind of fucked up to decide to pursue a career in family law. Even more so to build a firm on the reputation of your ability to skillfully destroy marriages. For a man who didn’t have much appreciation for the entire institution, it was more a matter of justice by way of practicality than a sense of spite. Well, maybe 15% spite. Overall, he did not care about the "sanctity" of marriage, in the sense that he was driven by the motivation to either uphold or destroy it.
Like most peoples’ baggage, it had started at home. John Winchester, to put it politely, was not suited for the strictures of being a father and a husband. To put it honestly, he was a drunk. More honestly, an asshole. It was hard to tell if he was an asshole because he drank, or he drank because he was an asshole. Dean suspected it was somewhere in the middle.
So when, on the summer break between his freshman and sophomore years of high school, his mom told him that she was going to file for divorce, it wasn’t a huge surprise. The fact that his dad apparently had an entire other family up North, well, that kind of was.
It seemed a pretty cut and dry case to him, seeing as his mom was the saint who had raised two children mostly on her own while her husband trucked and, apparently, fucked around America but his father’s lawyer felt differently. Mom hadn’t been able to afford anything more than the public defender, a nice but bumbling man— boy, really, fresh off of taking the bar and barely seasoned in court. Her finances were all tied up in the case but his dad? Well, he had a separate line of funding. Nobody said how much his attorney’s fees were, but nobody had to, the man's shoes were more expensive than all three of the suits on his mom’s side of the bench.
His father wasn’t a philanderer, a casual alcoholic, the perpetually empty seat next to his mom at school events and game days, no, he was a devoted father— to Adam. There were photographs, the three of them celebrating Adam’s birthdays, John in the stands at his little league games, transcripts of him at his parent-teacher meetings, for god’s sake. And of course the testimony, Kate’s— that John had tried to talk to Mary about separating after they first met, that Mary was jealous and selfish and refused, threatening to take full custody of the boys if he tried, that John loved them too much to let that happen so he had no choice, that Mary bled him dry, constantly asking for money— and here they entered into evidence years of letters and old voicemails from Mary telling John that they were short for that month’s mortgage, school fees, new clothes for the kids, bills for the doctor and the dentist, for antibiotics when Sam caught a series of nasty ear infections, for the countless mundanities of life, please, when would he be home? Conveniently skimming over her other words, retellings of stories, how they missed him, that she loved him. Those were all nothing more than manipulation and lies, of course. The kicker was Adam on the stand— cherubic and sweet, talking about how his daddy loved him and asking, voice trembling, if they were trying to take him away.
In comparison, Dean with his hair-trigger temper and his “anger issues” was used as another piece of proof. His furious testimony was nothing but hearsay and, by the way, look at his report cards: here, a noted “problem with authority,” there, “bright but unmotivated,” and why look, detentions for cutting class, for smoking on school property, for bad language, a 3-day suspension for fighting, and oh dear, he’s only holding a C average. A troublemaker, in short. If only he’d had a father figure to help. Instead he had Mary, who made several appearances in those reports as well, defending Dean, excusing his behavior they seemed to suggest, even telling a teacher to “go to hell” once. The part where the teacher told them that the only place Dean was ever going to get into was jail was glossed over.
Sam? Oh sure he was bright and polite, good grades, glowing school records, but he was young, malleable, and he loved his mother and brother to a fault. How could he ever say a bad word against them? His hesitation to follow Dean’s footsteps and outright defame John proved it. Mary had kept John away from him as much as possible, the boy barely knew his own father, not with his brother and his mother poisoning the well.
Dean wouldn’t ever forget the wan, shocked face of his mother, lost for words, sitting in that courtroom as her life was dissected and dismissed or the rage simmering in his stomach as he sat beside her and watched them take the truth and twist it into their lie.
When John’s lawyer approached them to set up a meeting to negotiate the possibility of an out-of-court settlement, Mary accepted. His terms were clear: he wanted the house, half of their joint bank account, and to only pay the minimum required amount of alimony and child support.
