The Largest Bets Ever Placed
No one without a gambling problem would recommend you go all-in on a bet. Whether it's the casino, the lottery, or sports betting, the odds of a massive payout are slim, and there are plenty of risks along the way. Even notorious gambling boss Meyer Lansky warned his friends against gambling (with a reluctant concession to blackjack, given its relatively high chance of winning something).
Yet for every million stories out there about someone who gambled and lost, or managed to break even at best, there's that one lucky son-of-a-gun who won and won big. And whether it's due to a dream of hitting those long odds, or the rush from a game of chance — or any other motive — some people put down huge sums of money when it comes time to place a bet. It's part of the mythology of Las Vegas that the Phantom Gambler (real name William Lee Bergstrom) placed three massive bets over four years, the last one being a staggering $1 million (lost) wager on craps.
But even the Phantom Gambler doesn't hold the all-time record for the most money wagered on a game of chance. It's a little tricky to determine the record holder, given inflation, the different odds in different games, and privacy policies. But here are some of the biggest reported bets in history ever placed (that we know of).
Floyd Mayweather allegedly bet $5.9 million
Some might say anyone who goes into combat sports professionally is taking a massive gamble; if rules and regulations help safeguard life, limbs (to say nothing of the rest of the body) will take some wear and tear. But if such a career is a gamble, it paid off for Floyd Mayweather Jr. "Pretty Boy," as he became known, is considered one of the greatest boxers of all time. Though retired since 2017, he maintains a hand in the sport through his Mayweather Promotions firm.
But besides his boxing career, Floyd Mayweather has a reputation for gambling. One of his other nicknames is "Money," taken from a youthful habit of throwing cash at the camera, but Mayweather has since applied it to his financial endeavors. He's gone on the likes of Fox Sports, for example, to share his gambling exploits, which involve both huge gambling wins and massive gambling losses (which you can deduct, if you ever wondered). At other times, he's tweeted photos of betting slips worth almost a cumulative $4 million, just to boast about his winnings. That figure, if buzz around the World Wide Web can be believed, was later topped by a single wager.
A widely circulated story in 2013 held that Floyd Mayweather put down $5.9 million on the Miami Heat to beat the Indiana Pacers. The rumor went unconfirmed before, during, and after the game. But Miami did win. Being the favorite by seven points, that would've earned Mayweather $6.49 million in profit on his alleged wager.
Mattress Mack McIngvale bet $10 million on World Series
Though his given name is James, Texas knows him as "Mattress Mack" McIngvale. He's the man behind Gallery Furniture, though his famous nickname stems less from his line of work than from the costume he wore in the wacky commercials that gave McIngvale and his store fame. Both have become institutions of the city of Houston.
McIngvale has received considerable media attention for his philanthropic activities, but he's also a gambler, sometimes for big money. He's indirectly wagered through his business; a promotional stunt repeated several times awards customers their money back for certain items if a given team doesn't win the World Series. These deals serve as potential offsets to some of the headline-grabbing bets he's placed in his time. In 2022, he placed a series of bets adding up to $10 million on the Houston Astros to win the World Series. (Read about how sports betting affects the economy.)
The Astros took the championship, and Mattress Mack won $75 million on his $10 million wager. However, his promotional deal generated $74 million in sales, which had to go back to the customers, meaning McIngvale didn't walk away with much. The following year, the reverse held true, as $10 million worth of bets on the Astros were lost when the team failed to reach the World Series again. But, all the mattress sales that didn't need to be refunded earned McIngvale $5 million in profit.
Kerry Packer allegedly tried to bet $100 million on a coin toss
"The Simpsons" has garnered a reputation (deserved or not) for predicting the future. Sometimes, it also seems less a satire of certain personality types than a documentary. Take the show's Rich Texan, for instance. In any given episode where he appears, he's an overblown send-up of stereotypes of the people of Texas. But he's also been used to spoof billionaire tycoons, those of a more eccentric and ostentatious bent than C. Montgomery Burns. In the latter guise, his betting, boisterousness, bullying, and brandishing of firearms aren't wildly off the mark from Kerry Packer, though the nationality is (Packer was Australian).
Packer was a media mogul and an outsized influence in Australian politics. But he tended to grab headlines for his outrageous antics, many of them connected to his gambling. This is a man who once insisted that a casino fire a croupier so that he could be allowed to tip her $800,000, then demanded she be rehired on the spot. His bets included £15 million spread among four roulette tables (he lost it all), $1 million on the Melbourne Cup, and winnings of $25 million from seven different blackjack tables.
One Packer gambling story, however, put him up against a real-life doppelganger for Rich Texan. Mirage casino boss Bobby Baldwin has said that a loud, pushy Texan once tried to get in on Packer's table. In making his demand, the Texan boasted that he was worth $100 million. "I'll flip you for it," offered Packer. The chastened Texan declined what would've been likely the largest bet in history, and left Packer alone.