A/N: Don't know why I gave Grimsley and Riley such a terrible past. What's done is done, I guess. It is the fate of Sir Aaron's descendants – to suffer forevermore. As always, unbetae'd.

A word of advice: The whole gist of this series is – how can I connect everyone through family bonds and/or pairings in one single universe?

Every chapter should focus on a character/pairing and in a headcanon. For example, this one is a headcanon regarding Grimsley's family-backstory (and Riley's, sort of), but there can also be relationship-backstories or journey-backstories or even career-backstories! I just want to fill in the gaps in the games. And what better way than to turn my headcanons into fic? Everything is headcanon and nothing hurts. For more information, contact me at tumblr, where I'll be glad to smother you in genealogical trees and opinions. My user name is "prolicide".

Chapter tags (as per AO3 standards): Alternate canon, dysfunctional family, family drama, character study, backstory, anachronistic;
Chapter pairings: Peripheral Riley/Cynthia and Grimsley/Shauntal;

.

.

Title: The Aaron Family As Seen Through the Eyes of a Skeptic
Character: Grimsley
Headcanon: Family Backstory

.

.

I.

There has always been bad blood between the Aarons; namely between the main family and the second branch. It's more noticeable when you look at things like old album pictures, but if you want to research deeper, then the oil paintings stashed away in the main family's mansion will suit you very nicely. You will not find a single portrayal of a second branch family member – they are bound to serve under the main branch by tradition and old contracts, and nothing more. The wealth and the fame of the main family is just that: the main family's.

Today, the Aaron family has been halved in size; arranged marriages and stubborn children are known to get along horribly, and the numbers have been diminishing ever since the latter half of the twentieth century. The fate of the Aarons rests on top of two heirs' shoulders: the main family's, Riley, who is expected to follow after his father's footsteps in business, and his first cousin, the branch family's only son Grimsley, who is expected to pull them out of debt and into the spotlight once and for all.

Although the two families are split by country borders (Sinnoh and Unova), the weight of the unspoken contract still hangs above their heads. If anything should happen to the main family, the second branch would be expected to take care of it. However, if anything were to happen to the main family's heir, then all the rewards would shift to the second branch.

Every single Aaron is quite aware of this.

VII.

Grimsley doesn't like Riley.

It's not just because Riley is free to do as he wishes, but also because the pressure piling down on him only has to do with his future career, which is something every Aaron offspring has to deal with. But family honor means a little less every passing decade, and Riley will be free to do as he pleases once his father gets older (even though his father's voice still isn't strong enough to sway him into taking his seat at the company where he works, Grimsley hopes that perhaps one day it will be, and that the other man will see what having no freedom feels like). Grimsley's family is slowly sinking into debt from an opulent life style, and it's his responsibility to keep it from happening. His father is dead; his mother has never worked in anything that isn't related to throwing parties.

Riley's father's only plight is the fact that his son has a terrible case of wanderlust.

Grimsley's mother knows best than to ask her son for anything; she's the one who owes him.

XII.

Grimsley takes the Elite Four job because he's good at battling and because it pays well, not because he necessarily wants to.

He can't afford a choice. His family is broke, after all.

IX.

The first time he's rewarded for something is when Grandfather falls ill for the first time.

They pack their bags and head for Sinnoh. The main family is kind enough to let them stay in the manor instead of in the house reserved for the branch family. His uncle greets him, but that's as far as he goes in admitting Grimsley's existence.

Riley thankfully isn't home.

His mother, daughter-in-law only, takes over the maids' duties and attends to the old man herself. He thinks it's demeaning, but presses his lips together and looks straight ahead when it's his mother who brings Grandfather his food and his medicine.

Grimsley still doesn't know what he's doing here. They all know that if Grandfather dies, everything is going to the main family.

At least the manor is calm. Stifling, yes, but quietly so.

One afternoon, when he is lounging in the library, nursing his fifth glass of wine, one of the younger maids comes calling for him. She calls him master instead of sir, a slip of the tongue. Grimsley doesn't correct her, but she gets it right the next times, when she leads him into Grandfather's room. She closes the door after her when they get there.

"Yeah?" Grimsley says, sitting down on the plush chair by the head of the bed. He resists resting his chin on his hand. That, together with the lack of proper address, would be his undoing.

"What have you done for the family lately?" Grandfather asks. His voice is tired and sickly-sounding, nothing like the austere tone that used to command his father around.

"I'm working to get my mother out of debt." Since none of you bother helping us. He doesn't say it but he knows his grandfather hears it. "Why the interest?"

"Your mother doesn't keep me updated."

