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Originally, Jess became Kendall’s assistant when she was fresh out of law school and looking for a temporary job with a cushy salary and health insurance. Two years into the job, she didn’t think she’d ever give it up. After having it consume her life, she almost didn’t know what she’d talk about with friends if she couldn’t complain about the dysfunctional Roys destroying anything and anyone that had the misfortune of crossing paths with them. Three years into the job, she’s starting to realize that she’s becoming one of those unfortunate people.
But we’re getting ahead of ourselves here.
Jess met Stewy during her first week on the job. Though she’d only been working for Kendall for four, maybe five, days, she had already encountered her fair share of uptight executives who threw hissy fits if the person they were meeting with arrived one minute late or if they didn’t get to sit down at their favorite spot at the board meeting table.
Stewy was nothing like them. Sure, he was filthy rich and stuck-up, but he was also brutally honest, barely even seeming remorseful when he told Kendall about gutting out failing companies. Jess had no clue whether he truly was as indifferent to the emotions of everyone around him as he seems, but whatever he was doing seemed to work for him.
After half a month of working as Kendall’s assistant, Jess’ initial ambivalent sentiments towards Stewy quickly morphed into ones of quiet irritation. Whenever Kendall wasn’t picking up Stewy’s calls, too busy wrangling with the unbearable weight of his family legacy by himself (Jess discovered this often took up more than half of Kendall’s daily routine), Stewy would bother Jess.
“Jess, what’s Kendall up to?” he would usually ask on days he was acting like less of a dick than usual. If Stewy was feeling like an asshole, he’d say instead, “Jess, I swear to god, if Kendall doesn’t pick up my calls, I’m going to storm into his office and cut off his dick.”
Either way, Jess would suck in a breath of frustration and calmly inform him, “Kendall’s busy right now. I’ll tell him to call you as soon as he’s free.”
She’d hang up on him before Stewy could start complaining about how Kendall is a shithead and should go fuck himself for ignoring him. With all the tasks she had been delegated daily, she didn’t have time to deal with Stewy’s bullshit.
A month into working for Kendall, Jess learned to associate Stewy with drugs. That seemed like the only reason Kendall kept him around. Whenever he thought Jess isn’t looking, Stewy took out his small baggie with whatever drug he was feeling that day and offered some to Kendall. She knew it wasn’t any of her business and that she shouldn’t get involved with whatever shady shit the two of them were up to, but she couldn’t help but automatically tense up a bit whenever Kendall asked her to make room in his schedule so he could meet up with Stewy.
Then, Kendall got sober because his habit was spiraling out of control and Rava refused to let him anywhere near Sophie and Iverson unless he went to rehab and got clean. Because he loves his kids, he began declining the drugs Stewy offered and turning his back so he didn’t have to see Stewy snort a line of coke off his phone screen.
That’s when Jess, one year into the job, realized she didn’t (and probably would never) understand the arrangement that Kendall and Stewy had. Their arrangement was much more than just getting high together. There were decades of history between them that she couldn’t even begin to understand.
Never being able to figure out what was going on between them wasn’t a good feeling, especially whenever Kendall said, “Uh, Jess, can you give us a second?” and Jess stepped out of the room to leave him and Stewy alone.
It was a strange feeling — Jess knew she should always be one step ahead of Kendall. She should be able to predict his next need, his next idea, and even his next lunch order. Yet every time Stewy came over, Jess had no choice but to relinquish control of Kendall’s airtight operations and hold her breath as she watched Kendall and Stewy disappear into a private meeting room and hoped that neither of them would accidentally burn anything down while playing with fire.
~
Jess was in love, once. Her name was Eloise, but she let Jess call her Elly. She smelled like strawberries. She was a typical Type A person with a work hard, play hard philosophy and an attitude that would make the most prolific professor at Columbia afraid to get into an argument with her. In all honesty, she was a little bit like Shiv.
