“One $20,000 heads-up poker match for lifetime bragging rights, everybody knows the rules.” That’s the premise as Barstool Sports founder Dave Portnoy squares off against longtime staffer Eric “Barstool Nate” Nathan in a livestreamed no-limit hold’em heads-up clash on Wednesday.
The showdown follows a Tuesday warm-up: a freeroll sit-n’-go featuring 17 Barstool personalities and popular slot vlogger “MrHandPay,” also set to stream. Nathan, a more seasoned player who regularly competes at the World Series of Poker (WSOP), has been angling for this duel for years — and now he finally has it.
The Heads-Up Match: Stakes, Structure, and Stream
The grudge match will run at $100/$200 blinds with each player starting 100 big blinds deep. Both players are putting up $20,000. Commentary on the broadcast is slated to be provided by Jeff Platt and Brent Hanks.
Key details:
- Format: Heads-up no-limit hold’em
- Blinds: $100/$200
- Starting stacks: 100 BBs each
- Buy-in: $20,000 per player
- Stream: On Barstool Gambling YouTube (King of the Felt livestream), with Jeff Platt and Brent Hanks on the call
- Date: Wednesday
Barstool Nate first challenged Portnoy in 2014, making this a rivalry 11 years in the making. Portnoy, better known for his pizza reviews and executive role than the felt, hasn’t been seen in public poker settings but has talked up his ability. Nathan didn’t mince words about perceived bankroll imbalance: “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.
Tuesday Freeroll SNG: DraftKings-Powered and Livestreamed
Before the heads-up clash, Portnoy and Nathan will join an 18-player sit-n’-go on Tuesday sponsored by DraftKings. The event is free to enter and will stream on the Barstool Gambling channel starting at 6 p.m. ET.
Prize pool:
| Place | Payout |
|---|---|
| 1st | $30,000 |
| 2nd | $15,000 |
| 3rd | $5,000 |
The field includes 17 Barstool Sports personalities along with “MrHandPay.” Expect appearances from PFT Commenter and Dan “Big Cat” Katz, while popular poker figure Ben Mintz — whom Portnoy hired, fired, and later rehired — is also in the mix. As Nathan framed it: “Me and Mintzy are probably the only two experienced players in the field,” Nathan said. “I think everybody knows how to play.”
Nate’s Edge — And His Boss’s Wild Card
Nathan, a former co-host of the Cracking Aces podcast, believes the heads-up format plays into his strengths and that the match could end swiftly: “It might not take more than 10 minutes,” he said.
He doesn’t expect Portnoy to outmaneuver him strategically but left room for variance — or a surprise coaching wrinkle: “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.”
Nathan also suggested Portnoy’s approach could hinge on mood and the marginal impact of the buy-in: “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. Still, he hopes Portnoy brings real focus for the sake of the show, predicting: “I think he’s going to play aggressive, regardless. He wants to push me around. He wants to bully me.”
Bragging Rights Now, Bigger Stakes Later?
Nathan’s “best case scenario” is a quick win followed by an immediate double-or-nothing rematch, ballooning the pot to $80,000. If Portnoy wins, however, Nathan says the bet stops there — he’s not bankrolled like the boss.
Perspective from the High-Stakes World
This in-house grudge won’t approach the nosebleed sums seen recently, such as the roughly $15 million splashed last month between Dan “Jungleman” Cates and Ossi “Monarch” Ketola during the Onyx Super High Roller Series. But for two competitive colleagues, this match carries lifetime bragging rights.
Portnoy, WSOP Talk, and Reality Check
Portnoy once teased a mega buy-in, tweeting he’d make “light work” of the $250,000 WSOP Super High Roller in 2024. He ultimately did not travel to Las Vegas for that bracelet event — nor has he been known to play public poker tournaments — leaving plenty of mystery around his true level. That veil lifts Wednesday, when he finally sits across the felt from Barstool Nate.
