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Being a nerd ran in the family.
As much as Leo would tease his brothers for being dorks or geeks it was an understood fact that there was a Hamato for every corner of nerdom— Donnie with his tech and chem of course, Mikey and his art, Raph and his plushie collection, their collective love of sci-fi.
Leo’s corner of geekness was chess of all things.
It started when he was little; their dad had found a mostly intact board with only a few missing pieces and brought it home, hoping it would entertain the boys at least a little. They had ended up helping Mikey replace the missing pieces as Donnie tried to learn the rules. Raph had tried to play first, Donnie explaining the rules as best he could with his limited six year old prodigy vocabulary and dad chiming in every once in a while.
Raph lost, to no one’s surprise, and dad had mentioned how it was a “clever man’s” game, so of course super smart Donnie was a natural at it. Mikey tried next, and dad was telling them about how it was a war strategy game or something, to train people to plan ahead.
Mikey lost too.
“Come on Leo, you gotta try now!” Mikey had told him, pushing him forward to settle across the board from his twin. It had been a quiet day back then, when some sort of weird bone-deep tiredness settled into his body and dried up his throat so no words came out, so Leo hadn't said anything.
Before Donnie could start the game, he spun the board around so he had the white pieces; the first move gave Donnie too many advantages, he knew that even when he was little.
Donnie wasn’t as expressive as the rest of the family, but everyone knew Leo’s blank smiles on quiet days were even worse. Maybe that had unnerved him, it being a quiet day, causing him to slip up in their little game of plastic and junk war.
It had been weird, as he moved the pieces along, how the tiredness slowly retreated from his bones and he’d felt himself perk up, having to carefully plan and guess what his twin brother was thinking. How, when he finally pinned his brother’s king down, the quiet of the quiet day was all but gone.
“Checkmate,” his scratchy little voice had said with glee, feeling more awake than he had in days.
His twin’s look of shock, his dad’s look of confusion, his other brothers’ cheers of delight, and the feeling of being awake, of an actual challenge making his bored mind finally start to work, even the faint tap of the piece to the board that made some part of his brain light up with delight— that had been the start of his love of the game.
When Mikey played against him Leo always took the black pieces; his little brother wasn't good at the game at all, mostly just mirroring what Leo did, so there wasn't much thrill playing Mikey, but it staved of the unending boredom that hit if he hadn't played for a few days. Raph also got the white pieces every time— he at least seemed to try to be strategic, but Leo was pretty sure the whole cause and effect of the game was lost to him.
At first he took the white pieces when playing Donnie, but after it started to get boring winning he let Donnie take them. Donnie was strategic too, and sometimes Leo lost to him, but after a couple dozen games, patterns started to become so glaringly obvious that the thrill was gone again. Donnie fell into patterns. His twin was smart, but at the cost of being predictable.
Dad was a bit more fun for a while. He’s pretty sure it was because dad was an adult, so he had more patience and knowledge than Leo, but for a good couple years dad was his favorite opponent after Donnie got boring, the few times he could get his dad to play. But the older he got, the worse dad got at being aware of his surroundings— Mikey thought something bad had happened and now that he didn't need to focus on the brothers it was hurting him.
Leo didn't understand that, just that dad had gotten boring to play against too.
By then he had gotten better at pushing through quiet days, so now they were just tired days, where if he couldn't convince his brothers to play a game with him he could just settle into a chair or some blankets and think. Could listen to his brothers around him and string together lines of reactions and thoughts. What if this happened? How would his brothers react if he did this? How would he do that?
He’s not sure when the masks showed up, or if he just always had them, but he's pretty sure when quiet days turned into tired days he started cranking up the ego mask. It made his brothers fumble when playing chess, so maybe it would work in real life?
It did.
In chess it made his brothers panic if they were unsure of what they were doing, if he bragged he was going to win, if he acted so sure of himself— but if they were sure they would win they would underestimate him, get sloppy.
It worked just like that in real life too.
Then April showed up, and he had a laser focus on a new partner to get rid of that tiredness. He held back for a bit, just a few weeks, he didn't want to scare her off after all. He joked and tried to get them to laugh, because getting people to laugh helped with the tiredness too; it took so much thought to get everyone cracking up, not the same as a good game, but enough to keep him from going back to quiet days.
Then, finally, he brought it up. He had to teach her the rules and that already lowered his hope for a challenge, but he let her start off white, and she played differently than his family, enough where he was able to get more thought out of it for a good couple months before the tiredness was back.
