AN: I've been threatening to create a KakaSaku Yakuza AU for a ridiculously long time. Here it is!

Update: this chapter has been lightly revised as of 2024.

"Would you like to make a bet, obaa-sama?"

"Sakura-chan."

"I give it one month before I'm sick of him."

"Sakura."

Tsunade barked her granddaughter's name in a crisp tone, the kind that wasn't to be argued with. In any case: only the dead argued with the Nidaime. Sensing the coming of the next great war, the clan members hunched over piles of cash dropped their idle talk, leaving the chattering of counting machines the only noise in the room. Nearby, the dim sounds of a televised fight played in the distance, but it had nothing on the sudden tension in the compound's counting room.

"Yes, baa-chan?" Sakura, as always, liked to give as good as she got. A younger member of the clan opened his mouth to speak, his nerves clearly shot. He'd barely managed an intake of breath before the closest aniki put a foot square on his chest in warning.

"Do you know how many people in Shikkotsu could speak to me like that?"

A sip of tea. "Let's see… there's probably me, Jiraiya-jii-chan, and then dear Uncle and Grandfather in heaven."

Tsunade snorted. Sakura was right. People didn't talk back, not to her. Not with her status as wife of the Nidaime of the Senju Group and inheritor of his title after death, supreme leader of the greatest Yakuza consortium in the West, the Slugger Princess, and of course constantly exasperated grandmother. Ironically, she felt the last to be the heaviest burden. Yes, Sakura had her figured out, but:

"You think I let Jiraiya speak to me like that? You've still got things to learn from me, girl."

The pink-haired woman beside her looked far too grown up to possibly be her granddaughter, but there was no justice in the world. Young children had young children: she'd been fifteen when Sakura's uncle was born, nineteen when the girl's father came screaming into the world. Sakura's own outsider mother had had the cheek to get herself knocked up at seventeen, so in reality, Sakura at twenty-three was doing well. Still. It wasn't pleasant to be reminded of her age, despite hearing that some of the other leaders and their wives had taken to asking where the Nidaime bought her face creams.

Green eyes crinkled in amusement at her tetchy reply, unaware of Tsunade's inner turmoil and the tension of the room at large. Sakura was likely thinking of her grandmother's husband attempting to speak with anything less than his trademark casual charm.

"Come on, you know I'm good for it, Tsunade-sama. A bet. You won't marry me off just yet."

Sakura had a gift for knowing exactly how much she could push things and she was exerting it now, leaning into Tsunade's side and shooting her a killer pout, her earnest eyes framed by long pink lashes. It was a curse how much the brat looked like Tsunade's first husband, Dan.

Sakura's father looked like him too, but he rarely smiled and never pouted, and on the rare occasions he'd shown up in the past to drag a teenaged Sakura away from his ancestral home he'd worn nothing but a snarling mask at the life he'd left behind. With her other child in a bloody grave, that left the young yakuza princess the only person who had the power to win over Tsunade, the underworld's hardest woman, with a mere look.

"Yes, I'm very aware you're good for money," Tsunade replied. "I know for a fact you've been going out at nights with certain foolish young clansmen, and taking part in those ill-advised baccarat mansion schemes."

She swept the room with fiery hazel eyes, daring any of the men to admit their part. There was an embarrassed cough as everyone except Sakura attempted to look natural. Everyone except Sakura miserably failed.

"I can't help it if there are people practically begging to be parted from their earnings, obaa-sama."

"You'll get bitten."

"I'll bite back."

Truly, Sakura was a girl after her own heart. But that was exactly why Tsunade had been setting up marriage meetings with the other big families in the country. There were too many fish for the pool; territory disputes were becoming an everyday occurrence, and if she didn't ally the Senju with another large group, creating a dragon amongst snakes, then the danger of being swallowed whole would only grow larger. She knew Sakura understood. After university, her granddaughter had willingly left the outsider lifestyle behind and dedicated her life to the Way of the Yakuza. It was just a matter of the right alliance, the right timing, the right person.

