Tom Dwan's $50,000 Chess Bet: A High-Stakes Showdown

In June 2007, during the World Series of Poker, a unique bet was proposed between Tom Dwan, David Benefield, and Greg Shahade. Tom Dwan bet $50,000 that he could beat Greg Shahade, an International Master, in a chess game where Greg would play without a rook. David Benefield was convinced that Greg Shahade could not be beaten even if he gave up his queen, while Tom Dwan thought he could beat Greg with just a few pawns.

Greg Shahade, along with his father Mike and sister Jennifer, are well-known in the world of games. Many chess players transitioned to poker during the poker boom of the mid-2000s, including FIDE Master Ylon Schwartz and Russian Grandmaster Alexander Grischuk. According to Jen Shahade, chess players naturally excel at poker because of their ability to devote themselves to rigorous study, practice, and pattern recognition.

David and Greg knew each other from the 2+2 poker forum and had mainly played online until this point. David reached out to Greg and asked how he would fare against a beginner if he started without a rook. Greg replied that he'd win virtually 100% of the time, which was music to David's ears. The agreement was that Greg would play for a 10% freeroll, plus $2,000 if Tom backed out for any reason. In 2007, $50,000 was a considerable amount for a prop bet. For chess players, that kind of money was unheard of outside of the top level.