Portnoy Tops ‘Barstool Nate’ in $40K Heads-Up Poker Showdown

Published on September 4, 2025|Last Updated on September 4, 2025 Author:Dusan Jovanovic
Dave Portnoy

Summary:

  • The long-awaited heads-up match between David Portnoy and Barstool Nate drew over 17,000 live viewers.
  • Nate, the more experienced player, made several shocking folds that commentators called “the worst in poker history.”
  • Portnoy capitalized on the mistakes, rallied back, and secured the $40,000 win.

The long-anticipated heads-up poker showdown between Barstool Sports founder Dave Portnoy and his employee Eric “Barstool Nate” Nathan finally unfolded on Wednesday night, ending with Portnoy on top in a $40,000 heads-up battle.

Heated Play with $40,000 Prize Money 

The ‘King of the Felt‘ match, streamed by DraftKings, was viewed live by more than 17,000 people at its highest peak. The contest with $20,000 each on the line and blinds starting at $100/$200 didn’t lack wild plays, questionable folds, and head-shaking moments.

Going in, Nathan, a World Series of Poker regular who is no stranger to live events, was the clear favorite. Portnoy, on the other hand, had some online experience from the PartyPoker days of the early 2000s but has spent little time at a live table. 

Nonetheless, Nathan admitted beforehand he expected his boss to play “wild and crazy”, which ultimately proved not to be the case.

Early action leaned Nate’s way, even though Portnoy managed to bluff him off the best hand with just jack-high. However, one bizarre moment saw Portnoy accidentally announce his hole cards, “10♦ 8♠”, loud enough for commentators to catch, though somehow Nate missed it and called anyway with the bottom pair.

“One of the Worst Folds I’ve Seen in My Life”

The swings came quickly, as Nathan pulled ahead after hitting a flush against Portnoy’s two pair, and at one point built a three-to-one chip lead. Yet he also made some puzzling folds that stunned the commentary team. The most infamous came when Nate laid down pocket kings on a dry board after facing a small river bet.

If he folds, this is one of the worst folds I’ve seen in my life”, said commentator Brent Hanks. Seconds later, Nate mucked his hand. “It’s the worst fold in the history of poker”.

Portnoy jumped on the momentum shift. “I’m a mental bully”, he joked to the booth during a break. “They’re going to crucify him for that”.

From there, Nate unraveled, passing on another chance to end the match when he folded top pair to a Portnoy shove, once again giving up the best hand. Commentators criticized him for playing “too passive” as his stack dwindled.

Three hours in, the blinds rose to $200/$400, accelerating Portnoy’s surge. Eventually, Nate shoved with the top pair only to run into a straight, sealing the win for his boss. Portnoy even offered him a chance to win it back on a spin of roulette, but the the bragging rights, the real win of the showdown, was already gone.

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Dusan has a keen interest in online gambling laws. Making his posts well worth a read to find where poker is legal and upcoming changes to the law..

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