Billionaire ‘Besties’ Crush Phil Hellmuth in Las Vegas Poker Tournament

Connor Richards
Senior Editor U.S.
3 min read
All-In Podcast Venetian

Phil Hellmuth may be one of the greatest tournament poker players of all-time, but the 17-time bracelet winner had a less-than-stellar performance in a private sit-and-go hosted by his All-In Podcast "besties" in Las Vegas.

The six-player sit-and-go, which took place over F1 weekend in the Venetian Poker Studio and recently premiered on YouTube, saw Hellmuth compete against podcast hosts and tech entrepreneurs Chamath Palihapitiya, Jason Calacanis, and David Friedberg, all of whom are good friends of Hellmuth, as well as high-stakes pros Alan Keating and Jason Koon.

Despite his short-handed experience and record-setting first-place finishes at the World Series of Poker (WSOP), Hellmuth was the first to fall in what Calacanis dubbed the first "Bestie Invitational Tournament."

"Nothing Better Than Hellmuth Not Winning"

Hellmuth's misfortune began about halfway through the hourlong turbo match in a hand against Palihapitiya, who PokerNews interviewed at the 2023 WSOP. Hellmuth bet all in with AJ on a flop of 425 as Palihapitiya called with J5, leaving Hellmuth's ace-high in trouble against top pair.

Somehow, the dealer found the 3 turn to give Hellmuth a miracle Wheel, but it was a short-lived victory as the 6 river gave both players straights for a chopped pot. No one was more excited to see the six land than Calacanis, who loudly cheered as Hellmuth sat back in silent disgust.

"Oh my god. That's so great!" Calacanis said before biting an unlit cigar. "Nothing better than Hellmuth not winning. There is nothing better than Hellmuth not winning. It's so great when he doesn't win."

Jason Calacanis
Jason Calacanis

Hellmuth, who stayed calm despite the playful jabs, would experience yet another rollercoaster runout as he moved all in with A3 to be pipped by A10 of Keating. Hellmuth was momentarily bailed out by the 432 flop before a ten on the turn secured his elimination in sixth place.

"Yes! Phil Helmuth loses. F*** yeah!" cheered Calacanis. "Awesome. Phil Hellmuth out first. This is what we live for, folks ... The world's greatest tournament player loses to Alan Keating, the wild man."

Last Laugh For Hellmuth?

The game included some colorful table talk, including Hellmuth bragging about getting paid to wear sponsorship logos and a story about Keating nearly getting in a fight at dinner the night prior. At one point, Molly Bloom of Molly's Game fame stopped by the studio and watched the sit-and-go action.

The match, which did not have any listed payouts, got down to Koon and Palihapitiya, who bested the high-stakes end-boss to win what Friedberg joked was the "first-ever Venetian five-minute turbo bounty."

Chamath Palihapitiya at the 2023 WSOP
Chamath Palihapitiya at the 2023 WSOP

Though he didn't fare well in the invitational, Hellmuth revealed to PokerNews he had much more success in a high-stakes private game with his "besties" that took place "somewhere in the Venetian" the same night.

"I (recently) went public saying I lost six times in a row filming ... and I won a big portion of that money back last night already," Hellmuth told PokerNews during an interview at the Big Deal for One Drop charity event on Nov. 21. "So people are like, 'Oh, Phil's lost his edge,' until they sit at the table with me, and then they're like, 'Ah, nevermind.' But yeah, you can't listen to the idle chatter."

Hellmuth shared additional thoughts on the All-In Podcast crew, who also filmed a podcast episode in the Venetian Poker Studio during their trip to Las Vegas.

"They kind of made fun of me on (a previous) podcast (episode). But like, I've brought Timothee Chalamet to their event, I've brought Tony Robbins to their event. And then they made fun of me and I said, 'I'm going to kill you guys.' And the next podcast they spent six minutes praising me."

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Connor Richards
Senior Editor U.S.

Connor Richards is a Senior Editor U.S. for PokerNews and host of the Life Outside Poker podcast. Connor has been nominated for three Global Poker Awards for his writing.

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