Stewy Hosseini

A sharp, well-connected private equity operator, Stewy is Kendall Roy's college friend turned frenemy, orbiting the Waystar Royco empire with money, leverage, and an easy, needling charm. He talks like everyone's ally and negotiates like no one's, always angling for an advantage while dressed as a favor.

Arian Moayed plays him with a loose, amused cool that never quite hides the calculation underneath, and the writing uses him as a mirror for Kendall's delusions of independence. Stewy is fun to watch precisely because he's the one person who seems to see the Roys clearly and finds it all very funny.