Barstool Sports Head Honcho Dave Portnoy to Prove His Poker Chops (or Lack Thereof)
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One $20,000 heads-up poker match for lifetime bragging rights, everybody knows the rules. That's the basic gist of what's going down at Barstool Sports on Wednesday when the company's founder, Dave Portnoy, takes on his longtime blogger, Eric "Barstool Nate" Nathan, in a livestreamed heads-up match.
Barstool Sports will also host a freeroll sit n' go on Tuesday, also to be livestreamed, with 17 Barstool employees and popular slot machine vlogger "MrHandPay," Nathan told PokerNews. But the main event may be the heads-up battle that has been 11 years in the making.
The stakes in the heads-up no-limit hold'em game will be $100/$200. Each player will start with 100 big blinds. Barstool Nate is the more experienced poker player, but his boss, who has been ducking his offer to play poker for years, has one advantage.
"Him and I are playing heads-up, 20k each, which is funny because he's worth like 10 billion dollars and I'm worth like 20k," Nathan said.
Poker Player Finally Gets His Opportunity
Barstool Nate, co-host of the former Cracking Aces poker podcast, first challenged Portnoy to a heads-up match in 2014. Portnoy, known for his pizza reviews as much as he is for building the Barstool Sports empire, has clashed with Nathan many times over the years, often insulting his longtime employee.
If the livestreams are a hit, Nate has an opportunity to show his boss that Barstool needs more poker content, something he's pushed for over the years. But, even more importantly, he can silence his confrontational boss.
"If we get a lot of viewers, hopefully this is just the beginning of poker content 2.0 at Barstool," Nathan said.
The match won't play as big as the $15 million splashed around last month between Dan "Jungleman" Cates and Ossi "Monarch" Ketola during the Onyx Super High Roller Series. But there will be lifetime bragging rights on the line between two competitive colleagues.
Nathan admits he has no idea if his boss even knows how to play poker. He believes there's a good chance the match will be a quick one even 100 big blinds deep.
"It might not take more than 10 minutes," he said.
Barstool Nate said that "best case scenario" is that he wins quickly and then challenges Portnoy to a double-or-nothing rematch for an $80,000 pot. If Portnoy wins, however, that will be the end of it because the sports blogger isn't bankrolled like his boss.
Portnoy, unlike his upcoming opponent, who regularly plays online and annually competes in the World Series of Poker (WSOP), doesn't appear to be an experienced card player. But Barstool Nate acknowledges he could have some tricks up his sleeve, such as secretly getting heads-up coaching from Doug Polk, although the odds seem slim.
"I think the only way he wins is a cooler situation," Nathan projects. "He's not going to outplay me, you know, it's not like he's in the lab looking at charts. It's not like he knows bets. I don't even know if he knows what bet-sizing is. I don't know. I know he knows the rules. But the only way he can beat me is, you know, I have aces, he has kings all in pre and he flops a king."
Barstool Nate made some other predictions about how Portnoy will approach the game, and one could depend on his mood on Wednesday.
"20k is nothing to him. I would say 20k is a rounding error in his bank account ... it's nothing. It's pennies on the dollar to him. So, I could see, maybe he wakes up, gets a bad night's sleep and he wakes up grumpy, I could see him just all in, all in, all in," Nate claims.
Nate's hoping Portnoy is focused and puts in some effort because it will make for a better livestream, which will be hosted by Jeff Platt and Brent Hanks.
"I think he's going to play aggressive, regardless. He wants to push me around. He wants to bully me," he predicts.
Mintzy in the Mix
Portnoy and Nathan will first compete in an 18-player Barstool Sports sit n' go sponsored by DraftKings on Tuesday. The buy-in is free, but there's a $30,000 cash prize awaiting the winner. Second place will pay $15,000, and the third-place finisher will take home $5,000.
The field will feature 17 Barstool Sports personalities, including popular poker player Ben Mintz, whom Portnoy hired, fired, and rehired within the past few years.
"Me and Mintzy are probably the only two experienced players in the field," Nathan said. "I think everybody knows how to play."
The tournament will feature many of the most popular Barstool Sports personalities, including PFT Commenter and Dan "Big Cat" Katz, co-hosts of the Pardon My Take sports podcast on Barstool.
Action begins at 6 p.m. ET on Tuesday over on the Barstool Gambling channel. Barstool Nate and Portnoy could get a taste for each other's playing style before the heads-up match a day later.
Portnoy has talked a big game about his poker abilities. He didn't just tease entering the $250,000 WSOP Super High Roller in 2024 — he tweeted out that he'd make "light work" of the tournament, which attracted some of the best poker players in the world.
Portnoy didn't come to Las Vegas for the bracelet event or any tournament. He's never been known to play in any public poker game. But he'll soon finally show the world if he's a competent player, or if he's as clueless at the game as Barstool Nate assumes.
