Work Text:
In a way, the Roys’ reign doesn’t really end, at least not for Jess. Every morning, she opens the news app and sees that one of the siblings, or at the very least, one of the family members, has made the headlines time and time again.
On this fine Thursday morning, Jess is standing in line at a bakery and reading an article about how Tom’s speech at a charity gala went awry because of a teleprompter malfunction, which of course led to him embarrassingly fumbling his way through his speech. She considers Tom part of the Roys because it seems like since he’s had a taste of the poison, he’s decided to down the whole fucking chalice.
Of course, Tom’s success came at the hefty price of Kendall’s downfall. Truth be told, some part of Jess still hoped that Kendall would have taken up the mantle, even though she quit her job because of how unbearable he had become.
“What can I get you?” The barista asks, seeming rather irked that Jess had been too occupied with looking at her phone to have her order ready.
“Sorry, um, I’ll have an espresso with an extra shot of caffeine,” Jess replies, and the barista fails at hiding his judgment at the amount of caffeination she requested.
“Throw in a croissant and put it on my Amex Black.” Turning around, she identifies the familiar voice as Stewy, who offers a wink as he hands his card to the barista over her shoulder.
Moments later, they’re standing next to each other in tense silence. Jess doesn’t know how to react to Stewy showing up or how she should have a conversation with him because the last time they talked was when—
“So, how have you been, since, you know, Kendall tried to drown himself?”
Though he appears unfazed on the surface, Stewy is unable to hide his genuine curiosity as he watches Jess, waiting for her reaction.
“Fine.” Jess doesn’t want to offer much, even though she feels like she owes him a detailed explanation.
Sensing Jess’ apprehension, Stewy explains, “By the way, I’m not stalking you or anything. I come to this bakery often. Ken and I actually used to come here all the time when we were younger and steal pastries from behind the counter. But look at me, I’m paying for my croissant now and living a more ethical life. That’s what being free from the hands of Waystar is like. I'm so glad that I don't have to deal with that sick fuck of a company anymore.”
“Order for Jess!”
Jess grabs her drink and Stewy’s croissant, which she hands to him, expecting him to take it and leave. Instead, he questions, “You work in equity research at Barclays now, right? Mind if I join you on your walk to work?”
“It’s a bit of a walk,” Jess says, but she follows him out of the bakery anyway.
“I’m sure your boss won’t mind if you’re, like, an hour late for work. If he does, I’ll talk to him. I’m 90% certain I probably have been with him in a bathroom at an underground party at some point,” Stewy pauses to finish off his croissant in three quick bites. “But seriously, tell me what’s been going on.”
Jess sips her espresso, wishing she could wince at the bitter taste like she used to, but it’s hard for her to find things that leave a bitter taste in her mouth after everything she’s been through at Waystar. “Nothing much. Just working and staying busy.”
“That’s good to hear.” Their conversation lapses into silence once again — Jess is a little weirded out because it isn’t like Stewy to be quiet. Then, she realizes what Stewy wants her to ask.
“How have you been?”
“I’ve been pretty good myself. Been thinking a lot about shit that I haven’t really thought about in a while.” Stewy crumples up the napkin in his hands and tosses it into a garbage can with ease. “Hey, remember what you said last time about why you kept working for him even though he’s a piece of shit? Did that change?”
As Jess glances down at her shoes to avoid Stewy’s scrutinizing look, she thinks for a moment about how to reply. At one point, Jess believed that neither unfounded love nor money had kept her from quitting her job and that she had a habit of always seeing the good in people, no matter how ugly the bad is.
Perhaps this still applies because looking back, she had made a million excuses, tiny justifications, for Kendall’s behavior. In comparison, to Logan, Kendall seemed like a saint but with Logan gone, well…
Stewy nods as if he can tell that Jess doesn’t really have the words to express how she’s feeling. “You know what? You don’t have to answer that. Hey, wanna hear something funny? Kendall got himself a new assistant, and get this, get this: he calls her new Jess.”
Jess’ eyebrows raise, and she’s unable to suppress a small chuckle. Stewy laughs along with her and adds, “Yeah, it’s crazy. She looks nothing like you. She’s, like, blonde with blue eyes, and I don’t even think she’s called Jess. As you can probably tell, he’s been going a little crazy without you there to keep him sane.”
“I’m not surprised. He literally called me at one in the morning during my birthday party to ask me to come to his office.”
Amused, Stewy smiles and asks, “Did you go?”
“Yeah, but I was definitely not sober enough to hide that I was super annoyed.” She shakes her head, recalling how annoying that incident had been.
“I’m happy that you’re free from that shit. After he fired you, he kept bothering me like crazy and getting pissed about how indecisive I was. Guess he didn’t like the taste of his own medicine.”
Jess knows that she shouldn’t ask about Kendall, but curiosity gets the best of her. “Have you talked to him since the board meeting?”
“Not really. Sent him a text or two to make sure that he’s still alive, but I’m just kind of done with dealing with white men for a while. Plus, sometimes, I wonder if forgiving him would make me as bad of a person as he is…” Stewy sighs, shoving his hands into his coat pockets. “But then I remember I’m a piece of shit too, and then I don’t care as much.”
Jess rolls her eyes but can’t hide her grin. She pauses when she realizes that they’ve reached her office building.
“Well, this is where we say goodbye.” Stewy sticks out a hand, and Jess shakes it. It feels odd to be so formal around him considering their previous interactions, but somehow, it felt like a fitting goodbye for now. “I would say call me if you need anything, but knowing you, you’re going to be fine.”
With that, Stewy turned around and walked away. As Jess watched him disappear into the crowd of New Yorkers crowding the street, she realizes that Stewy Hosseini would always be an enigma that she would never be able to figure out. Yet, for someone who’s as determined to find the answers for everything, she’s surprisingly okay with leaving it at that.
—
About a week later, Jess is walking towards the bakery before work as usual when she sees a familiar face through the window.
Sitting at a table alone, Kendall Roy has a croissant on the plate in front of him but doesn’t seem interested in eating it at all. He stares out the window forlornly, thankfully not in Jess’ direction, as if he’s waiting for someone he knows will never arrive.
The part of Jess that feels sorry for him wants to sit down next to him and catch up as if they’re old friends. Yet, when Jess looks at him, she gets flashbacks of watching him argue with his siblings about Mencken and yelling threats at Rava, who only wanted to protect their children, and that sympathy shrivels.
So, Jess holds her head up high and walks past the bakery, purposely not glancing in Kendall’s direction. She doesn’t want to know if he looks at her with crushed hope in his eyes because, truthfully, she still cares just a little.