Wanted: an assistant to a C-Suite executive at Waystar Royco. Responsible for all administrative duties, including scheduling. Must be technology-proficient. Will involve some travel. Must feel comfortable delivering messages on behalf of executive, putting up with executive’s inner circle, and participating in the acquisition and subsequent decimation of other seemingly hugely successful companies.
When Succession’s Jess Jordan (Juliana Canfield) saw that job description, she probably shrugged, thought, “Hey that doesn’t sound so hard, and it’s a foot in the door at one of the top media conglomerates in the country,” and clicked “Apply.” However she came to it, she got the gig, professionally attaching herself to Kendall Roy; she’s been performing the job with aplomb ever since. Jess is vital to the Waystar operation, as well as Kendall’s professional and personal well-being, and a keeper of many of the company’s and Kendall’s secrets.
However, Jess Jordan didn’t spring into this world from the forehead of Logan Roy—the Zeus of Waystar’s Mount Olympus—fully formed as an assistant god. She presumably had, and still has, hopes, dreams, a past, a future. Jess manages Kendall’s calendar, helps keep the business Kendall is dealing with running smoothly, and procures him drugs when needed. Jess has no on-screen life of her own—exactly, we can assume, as the Roys would prefer their employees. Yet she’s one of the most compelling Succession characters around (and she is almost always around) because so much about her remains a mystery. Why does she choose this life? (Perhaps because working for Waystar Royco is a résumé-booster and, hopefully, being at the beck and call of a messy, cocaine-fueled billionaire comes with a nice, fat salary, though the PTO seems subpar.) Does she sleep enough? (Doubtful.) Does she eat well-balanced meals? (It doesn’t seem like she has time to meal-prep.) Does she properly hydrate? (She must, because her skin is flawless—and speaking of, what is her skincare routine?) Who is Jess Jordan? Where did she come from? And where is she going?
We first meet Jess Jordan in “Shittshow at the Fuck Factory,” the second episode of Succession’s first season. When the episode opens, Kendall is in the back of a town car, filling his estranged wife, Rava, in on the Logan/hospital situation. Kendall mentions that he’s “here with Jess” and they’re stuck in traffic trying to get to the hospital. Jess is tapping away on her phone—she does this a lot—having perfected the vital executive assistant skill of listening/not listening. Crucially, this first time we see Kendall and Jess together, it is quite clear that he (a) does not care whether she’s listening in on his conversation, which contains information that the Roy family does not want told to the wider public just yet; and (b) is comfortable exposing his vulnerable, emotional self in front of Jess. Is Kendall crying on the phone in the back of a town car the worst or most vulnerable state Jess has seen him in? Almost definitely not. When Jess pops up later in the episode, she is seemingly the only nonmanagement Waystar employee there, situating her in Succession’s universe thusly: She is important, or at least more important.
There are other assistants in the Waystar corporation—including Cousin Greg the Motherfucking Egg, who started his journey to … wherever it is he’s going … as Tom’s assistant in parks and cruises. But Jess stands out. She’s one of the only assistants who’s nearly always present—not just at the office, which seems normal, as she works for the company, but around the family. She’s also one of the only people of color we see consistently in the majority-white world of Waystar and the Roys. She, like much of the other support staff, flits on and off screen, in and out of the Roys’ immediate vicinity but always in orbit. And yet, does Roman have an assistant? Does Shiv? Does Connor? If so, they aren’t around nearly as much as Jess.
Part of Jess’s near-constant presence has to do with which Roy family member she works for. Jess is physically always a step behind, but metaphorically often a step ahead, of Kendall Roy, who at the start of the show’s first season seemed the most likely successor to Logan. As the first season followed the ups and downs of Kendall’s pursuit of the Waystar throne, Jess was there, by his side, helping his pursuit as his steadfast assistant, even when his stock was way, way down.
These two are inextricably linked. In “Safe Room” in Season 2, Shiv said it best when Jess interrupted a meeting with Gerri to covertly show Waystar’s legal counsel something on her phone. After Gerri refused to indicate whom the interruption concerned, Shiv simply stated, “Well, Jess, so Kendall.” Kendall is Jess; Jess is Kendall. But more than that, Jess is there for Kendall, to a further extent than anyone else. When Kendall was fired in Season 1, we didn’t see Jess leave the company with him, yet there she was, two episodes later—in England, no less—helping him (and Stewy) with the hostile takeover/“bear hug” plans. What was Jess’s game here? Did she think Kendall would end up back on top? Did she just feel it her duty to keep assisting Kendall? Was Waystar still paying her? Was she truly on board with the bear hug? Also, did she get to attend any of Shiv’s wedding? I hope Jess got to at least drink some of that Wambsgans wine. Anyway, once Kendall is back in the Waystar fold, so is Jess—which means she probably never fully left it.
