The Craziest Bets Ever Made by Gamblers

There’s no getting away from it; people love a risky bet. Over the years, bookmakers have gratefully taken money put down on a host of outcomes, such as who will win the Academy Award for Best Actress and even at what point in the acceptance speech will the lucky recipient burst into tears. The political arena is not immune to this behavior, with elections particularly popular, and in recent times topics such as Brexit and the impeachment of President Trump have drawn considerable attention in the gambling sphere. Outlandish though this might seem, there are far weirder wagers that have been made.
Two men thinking about crazy bets.
Published on: 1 August 2019

Get Tits, Tased or Tattooed, All with One Bet

Seriously, these have been the results of some less fortunate flutters. Flutterers? Forget it. The point is, these guys really put even your most reckless gambles in the shade by putting everything on the line – families, careers, identities, even their physical well-being. Now, that’s upping the ante.

A possible gambling news headline.

Green Eggs and Gam-ble

Once in a while, there’s a bet with no losers. In 1960, Bob Cerf bet his friend Theodor Geisel that the latter would be unable to write a book using 50 or fewer words. This was no idle wager; Cerf was the founder of Random House, one of the world’s most successful publishing houses. And Geisel? Well, he took the bet and became one of the most famous children’s authors of all time, albeit under his pseudonym, Dr. Seuss. It seems that Cerf went back on his wager and never paid the forfeit, but it only amounted to $5 anyway so it’s safe to say that Geisel came out pretty well.

Take my Wife

Trial separation? Sleeping in different beds? Having an affair? None of those hold a candle to this bet when it comes to indications that a marriage may have run its course. Andrei Karpov was the unlucky man who, in a 2007 poker game against Sergey Brodov, wagered his wife on victory. Despite the desperation that doubtless drove him to such a decision, his spouse Tatiana was unsympathetic when she discovered his actions and immediately filed for divorce. Tatiana, it appears, was the major winner of the whole episode, as she subsequently married Brodov and declares herself happy with him – regardless of the fact that he won her in a game of poker.

Breasts for Brian

Ordinarily, a chest augmentation would not strike you as particularly strange or startling. However, Brian Zembic was anything but ordinary. A professional gambler whose high-stakes career helped make a healthy living for many years, Zembic took a bet in 1996 that would leave him decidedly top-heavy. A friend wagered that he would not get implants and, never one to renege on a bet, Zembic delivered. He was only supposed to keep them for a year but, 20 years later, he still has them and is beginning to worry about the threat of sagging. His story is recounted in Michael Konik’s book, The Man with the $100,000 Breasts…but then, you could have guessed that from the title.

Everything on Red

We’ve all had this fantasy, haven’t we? Walking up to a roulette table with literally every single cent to our name, and putting the whole lot on red or black. What, just us? Well, in any case, Ashley Revell from Kent in England has lived this dream. In 2004, he sold every possession and flew to Las Vegas, where he put down $136,000 – all the money he had in the world – on red. Amazingly enough, his luck was in and he doubled his money. Sensibly, he quit while he was ahead, tipping the croupier $600 and flying back to Britain to set up a poker website. “I’m not married and I haven’t got kids”, Revell said. “It’s almost like my last chance to go mad”. Way to put a depressing spin on it, dude. Anyway, he was not the first to try his luck in this specific manner; in 1994 another man from England sold his home for £147,000 ($190,000) and, unbeknownst to anyone, also flew to Vegas and staked the whole lot on red. He won as well. The lesson? Always bet on red. Ed Note: This is certainly not the lesson. Check out the best roulette strategies if you’d like to enjoy the game responsibly.

Tase Together, Stays Together

When the Green Bay Packers went head-to-head with the Chicago Bears in 2013, Illinois residents John Grant and his wife Nicole were put in a pickle. See, they were rooting for opposing sides; Nicole for the Packers, John for the Bears. Makes you wonder how they got together in the first place, given that Green Bay and Chicago share the longest running rivalry in the NFL, but I digress. Point is, this couple wanted to make an already spicy head-to-head all the more interesting. They agreed that the fan of the winning team would get to shock their spouse with a taser. When the Packers succumbed, Nicole didn’t really believe that her husband would follow through with the bet, but she was mistaken. After stepping outside, John proceeded to tase his wife not once, not twice, but three times. Understandably, Nicole responded by calling the cops. Less understandably, she later dropped all charges.

Nude Broadcast

Betraying a flagrant lack of patriotism, French television presenter Doria Tellier refused to believe that her country would qualify for the 2014 Soccer World Cup, and took a bet promising to do the weather forecast au naturel should Les Bleus prove her wrong. As it happened, the national team were made of sterner stuff and did make it to Brazil, presumably to the delight of Tellier’s viewers. True to her word, the 27-year-old reporter stripped down to her birthday suit to deliver the weather report, streaking across a football field for the cameras. Vive la France!

Ante on the Apocalypse

Predicting the end of the world has been a common pastime for as long as pastimes have existed. The Mayan calendar famously foretold that 2012 would see the Earth’s destruction (spoiler: it didn’t) and Jehovah’s Witnesses have been prolific in their attempts to predict the end of all things, with 1914, 1915, 1918, 1925 and 1975 all chosen at one point or other as the date of Rapture. Similarly, Londoner Matthew Dumbrell once took a million-to-one bet that the world would be no more by the year 2000. Obviously, we don’t want to poke fun at this man, but…how was he planning on collecting his winnings?

What’s in a Name

This is why some names should be prohibited. Of course, freedom of expression must be protected, everyone must be free to identify however they so wish, there is no question of that. However, when a man from New Zealand loses a bet and has to call him himself “Full Metal Havok More Sexy N Intelligent Than Spock And All The Superheroes Combined With Frostnova”, you have to wonder. Imagine the poor guy having to fit all that into a job application, or a tax form. Maybe he just goes by Havok?

Dying to Win

Faced with the prospect of owing £3,000 (Just under $4,000) in inheritance tax should he die before December 6th, 2005, Arthur King Robinson hit upon a novel solution. The 91-year-old retired solicitor from Devon went to bookmaker William Hill and put down £500 on odds of 6/1 that he would be dead by the end of the year. Happily, the morbid scenario did not come to pass, and the nonagenarian saw in 2006.

Tooshie Tattoo

A tattoo is probably one of the more common betting forfeits, but even so, there are stranger ways than others to get inked. Back in 2013, Will Hirons swore he’d get a tattoo of Andy Murray’s face should the Scot manage to win the Tennis Championships at Wimbledon. Of course, Murray duly took the crown, and Hirons got the British hero permanently drawn…on his left butt cheek. Basically, every time he now sits down, he’s sitting on Andy Murray’s face.

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