When Jess appeared in front of him in his office that next Monday morning, Kendall was almost relieved; she hadn't reached out in over four days, and the mortification from her silence nearly killed him. Her usual even countenance was burdened by a furrowed brow, and he watched her as she steeled herself into speaking.
"It's best," she started in a small voice, "to put aside…what happened…"
Kendall's face fell. His chest felt heavy with a seeping humiliation.
"…and it's prudent to…move forward within an entirely professional context," Jess continued, realizing she needed to brush up on her PR crisis communications, "and overcome …previous… unsustainable complications."
Kendall, in abject fear of appearing weak, immediately concurred, in a hearty, overly enthusiastic tone.
"You're quite right," he trained his eyes on her forehead to avoid direct eye contact, "I wholly agree."
Jess breathed in once, inadvertently revealing surprise, but went on with the improv exercise between the two of them, "It's not the …optimal road to go down."
"Quite right," Kendall nodded, tamping down the scream inside of him. He sat upright in his chair, as if a rod had replaced his spine. He pretended to be a robot. He waited, with his heartbeat in his ears, for Jess to tender her resignation.
"But that will change nothing here," she said, trying to find a firm tone of voice.
"Of course," Kendall was confused, but what else was new?
He laid his hands on the desktop ledger and tapped his fingers to give himself something to do. He couldn't contain the overflow—it was always impossible to do so in front of Jess. Kendall quivered, in spite of himself.
Jess moved to go, and he watched her have the slightest argument inside of herself and turn back to him.
"You know we can't do this—" her words seemed harried, uncontrolled. Kendall was in shock, "you're—married—"
"—Separated—"
"You have kids to—"
"Jess—"
"You're in recovery," she said with finality, "and I just—I just want you to stay safe. Above everything else."
Without waiting for a response or permission to leave, she opened the door, quickly glanced over her shoulder once, and went to sit at her desk. Kendall watched her go; she would go through that same motion—going from his office to her desk—exactly 2,540 times before they would leave Shanghai.
And another 7,830 times over the next couple of years at Waystar Royco in Manhattan. He would watch her each time, fighting the memory of the kiss. Day after day, she would dutifully complete her tasks with precision—and without judgment. Jess had grown to be an extension of Kendall, silently supporting, compensating, and double checking. She had learned to absorb information about him from context clues and silent looks; the deep, extended conversations began to ebb. Jess had all of the background intel she had needed; the time in the desert, the time in Shanghai, the intimate moments they shared with each other (when he haphazardly brushed his lips against her knee in forgiveness, good god, she had almost forgotten), the late nights-all informed every decision she made in her day-to-day duties.
Had it not been for those moments, which seemed so incredibly illicit when they would burst forth from her memory into her mind's eye while she sat at her desk (could they have truly been wrapped up in each other on that couch? Was that real?), Jess knew she wouldn't be able to do her job half as well as she did.
And she took a quiet pride in it. In the years after Shanghai, she kept track of his sobriety as much as his business. Three years and counting now—and back in New York, as strong as ever. And she was a part of it. She was able to keep him on the right path. Gone were the uncertainties, the late-night check ins—and they seemed so far from that moment she found him alone and unconscious on his bathroom floor. There was a light at the end of the dark tunnel, and Jess finally allowed herself a sense of relief, if not longing, for what could have been. She knew when he attended meetings, when he would see his therapist, and when he would meet with his sponsor. If they couldn't be together, they could at least have this.
For Kendall, Jess was the glass he had broken in case of emergency, and she had rescued him. He felt secure—for the first time in his life. He fought, every day, to keep from begging her, from kissing her, from tearing at her clothes helplessly, but he felt safe. Every time he watched her go from his office, he'd repeat to himself:
"Don't fuck this up."
But, of course, that would be against his nature, he surmised.
He shifted in his chair as he watched the clock to strike nine.
Kendall sometimes thought of Jess, and he didn't know why. She would merely appear in his head—and rarely left. He was busy thinking of her as he strode down the hall to the conference room. Fiona was there, waiting by the door.
Don't fuck this up.
"He's all set," she murmured, grabbing the handle and allowing him to step in. Kendall nodded curtly as he adjusted the lapel of his bespoke suit.
Let the succession commence, he thought.
It was official: Kendall was the heir apparent to the Waystar Royco empire. The Crown Prince, the Golden Child.
Jess had zero idea why Joan had contacted her for a meeting with Logan. At first, she responded with open times in Kendall's schedule.
"No," Joan's voice was maternal, dismissive over the phone. Jess glanced across the room. She could see the older woman tapping her pen on the desk in impatience. That was always a benefit and a downside to open office structure: you peer across the space to see the visual subtext from a coworker. "Your schedule. Mr. Roy wants to speak with you."
"…Excuse me?"
"In anticipation of the younger Mr. Roy's …promotion…" Joan's hesitation displayed her mixed feelings, "Mr. Roy thought it prudent to speak to you."
The meeting, which was at 9:30 the next morning, was mercifully short. Jess timed herself so that she was exactly one minute early. Choosing to wear her new suit—the one with the pencil skirt—with a sloping silk blouse, Jess knew she looked professional, put together, but also really, really good. Against her better judgment, she added a hint of eyeshadow. She was ready to play the game. She'd been practicing for years.
"I know that you've been looking after Kendall," Logan was blunt.
He didn't look up at her. Instead, he scanned the headlines on a folded newspaper in front of him.
Jess was thrown off by that choice of opening, which was probably Logan's goal, and she didn't immediately respond. Someone had noticed some of her work. And it was Logan. Jess struggled to keep her eyes from widening at the realization, almost embarrassed. Her handling of Kendall, she assumed, had been kept secret. She wondered: did he notice the intended, on-paper duties of her position?
"You've done a fine job," Logan declared, still reading, "and you'll get a raise for continuing to do so over the next few months as we prepare him for the …transition."
Jess gave him a small nod.
"He's not easy," Logan shifted in his chair and brought his attention up to her. He cleared his throat, "but he's got potential."
Kendall's father spoke of him as one would a wayward teenager, not a 39-year-old Vice President of a Fortune 500 Company.
"OK?" Logan tilted his chin downward and peered at Jess over his reading glasses.
"Yes, sir," she replied immediately, in a low voice.
"All right, then," he said, and went back to reading.
This signaled to Jess that the meeting was over.
It wasn't quite what she expected, but it was confirmed that she was now officially Kendall's nanny? She couldn't help but be stung by how this macro narrative was shaping up: woman of color holds hand of privileged white male in order for him to not screw up his capitalist birthright.
She rose from the Le Courbusier chair, uttered a quiet "thank you," and stepped out. This transition, she predicted, would be an absolute, unmitigated shitshow. She emerged from the meeting with more articulated loathing for Logan Roy than she ever had—not based on any one word he had relayed to her, but merely on a gut feeling, or perhaps a tiny voice inside of her head. She also emerged from the meeting with more loyalty for Kendall than he deserved, but Jess was certain that sentiment came from deep within her chest. Yet there was a new sensation brewing inside of her as well, one that belonged completely to her: ambition.