Chapter Text
It had just been like any other Wednesday morning when Stewy saw the notification in his email inbox.
Funnily enough, the invite had been sent to his personal email from his days at Harvard—the one that had preceded all the email addresses (a time before @maesbury and @goldmansachs and now @waystar), the one he used before he was a corporate vulture with his talons sunk deep into private equity, the one he used when Waystar was a problem looming over the horizon but definitely not his problem. It was only through sheer happenstance that Stewy had seen it in the first place, anyway. One of his friends from his university tennis club had simply asked for a couple of photos of them to use in their alumni newsletter.
Sure, man. Stewy texted back over his morning coffee, let me send you some pics.
Luckily, he had uploaded a few of his pictures on the cloud once Google Drive became a Thing and it didn’t take long before he found photos of himself and the men’s tennis team after a tournament—a bunch of sweaty young adults all huddled together, smiling wide and happy, under the blistering heat. He remembered that game. He remembered almost qualifying for the inter-university open, he remembered the absolute debauchery that followed in one of the frat houses. He remembered the drinks, the drugs, the girls, getting high on molly and maybe kissing a couple of his teammates, but most of all, he remembered going home to his and Kendall’s shared apartment to find him sporting a busted lip and a cut on his cheek.
“It’s nothing, Stew. He just fucking…I basically ran into him,” Kendall had shrugged then, slipping his hands into his pockets, hiding his trembling hands. “It’s all water under the bridge. I’m feeling pretty, you know, zen about this now.”
He remembered how Kendall shrunk into himself, and pushed food around his plate that night as if he had forgotten how to eat.
Stewy picked a few photos and swiftly forwarded them. He considered logging out and going about his day but couldn’t resist the urge to fuck around his inbox, as anyone with decades worth of information would.
And that was when he saw it—
From: Kendall Roy
Sent: February 3, 2023
Subject: Fwd: Invitation: Kendall’s Greatest Hits @ Wed Feb 8, 2023 11am (EST)
“This fucking idiot,” Stewy breathed out a mix of a laugh and a sigh of relief, feeling his breath catch in his throat as if his body couldn’t decide what to do. Greatest hits, he thought. Maybe in Kendall’s post-coke slash post-depression slash post-losing Waystar clarity, Kendall had finally decided to upload the Wu-tang Clan covers he had “sworn” he deleted from his hard drive. It’s Ken’s birthday all over again.
He should have declined the invite—in fact, he was about to. His thumb was already hovering over ‘decline’. And he would have tapped it had it not been for the fact that he hadn’t heard from Kendall since Roman and Shiv had committed fratricide during that board vote two months ago, despite his multiple attempts to reach out.
At least he’s alive.
It was already eight o’clock in the morning so Stewy only had three hours to reach Kendall. To his frustration, the invite had listed no other details—no location, no description, nothing. The only other thing that signaled warning bells in his head was that it continued on until some point in January the next year. After which, nothing else followed. Just an empty stretch of dates with trivial things such as birthdays and holidays scattered in between.
Stewy downed his coffee and tried to squeeze in a couple more bites of his breakfast. He headed to his bedroom to pack an overnight bag and take a shower, mentally listing all the urgent Waystar and Maesbury business he’d just have to delegate.
What a fucking shitshow.
Tom had asked him to take over the role of CFO for Waystar in the wake of Karl’s golden parachute. Stewy didn’t particularly find the role that interesting, even if it was pulling in enormous amounts of money into his bank account. Frankly, he didn’t even like Tom—hell, even Waystar—enough to be willingly complicit to Mattson’s puppetry. He viewed this position as a temporary stop-gap while he and Sandi figured out an exit plan. After all, with Logan dead, the Roy kids gone, and the rest of Waystar being chopped up and sold for parts, there really wasn’t much of a reason—financial nor sentimental—left to stay.
“Karla, hey,” Stewy greeted once his assistant answered his call, “I’ll need you to push back all my meetings to next week. Just leave me with automatic replies for now.”
He tossed a few days worth of clothing and his laptop in his carryon. “Motherfucker,” he grumbled, what do you even bring to a random as fuck Greatest Hits…thing that’ll end next year?
