Four Years Before

When he'd stepped off the elevator and saw her waiting with his morning coffee, she looked different. Somehow. He wasn't sure. This was an ordinary Monday, much like any other.

But she was different. Brighter? Maybe?

"Hey," he said, ready for the morning debrief as they walked to his office.

"Morning," Jess replied, handing him the cup and tapped her tablet.

He took off his sunglasses.

There it was. Glinting in the elevator bank light. The light that they'd had environmentally designed to not seem like it was fluorescent. (It was.)

Without even having to think about it, Kendall immediately knew what it was. He blinked as he was ambushed by a feeling. A feeling.

"Whoa," he murmured under his breath and indicated his sunglasses weakly, "maybe I should put these back on? …Heh…May I…"

May I? Jesus fuck. What am I, a fucking appraiser? He reached out and quickly retracted his hand.

Kendall watched Jess as she grew fleetingly self-conscious and withdrew her hand to her chest for a moment. He watched her make a small decision before presenting it to him.

"Uh—" he found himself tripping over his words as he surveyed the ring. It was fantastic clarity. Kendall noted that it seemed to overwhelm her finger, "congratulations."

"Thank you."

Jess watched him as his shoulders sloped a little. Kendall nodded once before they began toward his office. Instead of the usual debrief, or any instructions Kendall would give, they walked in silence. Jess grew mortified; what…was going on?

She felt like sinking into the carpet.

Jess took a breath as he stopped in his office doorway.

She glanced down at the tablet: "The meeting for—"

"—yeah, it's at ten?"

She nodded, stepping back toward her desk.

"OK." Kendall nodded back and managed a quick thumbs up before he slipped into the sanctuary of his office.

He took a breath for a moment. He had no right to her. He had no right to anyone, really. But he couldn't deny the hurt welling inside of him. He stood there frozen, unable to articulate why he felt what he felt and at a loss with what to do with it. All he knew was that it felt heavy, empty. Like he'd lost something.

Someone.

Kendall cleared his throat, disappointed in himself. He shook his head, swallowed the hurt, and sat down at his desk.

Present Day

Over the next month after Argestes, Jess found herself far from Kendall, both geographically and interpersonally. He'd gone off to England to visit his mother—and maybe link back up with Naomi Pierce, it seemed—and then back in New York for a short few days before jetting off to Scotland.

Kendall chose the first woman presented before him at the first preview of Willa's new play.

Jennifer, Tony said. He'd become the point person for Kendall's latest fling, making last minute arrangements for her to fly out to Dundee. And to fly her home a day later.

"First it was Naomi Pierce," Tony commented in a hushed voice to Kerry the day after they'd returned from the gala, "I was coordinating some dinners and such—"

Jess trained her eyes on her phone, mindlessly scrolling and pretending not to care, as they huddled in the C Suite kitchen.

"—and then it was this Jennifer—"

"The actress from Connor's gf's play?" Kerry asked as she shoved some roasted almonds into her mouth. A sorry excuse for lunch before an afternoon of escorting Logan to meetings.

"Yeah," Tony rubbed his chin in thought, "and then, in a flash, he wanted her gone. From the gala. And there's been nothing since. It's like he's pinballing around—I mean, he's always been…pinballing, I mean…you know…but now?"

"What do you think, Jess?" Kerry asked, dusting the salt off of her hands, "you always have astute reads on things like this."

Tony waited silently, his eyebrow daring to arch.

Jess shrugged. "I don't know."

"Come on," Kerry nudged, "no quip or witticism?"

"I mean," Jess finally glanced up from her phone and faced her friends. Her colleagues. Her comrades in arms, "yeah. He's sowing some sort of wild oats or something. Perpetual arrested adolescence or something."

They were silent as they looked at her.

"Well, anyway," Jess sighed, "we've got the D.C. brief in a minute. We should get going."

She slipped out of the kitchen and went down the hall, leaving Tony and Kerry to exchange one quick look before following her out.