Jess’s role in the bear hug situation is a microcosm for her larger role in the company: She sticks by Kendall, even when it’s unclear whether that’s her job anymore; she’s extremely on top of it all, even when something goes wrong (she accidentally sends the bear hug letter to an unknown printer in the castle, but realizes it and is trying to fix it a full 30 seconds before either Kendall or Stewy do); and she knows her own boundaries. When Kendall and Stewy are arguing over who will deliver the letter to Logan, Stewy says, “I mean, Jess could do it,” to which she just offers a low whine sound, never taking her eyes off the computer screen, in a way that clearly communicates, “Um, no, I will absolutely not be doing that, Stewy, you ass.” And it’s that moment—Stewy’s suggesting Jess—that makes Kendall agree to do it himself, suggesting he’s too loyal to her to send her to the Logan Roy guillotine. (P.S. Watch Jess any time Stewy is around. She hates him and usually expresses it only with her eyes. It is beautiful to watch.)
Lest we start to think that Jess assists Kendall out of personal admiration rather than the fact that it’s her job, however, let’s recall her reaction to Kendall’s wanting to “do a bit” at the Wrecking Ball in “Sad Sack Wasp Trap.” Jess dutifully taps away at her phone, likely getting in touch with the late-night guys as Kendall asked her to, but the nuanced look she gives her boss clearly says, “Are you sure you should do a bit?” Jess has a good poker face, but her eyes betray a concern that her boss might horrendously embarrass himself in ways his twisted narcissism will never allow him to realize. Which begs the question: Did he run his “L to the OG” rap in “Dundee” by her? The fact that it happened makes me think the answer to that question is no. She really should have traveled to Scotland; I bet she wouldn’t have returned DJ Squiggle’s calls.
There are yet more questions about Jess I would like answered. Where does she go when she’s not acting as Kendall’s right-hand woman? What does she do when she’s not at work? It seems unlikely, given the demanding nature of her job, that Jess has time to date, let alone cultivate a fulfilling romantic partnership, though the suits she typically wears to work could easily transition from day to night. Based on Jess’s role in helping Kendall decimate Vaulter, she’s probably not dipping into the alt-hipster startup dating pool, and considering her barely concealed antipathy toward Stewy, finance bros don’t seem to be her type, either. What of friends? She must have some, but again, it’s unclear when she’d spend time with these mysterious BFFs. Also, it seems possible—realistic, even—to assume that she’s genuinely Kendall’s best friend, and that’s basically another full-time job on top of being his assistant.
Just think of everything that Kendall has made Jess privy to—and everything that Jess has been made privy to because of her association with Kendall. She was there to put Sandy Furness in the secret meeting room; she was there when Kendall fretted over Logan’s health emergency; she’s both arranged for Kendall to get drugs and also helped clean up his self-destruction; she’s one of the only people on the planet who knew about Rhea’s secret meeting at Waystar; she was party to the aforementioned bear hug. Perhaps the only thing she doesn’t know about is Kendall’s Chappaquiddick incident.
So here’s the really important question: Will her position and how much dirt she’s accumulated because of it benefit her or bite her in the ass in the end? Because Jess has so much dirt. And while there’s no concrete evidence that she’s used it yet, she’s always there, tapping away at her phone, privy to so much of the professional and personal that touches Kendall Roy, and by extension, the other Roys. Of course, the length of her NDA could probably circle the Earth twice, but as Kenneth from 30 Rock eventually skyrocketed to the top of the Kabletown food chain, so could Jess be one of the most powerful people in the future Succession universe. Or, instead, maybe Jess Jordan will simply continue to be the most inexplicably loyal, hardest-working assistant in New York media. I just hope she gets to use some of her vacation days soon.
Jessica MacLeish is a pop culture writer and freelance book editor based in Brooklyn (but also on the World Wide Web, tweeting sporadically @jessmacleish).
Disclosure: HBO is an initial investor in The Ringer.