"She's just too busy. I'm sure she just forgets, sometimes." Grandfather's lips pull into a smile, and it's infuriating to see him pleased. Grimsley nods to himself. "She's never been the same since Father died. I'm sure you understand."

It's funny because it's a lie; his mother has never been the same, true, but the old man will never understand why. The old man's eyes dart to Grimsley's, and he keeps a level gaze. He's an elite, he does intense stares for a living. What is an old fool to a man who has nothing left to lose?

Grandfather doesn't take the bait.

"And what have you done for yourself lately?" he asks instead.

"Nothing," Grimsley replies, fingers curling around the glass' foot as he brings it to his mouth. "I'm always too busy doing things for someone else."

Grandfather doesn't die then.

They return home the next weekend, after he recuperates from his illness. His mother locks herself in her room for a week after that, eating in bed and getting up only to use the bathroom.

He gets a letter from the family's lawyer, signed and stamped over, telling him that he's a part of the will as of now. Grimsley laughs and chucks it in the bin. He thinks it's a shame the fireplace isn't lit.

XIV.

On Riley's wedding invitation, he writes 'thank you' on the corner, before he sends it. It's the only one he writes on, despite Shauntal's various complaints.

III.

When he's still an intermediate-level battler, just skimming the beginning of seventeen, his uncle expresses some interest in marrying him to someone important (but not too much).

His mother is the first to decline: she spends a full afternoon on the phone, reaching into his father's desk drawers sometimes. It's an unspoken rule that no one messes with his father's office. That's probably what tells him that this is serious business. It's the first time he sees his mother drunk; she spends one night up drinking, arguing with his uncle through the line. He doesn't blame her – it's only been one year and five months since the death of his father. She still wears black.

At sixteen, Grimsley already kind of knows his life is going to be rough, so when his uncle turns his pressure to him, he replies that Riley is single too. Why not marry him off? It would make more sense than marrying a member of the second branch, after all. His uncle withdraws only after Grimsley says he will never marry; he doesn't want his children to be put through the same kind of thing as he is being put through now.

It is that simple.

XI.

As soon as he gets into the Elite Four, he buys an apartment just off the end of Castelia.

He only goes home for Christmas after that.

V.

Before he joins the League, he wins his earnings in not-so legal poker matches. The casinos are fine too, but they pay less, so he avoids them. They're a waste of time.

He doesn't tell his mother how he scrapes by. It's enough to pay the maid and set the food on his table (and somehow pay for the house as well), and they leave it at that. Sometimes, though, he gets home in the morning and she is sitting at the end of the stairs, legs crossed and eyes on him as soon as he closes the door behind him. Those classical wooden stairs that give to the east and western wing, a study in polished opulence. He hates those stairs. They remind him of how big and empty his house is.

She only asks him where he's been once. Grimsley lets his keys fall inside the pocket of the suit he's wearing. It used to be his father's, but it's his now. He wants his own clothes, but between paying off loans and a new shirt, the choice is easy.

"What have you been doing? It's six in the morning," she asks, and her spine is as straight as the baluster behind her.

"My duty as a son," he says.

He thinks she smiles, but in the lavender light of the dawn, he can't be sure.

They leave the subject at that.

VI.

If anyone asks where he's learned to bet, he always changes the subject. Always.

IV.

He learns how to win without having to bet when he is still young.

A week before he turns eighteen, he is to set legal matters with the family's lawyer. His father's death has left too many loopholes, too many loose ends. He needs to inherit everything nice and proper so they don't have to waste time mulling over properties and contracts again. Grimsley wouldn't have it any other way. The less time he spends here, the better.

He spends the afternoons reading up on his family's backstory; it doesn't particularly surprise him that the founder of it lived two hundred years or so ago, given that they must be the only family in Sinnoh that works under the master-and-servant template. What does surprise him is how much alike Riley is to Sir Aaron, from the flip of his hair to his eyes. Figures, he thinks bitterly, setting the book aside. He doesn't read anything related to the Aarons after that.

During the three days he is there, he only sees Riley once, and it's not even inside the manor. It's on the streets. It's four in the morning and Grimsley's fresh out of the house, searching for the closest thing to a casino. He finds another kind of gamble instead.

The two of them are in an alley, leaning against opposite walls, dark spikes versus blond curls, midnight versus sunlight. Riley's hands are closed, the only time he's ever lost control in front of Grimsley, and so he commits it to memory and slips out unnoticed. His heart doesn't hammer inside his chest, but his jaw clicks into a smile.

He keeps it a secret until Riley turns twenty-six and remains unmarried. When the day of his birthday comes around, they gather in the main manor, as it is tradition, and Grimsley asks him about the champion of his region and watches him think the answer over before he says it.

Now the other man knows he knows.

He returns home in high spirits.

VIII.