Jess couldn't remember the last time she had been in D.C. A school trip, perhaps? She'd set up the Royal Suite for Kendall at the Four Seasons and secured a room for herself three floors below. Kerry and Tony had gotten rooms right next to hers, as well. There was talk of cocktails after the hearings—everyday.

The legal department and public relations had set up prep sessions for all top-level executives. Jess noticed that Kendall had been the only one to show up to every single one of them. And if she wracked her memory—Greg, too. After skipping the first session out of a misguided sense of early confidence, Tom Wambsgans had requested extra during his final hour, but none were given.

As they sat in the conference room waiting to go in, Jess watched Kendall flip his attention back and forth from the screen that streamed the hearing and his phone. He felt distant to her, which made Jess feel that something had been lost between them.

But it was what she had wanted, wasn't it? It was for the best.

Jess had half-expected him to be at her door with some made up issue that night before the hearings. But he wasn't there.

After a morning of monitoring Waystar stock in the holding room, she took her place behind Kendall and Logan before their questions.

Jess had prepared herself to listen to the age-old Roy spin. But there was no preparation for what she would witness.

The prep for the senators' questions didn't matter; he should've prepped against his own father. As Logan deftly threw the blame of the cruise cover up onto his son, Jess found herself, yet again, grappling with the ethics of her position.

Her mother had been right: working for Waystar meant working for the Roys. And this company, it seemed, was not one that Jess could try to change from the inside—as she had told herself at the beginning.

She watched from behind Kendall, as he shifted in his seat, bracing himself for the blows that would undoubtedly come to him: his own father had sold him out. And Jess watched. She felt powerless. How many times would Logan tear him down, dismantle him, to teach him a lesson? Or was there even a lesson? What she'd witnessed was insane to her.

How much more could Kendall take, she wondered. Surely he'd reach his limit.

He had never been one to express himself—not well, at least. Jess reviewed her time with him—her time being employed by Waystar. Five years, just about. Five years of steadily being knitted into Kendall Roy's life. He'd never once raised his voice at her; she'd watched him do it performatively from time to time around the office, but it was his mask.

The real Kendall kept everything inside, and she watched him for five years carry all of the unspoken words around with him, dragging them along, and she helped him carry his burden just as she'd helped him carry his bags.

And she had never been one to speak at length. Their relationship was one that had evolved (or devolved?) into looks, glances, vibes. Jess read the weight on his shoulders as he spoke to the committee. Something was shifting in Kendall at that moment. Something subconscious. Something shifted-along with the change that had occurred back in England, whatever it was. Whatever had made Kendall go back on the bear hug. Jess wanted to reach out—to hold him.

But, she pursed her lips, her chance had passed. It was too late now. Too late to go back and try again. Jess wondered if she had made the right decision in pushing him away. She sat, frozen, behind him.

The hours after the hearing were a whirlwind. Jess hung back as Kendall met up with Naomi right before they left the Russell Building; there was talk of going to the Capitol Hill Club for a celebratory drink.

"I can get back to New York tonight," Jess mentioned, trying to seem offhand while she inwardly wondered how she could keep Kendall out of prison.

"Oh—uh—" Kendall stammered as he stepped away from Naomi, "you don't have to—"

"I think I need to—" her words hung between them, and soon it hit Kendall that Jess had started to connect the dots. She was always three steps ahead.

He took a breath, heartened by her concern. Energized by it.

"Look," Kendall said in his fake voice, the one that he used on Lawrence Yee. The one that never seemed to work as intended, "it's—it's gonna be fine."

Jess looked at him silently, unconvinced.

"My—my dad said," he continued, "that we'll be regrouping on the yacht for a bit before the shareholder meeting for the next moves. It'll, it'll be fine."

"I'm gonna go back tonight."

"Uh-huh. OK." he cleared his throat as Jess' demeanor made his heart race—and not in the usual way.

Before dipping into the company car, Jess flashed a quick, curt smile toward Naomi, who returned a smile of the same kind.

