5 Most Ridiculous Bets Of All Time

5 Most Ridiculous Bets Of All Time

Gambling has become a massive global industry, generating an estimated revenue of $150 billion last year. Casino, poker and sports betting websites are dominating the internet and our fascination with a little flutter has even given rise to a whole new industry in the form of online betting comparison sites too.

But sometimes betting on a player’s score, or on the winning/losing team isn’t enough to satisfy some people. Sometimes you just have to take it one step further! Something like these…

5. The $10,000 Burger Challenge


Howard Lederer is a name famous in the poker world. This American professional has two World Series of Poker titles to his name and has earned over $5,900,000 by playing live poker tournaments. However, his hunger for winning was nothing compared to his hunger for food, and an overweight Lederer was told by doctors that he would need to get a gastric band and become a vegan to save him from an early grave.

Lederer heeded the advice of the doctors and lost more than 75 pounds. Seeing an opportunity to make some quick cash, fellow gambler David Grey bet Lederer the princely sum of $10,000 that he wouldn’t eat a cheeseburger. Unfortunately for Grey, Lederer easily wolfed down the burger and won the $10k. As they say, there’s no such thing as a free meal.

4. Gambling Against Cancer


When Jon Matthews was diagnosed with cancer, he decided to turn the bad news into a chance to make some serious money. Medical professionals told Matthews that he only had five months left to live but instead of resigning all hope he literally took a bet out on his own life.

In the first year following his diagnosis, Matthews made $8,300 simply by surviving. The following year Matthews kept keeping on and earned himself another $8,300 in the process. The odds on his life increased to 100-1 in the third year, meaning he could have made another $16,000. Unfortunately Matthews succumbed to his illness in May 2010, but went out of this world $16,600 richer.

3. Branson’s Drag Bet


Owner of Virgin Airlines and world famous entrepreneur, Richard Branson offered AirAsia chief Tony Fernandes an interesting proposition bet back in 2010. Branson bet that the Virgin Racing team would do better in the Formula One season than the debut Lotus Racing team. The stake? The loser would dress up in drag and serve on the winner’s airline for a day. Fernandes accepted the challenge, saying: “Bring it on, the sexier the better” and sending a mock-up of what Branson would look like as a female flight attendant.

In the end Virgin came in 12th to Lotus’ 10th, meaning that on the 12th May Branson took to the skies with AirAsia, “complete with make-up, a pair of heels and freshly shaved legs” for a charity flight from Perth to Kula Lumpur

2. Man Loses His Wife In A Card Game


When most people run out of money in a game of poker they simply have to exit with their head hung in a shame and a wallet feeling much lighter. Not Andrei Karpov though. When the Russian player was feeling a little short in a game of cards against opponent Sergey Brodov he made a bold move and put his wife up as a stake.

Luck was not on Karpov’s side and he ended up losing the hand, along with his wife Tatiana. She was so furious at being bet away that she divorced Karpov saying: “It was humiliating and I was utterly ashamed. But as soon as my ex-husband did that I knew I had to leave him.” Brodov literally won the heart of Tatiana and they ended up getting married. “Sergey was a very handsome, charming man and I am very happy with him,” she said, “even if he did ‘win’ me in a poker game.”

1. The Breast Bet


Professional backgammon player, Brian Zembic had a flare for taking up strange bets. After winning a $15,000 challenge that he couldn’t live in a bathroom for a month and sleeping in a box for a week to win $25,000, the Canadian gambler decided to take it one step further.

Whilst playing in a high stakes game, the talk once turned to boob jobs. Fellow gambler Jobo and Zembic disagreed over the seriousness of the operation and eventually settled their argument with a wager. If Zembic would be willing to get 38C breast implants and keep them for an entire year he would win $100,000.

After losing a serious amount of money on the stock market, Zembic decided to eventually take up the challenge. Hearing that Zembic has undergone the surgery Jobo tried to buy out the bet for $50,000, but Zembic refused. Not only did he keep the breasts for a year to win the bet but Zembic still has them to this day.

Although the breast bet has propelled Zembic into a celebrity status he says he will take them out if his six year old daughter wanted him to. He also seems to have learnt that living up to crazy dares isn’t everything. “The other day someone bet me that I wouldn’t cut off my own penis but I’ve since decided I’m not going to do it,” he said. “I’ve learnt that money isn’t everything.”




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