Tomorrow's meeting with the representative from the Uchiha group was another step in the right direction. Possibly.

The older woman paused, teacup to her mouth as she watched the yakuza princess beside her snort in derision and clap her hands together snappishly, prompting the men to resume their money counting. Whoever the right man was - she almost felt sorry for him.

Kakashi paused outside the compound, taking the proffered umbrella as he sent a cautious glance up and down the street. Empty, of course; no doubt the Senju group had sent round the circular to the residents, notifying them of the presence of another group's representative in the area. If the West worked anything like the East region - and he had his doubts, damned narrow streets - then the civilians of the district would be safely indoors. See no evil, hear no evil: if they weren't aware of the goings on of the yakuza in their midst, then it was all very easy to accept their protection and their sponsorship while ignoring the less savoury aspects of organised crime in the neighbourhood.

Or maybe Shikkotsu people were under more romantic notions of their lifestyle. He couldn't remember. He wasn't sure he even cared, just that today's meeting had been received with considerable pleasure by the Uchiha Sandaime Fugaku-sama. And what Fugaku wanted, Fugaku got, especially from his legendary Hatake lieutenant. Even if it meant Kakashi married some spoiled princess in place of one of the leader's sons.

The Senju man at the outer gate gave him an appraising smile as he avoided the puddles in the mud of the street; Shikkotsu was an old, old part of Fire country, the kind of place people could trace their foundations back six hundred years to some peasant who placed a hut in a field and declared it his home. So different from the Uchiha headquarters in Konoha's shining districts, except the high, imposing walls and liberal use of security cameras remained the same as ever.

They probably didn't even have dogs, a thought that kept Kakashi glum as he trudged through a disproportionately large garden accompanied only by the sound of pouring rain. The other Uchiha men he'd brought followed with the raised hackles of wolves out of their element, flicking nervous black eyes at the outhouses and store rooms of the Senju, spaces no doubt lined with men who were assessing their every move.

It was not the usual atmosphere that accompanied a potential suitor as he went to visit his bride.

But then, nothing about their lives followed the normal order of things. Watched by shadows as he went to visit a woman who ruled over those shadows. Himself a man of the darkness. It fit pretty well, and Kakashi allowed himself a small smile through his stoic mask.

Eventually they reached the traditional porch of the main house and his subordinates peeled off to follow the silent Senju who'd guided them. No doubt they'd be angry at being separated, but Fugaku had warned Kakashi that clans out here had ways and rules and he'd make a better impression by following them.

"Oh, he's wearing a suit?"

The voice was young and female with an unmistakable Shikkotsu twang. Kakashi glanced over his shoulder but the speaker had vanished; come to catch a glimpse and report back. It was only his exceptional hearing that had given them away in the first place.

"And isn't he kind of old? Is that white hair?" More girlish chatter as he was led through a sumptuous hall.

"Wow, a suit? Sakura-sama is gonna be pissed."

That was the granddaughter. The younger Uchiha heir, Sasuke, had cautioned him the night before that she had what they liked to dub 'a temper.' Kakashi spared a thought for how Sasuke knew that as he'd been successful in his refusal to meet her so far. Maybe they had mutual friends? He thought they were around the same age. Young. Probably too young for him. No matter - he knew she had a reputation for blowing men off after a few formal meetings. All Kakashi's duty entailed was a couple of attempts before he could reasonably return to the fold and give his regrets to the boss, feathers unruffled. Back to his normality, and whatever unfinished business the Uchiha decided to let him wrap up.

His everyday life, rather than escorting women who were almost too young and certainly too spoiled to be escorted in the first place.

After following an endless route that could only have been designed to confuse, they paused outside a door bearing the Senju clan crest in painted glory. The jade, dragon-like creature that gave the Senju its name swirled among the bamboo trees the region was known for, an imposing picture that impressed upon visitors the close link between land and underlord that had existed for hundreds of years. It was intricate in a way the Uchiha clan's crest was not, their simple fan starkly modern against this ancient imagery. With a slow nod, his guide left him to stare at the fierce brushstrokes for just long enough that it felt deliberate, but not long enough to be insulting. The Senju had distilled intimidation to its purest form.