From the first time she met Elly in her law class, Jess had fallen directly into her orbit. However, unlike others who had been drawn into the gravitational field of Elly, Jess could keep up with her. Both of them were at the top of their class, and though this would’ve normally sparked some sort of competitive resentment, Jess and Elly became the best of friends and in time, more than just friends.
They agreed to keep their relationship on the down low. Studying came first, but if it led to accidental make-out sessions and they still managed to get the highest scores in their class on notoriously hard finals, who were they to complain?
Even though they promised to keep it casual, Jess couldn’t help but imagine spending her future with Elly. They could be partners at one of the most powerful law firms in New York, or maybe even in the world. They could move into an apartment in Chelsea, Manhattan, and raise two cats together. They could have everything they wanted and still have each other.
It would’ve been nice if Elly shared the same sentiment. A month before they graduated, Elly had taken Jess to a fancy restaurant. When dinner was coming to an end, she began talking about how great the past few years had been, and Jess had thought to herself, This is it. She’s going to ask. Then, Elly declared, “So, I got a job offer at Santos & Davis LLP.”
“Oh, that’s great!” Jess smiled uneasily, unsure of what her girlfriend could be trying to segue into.
Unable to Elly lowered her eyes. “I really need to focus on my work when I get there. You know how competitive firms like this can be. So, um…”
“Oh.”
To be honest, Jess didn’t regret getting into a relationship with Elly — she just wished she saw the warning signs before the flood.
~
It’s no surprise Kendall’s under a lot of pressure. Of course, he is. Ever since he decided to spontaneously announce that he no longer sided with his father and wanted to bring light to justice, Kendall hasn’t had much time to do anything between meetings with concerned lawyers and inner-circle Waystar employees who were desperately trying to get him to back off. By extension, Jess’ own free time has decreased drastically.
That’s why she’s initially grateful when Kendall hires Comfrey and Berry as his PR assistants. More helping hands means a lighter workload for her, right?
Eventually, Jess grows worried when she realizes that she’s getting alerts that Comfrey is adding social events Kendall will be attending to the Google calendar without checking in with Jess beforehand. She can’t help but feel sidelined as she watches Kendall go to big events without her.
Sure, she knows that Kendall is bringing Comfrey with him because she’s trained specifically to handle PR, but after years of Jess bending over backward to manage countless disasters for Kendall, the least he could do was bring her to the charity dinner he had been invited to speak at.
It’s not even that Jess is jealous of Comfrey’s position — she just understands Kendall more than Comfrey does and worries that there’s no way this new PR assistant would be able to handle the insane amount of requests Kendall makes every day. But then, Comfrey flashes Jess a sly but cold smile when Kendall says, “Hey, Jess, feel free to take the night off. Comfrey will handle all my birthday stuff.” and suddenly, Jess doesn’t feel so bad for her anymore.
Plus, if Kendall insists she doesn’t have to work on his birthday night, she might as well take the opportunity to have a nice night in. She takes her face mask kit out from the fridge and lets it settle to room temperature as she flips through the shows and movies available on the streaming service. Nothing seems particularly interesting, but she picks a random National Geographic documentary about birds and plays it in the background as she prepares a face mask for herself.
Right when she’s finished applying her face mask, Jess gets a call from the last person she wants to talk to. She sighs, her hand instinctively flying up to press against her forehead out of distress, pausing in the nick of time when she remembers what’s on her face. Jess declines the call, places her phone face down next to her, and leans back into the couch, trying to release the tension from her shoulders.
Seconds later, her phone starts buzzing again, and she knows that he’s not going to leave her alone if she keeps ignoring him.
“Stewy, Kendall’s busy. In case you missed the invitation, he’s having his birthday party tonight,” Jess informs as she pauses the documentary and focuses on not sounding murderous.
“I know. I just got back from it. It was fucking awful. A total disaster. But hey, I was wondering if you wanted to come over.” Stewy hears the heavy pause on Jess’ end and quickly adds, “I promise I won’t talk business.”
