World Series of Poker prop bets range from the simple, like Brad Garrett's $2,000 last-longer bet with Everybody Loves Raymond friend and co-star Ray Romano, to the complex, like the points system that Jeff Madsen, Joe Sebok, and Gavin Smith came up with that led to Smith and Madsen showing up for Day 1 of the Main Event dressed as court jesters. Romano happily paid out his loss to Garrett when he busted out of the Main Event, and Garrett in turn donated the money to charity.
Smith and Sebok, who last year had a running bet on who had the best showing at the World Series, added 2 time bracelet winner Jeff Madsen into the bet this year. After losing last year's bet, Sebok had to wear a different costume for each day of the World Series, even though he busted on Day One. He started the event dressed as a bear cub (complete with diaper), a pun on his father Barry Greenstein's nickname of The Bear. Other costumes Sebok was forced to endure included Wonder Woman, Robin and Spiderman.
This year, the bet was that the winner would play the Main Event in a cape and crown, as the two losers played dressed as court jesters. The jesters were also supposed to bear the winner into the Amazon room at the Rio on their shoulders, but Gavin Smith was conspicuously absent for that bit, playing golf in Tahoe on Sebok's Day One.
Not all the bets involved funny tasks or charitable donations. With this many big-time gamblers in the building, the bets got very big very quickly. Eli Elezra laid 5-1 odds against a bunch of his Big Game friends, including Phil Ivey and Barry Greenstein that none of them would win a bracelet this year. Ivey reportedly put up $100,000 against Elezra's $500,000 that he would add to his bracelet total by the end of the series. Elezra not only won that bet when Ivey failed to win a bracelet during the Series, he also collected on a 10-1 bet with Barry Greenstein when he won a bracelet of his own in the $3,000 Stud Hi/Lo event. The side bet with Greenstein was worth more than the first place money in the tournament!
But the biggest and craziest prop bet of the 2007 WSOP didn't take place at the Rio. It's no surprise that Phil Ivey was involved in this one too, as his reputation for action is legendary. Erick Lindgren bet a host of friends, including Ivey and Gavin Smith that he could play four rounds of golf in one day, in the Las Vegas summer, walking the course, carrying his own bag, and shoot under 100 on each round.
Lindgren suffered mightily over the course of 72 holes of golf and over 16 miles of walking in the 100+-degree heat, but at the end of the day, he was $340,000 richer, if a little short on fluids. Lindgren barely made it through that prop bet with his health, but his wallet was a lot healthier when he was done, and his spot in the prop bet Hall of Fame was assured.