The Legend of Tom Dwan’s Very Expensive Chess Lesson

A $50,000 prop bet between Tom Dwan, David Benefield, and Greg Shahade still lives on as legend in the chess world. In the ensuing 15 years, the parallels between chess and poker have continued to grow.

David Hill
Apr 2, 2023
Tom Dwan (photo courtesy: PokerGO)

It was June of 2007, the World Series of Poker was in full swing, and two young poker players were taking a break from the action and sharing a meal at PF Chang’s. One of the players, David Benefield, mentioned he had been playing a lot of chess recently with another poker player who was pretty good at chess. That guy’s name was Greg Shahade, and he was an International Master, among the top 100 players in the United States. David felt like Greg was so good at chess, even if Greg gave up his queen – the most powerful chess piece on the board – David couldn’t beat him.

The other player, 20-year-old Tom Dwan, was unconvinced. He argued that with a queen up on his opponent, he could just trade off all the pieces on the board and use his extra queen to force a win. In fact, he figured he could beat Greg with far less than a queen, maybe even a couple of pawns.

“I thought he was way off, he thought I was way off, and so we had a proper opportunity for a fun bet,” remembers David. He proposed to Tom a bet: Greg would play without a rook, and if Tom could beat him David would pay Tom $50,000. Never one to back down from a good prop bet, Tom agreed.

If Greg’s name sounds familiar to you, it might be because he’s from a family that is well-known among players of games. His father Mike Shahade is a FIDE Master and in Philadelphia is sometimes called the “Mayor of Sugar House Poker Room.” His sister is Jen Shahade, a Women’s Grandmaster, the Mindsports Ambassador for PokerStars with nearly half a million dollars in tournament cashes, and the host of The Grid poker podcast.

The Shahades grew up playing games in their family, especially chess, but eventually found their way to poker. The poker boom of the mid-2000s brought a number of chess players to the poker tables, like FIDE Master Ylon Schwartz, who finished fourth in the 2009 WSOP main event, and Russian Grandmaster Alexander Grischuk, who became a regular in online nosebleed stakes and once considered poker to be his “second profession.”

According to Jen, chess players naturally excelled at poker because of their ability to devote themselves to rigorous study, practice, and pattern recognition, and in the early days found it easy to win. “That’s key. They know how to study a game. It’s not haphazard, they know how to structure it,” she explains. “Even poker, you can kind of structure into opening, middle game, and end game. Your opening ranges, your post-flop play, your play when you’re deep in a tournament, if you’re a tournament player. It’s very similar to how you would structure your chess weaknesses and strengths. Study your openings, make sure your repertoire is good and you know what you’re doing when you’re dealt Jack-Nine suited in the cutoff. The more preparation you do at home, the easier it is to play above the rim when you’re in action.”

For players like Grischuk and Schwartz, poker offered something chess couldn’t: money. Prize pools in major chess events paled in comparison to even some weekly online poker tournaments. Chess players devoted many hours of study to a game that offered very little financial reward, but poker offered a great deal of financial reward for very little effort. For some, the transition was a no-brainer. And in those days Greg and Jen Shahade found themselves playing a lot of poker.

David and Greg knew each other from the twoplustwo poker forum, in the single table tournament subforum. They had mainly played online to that point. David reached out to him and asked him “How would you do against a beginner at chess if you started without a rook?” Greg replied that he’d win virtually 100% of the time. That was music to David’s ears. He knew Greg was in town playing some of the WSOP events, so he invited him over to the house David and Tom shared with several other poker players. The arrangement they came to: Greg would play for a 10% freeroll, plus $2,000 should Tom back out of the game for any reason. Greg hemmed and hawed about having to change his flight home to make the game work, but secretly he was overjoyed. He considered himself lucky to get the call; after all, as he remembers it, “there were probably quite a few other strong players present in Vegas who would be glad to play a chess game for perhaps a bit less money.”

Why, you may wonder, didn’t Greg just back himself if he was such a lock to win? In 2007, even for young poker millionaires, $50,000 was a considerable amount for a prop bet. For chess players, that kind of money was outrageous. While plenty of chess players loved to gamble over the board, rarely did they play for more than $100 on a single game. And these were still the early days of the Shahade’s forays into poker, so it’s fair to say Greg wasn’t rolled for it, even if he did feel confident.

“Chess players don’t often have that much money,” Jen says. “The number one thing that will make you good at poker is if you have money. That’s number one. Because then you have more choice of games to play, and you have less aversions to losses.” She says that even if you play a game with a competitive edge over your opponent, if you’re gambling then your bankroll size could erase that advantage. “If you have $20,000 and you lose it, then you might not be able to pay rent. So having that mentality and then playing poker, it puts you at a huge disadvantage over somebody who doesn’t have that loss aversion.”