Shuffling through his nightstand, he packed his remaining stash of coke, valium, and after a moment’s hesitation, he grabbed his condoms and lube too, trying to ignore the knot that had made a home in his stomach.
—
Kendall’s Greatest Hits officially started in a private jet on the way to the Hamptons. Stewy and Kendall sat opposite each other, looking down at their phones. Kendall even had his headphones on, taking refuge behind his big shades, while Stewy sat there in a long sleeved sweater, with nothing to hide behind except his silence. Kendall had this faraway look again—as if he wasn’t really present. He sported a buzz cut too, his hair tinted a shade of gray. He’d looked older since the last time he’d seen him.
The silence was palpable, and maybe a little awkward. After all, Kendall didn’t even attempt to hide his surprise at seeing Stewy at his apartment lobby that morning.
“Yo, man,” Kendall had said, looking lost, pocketing a small packet of sunflower seeds into his jacket, “uh, no time to explain, let’s just hop in then. Talk later.”
There wasn’t time earlier in between being shuffled from one car to another and into Kendall’s private jet, and there definitely was time now, but it seemed like Kendall was hellbent on not making any use of it. He hadn’t even spoken a word or sent a look Stewy’s way since, not even acknowledging his presence. Even in the past, after mutually fucking over each other, one following the money, one following the family, moving across continents and marriages, they always seemed to gravitate towards each other, their gazes never refusing a chance to meet.
This time was different. The last time Kendall ignored Stewy like this was when Logan had forced Kendall to serve them dinner when Stewy came over after school, as if it were a punishment to a game Stewy was not privy to nor participating in. For a few days Kendall had refused to even look at him, looking down at the floor as they walked past each other in the hallway, until Stewy found him spending lunch break in the bathroom stall and coaxed him out.
There was a lot to acknowledge, and Stewy wondered if they were ever going to acknowledge them at all. It wasn’t lost on him that he had to broach them delicately, too. It was just too fragile and too loaded all at the same time—the invite sent to his Harvard email (the one he never opened), the fact that Kendall had ghosted him for two months, how he looked a lot smaller and sharper, shrinking into himself, his buzz cut and dead eyes, the tabloids with witness accounts that Kendall tried to jump into the Hudson river, the board vote, how Kendall dug his fingers into Roman’s eyes and grabbed his pregnant sister… Where do I begin?
“So, Kendall,” Stewy began, Kendall took off his headphones and shades, finally looking at Stewy. “What is this? You finally releasing your fucking Wu-Tang and Beastie Boys covers from the vault man? Kendall’s version style?”
It surprised a chuckle out of Kendall. Stewy was stunned by it too, and then his surprise settled into relief. He let out a breath he didn’t know he was holding.
“You prick, I never should have lent you my Macbook.” Kendall said, fiddling with his shades with a small smile.
Stewy had let enough time pass before knocking his shoe against Kendall’s, getting his attention again.
“You’ve got to give me something, Ken. You sent an invite to my Harvard email , that’s basically a non-invitation invitation if I ever saw one.”
Kendall shrugged, “Maybe I just wanted things to be like the old times. You know—Kenny and Stewy, going on epic adventures, kicking ass and taking names.”
“And I mean,” Kendall continued, gesturing to the both of them, “you fucking, saw it, you showed up, the stars are aligning and the world is, uh, healing, skin is clearing, moisturized, in my lane, whatever that means.”
“Okay…” Stewy said slowly. Kendall had that same look on his face again, the same mania he’d seen in the past and heard in the inflection of his voice, except this time the light didn’t quite meet his eyes. It was enough to rattle him again, worry and anxiety clawing its way up in his throat, but he managed to keep a calm facade.
“Cut the bullshit, Ken, you didn’t answer my texts or calls for two months. I heard you tried to jump in the Hudson. Now we’re on a jet to god knows where to do god knows what, and you look like shit. Is your head on straight, man?”
So much for being delicate.
A somber mood had fallen over them. And after a beat of silence, Kendall leaned forward with his elbows on his knees, looking down with his hands clasped together. He cleared his throat, and swallowed.
“Look, Stewy…” he trailed, at a loss for words, stubbornly refusing to meet his gaze, “There are just a few… things I just wanted to cross off my list, before—I never really planned on you… tagging along. I invited you on a whim, I didn’t know you’d actually see it.”
