Dave Portnoy to Finally Accept Barstool Nate's $20K Heads-Up Poker Challenge?

Jon Sofen
Senior Editor U.S.
3 min read
Dave Portnoy Poker

It appears Barstool Sports founder Dave Portnoy will finally put his money — and he has a lot of it — where his mouth is and face Eric "Barstool Nate" Nathan in a heads-up poker battle.

Barstool Nate, a longtime poker player, has been trying to make this match happen for a decade. PokerNews has asked Nate multiple times when the heads-up contest will take place, and he's never been able to give a definitive answer. But the former host of the Cracking Aces poker podcast seems confident his boss is ready to play him for $20,000.

Bartstool Sports Poker Battle

Eric Nathan Dave Portnoy Poker
Eric \"Barstool Nate\" Nathan

Nate revealed on X that a "tentative date" has been set for the high-stakes poker match. He has only disclosed brief details about the upcoming poker game.

"I'm hearing whispers and rumors that the 10-year-in-the-making, once-in-a-lifetime heads-up match, 20k each, me versus Dave is going to happen," Nathan said in a short video on X. "Possibly this summer. He's put it off for 10 years, so it wouldn't shock me if it doesn't happen. But I feel great. I think I'm a heavy favorite."

There's only one slight problem.

"I just need to find 20k cash."

Assuming Nathan comes up with the money to play, it appears he'll finally get his wish to face his boss after trying to make it happen for a decade. The exact date and location for the heads-up competition have not been released.

Will Portnoy Actually Play?

Portnoy, given a tentative date announcement was made, might no longer be able to duck his employee. But some Barstool Sports fans, aka "Stoolies," seem to think "El Presidente" will back out of the match.

"Bet he backs out, says he needs a mental health break from all the hate he’s been getting," @neonpantz tweeted.

Portnoy teased playing in the $250,000 Super High Roller at the World Series of Poker (WSOP) last year. He never showed up to play, but he tweeted out before the event that winning the bracelet against some of the best tournament players in the world would be "light work."

Nate's been trying to get his boss to play him for years. The two chatted on Bartstool's The Unnamed Show in July 2024 about a potential poker match. Both agreed to play.

Portnoy, however, said he wants the match to take place at Foxwoods Resort Casino in Connecticut, a legendary poker room. Barstool Nate said he'd like to have it livestreamed on PokerGO. That was a year ago, and it's unclear if those wishes have changed.

Barstool Nate will put aside the potential heads-up game against Portnoy to compete in the 2025 WSOP later this month. He also recently hosted a Barstool Heads-Up Poker Challenge, but dealt the game instead of playing against his colleagues. Portnoy didn't compete.

*Feature image courtesy of X/Eric Nathan.

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Jon Sofen
Senior Editor U.S.

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