He felt so sluggish and tired, maybe like how dad felt, he kind of just wanted to curl up and not move for a while too. But that was just how Leo was, so he kept it to himself, this never ending boredom he was always fighting off. It was easier to pretend tired days didn’t happen anymore at least, like they never existed in the first place.
Raph started going out alone finally, and he always brought back small little things for one of them when he did so— little scraps for Donnie and art stuffs for Mikey— and for a while he had nothing for Leo, not that Leo minded, he was to busy trying to get rid of the boredom by running through how April would have reacted if she met them under different circumstances, as well as a newfound mild interest in a medical textbook Donnie had found; it wasn't as non-tiring as chess, but it was better than just laying around and letting that tiredness pull his energy straight out of his shell.
He had been hunched over the book’s section on veins in the arm when Raph got back one day, tracing the veins in his own arm while trying to figure out how different the blood flowed due to the extreme differences in structure. He had ignored the sounds of Raph’s steps growing closer, biting down on the pencil he had been holding to press his fingers to his wrist, trying to find his pulse so he could doodle it into the book.
“Leo?” Raph had asked, and Leo held back a groan, slapping on his cheerful face, glancing up at his biggest brother, and making a muffled chirp of acknowledgement around the pencil in his mouth. “I um, I found you a gift, for your chess set, cus I know you broke your black castle—”
“Rook,” he corrected on instinct, putting down the pencil and actually paying attention now.
“Yeah, your black rook broke in your last game, and I know you were really upset about it so I uh…” the giant that is his brother doesn't finish the thought, just holds his hand out, and resting in his palm is a scuffed up black rook. It doesn't look like his old one, and picking it up Leo’s surprised by how cold it is, blinking at its weight and turning it over with wide eyes.
“Is this metal?” he asks. He hadn’t expected to actually be able to replace the piece any time soon, the poor battered plastic had finally split in half after Donnie knocked it aside in his and Leo’s last game. He holds the rook up to the light, feeling his smile turn genuine as it shines, soft delicate engravings slightly worn away by age but still clearly such high quality he can't help but feel giddy.
“Yeah,” Raph coughs a little awkwardly, rubbing his hands together as his fear stink starts becoming noticeable. “There’s this park with chess boards in it, so I’ve been checking it for any pieces someone might have forgotten, and I finally found you a new rook! Do you, uh, I mean, is it a good gift?”
He turns his attention away from the piece, holding it to his chest as he beams at his ever thoughtful older brother.
“It’s the best gift ever,” he tells him, shoving the book off his lap and jumping up to hug him, giggling a little— chess is his thing, none of his brothers find any real joy in the board that everyone agrees is Leo’s, so the fact that Raph not only noticed the broken piece but took the time to get him a new one? It felt like a nice little reminder that they cared. “Can we play a game now? Please? I wanna hear how it thumps against the board!”
Leo won that game too, but he wasn't really trying, too busy being entertained by the sound of his new metal rook hitting the board. It was a very nice sound.
He finds himself playing against himself sometimes, running through strategies and maneuvers; it’s not as fun or awakening as playing against someone else, but it’s enough to keep the tiredness at bay.
When it’s finally Leo and Donnie’s time to go to the surface alone— well, as alone as the twins could be when attached at the hip— Raph gave Leo directions to the park with the boards and Donnie agreed to check that first because it would be faster than Donnie wanting to check all the local scrap yards.
He didn’t find any spare pieces, but he did have to be talked out of taking one of the wooden boards, the pleasant sound of pieces hitting against wood instead of cardboard far too tempting for Leo’s finally not bored mind to resist.
The surface holds off the tiredness for so long. For almost a year there's so much to think about and plan for and turn over in his head to stave off that neverending boredom. Escape routes and backup plans for being seen and meet-up spots and so much more. Sure he had gone out before in brief sneak outs with his brothers, it’s how they met April, but being able to go whenever gave him so much to just chew on.
And just as he feels the tiredness sneaking up on him again, Draxum happens.
He’s not tired now, he's got even more to think about after all— battle plans and formations and traps and tricks and people to deconstruct and figure out.
But now, it’s almost as if there's, too much— so much to think about that suddenly he thinks of the worst before he can figure out the solution, plans that would crumble if he did the wrong thing, and has some other thought interrupting him before he can fix it. It’s too much, it’s not simple, he prefers it to the tiredness but he needs something simple, something to help him get his thoughts straight.
“Hey Don-tron?” he asks, the briefcase he kept his favorite game in gently tapping his leg as he leans on the doorway to his twin’s lab.
“What do you want ‘Nardo?” his brother’s sharp voice asks, but the fact that Donnie starts turning off whatever he’s doing instead of continuing to work tells Leo he’s welcome.
