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The Poker Player's Guide To Chess Gambling

A Peek At The World Of High-Stakes Chess


Jennifer ShahadeOne of America’s most famous chess games took place at the 2007 World Series of Poker in a luxury Las Vegas house. Greg Shahade, my brother, played chess against Tom “durrrr” Dwan for $50,000. Greg, an international chess master, played without one of his rooks (the most powerful piece aside from the queen) to compensate for his skill edge. David “raptor” Benefield looked on, with a heavy financial stake in the outcome.

After winning the match easily, Greg was the envy of the chess world. He later called the experience “surreal, as I remember my younger days of playing anything from $2-$10 per game, and being extremely happy to win fifty dollars from playing chess.” Greg was the natural choice to freeroll off the intersection of chess and nosebleed prop-betting. A SuperNova on PokerStars, known as “curtains” online, Greg secured title sponsorship from PokerStars for his pet project, the U.S. Chess League. The USCL is a yearly team competition of the top grandmasters and champions from 16 of the strongest American chess cities.

As the U.S. Chess League enters its seventh year with PokerStars, a federal court in Brooklyn recently declared that poker is a skill game. The New York Times reported, “In a ruling that goes to the heart of what it means to play poker, Judge Jack B. Weinstein…[reasoned that] poker is more of a game of skill than a game of chance.” The decision compared poker to chess in several instances, and used 415 million PokerStars hands from April 2010 to March 2011 to prove that given a large enough sample, skill checkmates luck.

More and more poker players have been asking me about chess lately, how to improve, and how to reasonably gamble on the game. The chess world is structured around a ranking system (ELO) that leaves little room for error and is published next to a player’s name at every tournament, as if lifetime wins and losses were taped onto a poker player’s forehead. A chess player rarely agrees to play for serious money against a higher rated player. Indeed, the night before the WSOP main event, a poker pro rated about 2100 asked me (I’m 2322) to play a blitz match. The stakes he proposed? $5 a game — a full .05 percent of the tournament we’d be playing the next afternoon!

Tom Dwan lost $50,000 to Jennifer's brother Greg at the 2007 WSOPTo give you an idea of some chess-poker player ratings, Greg estimated Dwan’s strength at 1000, while Greg holds an international rating of 2467. Chess prodigy-turned poker pro Jeff Sarwer was rated 1837 when he stopped playing and received a provisional rating of 2300 after resurfacing a few years ago in a rapid tournament in Poland. Dan Smith, EPT Barcelona high roller champ (and many other 2012 tournaments), is 2084. U.S. Chess Champion Hikaru Nakamura, who played in the 2011 WSOP is rated 2783, #5 in the world.

But as durrrr, curtains and raptor illustrated so dramatically, just because it’s hard to gamble on chess, doesn’t mean we shouldn’t try. Welcome to the ultimate degenerate’s guide to chess:

1. Brother, Can You Spare a Bishop?

As in the Shahade-Dwan game, you can alter the number of pieces each player starts with to handicap a chess game. The pawn is used to scale the rest of the army and set at one point. The knight and bishop are three points each, the rook is five points and the queen is nine points. Piece odds are best used for extreme skill discrepancies like a beginner versus a seasoned tournament player.

2. Dude, Where’s My Clock?

Most chess players use a double-sided clock for every game — when you are thinking, your time dwindles down. After you make a move you hit a button that switches the ticking pressure to your opponent. If you run out of time, you lose the game. Time limits range from a casual “blitz” game, in which each side has five minutes or less to a match for the World Championship, when each player has hours.

Players can also start with different amounts of time, ideally tweaked so that a stronger player loses on time as often as he checkmates. At the 2011 WSOP, the aforementioned grandmaster Hikaru Nakamura and a strong chess amateur and poker pro, Brandon Alan Lee, agreed to play a high-stakes blitz match. Brandon would receive two and a half minutes a game to Hikaru’s 30 seconds. Hikaru told me he was optimistic about his chances, but neither of us had a chess set or clock.

So I tweeted, “Need chess board and clock ASAP for some high stakes #wsop #chess action involving world #6 @GMHikaru.” We soon got a reply that led us to the Amazon room, which led us to the Rio parking lot, which led us to a van stuffed to the roof with boxes and bags. The generous soul we interrupted deep in a pot-limit Omaha bracelet event had packed all his belongings in his van soon after Black Friday to save money while chasing a few more dreams at the WSOP. We searched for what felt like hours in the desert sun and amidst socks and VHS tapes, finally located the clock and set. Finding the clock turned out to be harder than the match. Hikaru won the first few games so convincingly that he gamely accepted a buy-out.

