The Moment Dwan and Greenstein Played the Biggest Pot in TV Poker History

Images courtesy of PokerGO, 888poker Live

Poker games with nosebleed stakes and seven-figure pots have become somewhat normal over the last couple of years, but there was a time when only a select group of players were willing to gamble so high, especially with the cameras rolling. 

High Stakes Poker was the first TV show to bring such games to the big screen, as poker legends like Doyle Brunson, Phil Hellmuth, Daniel Negreanu, and Gus Hansen decided to give their fans an insight into the games they play on a daily basis. 

In 2009, the fifth season of High Stakes Poker shocked the poker world. The stakes were higher than ever, the lineups were full of old and new-school poker stars, and it was only a matter of time before records would be shattered. 

In episode six, the legendary “Robin Hood of Poker” went up against Tom Dwan, who was just a young online poker prodigy at the time, and the two played the biggest pot in the history of the game, up to that point. 

The record has been shattered many times since, but this legendary hand laid the foundation for many to come and showed poker fans just how big pots at the green felt can actually get. 

Barry Greenstein Goes Up Against the “Kids”

When season 5 of High Stakes Poker was being filmed in early 2009, Tom Dwan was a 22-year-old poker prodigy, and Peter Eastgate had just won the WSOP Main Event for over $9 million at the age of 23. 

It was these two “young kids” who went up against the legendary Robin Hood of Poker in a hand that would become a part of poker history forever. 

The stakes were already astronomically high for that time, when the newly minted WSOP champion raised it up to $3,500 holding A♠K♥. Next to act, Greenstein looked down at A♣A♦, the prettiest hand in poker, and bumped it up to a cool $15,000. 

Facing a 3-bet from a relatively tight player, many players would have folded the cards in Dwan’s position, but he decided his K♠Q♠ was good enough to see a flop for 15 dimes. 

Unfortunately for Barry, Eastgate decided not to 4-bet his AK, and the three players went to the flop, which brought Q♥4♠2♠, significantly improving Tom’s hand. 

First to act, Tom led out for $28,700, and Eastgate released his hand. Greenstain, on the other hand, decided to protect his Aces and raised it up to $100,000. 

The money quickly went in, as Tom took the aggressive route once again, and before anyone knew it, there was $919,600 in the pot, with the equity split down the middle. 

Oldtimer Refuses to Run It Twice

Once the cards were on their backs, negotiations started, as they so often do in high-stakes cash games. Tom suggested running the board twice, but Barry wasn’t interested in this idea. Instead, he offered to pull some money back, which wasn’t to Tom’s liking. 

In the years following this hand, Tom mentioned that he believed at the time his hand was a slight favorite, which is why he refused to take some money back. In truth, the two hands both had exactly 50% equity. 

In fact, given the equities and the dead money in the pot, both players would have benefited from simply splitting the pot right then and there. Yet, winning the biggest pot in TV poker history was an idea that appealed to both players. 

In the end, no deal was made, and the dealer ran the board just once. The turn card was the Q♣, which turned the tides in Tom’s favor and made him a massive 95% favorite, as Barry could now only win with one of the two remaining Aces. 

The river card was the inconsequential 7♦, and Tom “durrrr” Dwan dragged a pot worth nearly a million dollars. Of course, this was only the first of many such pots that Dwan would win over the course of his career, but one that certainly left a lasting impression on the 22-year-old poker phenom. 

Younger Generations Take Over the Scene

In 2009, online poker was already flourishing, and players like Tom Dwan and Peter Eastgate were a part of a whole generation of young players who were building up their careers. 

Yet, there is a big difference between grinding $20 SNGs online, which is what most players were doing at the time, and sitting across the table from one of the all-time poker legends, Barry Greenstein. 

While Eastgate’s presence at the High Stakes Poker table was fueled mostly by his recent WSOP win, for Tom Dwan, this was the beginning of a cash game career that he was always destined to have. 

He wasn’t the only one, either, as players like Patrik Antonius, Phil Galfond, and many others emerged around the same time and quickly started dominating the games. 

A new, more aggressive style of play emerged in this period, which completely changed the way poker is played, both in tournaments and cash games. 

Even this hyper-aggressive playing style has gone out of fashion since then, as a solver-based GTO poker approach took root in the 2020s, but players like Tom Dwan were the ones who dared take on established poker professionals and dream of becoming poker legends themselves. 

Today, the poker world is dominated by young players, with every new generation bringing a new approach to the table and reexamining the foundations set by those who came before, but the children of the Poker Boom, including Dwan, were the ones who showed the world it was possible in the first place.