Every bone in Jess’ body is screaming at her to say no and end the call. Still, in her heart, there’s a tiny spark of sympathy. The hint of worry Stewy hadn’t been able to conceal in his voice doesn’t go unnoticed. Against her better judgment, Jess turns off the TV and replies, “I’ll be there in fifteen minutes.”
~
When Jess arrives at Stewy’s apartment, she can tell from the wild look in his eyes that he’s already had more than enough to drink. Still, after he waves her into the ridiculously large and extravagant living room of his apartment, he pours himself another drink and gestures for Jess to sit across from him. She watches as Stewy sips his drink, quietly wondering whether she should ask him why he’d invited her over at an ungodly hour.
As she waits, she stares at the painting affixed to the wall above the dining table. It’s framed with pure gold, but there’s something sad about how it’s the only painting on the lonely wall and how it has to compete for attention with the gorgeous view provided by the window next to it.
“Can I ask you something?”
Jess nods slowly. She’s treading on enemy territory. It could also be friendly territory; Stewy promised no business talk. She usually relied on Kendall’s mood to determine whether Stewy was a friend or foe on a given day, but obviously, she had no way to measure that at the moment.
“What makes him worth staying for?”
She’s taken aback. Nobody has ever asked her that before, but plenty of people felt the need to tell her that no matter how high her salary was, it wasn’t enough to justify dealing with Kendall Roy and his family. Some people also suggested they thought she had Stockholm syndrome and fell in love with her captor — or in this case, her boss, though many would argue those two were equivalent in this situation.
Truth be told, it’s neither unfounded love nor money that keeps her from quitting her job. She just has a habit of always seeing the good in people, no matter how ugly the bad is.
“I think, deep down, he wants to do the right thing. Or, um, at least, he’s trying to.”
She wants to ask him the same question. After all, she hasn’t been able to figure out why he comes coming back for Kendall even though all they do is fuck each other over for the sake of profit. But under Stewy’s scrutinizing gaze, Jess squirms like a worm under a microscope and holds her tongue. Something is unnerving about the way he silently dissects people under his gaze. Jess has seen him do it to countless other people before — strangers, executives, and Kendall, even — but it’s bizarre experiencing it on the receiving end.
“The whole thing was so stupid.” Stewy yanks the rainbow bracelet from Kendall’s party off his wrist and tosses it onto the table next to the half-empty bourbon bottle. “He recreated his childhood tree house, but it didn’t even look like it at all. It didn’t even have the floorboard that we carved our initials into.
“You know what we used to do in that tree house? We used to get high in there as shit ‘cause he was always scared that Logan would smell the weed in the house and get pissed off at us. Fuck, we even had our first kiss in that thing, and he just fucking thought it would be a great idea to create a post-modern version of it for random strangers to walk through.”
At that, Jess raises her eyebrows, unable to hide her surprise. She had her suspicions before, but she didn’t know how far back the two of them went.
Too caught up in his own emotions, Stewy rambles on, “I don’t get it. He invited all these businessmen to his party like he wanted a networking orgy at his birthday party. I barely even got to talk to him.”
“Tell me about it,” Jess mutters under her breath as she reaches for the bottle, pours herself a glass, and tips her head back as she drinks.
“Now, we’re talking!” Stewy whoops as he takes a sip of his drink. He shakes his head, mostly to himself, as he muses, “He’s turning forty years old and he still doesn’t get it. I thought he did. I really did. I mean, he almost got it when he agreed to the bear hug, but he didn’t follow through. Dickhead.”
Jess’ surge of energy suddenly fades when the assistant remembers the aftermath of Shiv’s wedding. Calling him a shell of a man would be a kind understatement.
Kendall had been uncharacteristically stony for months following the wedding and barely responded to anything at all. She didn’t dare to push and ask about what could’ve caused such a drastic reaction. Whatever it was had changed him forever, and Jess feels more helpless than she ever has as she watches him slip further and further into becoming a shadowy imitation of his past self.