He meets Alder in a poker match. After he wins three rents' worth of him, the other man gives him his number.

"Anytime you want a cards partner," he says, scrawling his cell number across an errant napkin.

Grimsley misplaces it, and never finds it again.

It's a matter of luck that the older man finds him in Castelia one day. This time, he asks for Grimsley's number himself. Just to be sure.

X.

Grandfather dies when Grimsley is twenty-three.

He and his mother are cordially invited to the funeral. Grimsley doesn't want to go – what a surprise – but his mother sets her chin and sets her bags at the end of the stairs. His reluctant ones join hers the following morning. It's all about making her less depressed than before, because he couldn't care about his grandfather if he tried.

The moment they get to Sinnoh, his mother is whisked away into the kitchen, slipping into the matron role. Someone has to, and his uncle certainly isn't going to try. Grimsley slinks into the library, after greeting his uncle (it feels familiar, like greeting the doorman of his jail cell). He pulls a book into his lap and stares at the gardens outside, drinks in the sunset afternoon and the wine from his glass. He's never been so glad to be in a rich room, surrounded by two-floor windows and old bookshelves, surrounded by the smell of paper death.

The highlight of the day, not necessarily a good one, comes in the shape of Riley, sharp and blue, polished shoes quiet against the carpeted floors. Grimsley follows him with his eyes. He doesn't bother trying to come off as subtle. Why should he? Both of them know how Grimsley feels about Riley.

"Long time no see," Riley says, hands inside his pockets, casual. Grimsley doesn't answer, but he doesn't look away. He doesn't care enough to pretend that he is not ignoring him. And he wants Riley to know that. Riley, on the other hand, is undeterred. He continues, like it's nothing. It probably is, for him. What does it matter if Grandfather has died? His father has been the family head for quite a few years now. This is just making it official. "If you could have half of Grandfather's money, could you take care of your family's debt?"

Grimsley turns a droll page.

"You assume I want it." He laughs, but it's hollow and dangerous instead of sarcastic. He takes a sip of wine, to sweeten his voice. "A man has his pride. I might have taken your offer before, when I was just a kid and all of the main family knew I was waist-deep into shit. But now? What for? It's not going to make it all better."

"It would help."

"You know what would've helped? Helping out my father instead of watching as worked himself to death to pay off a debt that wasn't ours to begin with." Riley's shoulders twitch, just slightly. He is a far more emotional man than Grimsley. Maybe it has to do with being brought up under a stubborn old man and a frigid father. Maybe it has to do with his mother, the golden wife, who met death in the delivery room. Grimsley leans towards the latter. "You won't be able to buy my affections. I've lived my whole life looking out for myself. Paying off my debt – now that I've paid half of it – would mean nothing to me."

It's the first and last time they talk about money.

The next day, they have Grandfather's funeral. It's a quiet affair. Just him, his mother, his uncle and his cousin. The old man's picture comes in the paper and the town laments. The will is read and Grimsley declines the money Grandfather tries to leave him. Riley blinks when he says he doesn't want the main family's money. His mother and his uncle don't bat an eye at Grimsley's refusal to be further chained to his debt; they are made of sturdier stuff than Riley. Things go as they should, after that: Uncle inherits the house and the stock company, Riley inherits the future ahead, and the branch members nod politely and return home, a place five hours away.

His mother never does get the mention she deserves.

II.

He's fourteen when his father dies.

The papers talk about a family fallen from grace and little else. There is a small funeral, but no one from the main family comes. He's not surprised. They offer their condolences through the phone instead. His mother accepts them gracefully, and dresses in black for the next three years. Grimsley supposes he's meant to miss the smell of his father's cologne (when he dipped down to hug him, straight from work), or the way he rubbed his temples (when he was already growing tired of spending the night at his desk instead of in bed), or even the way he always told Grimsley that he was the one mistake he didn't regret making. He only gets that last one when he's twenty-seven and wants a family of his own, but he knows better than to hope. At least now he understands; he wouldn't be able to bring a child into the world under those conditions.

But by then he's grown tough and dry, with that naughty smirk glued on his face, meant to annoy, to disarm. It suits him for the gambling – but just the fun kind. No matter how gutsy or reckless he is, he's always going to steer clear of stock markets and bets that don't involve playing cards or dice.

It's the only lesson that sticks.

XIII.

Salvation is a letter in the mail.

It's signed by a notary, informing him that any ties that bind him to the main family have been dissolved as of a week ago. It's been a dull process, spanning across years, carried out in secret, paid in full—but all he's got to do with the main family now is kinship, not servitude. He reads it over once and then twice, and then he folds it carefully and drops it inside the first drawer of his father's desk.

It's the first time he laughs in years.