The Biggest Bets in History

The Biggest Bets in History


The gambling industry is one of the most lucrative in the world with millions of bets being placed around the world on a daily basis. Here is our look at the biggest bets ever made in the history of gambling.

The Suitcase Man

A Texas-born horse trader called William Lee Bergstrom earned himself the nickname of “The Suitcase Man” when he visited the Binion’s Gambling Hall and Hotel in Las Vegas, Nevada back in 1980. The reason for the nickname was that Bergstrom carried two suitcases with him including one that was full of cash that he planned to use to bet at the casino.

At the time, the casino had an offer that it would match any first time bet from a new customer. Bergstrom pulled out a staggering $777,000 from his suitcase and the casino was true to its word and matched the bet on a game of craps. Unfortunately, for the casino, Bergstrom won his bet only to then lose $1 million on a later bet.

Football Fan’s Own Goal


A Tottenham fan based in the UK was guilty of one of the biggest errors of judgement in football betting history when he wagered his entire mortgage on Spurs to win a game when they were leading 3-0 at half time against Manchester United on 29th September, 2001.

In a miraculous second half performance, the Red Devils scored five goals to turn the match on its head and leave the fan homeless. The reason for the fan’s ludicrously risky bet? It is alleged that he was trying to impress his new girlfriend and felt the result was a sure thing with only 45 minutes left.

Make sure your relationships and your bets don’t get involved, it can turn sour very quickly like this guy noticed. Also whether it’s online or land based make sure you read everything you need to know about gambling before you start betting.

Billy Walters and the $3.5m Bet

It is seen as one of the bravest bets in sporting history but ahead of Super Bowl XLIV in 2010, multi-millionaire Billy Walters decided to put his faith in the underdogs ahead of the big game. By faith we mean $3.5 million of his own money.

The bet backed the massive underdogs of New Orleans Saints versus the firm favourites Indianapolis Colts. The Saints prevailed as 31-17 winners in one of the biggest upsets in Super Bowl history and Walters was left counting the millions earned from one of the most ballsy bets in NFL history.

It’s All About the “Money” Mayweather

floyd-mayweather-showoff-moneyLegendary boxer Floyd Mayweather is just as renowned for his huge sporting bets as he is for his boxing achievements. The sports superstar frequently brags about his six-figure sports bets and his big wins. His boasting about his earnings and spending has seen him attract just as many critics as fans.

However, one bet that Mayweather will be most remembered for was his $5.9 million bet on Miami Heat to beat Indiana Pacers in game 7 of their NBA play-off series on 3rd June, 2013. Mayweather’s bet came in and he bagged himself a whopping $6.49 million in winnings to secure one of the biggest ever bet wins in US sporting history.

Scottish Independence Punt

Politics is often an attractive market for punters at the bookies but one political event captured the imagination of punters up and down the UK. This was the Scottish Independence Referendum. The forecast narrowly suggested a “No” outcome was favourite but it was too close to call with the odds changing on a daily basis. It was a referendum that even the political experts could not call an accurate judgement on even in the final days leading up to the vote.

It was the actions of one Scottish punter who place a staggering £900,000 bet on a “No” outcome winning the vote that was the most memorable moment of that vote. He bagged £193,000 in winnings on top of his bet as he correctly predicted the outcome. Sadly, he did not stop there and placed another massive bet of £200,000 on the following General Election resulting in a hung parliament. He lost.

A Wild World Cup Wager


The 2010 World Cup in South Africa smashed records for sports betting all over the globe as the online gambling market really came into its own and bookmakers all over the world fully capitalised on the growing online audience. It also saw one of the biggest losing bets in football betting history.

An anonymous punter decided to place a bet worth £417,000 on the World Cup Semi-Final match between Germany and Spain ending in a win for the Germans at odds of 10/11. It was a 73rd minute header from Carles Puyol that separated the teams to give Spain a 1-0 win and saw the punter lose his six-figure sum and missing out on a potential £800,000 pay out.

A Banzai Sky Dive Life Bet

One slightly unhinged Japanese sky diver called Yasuhiro Kubo decided to place a bet on being able to pull off a Banzai Sky Dive. This consisted of him flying up to 3,000 feet into the air in a plane, throwing his parachute out of the moving plane, waiting one whole minute, and then jumping out of the plane after it with the aim of catching it and putting it on before he hit the ground.

Now, what was the wager for this obscene and ridiculous bet? Only his bloody life! In spectacular and extremely lucky scenes Kubo managed to pull off the insanely audacious challenge and lived to tell the tale on 2nd September, 2000. Bets don’t come much bigger than that!