Dave Portnoy Defeats Barstool Nate in $20K Heads-Up Game

When Barstool put together a two-day poker event at Foxwoods—an 18-player sit and go followed by a $20,000 heads-up match between Dave Portnoy and Eric “Barstool Nate” Nathan—the draw was obvious. Eric “Barstool Nate” Nathan had been trying to make this match happen for the better part of a decade, and when it finally did, it came with a solid cash on the line, live commentary from Brent Hanks and Jeff Platt, and thousands of people watching on stream.

Both players had their moments early on—Portnoy made some unorthodox plays that somehow worked; Nate built up a lead and looked comfortable as the blinds increased, but the match didn’t stay balanced for long, and as the pots got bigger, the decisions got harder to explain.

The Build-Up: Years in the Making

For a long, long time, Eric “Barstool Nate” Nathan had been chasing one thing: a chance to take on his boss, Dave Portnoy, across the poker table. Nathan, Barstool’s in-house poker voice and host of the company’s Cracking Aces podcast, had pitched poker content to Portnoy for years while building a modest résumé of live results, including $63,495 in tournament earnings and a cash in the 2024 World Series of Poker Main Event.

Portnoy, by contrast, had virtually no live poker record. His connection to the game stretched back to the PartyPoker boom of the 2000s, but Nathan was the one with real tournament experience. The imbalance made the matchup compelling—Nate wanted to prove himself as Barstool’s poker guy, whereas Portnoy treated the whole thing as another chance to flex his competitive streak.

The grudge match was staged as part of Barstool’s new poker push, powered by a DraftKings sponsorship that tied poker content into the company’s broader gambling strategy. The week kicked off with an 18-player sit-n-go featuring familiar Barstool personalities like Dan “Big Cat” Katz and Eric “PFT Commenter” Sollenberger, with commentary from poker veterans Brent Hanks and Jeff Platt. Nathan and Portnoy both joined that event—neither made the money—but it served as an appetizer for the main event the next night.

By the time the two sat down at Foxwoods, it was the payoff to years of teasing, Nate finally getting the duel he’d demanded, and Portnoy stepping into a high-stakes spotlight he swore he didn’t need.

Early Game: Barstool Nate Takes the Lead

Eric “Barstool Nate” Nathan dictated the early action once the heads-up match began at $100/$200 blinds. He steadily grew his stack, forcing Dave Portnoy into tough spots and pushing the chip lead out to nearly three-to-one.

Portnoy managed a highlight early on with a check-raise bluff. Holding jack-high and a gutshot straight draw, he fired the turn and then bet $2,000 on the river, convincing Nathan—who had top pair of tens—to fold the best hand.

Still, mistakes piled up. In one pot, Portnoy accidentally announced his exact hand—ten-eight offsuit—while action was still live. Nathan, who had bottom pair of threes, didn’t pick up on the slip and paid off bets before folding.

Then came an even bigger misstep. On a board of 9♦-8♣-2♦-9♥-6♣, Portnoy held nine-four for trips. With $2,800 already in the middle, he inexplicably mucked his cards on the river without facing a bet. Nathan, holding king-eight for a weaker hand, was left puzzled but happy to take down the pot uncontested.

At the end of the first stretch, Nathan had the momentum, the chips, and the upper hand. Portnoy, though, hadn’t cracked. Even after giving away pots with unorthodox decisions, he still had enough chips to leave the door open for a swing.

The “Worst Fold in Poker History”

The hand that changed everything came with blinds at $100/$200. Nathan looked down at pocket kings and opened to $1,000, while Portnoy called holding king-nine. The flop of 4♠-5♦-9♠ gave Portnoy middle pair against an overpair, and the action started to build. Nathan led for $700, Portnoy bumped it to $1,700, and Nathan made the call, though his hesitation was obvious.

The 10♣ landed on the turn, and once again Nathan checked. Portnoy slid out $1,000, and Nathan called a second time. At the river the pot had swelled to $8,400, and after the 3♣ fell, Nathan checked for a third time. Portnoy bet another $1,000, a small stab that left everyone expecting an easy call.

Nathan, unexpectedly, went in the tank, and the commentators were stunned as the clock ticked. “If he folds, this is one of the worst folds I’ve seen in my life,” Brent Hanks said. Moments later, Nathan mucked the kings, and Hanks didn’t hesitate to say, “It’s the worst fold in the history of poker.”

Portnoy tabled his nine to rub it in, seizing the lead for the first time since the opening minutes. On break, he summed it up in simple fashion to Ben Mintz: “I’m a mental bully.” Nathan, meanwhile, looked shaken, and the booth kept hammering the point that the fold had broken his momentum.

The Collapse

After the fold with kings, everything seemed to slip away from Nathan. The steady confidence he had early on was gone, replaced by hesitation. Even when he finally picked up a hand worth playing, the nerves showed. With queen-jack on a queen-high board, he faced an all-in shove from Portnoy, who was holding just bottom pair. It was the spot that could have ended the match on the spot, but Nathan tanked and laid it down. The commentators were stunned, with Brent Hanks saying flatly that it looked like he had lost his footing.

The blinds then jumped to $200/$400, and the bigger pots worked in Portnoy’s favor. He started pulling in chips steadily, using the lead to push Nathan around and stretching his stack to nearly three-to-one. Nathan tried to push back with a bluff holding king-high, but once again it went the wrong way. The booth wasn’t shy about saying what everyone could see — Hanks and Mintz both pointed out how passive and lost Nathan looked, piling on as each hand slipped away.

At one point, Portnoy even leaned back and offered Nate a way out, suggesting he could surrender and keep his $20,000. The offer was brushed aside, but it was clear who was in control. Nathan’s pride kept him in his seat, yet the weight of the earlier mistakes was still hanging over him, and every pot seemed to tilt further in Portnoy’s direction.

Barstool Sports Founder Closes it Out

The end came not long after Portnoy had stretched his lead to three-to-one. Nathan, short-stacked, picked up ace-nine and finally connected with top pair on a board of Q♥-5♠-7♠-10♥. Portnoy, holding seven-four of diamonds, had flopped bottom pair and then improved to a straight on the turn. With $3,200 already in the middle, Nathan bet $1,200, Portnoy raised to $2,400, and Nathan pushed the rest of his chips in. Portnoy snap-called, and when the cards were tabled, Nathan saw the bad news.

There wasn’t much left to say. The players shook hands, and Portnoy leaned straight into the moment. Almost immediately, he offered to put the $20,000 he’d just won on a single spin of roulette, with Nate getting the money back if it landed his way. Filming restrictions killed that plan, but the idea carried over to a sports bet for the weekend instead.

Aftermath and Legacy

When it was over, Portnoy wasted no time claiming victory in the way only he can. “Killed ’em, which I knew would happen,” he told Ben Mintz in the post-game press conference. He added that Nathan had wanted the match for years, while he had barely played in more than a decade. “I tried to tell him. I didn’t want this, I didn’t want the match,” Portnoy said.

Nathan, for his part, faced the cameras with disappointment but tried to frame the night as a larger success. He admitted Portnoy had played better down the stretch, saying, “He played very poorly for an hour and then he figured out how to raise. He played pretty well for the last couple of hours.” But he quickly pivoted to the bigger picture, posting afterward that “poker content at Barstool works,” pointing to the two-day event’s strong viewership as proof that the effort had paid off.

King of the Felt pulled in more than 17,000 live viewers at its peak and brought Barstool personalities into the poker spotlight in a way that resonated with fans. Backed by Barstool’s sponsorship deal with DraftKings, the event gave the company clear proof of concept: poker content can draw attention and fit alongside its sports and gambling coverage.