Kendall took a deep breath, and continued, “We can, uh, put a lid on this. I could ask them to turn the plane around and have Fikret drop you off at Waystar and we can pretend this never happened.”
Stewy sighed, once again feeling a little out of place with Kendall and his grandiose plans. However, this time, Kendall offered him an out, one he would have welcomed on any other given day. Media outlets had caught wind of Gojo overstating subscription numbers not just in India, but in South East Asia, too. The stock price was plummeting and Mattson had his grip wrapped tightly around Waystar’s business segments, trying to squeeze out as much cash and profit needed to appease the shareholders. It was fucking bloody. They were divesting divisions every week.
But something was telling him that if he took this out, it would be the last time he’d ever be truly in with Kendall.
“And what things did you want to do?” Stewy asked.
“Uh, you know, visit a couple of places, try new things. Maybe swim with dolphins, visit a buddhist temple, I don’t fucking know. It’s dumb shit.” Kendall shrugged.
Another silence passed by, filled by the dull thrumming of the plane’s engine.
“And what’s after that, Kendall? You’ve got this whole thing scheduled until next year. What are you gonna do when it’s over?”
Kendall finally looked up and met his gaze in a show of honesty, and Stewy noticed his expression was completely void of any emotion. He had seen that expression before, he’d seen it when he returned to their dorm from his tennis tournaments, he’d seen it after Kendall would spend winter break with his father, he’d seen it while Kendall snorted enough cocaine to make his heart explode, he’d seen it the night before Kendall left for Shanghai, and when Kendall woke up in a hospital after an overdose. He’d seen it the day of the no confidence vote. He had looked into the same dull, lifeless eyes as Kendall had told him his father’s plan was better. He’d seen it as Kendall straightened his blazer after brawling it out with his siblings, when he walked back into the boardroom, attempting to save face, fully knowing it was over, and that he never had it.
“That’s it, Stewy”, Kendall’s voice was merely above a whisper, “and then it’s over. There’s no, uh, coming back for me. This is extinction level. I’m gone.”
For the second time that day, Stewy’s body couldn’t decide if it wanted to breathe back air into his lungs. He had always known, somehow, in the back of his mind, that this is how Kendall would have gone out. He had flirted too much with death for it to not happen that way.
Kendall’s Greatest Hits , wasn’t him trying his shot at a mediocre rap career—Kendall was trying to make sure he left on his own terms, as unserious as it sounded. He was going to have one last great year, to make up for all the shitty ones that preceded it.
Stewy dropped his face into his hands, at a loss for words. It was all so painstakingly Kendall. His heart hurt. He wanted to throw up.
“Ken.”
Some time passed as Stewy tried to slowly process what he had just heard. Kendall was careful enough to let the minutes go by as Stewy sat in front of him. Eventually, Stewy sat upright and asked the flight staff for a glass of the strongest whiskey they had on board.
Did Stewy seriously just sign himself up to go on one last morbid adventure with his…whatever Kendall was? Was he really going to watch idly by as Kendall placed a time limit on his own life? Did Kendall think that Stewy was going to sit there and watch?
That probably explained Kendall’s surprise and reluctance to keep Stewy on board. He was going to do this alone . That thought alone was enough to run chills down his spine. If Stewy hadn’t even opened his email this morning, he might have just gone through the year wrapped up in his own world, tunnel vision on Waystar, Maesbury, his growing pile of bills, only hearing of Kendall once his tragic death made the news.
“Look man, it’s okay. I’m okay. We don’t have to, you know, get into it. Right now.” Kendall leaned back into his seat, donning his shades and looking resolutely out the plane window.
Stewy could stop it. He should stop it. He planned on doing whatever it took to change the direction of the current. Give Kendall this one great year, and then some. Then maybe Kendall would develop an appetite for great years and would never stop going after them.
“I can’t believe you’re pulling The Bucket List on me, dude. I seriously fucking hate you so much.” Stewy said, as his body slowly recovered from the news, slumping down his seat, feeling heavier than ever.
Kendall had a small smile on his face. Stewy thought that he looked peaceful at that moment. Peace looked good on him.
Everything is so fucked.
For the rest of the flight, Kendall kept his gaze out the window, watching as clouds passed by, as if he was trying to memorize what they looked like.