Top 10 World’s Craziest Bets Ever Made

Top 10 World's Craziest Sports Best Ever Made

Gambling has been around throughout history and is still a beloved leisurely activity. However, gamblers will sometimes wager and put anything on the line, resulting in some of the weirdest bets ever made.

Here are some of the craziest sports bets placed by punters, as well as their crazier backstories!

The Stories Behind the 10 Craziest Sports Bets

Put It All on Red – Ashley Revell

Ashley Revell will go down in history as the man who staked everything he had on a single roulette wheel spin. Revell is a gambler from England who sold everything he possessed, including his clothes! In 2004, Revell was betting $135,300 – his whole life savings. He doubled his money, bringing his total to $270,600.

The Suitcase Man – William Lee Bergstrom

There is not much known about William Lee Bergstrom except that he once placed the largest bet in casino gaming history, totalling $777,000. There were notable limitations for anyone making their first bet in September 1980, when Bergstrom went to the Binion’s Horseshoe Casino. He had two suitcases, one full of cash and the other empty, ready to win. Then, he staked $777,000 on the Don’t Pass line, doubled his money, and then walked away. 

Beginner’s Luck – Patricia Demauro

Patricia Demauro was with a friend, John Capra, at the Borgata Hotel Casino in Atlantic City in 2009. Though Demauro was a novice, having played just once previously, that didn’t stop her from rolling the dice 154 times in a remarkable winning streak. Demauro never revealed her total winnings, but it’s safe to assume she won more than $100,000 that night.

The Luck of the Northern Irish – Gerry McIlroy 

Gerry McIlroy won £100,000 on a £200 wager he placed in 2004 that his 15-year-old son would win the Open Championship before turning 26. He wasn’t alone in his triumph; two of Gerry’s buddies also won £80,000 following Rory’s victory in 2014. They both staked £200 on Rory to win the Open in ten years.

A Trip to the Tracks – Richard Hopkins

In 1998, Richard Hopkins bet £200 that Lewis Hamilton would win a Formula One race by 23. Hopkins placed a second wager of £100 on Hamilton, becoming a Formula One world champion by the age of 25 and the third bet of £50 on Hamilton achieving both goals by the age of 25. Hopkins received a total payoff of £165,000 when Hamilton won his first race at the age of 22 and went on to win the World Championship at the age of 23.

The Taser Wager – John and Nicole Grant

John and Nicole Grant are a couple whose love for the NFL and betting got them on this list. The couple wagered on their favourite teams – the Bears and the Parkers – that night, and the winner would get the opportunity to tease the loser. John ended up winning. Perhaps Nicole was drunk when he did it, or she completely forgot about the bet, but once he cashed in on his winnings, she called the police on her husband!

Federer Fever – Nick Newlife

Tennis player Roger Federer won his first Wimbledon championship in 2003. In the same year, Nick Newlife bet £1,500 that Federer would win at least seven Wimbledon Grand Slams by 2019. By 2012, Federer had won the Wimbledon championship seven times. Unfortunately, Newlife passed away in 2009 before learning the outcome of his strange gamble. When Federer won his eighth Wimbledon title, he bequeathed his estate, including the betting slip, to the charity Oxfam, which collected the winning prize of well over £100,000.

The Magnificent Seven Races – Darren Yates

The Ascot racetrack was the venue for one of the most outstanding bets of all time in 1998. Darren Yates, who bet £67.58 and put all seven horse races into one wager, gambling that Frank Dettori, a famous jockey at that time, would win them all. Yates must have known his way around horse betting systems as Dettori won all seven races, and no one earned more than Yates, who earned £550,823.

The 50p Millionaire – Fred Craggs

In 2008, Yorkshireman Fred Craggs decided to celebrate his 60th birthday with a horse racing wager, but given that he bet just 50p, it’s safe to say he didn’t put much thought into it. Then he chose an eight-horse accumulator, with the only thing they had in common being exceedingly long odds. Every horse came in as anticipated on race day, and Craggs’ wager converted into a £1 million payment.

 A Winning Loss – Ted Forrest

Ted Forrest, a professional poker player in the United States, received a wild prop bet from his pals Mike Matusow and Justin Smith. According to the prop bet, Ted Forrest would win $2 million if he could lose 50 pounds (22.68 kg) before June 15, 2010. Ted was skin and bones and weighed roughly 60 kilos when he got on the scale two months later. He had reduced almost 23 kilograms and had accomplished the seemingly inconceivable feat of losing 26 per cent of his total weight, or roughly half a kilogram, virtually every day for two months.


Some people go a little too far when it comes to gaming. While they make for a good story, if you don’t want to be associated with some of the craziest sports bets of all time, try your hand at online betting. When you play online casino games or place bets on your favourite sports, you have a much better chance of winning without sacrificing your dignity (or anything else!).

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