And anyway, who could be sure Tom and David weren’t hustling Greg? He had never played Tom and had no idea what his actual strength was. “If my opponent simply happened to be a 1600-1700 level player, I would be a huge underdog to win.”

Before Greg and Tom played for the $50,000 they agreed to play one practice match where Greg would give up a knight rather than a rook. The practice match was for $5,000. They agreed they would play each with a clock; if Greg’s time ran out, he lost, but if Tom’s time ran out he could think for as long as he wanted and pay a penalty for every minute he went over his time. They also agreed to flip a coin before each game to decide what color each person would play and which of the two knights or rooks would come off the board.

Before the practice game began, Tom put two pawns on the board and demonstrated an “en passant” capture, a standard move in chess, and asked Greg if it was permitted. “This was another good omen for my chances.”

They played the practice game, and it only took Greg seven moves to find a checkmate. He may have been a chess player, but he was also a professional gambler. He had a little hustle in him as well. “I felt it would be poor form to checkmate him in just 8 moves, and may discourage any future action,” he said. So instead, he castled, prolonging the game a bit longer to give the appearance of parity. “I understand that this is very shameful.”

By move 17 the game was over, and any fears Greg had about Tom sandbagging his true strength were allayed. David took Greg aside to ask him how he felt about it, and what odds Greg thought he could realistically offer to get Tom to raise the stakes. Tom, however, came away from the practice game in no mood to press the bet. “I tend to not try to push people into making a bet they don’t want to make,” David says of the negotiations. “He was very happy to make the original bet as was I, he quickly passed on the next offer, fair enough.”

Instead, Tom asked that they change the terms of the bet to a best of three, to reduce variance. “I didn’t think there would be much variance and didn’t particularly care how many games he wanted to play, so it didn’t seem like a big deal to me,” David says. Greg, however, felt like if he needed to play more chess, he should be paid more money. He wanted another $2,000. “At this point I was even confident enough to put the money up myself,” he wrote. When all was said and done, they agreed on a best of three, $55,000 against $50,000, with Greg freerolling for $7,800.

The first game did not go anything like the practice game. After about fifteen moves Tom surprised Greg with a move. “I actually overlooked a move that my opponent saw. I assumed this would never happen under any circumstances, so I was a little rattled,” Greg wrote. Tom was playing much better in this game. “But part of me believed it was accidental, as he seemed so tentative and unsure with every single move he made.”

In the end, Greg won. That first game lasted 44 moves, and left both players a bit exhausted. While the game may have given Greg a brief and slight scare, David was unconcerned. “There were a few higher-level chess players there and I was just listening to them in the background. One of them was like ‘oh yeah Tom is drawing dead vs Greg in this spot’ and that was good enough for me to not worry much.”

The second game was a cakewalk, and Greg won after Tom let his time dwindle down to only thirty seconds.

Afterwards they all settled up, and Greg was surprised to see Tom take the loss in stride. “I think he thought it would be a bit easier, but he didn’t seem too bothered by it either way,” David remembers. “He’s always been pretty good at taking losses and this spot was no different.” Tom asked Greg if he thought he had a 5% chance of winning. “I didn’t know what to say,” Greg wrote. “I worked so hard during the games that I felt some sense of danger. Whenever you work hard during a chess game you need to worry a little bit. However, looking back, it’s hard to imagine him actually winning. He simply has to survive so many pitfalls and then after all of that he has to demonstrate the technique to beat me from a winning position.”

It’s now been more than fifteen years since that bet. In the ensuing years, much has changed for both games. Chess is only now, finally, seeing new financial opportunities through online content creation and an expanding player base that is beefing up tournament pools. Poker, meanwhile, has seen technology like solvers turn the game into something more akin to chess: a game where effort translates to ability. “The reality at the elite levels is that it’s quite boring,” says David, who still plays high stakes poker professionally. “The best have put in countless hours grinding sims attempting to get as close to GTO play as possible, similar to how chess players study with stockfish.”

“As soon as the advent of solvers came up, you started to study poker a lot more like you would study chess, and use the computer to analyze what you should do with each hand and try to remember the patterns,” Jen Shahade says. “I feel like it helped me in my understanding of the game and I was able to latch onto them very quickly. But it was also bad, because it meant that you just didn’t have time to study both games.”

Over the last fifteen years, the poker world has seen plenty of prop bets more outrageous and for more eye-popping stakes than this one. But in the world of chess, where prize pools still languish and gambling is still a novelty, this bet has become the stuff of legend – the triumph of one of theirs over poker’s elite.