"She's working hard today," she commented as they watched the SUV pull away.

"Hm?" Kendall asked her absently, very still.

"Your shadow."

"She's always working hard," Kendall, who had placed his sunglasses on to hide his eyes, watched the car disappear into the D.C. traffic.

Kerry was the one to mention to Jess that she'd gotten word from Kendall that Naomi would be joining him on the yacht.

"You…didn't know?" Kerry asked.

Jess shook her head, almost imperceptibly, sipping her martini. It was close to midnight at the bar, and she was ready to head uptown for the night.

Her work phone buzzed, face down, on the table between them. She and Kerry exchanged a quizzical glance at one another.

"Hm," Jess said, furrowing her brow as she surveyed the screen.

"What?" Kerry asked, interested immediately piqued.

"Kendall is calling me." This was weird. So many vacations he'd been on during her tenure-and no voice calls. And so late? There was the time difference-

"You're still up," Kendall said to her instead of a greeting.

"Yes."

"I need you to get a hold of Tony," he said plainly, "and round up the team for tomorrow. 9 a.m."

"OK…"

"I'm on my way home," he said, his voice so even that it made Jess shiver.

"OK." She whispered, waiting for the drop, thinking back to Logan and the hearing.

He gulped—may as well clue her in: "My dad—he thought it best—"

Looking back on that moment, Jess couldn't recall the words Kendall said to her. The feeling was too great, too much. The reeling sensation she had, in the middle of Stone Street on that perfect May night, overpowered any memory-making capabilities she once enjoyed.

She texted Tony as Kendall kept talking.

Plans were then set into place that night. A press conference. An announcement. Jess had nine hours. Kerry had appeared a distance behind her, having also gotten word.

"All right then," Kendall finished when everything was in motion, "estimated arrival time looks like 8 a.m."

"Got it. I'll have a car for you."

He must've felt the tremor in her voice. "You good?"

She took a deep breath, thinking of how poorly Kendall would fare in prison. "Yeah."

"Hey, Jess-"

"Yeah."

On second thought, maybe Kendall would thrive. Prosper.

"Don't worry."

"Sure," she said as she bit her lip. Her heart raced as she scrambled to put together some vision of what the near future would look like. Kendall in cuffs. FBI searches.

"I got this."

He had that ultimately ineffaceable Roy confidence. Jess marveled at it for the first time.

She wondered, in the back of her mind to keep herself from sobbing, what his plan really was.

"Your father's watching," Karolina said to Kendall.

Jess felt a sting of anger well up inside of her as she gauged Kendall's reaction. He was calm. Still. The emotion…

What was it? Not angry.

In that moment, she'd be angry for him.

As Kendall went down the hall to the room where the press had assembled, she trailed him, as his ever faithful familiar. The bulbs flashed as the hive of reporters started to buzz at the sight of him. And all Jess could feel was the void laid out before them. She kept searching Kendall, checking in with him, trying to find out some clue, some sense of how to feel, what to do.

She reached out, speaking with her touch:

I'm with you.

The heat from her hand on his shoulder centered him. With an exhale, Kendall glanced at her as if he were gulping water in the desert, shook his head at his own choices, and proceeded to the dais.

Jess took her place next to Karolina in the back of the room. She drew a deep breath as she let Kendall's words wash over her, bracing herself for what was to come. After all of this—all that he'd been through—his monster of a father would offer him up as a sacrifice? She felt sick.

But then, Jess, no longer listening to his words, watched as the muscles in Kendall's face shifted.

Her lips contorted against the pricking tears in her eyes as she tried to make sense of what he was saying, if what she was hearing—the incredulity of the crowd, Kendall's message—was actively real.

The press burst forth into harried cries and questions as Kendall stood, tearing his company line speech as he stepped away from the throng of microphones.

Jess took a moment, as Karolina spit curses into her phone next to her, to be in silent awe. But only a moment.

Because there was work to do.