Logan Roy has a way of collecting Lady Macbeths, and the next in line might be personal assistant-slash-potential baby mama Kerry Castellabate, played by Zoë Winters. Over the course of the third season of Succession, Kerry has gone from silently lurking in muted outfits at Waystar Royco meetings to boldly stepping out in sunshine yellow, girl boss mauve, and icy aqua blue, sarcastically razzing Logan’s children (who are about her age) in between serving up smoothies full of “gloop”-enhancing abilities to her boss and, it’s heavily implied, lover. Amid the many moves and countermoves that Succession tracked over the nine episodes in its third season, Kerry’s steady ascendency might be the most surprising. Will Logan’s quad of children have a new mommy — and a new younger sibling — when Succession’s fourth season grinds into motion next year?
The many assistants, employees, and fall-takers who populate Waystar Royco do most of the work that keeps the company running day-to-day, while Logan’s revolving inner circle of his children and established old-timers like Gerri, Frank, and Karl handle strategy, shareholders, and acquisitions. It’s rare to see someone from the former column crossing over into the latter, and yet there Kerry is by the time “All the Bells Say” starts, green juice in hand.
Succession has always been a fast-moving show, the narrative thrust of which has often been guided by offscreen events and the characters’ reactions to them: the cruises scandal and the Department of Justice investigation, Kendall’s moves to undermine his father and try to sway shareholder support his way, Shiv and Tom’s withering marriage. And yet even amid that established setup, Kerry’s rise and whatever relationship she’s cultivated with Logan has been quick, mostly unseen, and, Logan’s kids would probably say, catastrophic. In the immortal words of Michael Bluth: “Her?”
Yes, her! Like Jesse Armstrong has said before, Succession does not do red herrings. The show is deliberate in its plotting and thoughtful in its double-crosses. Gerri has always protected her interests, and Roman should not have thought otherwise. Tom has always acknowledged Logan’s power as impenetrable, and Shiv should not have underestimated that. And if one were to extend that reasoning, then Kerry’s first smile at Logan should have tipped us off. Brian Cox may have thought that Logan and Holly Hunter’s Rhea didn’t actually sleep together in the second season of Succession, but it’s harder to deny that something is going on between Logan and Kerry. That woman smirks like she knows something, and apparently what she knows is the purpose of maca root.
But first things first: Who is Kerry, and where did she come from? Kerry might potentially play a pivotal role moving forward, but she wasn’t introduced with any great fanfare. In fact, Logan seems to have a different personal assistant in the first season and partially through the second: Lucy, who appears in six episodes and doesn’t say much. She then melts away, as so many of Waystar Royco’s employees seem to, and Kerry enters in a similarly buttoned-down, mostly silent fashion in season two episode “Return.” In a gray dress and already rocking those severe bangs, Kerry presses play on a Maesbury Capital–emblazoned tablet that Stewy and Sandy sent to shareholders to convince them to vote against Logan.
“Return” is also the same episode in which Logan and Rhea maybe slept together, and because Succession was all-in on that story line, Kerry didn’t yet have much to do. She’s just another Waystar Royco body, appearing only one other time in the second season in the penultimate episode “DC.” She gives Logan a bottle of water, she watches Tom’s stammering, silly testimony before U.S. senator Gil Eavis (Eric Bogosian), and she doesn’t say anything.
Is Kerry already collecting intel to return to Logan and secure her position so she doesn’t get replaced like Lucy? Maybe, because by the time she reappears in season three, she’s firmly on the inside. Seated next to Tom during Shiv’s “Rape Me”–sabotaged speech and opening the Waystar Royco doors to the FBI in “The Disruption,” Kerry is played by Winters as alternately bemused and brusque. She’s professional, of course, but not cold; she seems willing to give Logan the fawning attention he’s not getting from Marcia or his children. Watch her face as she sits next to Logan on the private jet back from meeting with figuratively and literally multilayered shareholder Josh Aaronson (Adrien Brody) in “Lion in the Meadow.” Logan is double-talking the President about ATN’s increasingly critical news coverage, and when he puts himself on mute and leans over so that Kerry can listen to the Raisin’s whining, she is a little trepidatious — all wide eyes and a slightly open mouth — until she meets Logan halfway and angles her body toward his. Her little giggle at the president losing his temper is like a shared secret, and it’s only the first of presumably many that Kerry and Logan will share.
