The world of betting is constantly shifting and changing. We’re writing this article now and by the time you come to read it it’s possible that the biggest bets we’ve found that have ever been made will pale into insignificance compared to the ones that you know about.
That’s the nature of betting and the desire of people to constantly outdo each other and win more money.
Even so, the aim here is to look at some of the biggest bets that have ever been placed, looking at a range of different areas in which the bets have been won and lost.
The casino is a natural draw for the world’s biggest bettors, but it’s not as though sportsbooks haven’t seen their fair share of the action over the years, so we’ll look at bets placed there, too.
Mattress Mack Wagers $10 Million on the Astros
Jim ‘Mattress Mack’ McIngvale is a very well known figure in his native Texas, and thanks to what was believed to be the biggest sports betting win in history, he became a very well known figure all across America and beyond.
He is a businessman who found local fame through a succession of whacky TV commercials for his furniture store that was always running promotions, and he even managed to tie in his bets with his promotions eventually. It would work like this: Mack would offer all customers who spent $3,000 or more in his store their money back (so their items would be free), if his team won the game. If his team didn’t win the game, the items they bought were obviously still theirs to keep, but they had to pay for them.
In this way, Mack hedged his bets because if his bet won he would win lots of money, and if his bet lost the increase in sales throughout the promotion would boost the income of his business.
In 2022 he placed a series of bets of the Houston Astros to win the World Series, totalling a massive $10 million. They won. The payout was a staggering $75 million.
Although this is the biggest bet Mattress Mack made, he regularly wagers millions on different outcomes, so who knows what he has wagered in total over the years, but you can be sure that he will keep doing it.
Floyd Mayweather, The Boxer Betting On Miami
Floyd Mayweather boasted the boxing nickname of ‘The Money’, which he seemed to take literally when it came to his wager on the Miami Heat in 2013.
He was the highest earning athlete in the world at the time, so he probably wasn’t all that worried when he staked $5.9 million on the Miami Heat to win a basketball game.
They were up against the Indiana Pacers, with the presence of LeBron James meaning that the Heat were 7-point favourites before the match got underway.
Having signed a $200 million six-fight deal with Showtime, Mayweather went big on the Heat and was rewarded for his bravery; they beat the Pacers 99-76, having The Money $6.49 million in profit.
The Anonymous Man Who Bet £417,000 On The World Cup
The World Cup is one of the most watched sporting events on the planet, seeing countries from around the globe compete on the football pitch to prove that their nation is the best at the sport. It obviously sees huge sums of money wagered on the outcome of matches, but a British punter claimed the record for the largest amount staked.
He was looking at the World Cup semi-final match up between Spain and Germany and decided that the Germans were going to do what the Germans have almost always done and make it through to the final. He called William Hill’s telephone service and bet £417,000 on them doing just that at odds of 10/11.
He stood to walk away with £800,000 if the Germans defeated the Spanish and must have been at least mildly confident when the match went in 0-0 at half-time. Instead, Spain scored in the second-half and Germany were denied a penalty late on to take the game into added time. He lost his bet, delighting William Hill and other bookies after Germany had been backed widely.
Billy Walters, The Man Who Bet $3.5 Million
Born in 1946, Billy Walters started his his career as a used-car salesman at McMackin Auto Sales in Louisville. He sold around 32 cars a month, earning the equivalent of about $400,000 a year. He was soon head-hunted by a rival car sales dealership and eventually set up his own business, Taylor Boulevard Auto Sales.
Alongside his car sales, Walters also remained involved in sports betting and in 1981 decided to give up car dealerships altogether and settle on becoming a professional gambler. Part of that involved running a sports betting service on the side, which was illegal in Kentucky. When he was charged for doing so he decided to move to Las Vegas with his wife, Susan.
He soon began to win big, turning $2 million at the Golden Nugget Casino into $3.8 million after noticing a bias on one of the roulette wheels. During the 1980s he also joined The Computer Group, which used computer science to analyse sporting outcomes. During a period of 39 years betting, he only spent one of them in the red.
All of which is to explain why his bookmaker should have been worried when Walters approached them and asked to placed a $3.5 million on the New Orleans Saints in the Super Bowl XLIV. It’s possible that they didn’t panic because Walter often used runners to place his bets in order to avoid having them refused by bookies who knew what he was capable of.
He won the bet when the Saints won the Super Bowl for the first time, defeating the Indianapolis Colts 31-17. His history has been marred since, though. He was sentenced to 5 years in prison and a $10 million fine for insider trading when he used non-public information provided to him by Dean Foods to earn money.
William Lee Bergstrom, The Phantom Gambler
Where else to start when it comes to casino betting but with the man commonly known as The Suitcase Man? Also occasionally referred to as the Phantom Gambler, William Lee Bergstrom was born in Texas and graduated from his local high school in Austin in 1969. He majored in electrical engineering and attended Texas Tech University, leaving in 1971.
He then went to Texas University but dropped out in 1974, making a living by selling and owning property in his home state. On the 24th of September in 1980, he travelled to Las Vegas and entered Binion’s Horseshoe Casino with two suitcases. One of them was empty, but one of them contained $777,000 in cash.
