Kylie Jenner just got called to the table.
On Monday, March 30, Sam "Señor Tilt" Kiki took to X with a message aimed directly at the 28-year-old beauty mogul, offering her a seat and $500K with her name on it. "I hold the record for most ever won in a full season of High Stakes Poker and the largest single day win," Kiki wrote. "I, too, like splashy pots."
The post was a direct response to Jenner’s viral poker tutorial with Vanity Fair earlier this month. In the video, the Kylie Cosmetics founder walked viewers through the basics of Texas Hold’em and revealed she picked up the game two years ago on a trip with friends. "All the boys were playing poker and I didn't really understand it," she said. "They just taught me how to play. And then I started watching tournaments and that's when I became obsessed."
Jenner, who hosts regular poker nights at her Hidden Hills home with boyfriend Timothée Chalamet and his friends, said she prefers players who "juice the pot" and "bet a lot of money."
Kiki appears to fit the bill. The founder of MonkeyTilt, an entertainment and betting company backed by $51 million in funding, currently holds two all-time records on High Stakes Poker — the iconic cash game series that airs on PokerGO. The show's CEO Brent Hanks confirmed the records last week and has called Kiki "the most dangerous recreational player on the planet."
The challenge wasn't just for Jenner either. "Bring Timothée," Kiki wrote. "I'll teach you both everything the Vanity Fair video left out. Then we all compete on @PokerGO with a few of our mutual friends."
While it’s unclear exactly which “mutual friends” Kiki had in mind, there’s already some overlap. In February 2025, Kevin Hart joined Chalamet, Jenner, Kid Cudi, and Tobey Maguire at a pre-Oscars poker night at Chateau Marmont. The Jumanji actor later sat across from Kiki during Season 15 of High Stakes Poker, where Señor Tilt won approximately $424,500 from him in a single hand.
"Similar to what 'Drive to Survive' has done for Formula 1, I'd like to do for poker," Kiki told Market Realist last year. With Jenner’s 390 million Instagram followers and Chalamet fresh off a Best Actor nomination, it’s the kind of crossover Kiki has been pushing for.
