Timothée Chalamet Pulled Into $500K Poker Challenge by Pro Sam ‘Señor Tilt’ Kiki
Timothée Chalamet and Kylie Jenner have unexpectedly been pulled into a high-stakes situation after she starred in a viral video. A record-breaking poker pro, Sam ‘Señor Tilt’ Kiki, has issued a $500,000 challenge to the superstar couple, leaving fans waiting to see what will happen next.
The Viral Video That Sparked A Fascinating Challenge
On March 11, 2026, Vanity Fair's YouTube channel uploaded a video in which Kylie Jenner was shown talking about her "hidden talent," playing poker. In the opening minutes of the video, she revealed how her passion for the game began. "Two years ago, on a friends trip, all the boys were playing poker, and I didn't really understand it. They just taught me how to play, and then I started watching tournaments, and that's when I became obsessed."
From there, Jenner went on to explain the rules of poker. The video's release came months after E! News published an article about Jenner's mom giving her a casino-style poker table for her 28th birthday. The outlet also reported that Kylie Kenner had previously played poker with Tobey Maguire, Kevin Hart, Nathan Fielder, Marcus Mumford, and her boyfriend Timothée Chalamet.
Following her Vanity Fair video, Jenner and Chalamet both became the subject of a challenge from a gaming professional. For poker fans, it will be fascinating to see how the celebrity couple will, or won't, react to the challenge.
The $500,000 Poker Challenge Explained
18 days after Kylie Jenner's poker video was uploaded, the professional poker player, Sam ‘Señor Tilt’ Kiki, reacted on X. Alongside reposting the video, Kiki wrote to Jenner that he has $500,000 and a seat at a poker table waiting for her. He then encouraged the reality show star to bring her A-list boyfriend, Timothée Chalamet, with her, and offered to teach them both everything he knows about playing poker.
"I have a seat and $500k with your name on it. Bring @RealChalamet. I’ll teach you both everything the @VanityFair video left out. Then we can all compete on @PokerGO with a few of our mutual friends."
Considering Jenner and Chalamet's reported interest in the highly strategic card game, the opportunity to learn from a pro seems like it should be very exciting for them.
Who Issued the $500K Poker Challenge
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.
— Señor Tilt (@senortilt) March 29, 2026
I have a seat and $500k with your name on it. Bring @RealChalamet. I’ll teach you both… https://t.co/dj8ZmYADqQ
Alongside inviting Timothée Chalamet and Kylie Jenner to play poker with him, Sam ‘Señor Tilt’ Kiki's X post featured the following brief description of who he is. "I’m Sam Kiki. I hold the record for the most ever won in 17 seasons on High Stakes Poker."
A recent Sports Illustrated article detailed what makes Kiki a record-breaking professional poker player. It detailed that he won more money in a single pot and cumulatively across a season of High Stakes Poker than anyone else ever has in the show's history. The same article also revealed that, on top of being a poker pro, he is also the founder and CEO of Monkey Tilt, an entertainment and betting company that raised $51 million from investors.