Jennifer with a chess roulette wheel. Credit: Betsy Dynako for the STL Chess Club3. Roulette Chess

Combining chess with chance dates back to ancient precursors, in which the throw of a die determined which piece a player could move. I created a roulette chess wheel with curator and artist Larry List for a 2009 exhibition, “Chance Aesthetics” at the Kemper Art Museum in Saint Louis. The wheel incorporates graphics inspired by chess master and artist Marcel Duchamp. It is also a playable game. Before each move, you spin the wheel to determine which piece you can move — most spokes have two choices on them and the pieces are distributed to promote game flow. Like guessing whether a flop is red or black, the wheel can also be used for less skill-oriented side bets. My advice? Always bet on the bishop.

4. Heads-up Poker Chess

A pure way to combine chess and poker is a chess match with poker chips at stake on each game. For instance, we could play ten games of chess with 100 poker chips for the winner of each game. If I win the match 6-4, we’d go onto a heads-up poker match with me starting with 600 chips and you with 400. This system can be modified to include multiple players and to increase the weight of either poker or chess.

Jennifer plays Kenny Shei, with Terrence Chan looking on at 2012 WSOP. Credit: Rodney Chen5. Chinese Poker Chess

I ironed out the rules of Chinese poker chess at this year’s WSOP. The two games merge well. Both can easily be played head to head on a small table and it makes sense to reward players who set their Chinese hands quickly. The hybrid starts with two-player Chinese poker. Whoever sets her hand first hits the other player’s clock. The slower player must set his hands before he makes his first chess move, while his clock is ticking down. The game works best with super-fast time controls aka “bullet”, because otherwise it skews too heavily in favor of chess skill. I was usually slower than my opponents at Chinese, but better at chess.

So we’d play one minute games and as I thought an extra 20 to 30 seconds on my settings, I’d have to win the chess game in about 30 seconds. The chess game is worth three points; beating your opponent in Chinese is worth two points; sweeping Chinese is four. You get a bonus point for sweeping the Chinese AND winning the chess game.

I usually played this hybrid with Chinese low (five-card high hand in the back, five-card low hand in the middle and three-card high hand in the front) but it could be played with Chinese high, or even 17 (five-card high hand, five-card low hand, four-card Badugi hand and a three-card high hand.) We could even merge chess with the latest Open Face Chinese craze, but isn’t open-face enough like chess already?

Try one out yourself. Even without $50,000 at stake, you may find your brain straining in a way that reminds you of your favorite skill game.

Jennifer Shahade is a two-time U.S. Women’s chess champion, author and editor of She writes for PokerStarsWomen, produces videos at and and is a member of the Grindettes. Find out more on and follow at



almost 2 years ago

A 400 point Elo differential generally indicates that the lower-ranked player will lose 100% of the time. With a rating 1467 points higher than Dwan, Shahade could have played him at queen odds and won easily.


almost 2 years ago

Greg has a rating usually just under 2500 mark. Is Dwan's rating seriously around 1000? That's a really, really terrible ELO. With a rating like that you shouldn't even be considering competetive chess, let alone gambling. First learn how the pieces move!


almost 2 years ago

Here's a comparison between chess and poker. A chess international grand master plays 1 million matches against beginners will win 100% of the matches. The best poker player in the world plays 1 million heads up matches against beginner poker players will win no where near 1005 of the matches. Chess is a game of skill poker is a game of randomness with some luck and some skill.


almost 2 years ago

I agree that chess is purely a game of skill (except for flipping a coin or choosing pawns for the slight advantage of playing the White pieces, which is random, and analogous to having position in a given poker hand).

That said, luck is a much smaller factor in poker than you might think. Everyone gets the same cards in the long run: knowing how to play them is the difference between the pro and the amateur. Does chance matter on individual hands? Sure. But no human is inherently "luckier" than another: the skilled pro will always prevail over the amateur in the long run.


almost 2 years ago

I understand what you are saying Joe8 but in the example I used it does not matter what color the Master starts with against a beginner he will win every time. In poker I hear people saying things that will happen in the long run. Reality is there is no such thing. Alive player playing 10 hrs. a day 5 days a week will have to play35 yrs. to play 5 million hands which is not really large sample. Each hand is a random individual event that the previous and future hands have no effect on. In supposed long run the law of averages favors neither player. Will Phil Ivey beat a random beginner, it depends a lot on how those random cards are distributed. Even if he has edge in experience and is technically better the randomness of that card distribution evens the playing field which makes this comparison poker to chess silly. Chess is a game of pure skill and poker is a game random cards,luck and skill. With the randomness being a larger part of the game then luck or skill.


almost 2 years ago

A better game to compare internet poker to would be bingo where in both instances a player buys more entries trying to increase their chance of having a winner.


almost 2 years ago

I would add one warning to the Chess player... if it is your $50,000 that you will lose, the odds may change slightly. Perhaps making Chess more comparable to Poker than you would think.


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