“Need to clear my head and was wondering if you’re open for a quick game?” He holds up the case a bit as his twin turns to look at him, glancing between the case and Leo. For several long seconds it’s silent before Donnie waves a hand at one of his desks.
“Clear off the one with the metal scrap on it, nothing breakable on it,” he hums before he turns around and goes back to shutting things down.
Leo lets out an internal sigh of relief, moving to do as he’s told.
A game against Donnie is predictable, reliable, with the same paths and mistakes because it takes at least three tries before Donnie learns a lesson that’s not about tech or chem. It’s not great when trying to fight off the tiredness, but as Donnie settles across from him and leads with the same move as always, Leo can’t help but feel something in his soul settle, thoughts untangling as he goes through the familiar waves and motions of a game of chess against his twin.
“Checkmate,” he hums at the end, feeling like he can breathe again as Donnie swears under his breath.
He makes a habit of it now, whenever his thoughts start to crush his lungs, to settle in the lab or the atrium or the kitchen— or now ever so rarely in the tv room— and just play a nice calm game of chess against his family. Not to get rid of the tiredness, but to wrangle his thoughts back into neat black and white checkered patterns.
His interest in how different their biology was came in handy now; he never thought he would have to know how to properly splint their bones, or how to heal minor shell fractors, or need to recite under his breath exactly how long they could go with open wounds.
When Shredder came around, Leo thought maybe this is what normal feels like. It’s a gross thought, but as he pulls and tugs at Big Mama’s strings, makes her dance like a puppet as she clearly sees him as nothing more than a dumb little kid, he cant help but be delighted.
He learned as a kid playing chess that acting cocky can make your enemies make one vital mistake: underestimation.
He doesn’t think she really got rid of Shredder, but there's not much he can do other than what he's always done.
Think.
The tiredness is creeping up for a while, edging at his mind and starting to drain him away, forcing him to try harder and harder to keep up his mask when all he wants to do is settle into something soft and think.
And then Mikey does what Mikey does best, and gives Leo even more to think about.
Baron Draxum is complicated to Leo, because Leo can see his patterns, and those patterns aren't that of someone redeemable, yet Mikey is trying so hard anyway, so Leo leaves it be. Baron won't be Leo’s problem, so it doesn't matter.
“Have you played a game against other dad yet?” his only little brother asks him one day as the two of them are playing a match, and it takes everything in Leo to not flinch.
“No, check,” he answers honestly, and he doesn't plan to. Chess is for family and, while Mikey might call him other dad, he’ll always be ‘the guy that threw him off a roof’ to Leo.
“Why not? He’s smart like you and Donnie, maybe even as smart as you and Donnie, maybe you got your smartness from him and he can give you some difficulty? I mean you don't say it but we all know playing against us isn’t enough sometimes.”
“Enough what? I like playing against you guys. Check.”
“Yeah you like playing against us to clear your head, not for, I think the word’s ‘stimulation’? I read about it a while ago, we aren’t hard enough for you and you’re always bored, even if you’re good at hiding it.” Mikey picks up a bishop, pointing at Leo, almost accusatorily. “It’s hard to tell but you've been laying down more lately, and you get all irritated if you haven't had a game that made you pause in a while, maybe Draxum can give you that!”
“I don’t get irritated,” he huffs, watching Mikey place down the bishop and then moving his own piece. “…but if I agree to play a game, will you drop it?”
“Mhm!” Mikey agrees, watching Leo make his move.
“Fine, and checkmate.”
“Oh come on!”
He has to explain the rules of chess to Baron, and even then the yokai is only interested when Leo mentions how it’s technically a war training game. Mikey was wrong in the end— Baron’s predictable. Maybe it’s just because it’s the first time the other has played the game, but it’s one of the few times where Leo’s actually bored of his favorite game. Maybe he had been hoping Mikey would be right, and he could finally get some kind of challenge for the first time since he was little.
He finds some joy in the lair games trick, feels delight as everything falls into place and his carefully constructed plans fall into one another. Could he have just asked Donnie to soundproof his room? Oh sure, but he had to find his entertainment somewhere, and it was an honest surprise when Donnie won instead of Raph like he planned. He had been planning on getting Raph to win so he would get why Leo wanted to change rooms so he would ask Donnie to proof the room and then, Raph being Raph, would switch the rooms back. The tie breaker and Donnie actually putting up a pretty good fight was a delight to his tired mind.
He makes sure to tell Donnie that, after the reason he offered up his room is revealed; his brother’s own surprise and joy echoes into Leo’s until they’re both flapping their hands as Donnie talks about how he’s going to proof Leo’s room.