Straining, Kakashi could hear a few hurried footsteps leave the room - final preparations - before the paper door slid back and he had his first glimpse of the occupants.

The Nidaime he'd seen before. Tsunade was a figure at the very top of their world, drawn back from retirement by the sudden death of her son the Senju Sandaime and strong for it, beautiful even as she approached the winter of her life. She wore the green haori she was known for over a kimono that matched the brown of her eyes, which were currently sweeping him from head to toe in frank assessment.

Sakura, he'd seen only in pictures. She was Tsunade remade in youth, touched with the pink colouring of her civilian mother and styled after her namesake in a cerise kimono with blossom embroidery.

It didn't suit her. He kept his face blank as she bowed from her seated position - just a touch too lightly, but then she had most of the power here - and he sat across from her in a semi-formal stance.

"You're wearing a suit," she remarked.

Kakashi looked down at his clothes. For some reason, this was the third time his attire had provoked commentary. Was there something wrong with it? Dark grey with just a tinge of purple in the lining, a sombre forest green tie to match Shikkotsu sensibilities; Fugaku had warned him away from anything over the top. Shikkotsu yakuza wore their exuberance in their tattoos rather than their threads, he'd said. But the suit had passed muster at home - why not here?

"Yes?" he hedged.

He watched as Sakura sighed, ignoring the very obvious pressure Tsunade was applying to the hand closest to her side.

"You've come to meet us," Sakura muttered, gesturing to the ornate reception room, "in a suit?"

Kakashi paused. "... and you'd rather I…?"

The two women exchanged a look fraught with significance he didn't understand, before Tsunade coughed lightly and passed him a cup of the tea she'd been preparing. The inconspicuous guards in the corner shook with silent amusement, but he managed to ignore it as they exchanged more formal greetings.

It was the kind of discussion that hovered delicately between small talk and information exchange but all the while Sakura stayed silent, sipping her own tea with such grace Kakashi knew it had to be contrived. For some reason, the Senju heir truly was pissed.

"You honestly didn't think to wear traditional clothing to a traditional marriage meeting?" Sakura finally interjected.

Tsunade's expression was unreadable.

Ah... really? Kakashi thought sourly.

It was half shallow and half damned Senju rules, but it was irksome. Judge him for his character, his history, and his accomplishments as a leader in the Uchiha clan. Not for his trousers. Kakashi said nothing after she spoke but he'd tensed and it didn't go unnoticed, both women directing their keen gaze at his disgruntled shifting.

It was time to defuse; what would Fugaku say?

"I see now that I should have, and I'm sorry for it."

Pausing for effect, Kakashi continued, "would you like me to return another day?"

If he left now he'd be in time to meet Obito and spend the night in the members club. Definitely a more tempting prospect than the spoiled doll in front of him.

Sakura blinked, clearly surprised at his quick (if insincere) apology. She probably had him pinned down as a boorish Konoha idiot and though he didn't particularly care it was gratifying to see the wheels turning as she looked between him and the Nidaime.

"No, that's some journey…" she managed, trailing off. "We couldn't possibly…"

All three yakuza leaders sipped their cooling tea in uncomfortable silence, a tense stand-off that he dared not break. Tsunade had a small smile on her face. Kakashi didn't think it was a happy one.

Sakura cracked first. "Tsunade-sama, Kakashi-san, please excuse me for a moment."

The thin blonde arch of Tsunade's eyebrow managed to convey a hundred warnings but she didn't say anything. Permission granted, apparently, though for what Kakashi couldn't fathom. Sakura swept out of the room, all elegant movements and unflattering kimono sweeps, and he was left with the terror of a generation of the underworld.