At the time, Binion’s had a policy of honouring a bet of any size if it was the bettor’s first wager at the casino. Bergstrom hadn’t been there before but took Benny Binion up on his offer and staked the entire $777,000 on the Don’t Pass line of a craps table. The shooter established a point of six, then sevens out within two rolls, making Bergstrom’s bet a winning one.
The empty suitcase was soon filled with his winnings, which the Phantom Gambler promptly picked up and departed the casino with. Benny Binion later reported that he had borrowed most of the money that he used for the bet, planning to commit suicide in the event that it had been a loser. It wasn’t, so he travelled the world for some years instead.
Remarkably, when Bergstrom returned to the casino in 1984 and placed another bet on the Don’t Pass line, he won again. This time the bet was worth $538,000 and as a result of his victory he took him mum to see Willie Nelson in concert. He even won another $117,000 on more craps bets, adding more money to his pot.
His luck finally ran out in November of that year. He arrived at Binion’s with a suitcase filled with $550,000 in cash, $140,000 in gold and $310,000 in cashier’s cheques. He opted for the Don’t Pass line again, but this time the shooter threw a seven on the come out roll, meaning Bergman lost $1,000,000.
Whilst it isn’t the biggest bet ever placed, $777,000 was worth a lot more in 1980 than it is nowadays. On top of that, the move has gone down in Vegas folklore and inspired numerous different awards and prizes in Sin City. Just a few months after losing the money he committed suicide, though it’s believed that was because of his sexual orientation rather than the loss.
Kerry Packer, The Billionaire Bettor
Kerry Packer might well have proposed the largest ever bet in Las Vegas, even if the bet didn’t actually take place. Packer was a billionaire and was so generous with his money that it led to the coining of a phrase that if Kerry Packer was in town then no one in the casino business called in sick. When he was rushed to hospital after becoming ill in 1990, he tipped the ambulance crew $1 million for looking after him, for example.
It’s believed that Packer was personally responsible for Aspinall’s in London going bankrupt after he won so much of their money, which led to him being banned from a host of venues around the world. The MGM Grand wasn’t one of them, but the manager might well have wished it had been after allowing him to play blackjack for $500,000 a hand and losing $26 million in one evening.
The wager that gets Packer’s name onto this list, though, came about when he was gambling at a private table in the Bellagio on the Las Vegas strip. A Texas oil tycoon approached and him and asked if he could join the table, but Packer refused. The Texan was enraged by this, soon boasting that he was worth as much as $100,000,000.
Packer, never one to pass up an opportunity and aware that losing one hundred million dollars wouldn’t have much of an impact on his personal fortune, apparently looked the tycoon in the eye and said, “If you really want to gamble, I’ll flip you for it.” Perhaps somewhat unsurprisingly, the Texan declined the offer so the bet never stood. Even so, $100 million has to be one of the biggest bets ever.
Ashley Revell, The Man Who Bet Everything
In terms of gambling, large bets tend to be relative. For proof, look at the story of Ashley Revell. Born in Maidstone in Kent in 1971, in 2004 he decided that he was going to sell all of his possessions in order to place a bet on the single spin of a roulette wheel. The idea was formed in a pub when a friend said the simple sentence, “Wouldn’t it be great if we went to Las Vegas and bet everything on a single spin?”
The next day, Revell began the process of selling all of his possessions, despite the protestations of family and friends. Though he didn’t own a house he did have around £10,000 in savings as well as a nice car, a good watch and expensive golf clubs, all of which he was able to sell via auction. For smaller items he decided to set up a car boot sale, selling everything from his school cricket jumper to some ties.
Within six months he’d sold everything that he possessed, garnering the attention of Sky along the way. By the time he got to Las Vegas all he had was a hired tuxedo that he wore, having wired £76,840 to the Plaza Casino and Hotel in advance. The casino gave him a large stack of chips which he took up to the roulette table and placed it all on red.
The bet won, landing him with £153,680. When he got back to the UK he bought a motorbike and a trip around the world, on which he met the woman that became his wife. Whilst it’s not even close to being the largest bet ever placed in real terms, it was in the sense that he wagered every single thing that he owned, which is pretty impressive in real terms.
Terrance Watanabe, The Man Who Lost $127 Million
When it comes to betting, sometimes you don’t need to bet it all in one go to see money slip through your hands. That’s what Terrance Watanabe discovered back in 2007 during a period betting big in Caesar’s Palace and The Rio. The man who inherited the Oriental Trading Company became a philanthropist after resigning as the company’s CEO in 2000.
Nowadays he’s considered to be the biggest whale in Vegas history, largely thanks to what happened in Sin City in 2007. Most of his losses were at the poker tables, where those he was going up against couldn’t believe their luck. He kept on losing to the point that at the end of the year he was $127 million down and owed Caesar’s a further $14.75 million.
The company had to take him to court to get the money from him in the end, at which point it was alleged that they allowed him to gamble whilst intoxicated and fed him painkillers to keep him at the tables. Whether that was true or not, we do know that the New Jersey Gaming Control Board issued a fine of $225,000 to Caesar’s Entertainment Corp for their behaviour.