He didn't know that being something Leo hadn't thought of would delight his twin so much, but if it made sure Donnie didn’t have a sudden inferiority shut down Leo wasn't going to complain.
When Cassandra joins the family no one’s really surprised.
Casey has always been more of a fun rival than a villain to them— her intensity always startled Leo and gave him all kinds of new scenarios to play with. And now that she's their friend, hockey has been added to the repertoire of sports the family plays. They’re actually sitting down after one such game when the topic of hobbies suddenly pops up.
“And what about you blue one, you've been quiet.” She stares at him as he comes out of his head, glancing at her.
“Naw, it’s embarrassing,” he waves her off. He doubts she’d be a challenge if both his twin and the person who made the ooze leave him bored. She seems too… energetic to like chess anyway.
“It’s chess,” Donnie betrays him, “he’s been addicted to it ever since we were six.”
“A good hobby,” she nods, surprising all of them. “I do not play it often, but I do enjoy crushing my enemies in a game of wits.”
“You like chess?” April asks, voicing what they were all thinking; some bored, tired, and pacing beast in Leo’s mind perks up at the chance of a reasonable opponent, someone he would at least have to think harder for. “You, Cassandra Jones, like chess?”
“Yes,” Casey confirms with a sharp nod. “It is hard to find worthy adversaries, but when I can, it is very enjoyable.”
“You and Leo have to play a game!” Mikey chirps, an excited trill in his throat as he glances between Leo and Casey. “He’s always complaining about how we suck at it!”
“I do not!” he finally defends himself, rolling his eyes. Though, he will admit, he hopes Casey isn't just talking to talk. She isn’t the type to do that but still, if she is any good it would be nice to have a chance to chase the tiredness off. It’s only grown worse since the defeat of Shredder.
After a few more hours of playing on the ice they end up in the lair, Leo setting up the board as the family for some reason gathers around with blankets and popcorn. They’re way too excited for what’s probably going to just be Leo’s boredom increasing again.
Casey settles behind the white pieces without prompting, Leo settling into his own space.
She moves her knight first, and Leo perks up, shifting to straighten up from his normally lax position. Ok, so she at least kind of knows what she's doing, that at least means he’s going to have a game he’ll enjoy this time. He ignores the slight gasp from his family, countering with his own knight.
He’s not sure what his family thinks they’re doing, why they all seem so stunned when he straightens up. Oh he can guess— over the years his lax half paying attention pose has been standard to show how, as much as he liked the game, he wasn't having as much fun as he wished for.
Casey is an aggressive player, she's quick to get him on the defensive, and her face is set into a hard scowl so he can’t get a very good read on her. He manages to get himself some breathing room, and he feels alive, the quick and soft click of plastics and metals from his missmashed chess set pinging whatever signals in his brain to make him feel good; he doesn’t have long to think before she's got him backed up again.
It’s great, and everytime he grabs one of her pieces a sting of pride zips through his soul. This was difficult, he was having to think and think quickly, he had mostly tuned out his family who were now whispering between each other some kind of commentary about the match.
“Believe I play chess now, blue one?” Casey smirks as Leo’s eyes flit over the board, figuring out his plan of attack.
“Oh I never doubted,” he admits, sliding his rook and managing to knock down one of her knights, “I just wasn't expecting you to be on my level.”
She clears away one of his pawns with a laugh.
“Check,” she says.
His family gasps, erupting into whispers, and Leo can’t stop the grin from growing on his face— he hasn't been checked since he was, what, eight?
“Clever,” he admits, moving his bishop and trying to mask the joy in his voice, “and check right back.”
More excited whispers, he’s pretty sure Mikey murmurs something about it all coming down to this last move. He's not sure if that's true, if she plays it right she might manage it, but one wrong move and Leo’s got her, so it’s just a matter of…
“Checkmate,” she says, flashing a smirk as she kicks over his king.
His family erupts into roars of disbelief, and Leo can’t help but laugh. He hasn't been beaten since he was seven, and what an odd feeling to be glad you lost. He looks over their board, baffled by it. He feels awake and excited and delighted .
“We have to play again,” he demands, and Casey rolls her eyes at him, but there’s delight in her eyes too.
“Deal, next week sunday?”
“Perfect.”
Playing Casey is fun, is the thing. He's never quite sure what she's doing, and she clearly doesn't know what he's doing either. Donnie ends up setting up a chalkboard in the new main area of the lair and keeping tally, marks growing and growing the more games the two play; they’re nearly equal most of the time. Once Casey managed to jump ahead two games, but Leo managed to catch up quickly enough.
