Eric 'Barstool Nate' Nathan finally got his heads-up dream duel with Barstool founder Dave Portnoy in a livestreamed poker showcase on Wednesday night, but the dream matchup went south for Nathan, who lost his $20,000 buy-in after roughly three hours of play.
"Killed ‘em," Portnoy told host Ben Mintz in the post-game press conference. "Which I knew would happen."
Nathan had chased this match for the better part of two decades. He finally got his wish in a two-day poker showcase featuring an 18-player livestreamed tournament on Tuesday and a heads-up battle with Portnoy on Wednesday. Both shows, which were anchored by Jeff Platt and Brent Hanks, captured a lot of viewers and brought potential new fans to poker, validating 15 years of Nathan pitching the game to his boss. But that win is now overshadowed by the loss he took from Portnoy, who won't let it go any time soon.
"He plays a lot of poker," Portnoy continued. "I’ve played twice in fifteen years. I tried to tell him. I didn't want this, I didn’t want the match."
The post-loss plan called for taking the money to a nearby roulette table, where Nathan could get his buy-in back if Portnoy won on a single roll. If he lost, both would leave empty handed. The plan later changed due to filming restrictions and the money will linger on a sports bet this weekend. "I don’t even want his money, to be honest. But you have to take it, as a man of honor you have to take the money."
It was a rough night with silver linings for Barstool Nate. The worst fold Hanks has ever seen?
The match wasn't all Portnoy, by any means. Nathan jumped out to a lead and his confidence was growing, but that's when he made what Brent Hanks called the worst fold he's ever seen.
Nathan picked up pocket kings with blinds at $100/200 and raised to $1,000 ("I'm just going to keep raising, Dave."), bringing in Portnoy and his 
. The flop was 
and Nathan tossed out another $700, which Portnoy raised to $1,700.
"Why?" Nathan asked out loud before he called. The first sign of trouble.
The turn was the 
and Nathan, who seemed to be frozen in his tracks, check-called a $1,000 bet from Portnoy. A 
on the river meant nothing and Nathan checked before Portnoy tossed out $1,000 with top pair and the worst hand.
"Insanity," Nathan muttered. "Flop a set?"
No one considered that he would fold a $8,400 pot to a $1,000 bet with an overpair, and Mintz refused to even considered it. But that's exactly what he did, giving up the pot and the lead.
The beginning of the end
Nathan didn't sputter away immediately. The two players traded the lead until Nathan crumpled under Portnoy's momentum for good in what the commentators called "full-blown spazz mode."
The flop had 
and Nathan had 
, but that didn't stop him from raising Portnoy's $1,000 bet to $2,500. Portnoy called with 
and the turned a third eight, setting up a $3,000 bet that Nathan couldn't call. It left him with around $10,000, well behind Portnoy's $30,000 and change.
A few hands later, with just $6,700 left, Nathan raised to $800 with 
. Portnoy called with five-four and picked up a straight draw with the 
flop. Nathan tossed out $800 after Portnoy checked and a call brought the 
of destiny for Portnoy's straight. Nathan bet $1,200 and Portnoy raised to $2,400, prompting a shove from the short stack. Portnoy snap-called and that was it for the challenger.
Nathan had his chance to explain during the post-game scrum.
"He played very poorly for an hour and then he figured out how to raise," Nathan told Mintz. "He played pretty well for the last couple of hours."
"I knew the result walking in here," Portnoy said further. "I knew there was no way he was going to beat me."
Throwing the poker loss to the side, the rest of the week was a big victory for Nathan. The two-day poker event at Foxwoods was a success and Barstool personalities fit right into the livestream poker vibe, as he had predicted.
"Everyone is stoked," Nathan said on X. "And poker content at Barstool works!! $20k comes and goes but proof of concept is forever."
