A Decade-Old Grudge Match Delivers Drama
The long-simmering poker grudge match between Barstool Sports founder Dave Portnoy and his colleague Eric “Barstool Nate” Nathan finally ignited on Wednesday, and it didn’t disappoint. Playing a $20,000 buy-in, winner-take-all heads-up bout on King of the Felt, presented by DraftKings, the pair battled for a $40,000 pot before Portnoy sealed the victory.
The stream drew more than 17,000 concurrent viewers at its peak. The match opened at $100/$200 blinds and featured a blend of cagey lines, head-scratching decisions, and one all-timer of a fold that left the commentary booth in disbelief.
Barstool Warm-Up: Freeroll Action on YouTube
On the eve of the showdown, Barstool Sports hosted a three-table, 18-player freeroll sit-n-go for staff on the Barstool Gambling YouTube channel. Both Portnoy and Barstool Nate took part but failed to cash. Portnoy did, however, make a standout laydown with A♦K♥, correctly folding to an all-in on a 5♦A♥6♦ flop against bottom set. Ethan Kamps won the event for $30,000.
Experience vs. Instincts
Nathan, a regular at the World Series of Poker (WSOP), brought the deeper live résumé. Portnoy’s background traces to the online boom era—he played in the 2000s on PartyPoker—but he has limited live experience. Contrary to what Nate predicted in a pre-game interview earlier in the week, Portnoy’s approach was more measured than manic.
Early on, Nathan took the initiative, but Portnoy snatched a pot by min-check-raising a turn with a gutshot and jack-high, then firing $2,000 on an ace river to get a fold from Nate’s top pair (tens).
The strangest sequence arrived when Portnoy, possibly unintentionally, announced his exact hand—10♦8♠—and the broadcast team heard it while Nate seemingly didn’t. The flop fell 3♠8♥6♥. Portnoy, with top pair, bet $600—more than the pot—and Nathan called with A♣3♥. After the 7♣ turn and another $600 from Portnoy, the booth tried to save him some pain. “Nate, he told you his hand,” commentator Brent Hanks said. This time Nate folded, but the earlier call had already cost him chips.
Moments later, with the board showing 10♠4♣9♥5♣, Nate bet $600 holding 6♣2♣. Portnoy raised to $1,200 with 9♠4♥. The river 8♣ completed Nate’s flush; Portnoy bet $1,000 and then called a raise to $3,500, flipping the match as Nate surged to better than a 2:1 chip advantage on the back of a rough beat for his boss.
On the very next hand both players flopped top pair, but Nathan held the superior kicker. An ace hit the turn, Portnoy fired a small $400, and Nate laid down the best hand—another fold that baffled the booth.
Then came a pivotal pot: Nate opened 8♦4♦ to $400, Portnoy defended 5♥2♣, and the flop came 10♦2♦3♥. Nate bet $400 and got called. The turn paired the board with the 3♥, and Portnoy led $1,000 with his deuce; Nate called with the diamond draw and hit the 5♦ river for a flush while Portnoy improved to two pair. After Portnoy bet $1,000, Nate raised to $4,000. Portnoy found the strong fold but slipped to a 3:1 deficit.
When the Wheels Came Off—and Back On
The oddities continued. With the board reading 9♦8♣2♦9♥6♣ and $2,800 already in the middle, Portnoy held 9♣4♣ for trips—and mucked his hand before either player acted on the river. Nate, holding K♦8♥, looked perplexed but scooped the pot uncontested.
Irritated by the pace, both players agreed to bump the blinds to $100/$300. That change sparked Portnoy’s comeback. On a four-diamond board, he made a low flush that still eclipsed Nate’s, trimming the gap to under 2:1. One hand later, Portnoy rivered a flush to crack Nate’s trips and collect a $5,600 pot.
Then came the hand that will live on in highlight reels: in a preflop-raised pot to $1,000, Nathan picked up K♠K♣ against Portnoy’s K♦9♥. The flop fell 4♠5♦9♠. Nate continued for $700 and faced a raise to $1,700 as Portnoy drew to a two-outer. Nate called. The 10♣ turn went check, $1,000 from Portnoy, call. The river brought the 3♣—a seemingly blank. Same action: check from Nate, $1,000 from Portnoy. Nate tanked, stunning the commentary team.
“If he folds, this is one of the worst folds I’ve seen in my life,” Hanks said, just seconds before the cards hit the muck. “It’s the worst fold in the history of poker.”
Portnoy tabled K♦9♥ and seized the lead for the first time since the opening orbits. The reveal sent Nate reeling. “We just witnessed an absolute disaster,” Hanks said as the players took a brief break.
Backstage, Portnoy leaned into the psychological warfare. “I’m a mental bully,” he told commentator Ben Mintz, adding, “They’re going to crucify him for that.”
Can Portnoy Take Over?
Nathan wobbled after the kings hand, with the commentators—Brent Hanks, Ben Mintz, and Jeff Platt—remarking on the apparent mental toll. Still, he answered with a sharp laydown, folding a flush to a bigger flush facing a $2,000 river bet.
Momentum whipsawed again when Nate bluffed a sizable pot with king-high, pushing Portnoy off middle pair and effectively resetting the stacks to near starting depth.
Nate soon had a chance to all but end it. On Q♥5♠7♠10♥ with Q♣J♦, and $4,000 already in the middle, Portnoy shoved holding 7♦4♦. Drawing to just four outs, he was in bad shape—until Nate tank-folded the best hand. “He is playing so passive. He clearly didn’t seek out any coaching,” Hanks said.
Three hours in, the players agreed to accelerate again, moving the blinds to $200/$400. The change turbocharged Portnoy’s march to a 3:1 lead. The commentary grew increasingly critical of Nate’s lines, with Mintz occasionally piling on.
The Finish: Offer Declined, All-In Decided
With the edge widening, Portnoy offered Nate a chance to surrender without paying the $20,000—an easy gesture from a man who reportedly has a nine-figure net worth. Nate declined and soon slid further behind. The booth suggested he had “checked out” and “given up.”
The end arrived with Nate’s A♠9♣ making top pair on the flop, only for Portnoy to turn a straight. With $3,200 in the pot, Nate bet $1,200, faced a min-raise to $2,400, and then an all-in shove. Both players—who had traded their share of pre-match jabs—shook hands as Portnoy closed it out.
In a final flourish, Portnoy offered to put the $20,000 he’d just won on a single spin of roulette, promising that if the spin fell Nate’s way, he’d get his money back. The cash stayed with Portnoy—and so did the bragging rights.
Result and Payout
- Format: Heads-up, $20,000 buy-in each, winner-take-all
- Blinds: Started $100/$200; later increased to $100/$300 and then $200/$400
- Peak audience: More than 17,000 concurrent viewers
- Broadcast: King of the Felt, presented by DraftKings
| Player | Outcome | Net Result |
|---|---|---|
| Dave Portnoy | Winner | +$20,000 |
| Eric “Barstool Nate” Nathan | Runner-up | -$20,000 |
