Sam 'Señor Tilt' Kiki Issues Kylie Jenner, Timothée Chalamet Poker Challenge After Viral Video

Sam "Señor Tilt" Kiki, who recently broke two all-time records on the televised cash game series High Stakes Poker, publicly challenged Kylie Jenner to a game this week — and invited her boyfriend to join.

Kiki, who is a poker star and founder of the entertainment and betting company MonkeyTilt, posted the offer on Sunday on X, told the model mogul he has a $500,000 seat waiting for her:

May 31, 2025; Indianapolis, Indiana, USA; Timothee Chalamet and Kylie Jenner are seen in attendance during game six of the eastern conference finals between the Indiana Pacers and the New York Knicks for the 2025 NBA Playoffs at Gainbridge Fieldhouse. | Trevor Ruszkowski-Imagn Images

"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."

Hey @KylieJenner — I’m Sam Kiki. I hold the record for the most ever won in 17 seasons on High Stakes Poker. I also hold the record for largest single day win. I, too, like splashy pots.

I have a seat and $500k with your name on it. Bring @RealChalamet. I’ll teach you both… https://t.co/dj8ZmYADqQ
— Señor Tilt (@senortilt) March 29, 2026

The message was a direct response to a viral poker tutorial Jenner recorded with Vanity Fair earlier this month (see video below). In the video, the Kylie Cosmetics founder explained she picked up Texas Hold'em two years ago while traveling with friends.

"All the boys were playing poker and I didn't really understand it," Jenner said. "They just taught me how to play. And then I started watching tournaments and that's when I became obsessed."

Jenner, 28, said she now hosts regular poker nights at her Hidden Hills, California, home with boyfriend Timothée Chalamet and his friends, and that she favors players who "juice the pot."

Kiki extended the invitation her Oscar-nominated actor boyfriend as well.

"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."

The two sides may more in common in this arena than it first appears. In February 2025, Kevin Hart attended a pre-Oscars poker night at Chateau Marmont alongside Chalamet, Jenner, Kid Cudi and Tobey Maguire. Hart later appeared on Season 15 of High Stakes Poker, where Kiki won approximately $424,500 from him in a single legendary hand.

PokerGO CEO Brent Hanks confirmed Kiki's records last week and has described him as "the most dangerous recreational player on the planet."

Kiki has been vocal about his ambitions beyond the felt. "Similar to what 'Drive to Survive' has done for Formula 1, I'd like to do for poker," he told Market Realist last year.

Jenner has 390 million Instagram followers alone while Chalamet received a Best Actor nomination at this year's Academy Awards where he and Jenner attending the Vanity Fair Oscars Party.

A game with the those two and Kiki would certainly be epic and cause a stir across social media.