While the majority of gamblers put down small stakes, that kind of money is barely worth thinking about to high net worth celebrities. Meaning what is casual gambling within their bankroll for them, will look outlandish and extreme compared to most. Many celebrities are know fans of poker, blackjack and sports betting, but these are the biggest gamblers of them all.
From top athletes to CEOs to music stars and Hollywood actors this list is diverse. Although their are probably bigger bettors out there, these six famous figures have never been shy about documenting their high stakes gambling exploits.
Michael Jordan Puts Down Millions on His Own Golf Games
Easily the most famous basketball player of time, and now billionaire thanks to his commercial deals and brands like Air Jordan, Michael Jordan is also a rather prodigious gambler. He has been known to put down hundreds of thousands on casual golf games against his rich and famous friends, and has been repeatedly spotted at casinos across the US.
Luckily, you don't have to be a billionaire sporting legend with a private bookmaker to enjoy a bit of online casino action. Modern gambling sites are available 24/7 with low deposit minimums and top quality games that can be played at all stakes. Plus great bonuses and promotions to get you up to speed quickly.
Tobey Maguire Put on High Stakes Hollwyood Poker Games
The Spiderman star actor Toby Maguire had a famous penchant for poker, that eventually ended up making the story for a whole movie. In the mid 2000s Maguire was key player in organizing high stakes Hollywood poker games. Maguire and Leonardo Di Caprio, alongside a few others, would try to convince Hollywood execs and Silicon Valley elites into cash games playing for eye-wateringly high stakes.
Maguire's assistant in running the games – Molly Bloom – eventually published a memoir documenting much of what happened in that period. The book, Molly's Game, was eventually also made into it's own Hollywood flick.
Drake Loses at Sports Bets and is Called Cursed
The Canadian rap superstar Drake has been known to put down huge sports bets, and is even sponsored by an online casino brand. Interestingly, for a long while Drake's sports bets were so unsuccessful people began discussing a so-called "Drake Curse" on social media. Just some of the rap hitmaker's biggest bets he has claimed include:
- $40 million won playing online roulette while at Dave & Buster's on his birthday
- $2 million lost on Israel Adesanya at UFC 281
- $2.3 million won on Paddy Pimblett and Molly McCann to win at UFC London in 2022
- $1.2 million lost on Jake Paul to beat Tommy Fury
Dana White Beats Las Vegas Casinos for Millions
The UFC founder and billionaire businessman is also a frequent high stakes gambler in Las Vegas. White claims to put down hundreds of thousands of dollars per hand on baccarat and blackjack. He says he once beat Las Vegas casino Caesars Palace for $3 million in a single night, and has been banned from several casinos in Sin City.
However, White has also been open about his losses. He apparently once lost several million dollars gambling at Las Vegas' Palms Casino Resort. He has also appeared on other famous gamblers streams, like Adin Ross and the Nelk Boys, and is closely acquainted with Red Rock Resorts owners Frank and Lorenzo Fertitta.
Floyd Mayweather Jr. Lives up To His Nickname
When you're nickname is "Money", you've probably got enough of it coming in to have a few big splashes gambling. World champion boxer Mayweather has claimed to gamble as much as $100,000 a week betting on sports, and has put down millions on big events including the Super Bowl. You can confirm this yourself, because he literally posts the receipts on his social media.
Mayweather has been known to bet on celebrity boxing, as well as getting involved in the ring. Such as when he earned millions fighting Jake Paul. Some of Mayweather's biggest sports bets he has posted online include:
- $5.9 million on the Miami Heat to beat the Indiana Pacers in the NBA Finals in 2013
- $800,00 on the Arizona Cardinals, which won him $1.5 million
- Multiple large bets of $50,000 plus against Conor McGregor
- $1.8 million on an NFL parlay including the Seattle Seahawks and the Indianapolis Colts
Phil Mickleson Allegedly Gambled $1 Billion Over 30 Years
While he might be the least famous name on this list, to non golf fans at least, Phil Mickleson's betting is apparently up their with the biggest names. The multiple championship winning golfer was good friends with infamous sports bettor turned bookmaker Billy Walters – until Walters' memoir elaborated on Mickleson's alleged betting activities.
Although known in golfing circles to be a bit of a gambler, fans were shocked to hear Walters allege Mickleson had gambled nearly $1 billion over the course of 30 years. Mickleson apparently tried to bet on Team USA to win the Ryder Cup in 2012, while he was playing in it.
Since the revelations Mickleson has opened up about his gambling on social media, and has apparently stepped back from betting in recent years.
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