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Top-10 craziest prop bets

21 Feb 2011

By Aaron Todd
The human race has a long history of making crazy bets. Brian Zembic once won $100,000 when he had breast implant surgery. And yes, Brian is a man. And as of five years ago (the bet took place in 1996) he still had them, even though the bet only required him to keep them for a year.

Crazy prop bets often occur between high stakes gamblers, but some of the best bets have come from people who are much more famous for other things. Dr. Seuss, for instance, won $50 for penning Green Eggs and Ham with just 50 different words.

In recent weeks, prop bets have received increased attention thanks to a high-profile bet between two online poker pros (see number four on this list), which of course, leads me right into the top-10 craziest prop bets.

Disclaimer: Many of these bets are unhealthy, unwise and unsafe, and my description of them is in no way an endorsement to give them a try. But of course, their extreme nature is part of why they made the cut.

10. Ted Forrest vs. Mike Matusow weight loss bets
Last summer, Ted Forrest won a whopping $2 million prop bet with Mike Matusow by dropping 50 pounds in just a couple of months to tip the scales at a scant 138 in the middle of the World Series of Poker. Forrest told ESPN's Gary Wise that to win the bet he didn't eat for 10 days, then ate "a kiwi, a tomato and five or six raspberries" in the last few days to build enough energy to work out.

The two had previously bet on Matusow's weight loss, and Forrest had to fork over $100,000 when Matusow dropped from 241 to 181 pounds.

9. $10K to eat a burger
On the poker circuit, it's well known that Howard Lederer is a vegetarian. So David Grey thought he had a sure thing when he bet "The Professor" $10,000 that he couldn't finish a hamburger. Grey was left eating his words after Lederer easily downed the burger. Lederer tried to make a "double-or-nothing" bet by giving Grey – who hates olives – a chance to eat a few to even the score. But Grey apparently hates olives more than he hates losing five figures, because he passed on the opportunity and gave up the cash.

8. Cheers beard growing contest
The first of two bets between fictional characters to make the list is one of my favorite episodes of Cheers and involves the gang growing beards for a month. Sam, Norm, Cliff and Frasier each throw in $20, agreeing to let Carla judge the entries on "length, body, fullness, luster, sheen and bounce." All of them do pretty well, but Cliff has a little bit of trouble until he finds some "industrial adhesive products."

7. WSOP last longer
When an online poker room runs a "Craziest Last Longer" promotion, you'd hope that the winners would make this list. And Gregg Mardirosian and Justin Leichter certainly fit the bill. The duo was entered into a $1,000 World Series of Poker event last summer, and the player eliminated first had to get a tattoo of the UB logo and find and marry a woman in Las Vegas before coming home.

6. ESPN's "The Nuts" prop bet challenge
Okay, this one wasn't all that crazy or extreme, but the resulting video was. Daniel Negreanu, Erick Lindgren, Billy Gazes and Josh Arieh competed in four silly competitions for a "Prop Bet Championship." ESPN's footage of the field goal kicking portion of the competition (embedded below) is perhaps the most entertaining two minutes of poker coverage ESPN has produced. And if you want to see who won, check out part three of the series.

5. Lindgren golf prop vs. Gavin Smith
Lindgren is no stranger to prop bets, and his June 2007 bet with Gavin Smith (among others) that he could shoot four consecutive sub-100 rounds of golf at Bear's Best, a Jack Nicklaus designed course, while walking the course and carrying his own clubs in the Las Vegas heat received a lot of attention. Lindgren ended up winning the $340,000 bet fairly easily, but in the end said that he wouldn't do it again, because it took a lot more out of him than he had anticipated.

4. Seventy miles on a treadmill in 24 hours
Ashton Griffin, a young online poker player who has posted incredible results in both tournaments and cash games on both PokerStars and Full Tilt Poker, recently won $300,000 when he ran 70 miles in a 24-hour period on a treadmill. The craziest part of this bet? Griffin laid 3:1 odds, meaning that had he lost, he would have owed those who bet against him $900,000. I know some pretty incredible endurance athletes, but I don't think any of them are crazy enough to try something like this, especially if they have to lay 3:1.

3. Charles Barkley vs. Dick Bavetta in a foot race
During the 2007 NBA All-Star Weekend, TNT commentator/Basketball Hall of Famer/noted gambler Charles Barkley took on long-time NBA referee Dick Bavetta in a footrace. The challenge arose when Barkley criticized Bavetta, claiming he could run faster than the veteran ref could. Bavetta didn't take kindly to the criticism, saying he'd bet $5,000 that he could beat Sir Charles in a race. Eventually, the NBA and TNT found a venue for the challenge during All-Star festivities in Las Vegas, with the league and the network offering a total of $75,000 to the winner's charity. Whether Bavetta and Barkley ever put their own skin on the line (other than the skin from Bavetta's knees, which he scraped diving for the finish line) was unclear.

2. Seinfeld "The Challenge"
The second fictional bet in this top-10 list is likely the most famous bet in TV history. The gang from Seinfeld makes a last-longer bet on who can remain the "Master of their domain" the longest. The best part of this bet is George's insistence that Elaine give them 2:1 odds because she's a woman.

1. John Hennigan vs. Des Moines, Iowa
John Hennigan has won two World Series of Poker bracelets. He's amassed more than $3.2 million in lifetime poker tournament winnings. But he couldn't manage to live in Des Moines, Iowa, for six weeks for a six-figure payday. In fact, Hennigan came home after just two days. If the folks – yes, multiple people bet on this – who bet against Hennigan would like to make the same wager against me, I'll happily take the action.
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