It’s forty two to forty one in favor of Leo when the krangg happen and Leo winds up forced on bedrest while he heals.
It’s fair, really, as the medic he's very aware of how much is wrong with him: cracked shell, most of his ribs broken, a pierced lung, some major internal bleeding, a dozen fractures in his skull, some bruising and cuts for flavor, with one hell of a concussion to top it off.
But also as the medic it’s his job to be the worst possible patient.
“I’m booooored,” he whines to his twin, who is currently checking over his chest.
“Whatever will you do,” Donnie mutters, rolling his eyes. Leo can see other Casey peering around Donnie, worried expression apparent. “If you hadn't hidden your injuries maybe it wouldn't be this bad.”
“This punishment is both cruel and unusual,” he gripes, glancing at Casey number two with an idea. “Hey Casey, can you go grab something for me?”
“Oh sure sensei,” Casey answers, standing at the ready.
“No you will not, that very much depends on what it is,” Donnie corrects the teen, glaring at Leo with no small amount of disdain and some hidden worry.
He can try to hide it all he wants, Leo knows his twin
“I just want to see if he can find my chess set Don-tron, jeez.” He sticks his tongue out. “Might as well have it ready for when Casey gets here.”
“Leo she’s not going to be here for another hour, she was helping with clean-up remember?” Donnie mumbles at the same time Casey points to himself in confusion.
“Not you kid, Cassandra,” he waves the kid off, turning back to Donnie. “But, brother of mine, consider this, I’m boooooored, and it’s not like I can hurt myself playing chess!”
“You want to play chess, with a concussion,” Donnie says like he's an idiot.
“Yes,” Leo tells him, like an idiot.
“Hey dumb question,” Casey two speaks up, hand half raised cautiously, “but what’s chess?”
Leo can feel his world record-scratch at the same time Donnie turns to second Casey— he needs a better name, Cj? Cass? Eh he’ll workshop it. He can practically see his twin brother’s expression of confusion. He can also hear Mikey, who had apparently entered the medbay at some point, start laughing.
“Future me was a failure,” Leo finally manages to declare, Mikey’s laughter growing in intensity as even Donnie starts to chuckle under his breath. “I mean, I didn't even teach you chess? That’s bullshit!”
“Oh me gosh I have to, oh me gosh April, Raph! You have to hear this!—” Mikey calls out, laughing again when he sees Casey Jr’s confused and worried face. Yeah Jr worked, Cj too.
“What? Why? What is it?” Cj asked, glancing around in clear confusion.
“Chess is a certain someone’s all time favorite game,” Donnie huffs, finishing Leo’s bandages and leaning back. “It’s just funny to think he and Casey didn't pass that on to you, what with the sensei and mom nonsense.”
“Now you have to let me play,” Leo jokes, gesturing at Casey. “This is an atrocity! A straight up crime! A mistake of seismic proportions! He can't be my student and Casey’s kid and not know how to play chess!”
“He doesn’t know how to play chess?” It’s April’s shocked voice this time, Leo glancing over to the door where her and Raph stand.
“I know where your set is, I can go get it?” Raph offers, scurrying off at Leo’s thumbs up.
“Is it really that big of a deal?” Cj asks.
“Yes!” Everyone choruses, even the faint sound of Raph retrating down the hall echoes the word.
The family has mostly settled into the medbay when Cassandra finally arrives, pushing into the medbay and staring at the clear audience settled on one side with all their typical snacks for chess night. Her apparently future kid is sitting on the cot next to Leo, who's holding up a rook.
“Now there’s a lot you can do with a rook, hey Casey, yet not much at the same time.”
“What are you doing?” Casey can’t help but ask, drifting over to the chess setup and taking her seat, making a move almost absentmindedly.
“Future boy doesn’t know how to play chess,” Leo informs her as he sets the rook down and moves one of his own pieces.
“ What?” She hisses, and Leo’s delighted to see she had the same response as him.
“I know right? So I’ve been teaching him the basics while I waited for you to get here— oh I’ve got a concussion by the way so might take a bit longer to make a move than normal.”
“I don’t care, where did you leave off? I need to make sure you don't miss anything!”
That game is softer than they normally are, with both Casey and Leo explaining their every move to Cj. Casey wins to nobody’s shock, Leo was concussed after all.
Also to nobody’s surprise, Cj asks for next game, and he loses, because he just learned how to play and he's probably still confused on the rules. But Leo can’t help but smile.
Because Cj plays just like Casey does.