Crazy Prop Bets

Sports have always been a ripe field for proposition wagers: “Betcha can’t make the green in two” or “Ten bucks says a woman sings the National Anthem at the next game.” It’s not simply about winning or losing a bet. It’s also about making or taking the “dare,” being right or proving a point, and in many cases bringing somebody down a notch by showing up weaknesses or making him/her look foolish.

But there seems to be something about poker that drives players to take prop betting to crazy levels— bracelet bets, cross-dressing bets, tattoo bets…. Perhaps it’s the way big money is won at the tables or a feeling of invincibility that develops among great players. Maybe it’s just the “frat house” atmosphere of being in close competition with the same boys and girls at the table so often. Whatever the cause, it certainly has led to some wild wagers over the years. Here are eight of the zaniest:

  • Ivey vs. Beal – Most folks have heard how in 2006 Phil Ivey, with the backing of the “Corporation,” defeated billionaire banker Andy Beal in three days of heads-up poker for a whopping $16.6 million. What’s less well known is how the two also wagered on coin flips as side bets, to the tune of $70,000. Yes, Ivey won the chump change, too.

  • Grey vs. Lederer – Everyone on the poker circuit knows Howard Lederer is a vegetarian. David Grey thought he’d pick up some easy money by betting the “Professor” that he couldn’t down an entire hamburger. How wrong Grey was, to the tune of $10,000.

  • Lederer vs. Grey – Being a good sport, Lederer decided to give his benefactor a chance to even the score. The Professor knew Grey hated olives, so he offered the two-bracelet winner double or nothing if he’d just eat a few. This time, Grey wasn’t about to lose. He declined the wager and let Lederer keep his cash.

  • Lindgren vs. Smith et alia – In 2007, David Lindgren bet Gavin Smith, Phil Ivey and others that he could shoot four consecutive sub-100 rounds of golf from the pro tees at Bear’s Best, a Jack Nicklaus designed course, in one day, walking the course, carrying his own clubs and playing in 100ºF heat. That wager cost Ivey $200,000 and Smith et alia an additional $140,000.

  • Hennigan vs. Des Moines – Las Vegas-based John Hennigan has two WSOP bracelets and over $3.2 million in poker tournament winnings. A group of players pooled together over $100,000 to wager that the desert-dweller couldn’t manage to live for six weeks in Des Moines, Iowa. Hennigan must have found leaving Southern Nevada unbearable; he lasted only about 48 hours in the Hawkeye state’s capital before flying home.

  • The Ultimate Ultimate Bet – To score free entries to the WSOP in 2010, Gregg Mardirosian and Justin Leichter struck a deal with Whoever of the two got knocked out of the tournament first would pay for it by getting a UB logo tattoo and then finding and marrying a woman in Las Vegas before coming home, ala “The Hangover.” Leichter finished 52nd in his event, just out of the money. Mardirosian didn’t do quite so well, unless a free ink job and a new relationship counts as winning.

  • Forrest vs. Matusow – Back in 2008, Mike “The Mouth” Matusow weighed about 250 pounds. Ted Forrest bet him $100,000 he couldn’t get down to 181 pounds within a year. Matusow did it, alright, setting the stage for a rematch two years later.

  • Matusow vs. Forrest – For the sequel in 2010, it was 5’11” Forrest who had to lose the weight, from 188 pounds to under 140 before the end of the World Series of Poker in July. That gave Forrest only a couple of months, so Matusow laid odds of 20-to-1 against $50,000 it couldn’t be done. In fact, the Mouth was so sure the feat was impossible, he added a second deadline in September at odds of 10-to-1 against $100,000 more. Incredibly, by fasting and jogging 16 miles a day, Forrest weighed in at 138 pounds before the WSOP concluded—a $2 million prop bet that neither player will ever forget.

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