“I didn’t get him a birthday present. He can have anything he wants. He can have a million designer watches, sports cars, whatever. I mean, he even got himself a rich Barbie-looking girlfriend who will tell him whatever the fuck he wants to hear!” He laughs, though Jess can’t seem to tell what exactly about the situation is funny.
“But no matter what he does,” Stewy leans closer to Jess as if he’s telling her a secret, “he knows nothing will make him feel alive like I can.”
~
For a while, Jess assumes the birthday party would be the worst of Kendall’s downward spiral. She finds a plethora of articles from gossip blogs about how disappointed all the party guests were before she remembers that it isn’t her job to check the optics or try to salvage his public image. Frankly, she’s not even sure what her job requires her to do anymore. Kendall has essentially benched her while he’s with Comfrey in Italy at his mother’s wedding.
He keeps promising that he’ll be fine without her, but he also spontaneously shaved his hair off and won’t answer any of his calls, so Jess doesn’t know if he’s in the right state of mind to be making remarks like that. Still, she agrees to stay in New York and manage Kendall’s schedule from afar.
On the bright side, without the need to be at Kendall’s beck and call, Jess finds more time for herself. She only has to answer a call or scan through his emails once or twice a day at most, which is why she’s caught off guard when she gets a call from Comfrey as she’s getting ready for brunch with her friends. She checks the time on her phone: 10:24 am, so it must be 4:24 pm in Italy.
Jess answers the call, wedging her phone between her ear and shoulder so she can adjust the straps on her wedges. “Hello?”
“Jess, Kendall just— I don’t know, uh, I don’t know what to do.”
She hears the panic in Comfrey’s voice and freezes. “What happened?”
“I found Kendall in the pool, and he fell off his floatie, and he… he was—” Comfrey can’t seem to bring herself to say it. Jess’ blood runs cold.
“Did you pull him out? Is he safe now?” Jess asks as she undoes the straps on her wedges and hurries over to her laptop.
“He’s fine, now, I think. He’s at the hospital. They’re keeping him overnight, but, um, I don’t really know why. I can’t really figure out what they’re saying. I don’t understand Italian.”
“You know, Google Translate is a great resource,” Jess dryly suggests, her anger briefly seizing the best of her. She swallows her frustration, trying to clear her mind and approach the situation as rationally as she can. “What hospital is he at?”
“Um, I think it’s called the Maria Beatrice Hospital. In Florence. They just checked him in.”
“Okay, thanks for letting me know. Keep an eye on him, and send me updates.”
With that, Jess hangs up and types in the hospital name to find the phone number and pull up Google Translate in another tab. The next half-hour consists of Jess reading the choppy Italian to English translations provided by the site and responding by repeating the Italian translations that Google spat out for her in response to the English phrases she types. It’s possibly the most tedious task she’s ever had to do on behalf of Kendall, which means a lot considering he once asked her to acquire a snake for his son during the time Iverson had been obsessed with reptiles.
In the middle of the conversation, she also quickly crafts a “sorry, something important came up” text to apologize to her friends for missing brunch. She promises to reschedule and spend time with them sometime soon, but honestly, once she ends the call with the hospital, she doesn’t feel like speaking to anyone for the next month.
And that’s when she gets a call from Stewy. Jess stares at the caller ID on her phone for a second, and, against her better judgment, she picks up.
“Hey, Jess. I haven’t heard from Kendall recently. Is he doing okay?”
There’s a quiet beat as Jess opens her mouth, instinctively prepared to evenly recite the line she’s repeated a thousand times: “Kendall’s busy right now. I’ll tell him to call you as soon as he’s free.” Instead, she surprises both Stewy and herself when a sob comes out instead. She covers her mouth, attempting to collect herself and slow her breathing.
