Gambling has a knack for pushing boundaries, doesn’t it? With the right platform—be it a top-rated online casino or a land-based gaming house—you might stumble across bets so bizarre they leave you scratching your head.
Believe it or not, wagering on the weird and wonderful is far from a modern invention—it’s been a peculiar pastime for decades!
Intrigued by the strangest bets placed over the years? Let’s dive into some of the most outrageous ones.
1. The man with the suitcase
Let’s start with the incredible story of William Bergstrom, better known as the Suitcase Man or The Phantom Gambler. Bergstrom wasn’t just any gambler—he was a legend in the world of high-stakes betting.
In September 1980, he walked into Binion’s Horseshoe Casino in Las Vegas, Nevada, with two suitcases. One was empty, and the other held a jaw-dropping $777,000 in cash.
At the time, casino owner Benny Binion had a policy: no matter how big the wager, the casino would honour it. So, Bergstrom placed an audacious dice bet… and won.
He walked out with his suitcase now filled to the brim with winnings. Rumour has it he was prepared to end his life if he lost, but that wasn’t the case, at least not yet.
Bergstrom vanished from the casino scene for a few years, only to return in March 1984. He bet $538,000 and won again. But his luck didn’t hold forever. In November of that same year, he bet a whopping $1 million—and lost.
Tragically, shortly after this defeat, he ended his life. Whether it was the loss or something deeper that drove him remains a mystery.
2. Betting on the apocalypse
Ever wondered if someone’s ever tried to bet on the end of the world? Well, John Gillies from the UK did just that. He wagered £1,000 that the world would end before the year 2000. Sounds absurd, right?
But here’s the kicker: Gillies won—not because the apocalypse happened but because the bookmaker, who was a friend of his, passed away before the new millennium. Talk about a morbid twist of fate!
3. The snail racing championship
Leave it to the British to turn snail racing into a spectacle! Every year, Norfolk hosts the World Snail Racing Championship, an event that draws participants and spectators alike. Naturally, where there’s competition, there’s betting. Enthusiasts place their wagers on the snail they believe will cross the finish line first.
It’s quirky, it’s fun, and it’s yet another example of how humans can turn anything into a betting opportunity.
4. Rolling with the cheese
If you thought snail racing was peculiar, wait until you hear about the cheese-rolling tradition in Gloucestershire, England. Every year, daredevils chase wheels of cheese down a steep hill, risking life and limb for glory.
Spectators, of course, get in on the action by betting on which chunk of cheese—or which competitor—will make it to the bottom first. Certainly one of the most exciting and strangest thing you can bet on! Who knew dairy could be so thrilling?
5. A cheeseburger worth $10,000
Howard Lederer, a professional poker player nicknamed "The Professor," was known for his calculated gameplay and vegetarian lifestyle. But even he couldn’t resist the allure of an unusual wager. After a game, fellow poker pro David Grey challenged Lederer to eat a cheeseburger for $10,000.
Without a moment’s hesitation, Lederer accepted. Despite attempts to back the other out, neither budged. Lederer ate the cheeseburger and pocketed the cash.
But that’s not the end of the story. Apparently, Lederer later offered Grey a chance to win his money back—if Grey would eat just two olives. Whether Grey took the bet or not remains a mystery, but one thing’s for sure: poker and its players know how to keep things interesting!
6. Betting it all on red
Roulette has always been a game of high stakes, but Ashley Revell took it to an entirely new level. In 2004, the English gambler sold all his possessions—yes, even his clothes—leaving him with $135,000 in cash. With everything he owned riding on this moment, Revell headed to Las Vegas.
At the roulette table, he placed every cent he had on red for a single spin. The ball spun, the crowd held its breath, and Lady Luck smiled. The ball landed on 7 red, doubling Revell’s money. He walked away $270,000 richer and with a story for the ages.
7. Wagering on Kim Jong-Un
When it comes to betting, even world leaders aren’t off-limits. North Korea’s Kim Jong-Un has inspired some truly bizarre wagers over the years. Paddy Power, a well-known bookmaker, once took bets on when he would step down, with some predicting he’d remain in power until his death or around 2031.
But that’s not the strangest part. People have even bet on whether Kim Jong-Un would challenge US President Donald Trump to a round of golf. Both are known golf enthusiasts, after all. Politics, golf, and gambling—who knew they made such a compelling trio?
8. Betting on Doomsday
If you’re convinced you know when the world will end, Paddy Power has a bet for you. For a $50,000 stake, you can predict the exact date of the apocalypse. The only catch? Well, if you’re right, there might not be anyone left to cash in on your winnings. It’s a gamble in the truest sense!
Wanna bet?
From million-dollar wagers to snail races and cheese chases, the world of betting is anything but boring. With the right bookmaker and a penchant for the peculiar, it seems there’s no limit to what people will wager on.
So, whether you’re into roulette or just curious about the next bizarre bet, rest assured—there’s always something to keep you entertained at land-based or online casinos alike.
Article by Deni
CasinoWow Contributor
Hi, I’m Deni and I am here to ensure you have all the information you need to make informed decisions about online casinos and games and, of course, have fun while doing it. I do so through in-depth research and a keen eye for detail resulting in comprehensive reviews and engaging articles. Let’s explore the iGaming world together!