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Playing the $250,000 Super High Roller turned out to be a bad bet for Sean Perry.

The self-proclaimed sports betting guru arrived on Monday to enter Day 2 of the largest buy-in tournament at the 2025 World Series of Poker (WSOP). He lost all of his chips about five minutes after he sat down. But he’ll have an opportunity to win it all back soon (or lose more).

Poker-Playing Sports Bettor Gone in the Blink of an Eye

Perry took his seat inside the Horseshoe as one of the 63 entrants chasing the $4,752,551 first-place prize. That wad of cash won’t be going his way after he ran into a big pot against Bryn Kenney during the first orbit of his session.

The hand, as captured by PokerNews live reporter Tim Baker, began with Perry raising to 100,000 from the cutoff with A*♠10♦. Kenney, poker’s all-time live tournament cashes leader ($75.7 million), three-bet to 275,000 from the button with K♦Q♣*. The original raiser then moved all in for 750,000 and received a call.

Perry was slightly out in front but only a 3/2 favorite to double-up. But the board ran out 8*♠2♥5♠Q♦J♣*, giving Kenney top pair, enough to scoop the pot. That meant the former poker pro who still occasionally pops up at the WSOP was out of chips minutes after entering the tournament. Kenney had over 2.4 million chips at the time of publishing, an average stack size.

PokerNews will continue to provide live reporting coverage of the Super High Roller throughout the event. There were 38 players remaining when this article was published. Ben Tollerene held the chip lead, while other big-name pros such as Daniel Negreanu, Martin Kabrhel, and Phil Ivey were in the mix.

Chance to Win it Back

The good news for Perry is that he can quickly make back the $250,000 he lost in five minutes. That, however, depends on if the Oklahoma City Thunder can defeat the Indiana Pacers in the NBA Finals.

The Thunder tied up the best-of-seven series at 2-2 on Friday with a 111-104 road victory. Perry wagered on Indiana at +6, losing by a point. He has a $650,000 wager on the Thunder winning the series, which would pay him back more than he lost in the Super High Roller.

Game 5 takes place in Oklahoma City at 5:30 p.m. PT Monday night on ABC. The Thunder are favored by 9.5 points, according to ESPN. Many NBA experts have predicted the winner of Game 5 will go on to win the series.

Perry is often criticized by the high-stakes poker community for selling sports betting picks. Shaun Deeb, who feuded with Perry during a recent WSOP high roller event, is among those who’ve called him out for being an alleged “scammer.”

In this Series

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