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In “What It Takes,” the Roy family goes to Washington, D.C. to crown the next Republican presidential candidate—of course, after their own interference with coverage on their conservative news network, ATN, convinced the current, temperamental president not to run again. It’s a pit of vipers, so naturally, Logan Roy (Brian Cox) is in his element. But as the episode pokes at the unsavory underbelly of American politics, other characters find themselves taking to the environment, too.
Zoe Winters plays Kerry, Logan’s executive assistant, who has begun to assert herself at meetings, tossing off bold statements to the great delight of Logan and the great consternation of his children, who are worried that they might have to compete with an office flirtation for their father’s attention. It’s a sudden move to the forefront for the character, who has been hovering in the background since the end of season two.
“She joined at the height of the scandal in the cruise ship division,” Winters tells Sonia Saraiya on this week’s episode of Still Watching. “I have always been fascinated by the fact that she would choose to join the company at that point—she would fasten herself to this dysfunction media dynasty as they’re facing this investigation.” Winters, who also played a conservative operative in the buzzy Will Arbery play Heroes of the Fourth Turning, looked to operatives like Ann Coulter, Candace Owens, and Tomi Lahren for inspiration.
“I really feel like Kerry has some terrifying political positions,” Winters adds. “She is obsessed with winning.” The close relationship Kerry has with Logan stems partly from how dazzled the younger employee is of Logan’s success, ruthlessness and all. You can hear much more of the conversation with Winters in the episode below:
And of course, it wouldn’t be a convention of conservative windbags without Connor Roy (Alan Ruck) doing the rounds. (A bewildered Shiv (Sarah Snook) comments that in a room full of Timothy McVeighs, her hapless older brother looks like a Roosevelt.)
Justine Lupe plays Willa, Connor’s girlfriend with theatrical aspirations, whose play last season was a dismal failure. The state of Connor and Willa’s relationship has been a bit of a mystery, but so far in season three, despite the general chaos around them, Connor and Willa have been an inseparable unit—from holding down the Balkans to schmoozing in D.C. We spot her writing a play on her iPhone before fielding lecherous advances from organizer Stephen Root, whose attention, however unwanted, is good for Connor’s campaign.
“That’s what we all run up against sometimes,” explains Lupe. “How do I float through this moment … not allowing it to get too far, and yet making the other person feel calm?” Willa, to her credit, knows her way around these situations. “She was an escort. She went out with these guys. She knows how to be the easygoing … best-date-ever kind of girl,” Lupe adds.
Lupe also speculates with Still Watching on what’s keeping Connor and Willa together. She doesn’t think it’s ambition to be a political wife, or anything like that. “She’s headstrong. And she’s like, and she is protective of herself and she’s and consequentially because she’s tied to Connor. There is like a protectiveness of their thing together,” Lupe says. “And the level of denial that she has is so well-matched to Connor’s denial. I was so pleasantly surprised to see that she’s still just like typing away—like, ‘okay, I have to be here, but I’m going to be like working on my thing again.’”