“The house?” Mary hissed at him, “You want the goddamn house? My name is the only one on the deed. I found that house, I gutted it down to studs, and I rebuilt it with my own two hands. Now you want it for, what? A heartland vacation home for your second family?”
“I want to sell it,” John said.
“You keep that house and you’ll be the only one living in it,” he said.
“Are you threatening me?” Mary asked.
John smiled meanly, “No. I’m informing you. If you don’t agreed to these terms, I’ll fight to be granted sole custody and,” he leaned forward, “I think we both know that I'll win.”
“All these years and I couldn’t pay you to be a father to the kids, I never thought I’d be happy about it,” Mary’s eyes were fire and ice, cold enough to burn, “but now I know what kind of man you really are and it makes me think they’ve got an angel watching over them that saved them from you.”
John’s jaw tightened, “I don’t care about whatever fantasies you’re spinning for yourself. The house or the kids, you chose.”
“After that display, that charade, in court? They hate you, John, they’ll never agree.”
“You’re a fool if you think their opinion will make a difference. They’re both minors, they don’t know what’s in their best interests. Dean is just so troubled, isn’t he? Seems like he could use a more stable environment. Two parents, a steady income, with a nice house in a good school district or a single mom who’s going to need to find a full-time job to keep a roof over their heads? His little outburst on the stand combined with his track record? It won’t be hard to establish that you’re an unfit parent. Of course, it’s only a couple of years until he’s 18 but what about Sammy? He’s still a kid. How much are you willing to bet that he won’t change his mind? After a decade of playing happy family with two loving parents and a kid brother looking up to him, what would he ever want to do with his mean old biological mother who tossed him aside in the divorce?”
Mary was white as a sheet, standing like the only thing keeping her upright was sheer force of will and a spine of steel.
“You’re a bastard, John Winchester, and I hope I live to see the day when your house of cards falls down on you.”
She picked up the pen. “You, lawyer asshole, I don’t ever want to see him again. He can’t call, he can’t write, and he can’t ever see the boys. If, for some ungodly reason, they ever want to get in contact they will reach out, not the other way around. He revokes all his parental rights and in return he gets the house. It will be sold by a third party since he will be gathering his belongings and leaving the state as promptly as is possible. I will receive back the original amount of money I paid for the property, plus interest, from the sale. Alternately, if he wishes to have all the proceeds then I get to keep the amount currently in our joint bank account, of which I will become the sole holder. Don’t argue, jackass, it’s pocket change to you. I’m making sure we don’t starve to death. You redraw up the terms with my provisions and I’ll sign it.”
In that summer, somewhere among his family picking through the wreckage of their old life to slot it away in storage boxes, and trying to reassemble it in a cramped studio apartment, Dean made a decision. One thing was for certain, no one ever called him unmotivated again.
“His name is—”, Castiel hovered delicately over the word for a second, before his shoulders slumped forward slightly and he finished, “Dick.”
Dean caught a very unprofessional snort of laughter halfway through it escaping from his throat and attempted to cover it up with a badly faked cough. Judging from the slightly amused look on his client’s face, he hadn’t succeeded.
Cas waved away his apologies with a hand before he could even start to make them.
“No need,” he said, “It’s har— difficult not to, for most people. He’s very sensitive about it.”
Dean generally tried to keep these first consults impersonal, sticking to just the facts until they’d 100% decided to work together, it helped decrease the number of people who burst into tears, for one. He still had a stock of 3-ply kleenex in his bottom desk drawer, of course, he was a divorce attorney, tears were part and parcel of the profession. This one didn’t look like a cry-er though and he was too curious not to ask, “Why not just change the name?”
Cas sighed, “It’s family tradition. Which is the sort of thing both of our families consider to be compulsory. He’s actually Richard Roman IV, to be precise.”
Dean paused and tried to stop himself from making the joke, he really did. “So, what you’re saying is he comes from a long line of Dicks?”
“In every manner of speaking,” Cas replied.