Dave Portnoy Induces 'Worst Fold in Poker History,' Wins $20K Heads-Up Match
Table Of Contents
The poker grudge match a decade in the making between Barstool Sports founder Dave Portnoy and his employee, Eric "Barstool Nate" Nathan, finally took place on Wednesday, and it was quite the battle for a $40,000 pot, with the former coming out victorious.
King of the Felt, presented by DraftKings, lured in more than 17,000 concurrent viewers at its peak. The game — a $20,000 buy-in heads-up contest starting with $100/$200 blinds — provided some unconventional plays, and some moves from both players that would make any seasoned pro scratch their head.
Portnoy didn't play nearly as wild and crazy as Nate anticipated in a pre-game interview with PokerNews earlier this week.
Barstool Sports, on the Barstool Gambling YouTube channel, hosted an 18-player freeroll sit n' go for some of its employees on Tuesday. Barstool Nate and Portnoy both competed, but neither cashed, although Portnoy made some strong plays, including correctly folding with A♦K♥ to an all-in bet on a flop of 5♦A♥6♦ against bottom set. Ethan Kamps ended up winning the tournament for $30,000.
The three-table sit n' go was an appetizer for a heads-up match the following day between Barstool Nate and his often critical and confrontational pizza-reviewing boss.
Experienced Poker Player Hitting Hands
Nathan, a regular at the World Series of Poker (WSOP), is the more experienced player in this heads-up match. Portnoy, however, played online during the 2000s on PartyPoker, but doesn't have much, if any, live poker experience.
The early battle went mostly Nate's way, although he did get off a solid bluff. Portnoy min-check-raised with a gutshot straight draw on the turn and just jack-high. Nate called with top pair. An ace landed on river, no help to either player, and Portnoy bet $2,000 with jack-high. Nate had a pair of 10’s and folded the best hand.
But the match would quickly turn south for the wealthy entrepreneur. Portnoy, perhaps accidentally, in one hand, announced his hand — 10♦8♠ — and the commentators picked up on it. But, apparently, his opponent didn’t. The flop came out 3♠8♥6♥.
Portnoy, who flopped top pair, bet $600, more than the size of the pot. Nathan, who had A♣3♥ and was clearly unaware that his boss verbalized his hand, called with bottom pair. The turn was the 7♣, and another $600 bet ensued.
“Nate, he told you his hand,” commentator Brent Hanks said.
Nathan wisely folded this time around, but failing to notice Portnoy’s misstep cost him some chips.
Moments later, on a board of 10♠4♣9♥5♣, Nate bet $600 with 6♣2♣. Portnoy then raised to $1,200 with 9♠4♥. The river was the 8♣ to complete the flush. Portnoy bet $1,000 and then called a raise to $3,500, putting Nate out in front by more than a 2:1 advantage thanks to a bad beat.
Both players would flop top pair on the next hand, but Nate had a better kicker, only to make a fold with the best hand on the turn that confused the commentators when an ace landed and Portnoy made a small bet of $400.
There would be another crucial early pot that could have gone worse for Portnoy. Nate, holding 8♦4♦, raised to $400 preflop. Portnoy called with 5♥2♣, and the flop came out 10♦2♦3♥. Nate again bet $400, and received a call.
The turn was the 3♥. Portnoy decided to bet $1,000 with a small pair. His opponent, sitting on a flush draw, called and hit the flush on the 5♦ river, which gave his opponent two pair. Portnoy bet $1,000 and then faced a raise to $4,000.
Portnoy would make a strong and correct fold, but fell behind 3:1 in chips.
Action Gets Weird
The match would feature some strange hands, starting with one pot where Portnoy, with 9♣4♣ on a board of 9♦8♣2♦9♥6♣ for trips, just mucked his cards before either player had acted on the river with $2,800 in the pot.
Nate, holding K♦8♥ for an inferior hand, was confused, but took down the pot due to his opponent folding without facing a bet.
Both players would soon agree to raise the blinds to $100/$300 after Portnoy began showing frustration with the pace. Portnoy would, soon after, begin to battle back when, on a board with four diamonds, he hit a low flush that was still bigger than Nate’s flush.
Nate’s lead dropped to less than 2:1 for the first time in quite some time. One hand later, Portnoy rivered a flush to crack Nate’s trips for a $5,600 pot.
Luck would, it seemed, return to Nate’s side with K♠K♣ against K♦9♥ in a preflop raised pot to $1,000. The flop came out 4♠5♦9♠, and Nate continued for $700. Portnoy raised to $1,700 drawing to a two-outer.
Nate just called before the 10♣ appeared on the turn. Following a check, Portnoy bet $1,000, and his employee called to see the uneventful 3♣ on the river.
The same action as the turn transpired on the river, with Nate checking and facing a $1,000 bet. But this time he’d go into the tank, which confused the commentators who were shocked he hadn’t willingly put more chips into the pot with pocket kings on a relatively dry board.
Nate would shock announcers Brent Hanks, Ben Mintz, and Jeff Platt even more when he did the unthinkable and folded his cards.
“If he folds, this is one of the worst folds I’ve seen in my life,” Hanks said, right before the fold. “It’s the worst fold in the history of poker.”
Portnoy, who had regained the lead for the first time since a few hands into the match, showed his cards, which put Nate on tilt.
“We just witnessed an absolute disaster,” Hanks continued before the players took a short break.
“I’m a mental bully,” Portnoy told commentator Ben Mintz during the break as to how he conned the more experienced player into folding. “They’re going to crucify him for that.”
Can Portnoy Take Over the Match?
Barstool Nate began to unravel a bit following the questionable fold. Even the announcers, all experienced poker players, continued to harp on the fold and suggested the play left Nate mentally shook.
But Nate did impress the trio of announcers when he folded a flush against a better flush when facing a $2,000 bet on the river. Portnoy, however, was beginning to build a lead. But his opponent started to pick up some momentum and bluffed off a sizable pot with king-high, forcing middle pair to fold, leaving both players back to right around starting stack.
Nate had an opportunity to essentially end the match with Q♣J♦ on a board of Q♥5♠7♠10♥ when his boss, holding 7♦4♦, moved all in with $4,000 in the pot. He tanked before once again folding the best hand. Portnoy was drawing to just four outs, but still scooped the pot.
"He is playing so passive. He clearly didn't seek out any coaching," a critical Hanks said.
Three hours into the match, and the stacks were still nearly even. The players then agreed to raise the blinds to $200/$400 in hopes of speeding up the action again. All it did was speed up Portnoy's ability to build a lead that would grow to 3:1.
Hanks continued to trash Barstool Nate's game, making critical comments during nearly every hand dealt. Mintz even piled on at times.
Portnoy, pulling away, made an offer for his opponent to surrender and not have to pay the $20,000. The money is pennies to Portnoy, who has a nine-figure net worth, according to Yahoo.
Nate declined the offer, and would fall to an even larger deficit. His frustration turned into full tilt, which led the commentators to claim he "checked out" and had "given up."
Barstool Nate lost his opportunity to end the match earlier, and he'd pay dearly for it inevitably. The University of Maryland graduate, with A♠9♣, flopped top pair, but his opponent hit a straight on the turn with $3,200 already in the pot. Nate was drawing dead, but he bet $1,200 only to face a min-raise to $2,400.
That was followed by an all-in raise, and the two competitors, both who talked some trash before the match, shook hands. Portnoy then offered to bet the $20,000 he won on a spin of roulette, and if it were to go Nate's way, he'd get the money he lost back. But he lost the priceless bragging rights for good.