From that point on, practically wherever Logan is, Kerry and Logan’s trusted security guard, body man, and fixer Colin (Scott Nicholson) are too. In “Retired Janitors of Idaho,” the three begin the day in Logan’s Fifth Avenue home together. Logan trusts Kerry with telling him “what the temperature is amongst the shit-munchers,” and she is the only one who knows about his UTI. Logan relying on Kerry to respond to his health needs, given that this series started off with Logan’s stroke sparking all this familial infighting, is a big deal!
This is also the episode in which Kerry finally speaks to other people within Waystar Royco, adopting a somewhat negging tone that fits right in with how Logan interacts with his employees. “I think it’s kind of urgent,” she says in a deadpan response to Frank, Tom, Gerri, Karolina, Hugo (Fisher Stevens), and Roman trying to figure out who should talk to the president. “I think your dad wants a word,” she says to Kendall before grinning at his “Am I grounded, Kerry?” question and abandoning him in a crappy, rundown room with a scratched-out “Customer Friendly Office” plaque on the door. Kerry already doesn’t mind pushing the Roy successors around in service of Logan, and she only grows more comfortable with it as their relationship deepens.
The second half of the season catapults this dynamic to the forefront, but in typical Roy–children fashion, Shiv and Roman are so wrapped up in their incest jokes and power struggles that they don’t really grasp what’s directly in front of them. In “What It Takes,” Roman treats Kerry like a disposable sexual conquest for Logan, while Shiv refuses to believe that they could be hooking up at all. Kerry is laughing at all of Logan’s jokes, casually walking around the suite in which the inner family is assembled (and where Logan sleeps), and eye-fucks this man over a hideously overstuffed cream-colored couch in the most unsettling moment involving a piece of furniture since BOB crawled toward the camera in Twin Peaks. And still, Shiv needs to be told by Roman, “Looks like your polling was off again,” to really understand that her father has made space in his life for someone to whom he will give more influence and importance than them.
And Kerry, bless her heart, loves it! This woman lives for the drama. At a certain point, Winters’s face just gets frozen into a perpetual smirk, and there is something thrilling about how thoroughly, like Logan, she does not give a single, solitary fuck about what people think. In “What It Takes,” she smirks at Roman and Shiv as she walks with Logan into his bedroom.
In “Too Much Birthday,” she smirks at GoJo and Lukas Matsson (Alexander Skarsgård) with, “He thinks he’s a genius. He’s made one good piece of tech. Fuck him,” and Logan backs her up with “‘Fuck him’ is good tactics.” In “Chiantishire,” wearing a blue suit that matches Logan’s suit jacket (which in turn matches Roman’s pants; the three of them have a strange outfit-symbiosis thing happening in Italy), she smirks again as she saves Logan from having to chat with Caroline’s new husband Peter Munion. Kerry is thoroughly pleased with herself, and “All the Bells Say” reveals why: She’s trying to get pregnant.
On the one hand, maybe this theory isn’t true since it comes from Connor, who is irritated with his siblings for not acknowledging him as the eldest son, and who makes sure to punctuate his news about their father’s “sperms like little catfish” with the dig, “I guess he really doesn’t rate you guys.” (Alan Ruck digs in the knife with the flippancy of his line delivery.) On the other hand, Kerry sure is giving Logan a lot of grossly colored juice that could be full of virility boosters! Think of what Roman says in “Too Much Birthday,” when he sees Kerry drawing the blinds in Logan’s office: “She’s gonna give birth to dad’s baby while we chant a Satanic mass.”
If everything that eventually happens in Succession is previously foretold, then maybe a Kerry pregnancy isn’t utterly out of the question. She’s gone from wearing blacks and grays to purples, reds, pinks, and yellows — hues of royalty, romance, and optimism. She emphasizes to Roman that he’s just one heir, not the heir. (“Let me grab a couple of kids’ menus.”) She might even have some sort of understanding with Marcia, since the women cluster around Logan in the episode’s final act instead of breaking ranks. If Logan is serious about selling off Waystar Royco and starting again, is another chance at a familial legacy that absurd to imagine? (And, will a potential future child have better standing within whatever the new GoJo–Waystar Royco is than Kendall, Shiv, and Roman, who have now seemingly been pushed out?)
Of course, this is where we must acknowledge that all the Roy children are deeply screwed up mostly because of Logan. Connor is delusional. Kendall is an addict. Roman can’t fuck. Shiv is a moral vacuum. What hope does this baby, who might be born old and already attached to a walker, have? So the question about Kerry might not be “How did she begin her dalliance with Logan?” but “How does it end?” All of Logan’s relationships eventually do, and that’s the real supermajority on Succession.
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