Top 5 of The World’s Stupidest Bets Ever

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Discover 5 stupid bets that people won as insanely as possible. Learn about the man who got a breast to win a bet and much, much more!

Betting is an insanely old form of enjoyment whether it is professional or just between friends. It has also led to those who are addicted at winning so much so that they are willing to go to any lengths.

We live in a mad world where most bets have been drastically reduced to drunken frat-boys that usually end in stupid YouTube videos where pain is the main thing. This is actually something new. Back in the day, wagers were an art form dominated by crazy dudes ready to risk their short lives in incredible stunts, all because someone bet them that they could not do it. And we’re happy about this, otherwise we would be missing a few magnificent stories.

Over the last few decades, there have been instances of people making some really stupid bets. Here are the top five which will blow your mind.


5. Taking on an Insane Golf Challenge

Huck Seed is widely regarded as one of the greatest gamblers of all time and he attained much of his popularity after winning the 2016 World Series of Poker. It is fair to say that Seed does not make a bet unless he is 100% sure of winning. He was once given the chance to bet on scoring 100 on a desert golf course with numerous other difficulties thrown in. Seed was asked to get this score while only having a sand wedge, five iron, and a putter. Things were made even worse when it was revealed that the bookie would be choosing the day.

On a ridiculously hot Las Vegas desert day, with temperatures touching 120°F, Seed entered into the course and managed to do the unthinkable. He managed to achieve the target after just six rounds, thereby teaching a lesson not to mess with the best.

4. Betting on a Burger with Howard Lederer

The World Series of Poker is regarded as the highest crown for any gambler. If so, Howard Lederer would take his position as one of the fiercest gamblers in the world after having won the title two times. He has already earned a whopping £5.9 million just by playing poker. His hunger for gambling, though, may be slightly smaller than his hunger for food. Overweight Lederer was advised by his doctors to go vegan in order to reduce his weight. Sticking to the advice, Lederer went on a massive diet that led to a drop of 79 pounds.

David Grey, a fellow gambler, saw this is an ideal opportunity to make some money (of course, OddsDigger.com wasn’t invented back then). He offered $10,000 to Lederer if he was to finish a rather big cheeseburger. Grey was confident that Lederer would turn down the opportunity, but it became one of the disastrous and easiest ways to lose $10,000. Lederer finished the meal and pocketed a cool $10,000.

3. Getting a Tattoo of Andy Murray on a Private Spot

There used to be a time when Andy Murray just did not seem to have the luck to become a Grand Slam champion. After finishing in a series of Grand Slam events as the finalist, there were not a lot of bets on Murray to win a title in 2011. However, the Scotsman managed to win his first ever Grand Slam with the Australian Open title that year. In a sport where passions run high, it was not surprising that one of Andy Murray’s fans came up with a stupid bet, that he is likely to regret for the rest of his life.

A young British fan, Will Hirons, claimed that he would tattoo an image of Murray on his arse, if the Scot was able to win the title again in the subsequent year. As history would show, Murray ended up winning the Australian Open again in 2012.

2. Losing a Wife over a Game of Poker

Losing and winning are part and parcel of poker, but sometimes the value of a loss is difficult to quantify. Players have a tendency to go beyond money when it comes to stakes in a game of poker, but Andrei Karpov will probably regret such a tendency. In a game of poker against his friend Sergey Brodov, Karpov was suddenly left short of money and decided to put his wife as the stake instead. Incredibly, Brodov did not turn down the offer and the game continued.

Even then, luck was not Karpov’s side, he ended up losing the game and, subsequently, his wife. The loss turned out to be permanent, as his wife ended up divorcing him. To make matters even worse for the punter, his wife ended up marrying Brodov. It certainly takes its place as one of the greatest losses in a poker game, for who is a different question, and possibly the second worst bet stake in history.

1. Man Gets Breasts to Win a Bet

Brian Zembic has a reputation for being a tough guy to win, when it comes to a bet. The professional backgammon player lived up to his reputation when he accepted a bet from his friend to have a fake pair of breasts implanted for one year. Zembic stood to win $100,000, but no one believed anyone would do it, no matter for how much. At least, that was what his friend thought before Zembic accepted the offer. Zembic went on to live with the fake breasts for almost 20 years before recently removing them.

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