"Ah…"

Tsunade held up a hand, cutting him off. "No need to apologise, Kakashi." She smiled and this time it was genuine, if a little sharp. "There's no real harm done; I think she might just be put out that she didn't get to see a Konoha interpretation of traditional men's clothing."

Then, incredibly, the Slugger Princess tilted her head forward an inch. "Please forgive her - I've spoiled her."

Kakashi hurriedly bowed back, deeper by far. "Osu, ma'am!"

Spoiled grandchild or not, he had nothing but respect for the Senju head and he wasn't going to disdain the honour she'd shown by bowing her head to him.

"And I'm sure Fugaku's done his research - you know she wasn't brought up like us."

There was nothing to say to that because it was true on both counts. To admit Sakura's outsider upbringing might be rude and to try and deflect would be an obvious lie, so instead Kakashi simply acknowledged that the Nidaime had spoken before taking another sip of his tea. It was good stuff. Could Sakura make it the same? Doubtful.

"Either way, will you head back today?" Tsunade continued, admirably forging ahead despite the absence of the very person the meeting was for. "Jiraiya is sorry to have missed you."

Jiraiya - Tsunade's itinerant second husband, the man who was both the perfect image of the Yakuza Way and yet somehow separate from it. The only man in the underworld who could wander from clan to clan and be welcomed like family everywhere; yes, Kakashi was sorry he'd miss the old toad too.

"Unfortunately, yes."

It wasn't wholly true - no way was he staying overnight in Shikkotsu, but since she hadn't specified whether he was heading back to the Uchiha compound… it wasn't a lie, either. He was heading back, only most likely to one of Obito's nights at Bar Yellow Flash.

"Maybe I'll have time to see him on the next visit."

"Gods, he'd like that." Tsunade snorted, all semblance of formality gone and prettier for it. "I'd show you the texts he's been sending me all morning about missing the White Fang's son, but I'd rather not embarrass myself."

Kakashi grinned as the guards in the room whipped their heads around at the mention of his father. Before his death, Hatake Sakumo was a shadowy figure even in a world hidden from the light. As the Uchiha Nidaime's right hand man, Kakashi's father won the right of the Hatake clan to stand at the very forefront of Konoha's criminal world: at the same time, he'd never revealed himself to it.

Sakumo had lived more like an assassin than a thug. No wonder the older Senju men were on their guard.

"I've brought some Myoboku sake for Jiraiya-sama as an apology - please do share it with him."

Tsunade clapped her hands appreciatively and looked towards the ornate lacquered cabinet against the opposite wall, clearly contemplating sampling the drink before the man in question returned. Kakashi ducked his head and grinned - of course Tsunade was a sake hound, he'd heard rumours but never witnessed the truth - and was about to suggest relieving his men of an extra bottle when the door behind him slid open and he felt a draught of cold air on his back.

"I've returned," Sakura's voice announced behind him, rather unnecessarily. As if anyone else would dare interrupt their leader in a meeting. He stifled a sigh; she was worse than Sasuke had said. Temper and attitude rarely mixed well.

And then she went back to her seat and Kakashi forgot what he was about to say next.

Gone was the formal, ill-fitting kimono. Gone were the awkward kanzashi that warred with the natural beauty of her hair. Sakura had left the room a girl wearing clothes heaped onto her like a doll and returned to it a young woman who knew what she looked good in. Dark green trousers paired with a silk shirt the same hue, tailored enough to hint at the underneath while giving nothing away. A scarf around her neck in the Senju colours, boldly knotted but formal at the same time. He blinked. She still had on the immaculately white tabi socks, but now there was something damned near naughty about them when paired with the easy, androgynous elegance of the rest of her outfit.

Sakura tilted her head and smiled, letting the curtain of her soft pink hair fall over a keen jade eye. The very angle it fell was calculated.

"A suit," she explained, unmistakably mischievous. "And now we match."

Shit. A match? Kakashi was suddenly worried that he might have met his.

AN: Let me know your thoughts! I'm going for a Kyoto / Tokyo divide here with Shikkotsu and Konoha.