To her shock, Stewy patiently waits until she’s calm enough to speak coherently. “Kendall almost drowned.”
“What? Did he overdose?”
“The hospital said he didn’t have drugs in his system,” Jess informs. She wishes she could see Stewy’s reaction because even though she can tell he’s stunned, she can’t tell if he thinks that it’s worse that Kendall had done this out of his volition.
Stewy sighs. “Okay, that’s it. I’m going to get a private jet for us to get to Italy.”
“Don’t do that. The hospital isn’t letting any visitors in. He’s there for his mom’s wedding with the rest of his family, and I don’t think the press knows about his… incident yet. Let’s just— we shouldn’t try to make this a big deal,” Jess insists, although she can tell that her tone is so disingenuous that she has a hard time believing her own words.
“Then why would you tell me about it if I can’t fucking do anything about it?” Stewy snaps. Thankfully, he quickly backtracks. “Sorry, I didn’t mean that. Thank you for letting me know.”
“I just thought that if anyone would understand, it would be you,” Jess says.
Stewy falls silent for a moment, and Jess is worried that she might’ve scared him off. Then, he starts talking. “This isn’t the first time something like this happened. When we were in college, there was a night when he was taking a lot of stuff at this party we were at. He just called his dad earlier, and he was in a really awful mood. It got pretty bad towards the end of the night, and I had to make him throw up before it got to the point where we had to call an ambulance. I was fucking terrified, but he was okay. I know it’s really bad right now, but he’ll be okay this time too.”
“I know.” Jess wishes she could find more words to express her unwavering faith in Kendall’s ability to stand up after getting knocked down over and over again, but she knows that Stewy has seen it enough times to know it himself.
“I think this is the most I’ve heard you talk. Like, ever.”
Jess still feels like the wind has been knocked out of her, but she inadvertently chuckles at Stewy’s remark. “He really scared the shit out of me.”
“He tends to do that.” Stewy says it jokingly but Jess detects a hint of honesty in his tone. “Listen, I have to go, but if you need anything, call me. Take care of yourself, ‘kay?”
“Will do. Thanks.”
Standing up, Jess walks over to the large window in her living room and stares at the cluster of buildings afar. The sun is high in the sky, shining down on all the silver office complexes that look eerily similar to one another. She tries to spot the Waystar Royco headquarters, but she can’t seem to recognize any of the buildings from afar at all.
~
When Kendall comes back flanked by his siblings, Jess figures that they had planned to return with the blood of their father on their hands. Instead, they arrived with incarnadined knife handles sticking out of their backs, glinting in the bitter moonlight. She refrains from making any comments when Kendall tells her that he’s fired Comfrey, but when Kendall’s not looking, she can’t help but break into a small, victorious smile.
Jess pretends she doesn’t notice the sour look on Shiv’s face when she mentions that Tom had contacted her, looking to speak to Kendall, just before the siblings had returned to New York. She doesn’t flinch when Kendall instructs, “Tell him that I’m not going to speak with him and that he can go fuck off because he’s a fucking coward and pathetic asshole.”
“Got it.” She begins typing up a polite but firmly worded message to send Tom.
Although she doesn’t ask what happened with Tom that would’ve caused such a visceral reaction from the siblings, she figures it has something to do with Logan and shifting alliances. She doesn’t need Kendall to tell her to leave the room either when he, Shiv, and Roman sit down in the living room.
“Oh, and Jess?”
Pausing and turning around to face her boss, Jess offers an inquisitive look, waiting for her next instruction. Kendall pauses, glancing down at his hands as he considers something for a moment. Nodding, he looks at her and says, “Schedule a meeting with Stewy as soon as possible.”
Jess flashes a quick thumbs up, exits the room, and closes the door behind her.
Not that any of the Roys would notice, but when Jess welcomes Stewy into the apartment later that evening, there’s not a hint of animosity hidden in her smile. Stewy pats her on the shoulder on his way in, and she knows that he can tell too.