10 Crazy Proposition Bets - Hellmuth, Huck Seed, and More

There’s nothing quite as exciting as the ‘ol proposition bet. These wagers have been popular for years in bars and on golf courses, and nobody seems to love them more than professional poker players. In fact, some of the most profitable (and most unusual) proposition bets have been thought up and carried out by these card-playing gamblers.

The next time you’re hanging out with your friends and someone wants to make a prop wager, you can throw out one of these classic wagers and watch your friend’s face turn white. These bets are not for the faint of heart.

1. THE VEGAN PROPOSITION - It’s a well-known fact with the poker world that Howard Lederer is a vegetarian. So Davis Grey made him a $10,000 bet that the poker pro wouldn’t eat a cheeseburger. Lederer, without hesitation, devoured one and found himself $10,000 richer. Grey hated olives, so Lederer offered him a chance to keep his money. All he had to do was eat some of those little green items with the funky-looking pimento inside. Grey decided to pass and tossed Lederer the money.

2. THE WEIGHT WATCHERS BET - Venerable poker legend Doyle Brunson used to have a serious weight problem. And over the years, he’s literally lost hundreds of thousands of dollars on wagers involving his weight. But in 2003, he was offered 10/1 odds by a group of gamblers on a $100,000 bet. All he had to do to win was get below 300 pounds. Using the Atkins Diet and Weight Watchers, Brunson got below the target weight and picked up over $1 million in winnings.

A similar bet occurred between Erick Lindgren and Mike ‘The Mouth’ Matusow just before the 2005 WSOP. They wagered $20,000 on who could lose more weight. Matusow lost 17 pounds, but he still lost by two pounds when Lindgren convinced him that he couldn’t lose any more. Matusow fell for the trick and slacked off, allowing Lindgren to win by the slimmest of margins.

3. THE IOWA BET - John Hennigan loves the action of the big city, especially the action at the local casinos. But when a group of friends bet him six-figures that he couldn’t spend six weeks living in the sleepy city of Des Moines, Iowa, Hennigan couldn’t pass up the offer. Planning to work on his golf game, Hennigan only lasted two days before he ran screaming back to the big city.

4. THE GOLF BET - Phil Ivey is not a particularly good golfer, while Erick Lindgren is supposed to be quite talented. But ever the optimist, Ivey has bet his fellow poker player $500,000 that he can beat him in 72 holes of golf sometime in the next eight years. According to sources, Ivey has been improving as of late and is beating Lindgren from time to time.

5. THE BLIND BOWLER BET - The legendary Amarillo Slim used to tell a story about a man who tried to bowl blindfolded and his inability to break 100. When someone would bravely claim that they could do it, Slim would happily place a bet with the sucker, knowing that a blindfolded individual becomes incredibly disoriented.

6. THE BIG BOOB BET - Perhaps the strangest bet has to be the one taken on by Brian Zembic, a player noted for his skill at poker, blackjack and backgammon. In order to win $100,000, he had to get 36C breast implants and wear them for 1 year. He won the bet and then decided to keep the fake boobs attached.

7. THE FISTFIGHT BET - A much younger Johnny Moss once found himself in a bar next to a man who claimed to have never lost a fight. Moss’ friends offered him 15/1 odds that he couldn’t knock the man out. Ever the gambler, Moss sucker punched the man in the hopes of an easy win. It didn’t work, and Moss got several broken bones and a trip to the hospital for his trouble. Moss’ take on the whole affair? “15/1 was too good to pass up.”

HUCK SEED - KING OF THE PROP BET

8. THE BEARDED BET - Huck once wagered that he could go a year without shaving. The former World Series of Poker champ was doing fine until an unexpected death forced him to shave for the funeral.

9. THE POINT BREAK BET - Phil Hellmuth and his pal, Huck Seed, were relaxing near the ocean. Phil bet his buddy that he couldn’t stand in the ocean, up to his shoulders, for 18 hours. With $50,000 on the line, Huck simply couldn’t pass up the opportunity and waded out into the cold water. He lasted three hours.

10. THE GOLF BET - Huck was once bet six figures that he couldn’t break 100 on a desert golf course four times in the same day using only a five iron, sand wedge and putter. His opponent also got to pick the day and predictably waited until the temperature was around 120 degrees. But that didn’t stop Huck, as he got the needed scores and collected his money.

While most of us aren’t as ambitious as Huck Seed when it comes to wagering, we still enjoy a little proposition action from time to time. Luckily, Bodog has all your prop needs covered. From unusual celebrity bets to wagers on who will get whacked on the Sopranos, there’s more than enough to keep you busy. And none of their bets involve you having to wear fake breasts for a year.

10 Crazy Proposition Bets - Hellmuth, Huck Seed, and More