Tom Dwan, one of the most recognizable faces of the poker boom era, has been involved in some of the most unforgettable hands ever played. From scooping the biggest televised cash-game pot in history to clashing with BetRivers Poker ambassadors Phil Hellmuth and Phil Galfond on High Stakes Poker, Dwan has carved his name deep into poker lore.
One of those iconic moments recently resurfaced during a Q&A session on the Run It Once YouTube channel, where Dwan revisited the thought process behind one of his most famous bluffs.
Forcing Two Better Hands to Fold
Among Dwan’s most talked-about hands on High Stakes Poker was the one where he managed to make two superior holdings—belonging to 2008 WSOP Main Event champion Peter Eastgate and Poker Hall of Famer Barry Greenstein—hit the muck.
The hand began with Greenstein opening to $2,500 holding A♥ A♠, prompting a wave of callers and creating a classic family pot. On the 10♦ 2♣ 2♠ flop, Greenstein fired $10,000. Dwan responded with a bold raise to $37,300 holding Q♣ 10♣, clearing out most of the table. Eastgate, however, cold-called with 4♥ 2♦ for trips, and Greenstein came along as well.
The 7♦ turn checked to Dwan, who unloaded $104,200 into a $133,500 pot. Remarkably, both Eastgate and Greenstein folded, surrendering the pot to Dwan.
As the chips were pushed his way, Eli Elezra remarked that Greenstein had folded the best hand. Dwan immediately disagreed, insisting Eastgate had been ahead—a claim he later explained during the Q&A when asked how he reached that conclusion.
Spotting an Opportunity
“I didn’t know that,” Dwan admitted. “But it made sense that Eastgate had a deuce.”
Dwan explained that he believed Greenstein continuation-bet the flop too often, which inspired what he openly described as a “really f****** weird” flop raise.
“On paper, it’s terrible,” Dwan said. “Put it into a solver and it’s probably awful—though I never did.”
When Eastgate called the raise, Dwan assumed the hand was over. That feeling only intensified when Greenstein also called.
“I thought my money was gone. I was basically ready to leave the casino,” Dwan said. “But when Greenstein called too, it didn’t add up. Once Eastgate calls, he almost certainly has a deuce. That’s when I thought, maybe I actually have a spot here.”
At that point, Dwan decided the bluff might be profitable.
“I’m not even sure it was technically correct,” he admitted. “I’d been running hot online and live, and looking back, I don’t know if it was really plus EV.”
Still, Dwan trusted his instincts.
“If there’s a spot where everyone thinks I’m punting $50k, but I think I’m risking $2k, I’m just gonna go for it and hope.”
Why Eastgate Let It Go
A major factor behind Dwan’s confidence was his extensive history with Eastgate.
“He was really good,” Dwan said. “We’d played a ton of $25/$50 online, though the stakes on High Stakes Poker were big for him.”
Dwan also believed recent results mattered more than the actual cards.
“I’d probably been winning like 10bb/100 against him over the last month. It was one of the best stretches I ever had versus anyone,” he said. “I just didn’t think he’d find the call.”
That read proved spot-on.
“I figured he’d just say, ‘screw you, Tom,’ and fold,” Dwan said. “And that’s exactly what he did.”
Almost Forgetting Greenstein
Once Eastgate folded, Dwan felt the hand was essentially over.
“I thought, once Eastgate folds, I win,” he said. “I kind of forgot about the rest.”
Even as Greenstein went deep into the tank, Dwan still expected a fold.
“Even if he calls 10% or 20% of the time, that’s just lighting money on fire,” Dwan said.
Looking back, Dwan remains confident in his read.
“I was 90% sure Eastgate had the best hand,” he said. “Greenstein had an overpair, and Eastgate almost certainly had a deuce.”
The bluff succeeded, the reads were accurate, and the hand stands as one of the defining moments in Tom Dwan’s rise to poker superstardom. ♠️
