Biggest Wins Betting Outside the Box

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Humans love to speculate about future events. Whether it’s the next Oscars or the winner of the Super Bowl, there’s likely a wager involved. Whether the stakes are high or totally informal, it’s human tendency to make predictions.

The British, in particular, are known for their healthy betting culture. They regularly bet on football leagues and other popular sports like rugby, but also on things like cheese rolling or what color tie the Prime Minister will wear to an event.

But it isn’t only the British. Around the world, 1.6 billion people gamble regularly, while 4.2 billion gamble at least once every year, according to a gambling rates study by

Though gambling isn’t the same as sports or events betting, it goes to show that people grapple with future uncertainty by injecting some excitement into the situation. Whether this involves some financial planning or winning simple glory, if there’s uncertainty, there’s likely a bet involved.

Let’s take a look at the biggest wins over recent years, as well as the strangest bets around the world.

Biggest Wins

A resident of New Jersey, Jona Rechnitz, placed a wager on a safety position scoring the first touchdown in the Super Bowl—and won on the bet… twice. In 2012, he turned a $1,000 bet into $50,000. In 2016, he turned $500 into $25,000 on the same bet. 

For those who don’t know, the NFL’s Super Bowl is the most popular sports event in the US, with over one hundred million viewers and millions of dollars in wagers. As sports betting expands in the States, the availability of sites offering risk-free wagers on major sports leagues and events like the Super Bowl will increase.

In the past, major bets in the US, like Jona Rechnitz’s big wins on safeties, could only ever happen in Las Vegas. Meanwhile, back in the UK, such bets take place at in-person shops all the time.

Recently, a punter made a 30-pence 15-way parlay bet to predict the winning team of the next 15 soccer matches. Roofer Mick Gibbs managed to correctly predict the outcome of the next 15 games and was able to turn his 30 pence (around 50 US cents) into £500,000 (645,000 USD). This is a prime example of wagering for fun without imagining a massive payout. For this reason, both Rechnitz and Gibbs often make lists for craziest winnings in betting history.

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Oddest Bets

Any punter who spends time wagering on sports and consulting with expert analysis to increase their odds has likely seen long lists for prop bets. Known as ‘proposition bets’ in the industry, these cover specific outcomes within an event.

For example, common prop bets on the Super Bowl include who will score the first touchdown and what the National Anthem singer will wear. Beyond the world of prop bets, the wagers only get weirder.

As mentioned above, cheese-rolling is a hobbyist sport that involves brave athletes attempting to race their own wheel to the bottom of a hill without falling. Given the hilarity of the sport, it’s a rewarding event to watch and bet on.

Wife-carrying is another quasi-sport that enjoys a strong wager culture. The sport involves a bit more prestige and fitness than cheese rolling and even has its own World Wife-Carrying Championship that’s televised internationally. Some sites even offer guides on how to win money betting on wife-carrying.

Moving out of the west, common bets become even stranger for those unfamiliar with another culture. In Taiwan, for example, betting on the life expectancy of people may seem a bit grim. However, the trend is currently gaining popularity in Russia. 

Other crazy bets include whether or not UFOs are real and when alien life will be discovered. However, these bets include a variety of other factors, including a year of discovery, a method of discovery, and a place of discovery.

Given the wide range of opinions on such topics, ranging from the absolute impossibility to people believing they’ve seen a UFO themselves, bookmakers have plenty of business.