Gambling is a great leveler. Whether rich or poor, famous or anonymous, we all like to have a little something riding on the turn of a card or the outcome of a sporting event. In that regard, celebrities are just like the rest of us – albeit, to a degree. They like to gamble, they deal with ups and downs, they do everything in their power to win. 

That said, things get different when you factor in sums on the line and notoriety attached to their wins or losses. Wagers are eye widening and reports of money on the line make headlines. Here then are some of the world’s most famous people who like to gamble big, what they play and how they handle outcomes.


The media loves writing about Ben Affleck grabbing coffee or enjoying dinner with J-Lo. So, when he plays blackjack – with her at his side or solo – everyone takes notice. And that would include casino surveillance snoops. 

Such was the case in 2014 when he got backed off from the high-limit tables at the old Hard Rock (now known as the Virgin) in Las Vegas, where he was supposedly spreading from $100 to $10,000 per hand in a double deck game. 

Unless you’re terrible, the casinos will take notice. Apparently, he is not terrible. He was card counting and winning. Underscoring that celebs in casinos really are like the rest of us, he was asked to stop playing blackjack. 

More recently, in 2021, Affleck was spotted firing it up at the high limit tables of Wynn Las Vegas. If dealers love him more than casino enforcers do, it’s because he’s what’s known as a George (Vegas lingo for a generous tipper). On one occasion, he is said to have tipped out most of his Hard Rock winnings. Another time, it’s been alleged, he and Matt Damon wrapped up a Mirage session by giving away money to fellow gamblers. Nice guys!


Watch an Ashton Kutcher movie, and it would be easy to wonder whether or not the actor is as goofy in real life as he often is on screen. In Las Vegas, that definitely is not the case. 

In fact, he’s made a killing by wagering on NCAA football. But it’s more complicated than that. Kutcher is not lucky, he’s smart. Or at least smart enough to align himself with the right people.

As Kutcher told Esquire magazine, “I used to place bets for the largest national sports betting syndicate in America. I basically just placed bets for half a season. We cleared like $750,000 in four weeks of college football.” 

Soon after going on the massive heater, he found himself persona non grata in sports books. Despite the rebuffing, and not hinting at whether or not he still gambles in Vegas, Kutcher said, “It was pretty fun … but they eventually caught on.”

Celebrity gamblers


Tiger Woods is not the kind of guy who’s going to play low-roller blackjack. It’s been reported that he has a $1 million line of credit at the MGM Grand’s ultra-luxe Mansion – and that was a number of years ago. It might be even higher today. 

Phil Hellmuth, a sometime blackjack compatriot of the golf superstar, once told me, “Tiger is excellent at blackjack. He bears down a little bit, pays attention and plays perfect basic strategy. He takes his losing hands well and doesn’t get upset, though you do see that extra bit of focus at times. 

“I remember having a 13 against the dealer’s 2 and not being sure what to do. Tiger immediately told me to stand – and he was right. It’s the correct play” – unless one is card counting, like Affleck, and the count is -1 or lower, which would command hitting. “I said, ‘Aren’t you supposed to be a dumb golfer?’ He cracked up. I remember that Tiger won big that night. I’m not going into the number. But, if I say big, of course it was six figures.”


The former NBA star’s gambling habits are all too well known. He’s never hidden his gaming proclivities, nor did Wynn Las Vegas when the joint sued him over a $400,000 marker that went unpaid.

Barkley settled up with the Wynn and had to fork over an additional $40,000 to the Vegas District Attorney’s office (amazingly, the DA there has a division devoted to collecting unpaid markers and receives an extra 10 percent for its trouble). 

Barkley has come clean about having lost $1 million over the course of a day on at least 10 different occasions. Conversely, on the more positive tip, he won the same sum five or six times. He’s described his gambling as a “bad habit,” but vowed that he will not stop doing it because it’s “my life and it’s my money.”

Fair enough, though there was at least one instance when his breakneck wagering caused a pro golfer to cry. Such was explained by Andres Gonzales on the Golf magazine podcast Subpar. Gonzales, a PGA tour pro, was alongside Barkley in a casino, and, as he put it, Barkley was “putting 10 grand down on a blackjack table.” Then he’d be “turning around, putting 10 grand down on craps … he was stressing me out, man.”

That led to a panic attack and tears for Gonzales. Barkley, always hungry for action, tried convincing Gonzales to golf against him for money. Gonzales did not elaborate on his response, though the terms would have been characteristically terrible for Barkley: he wanted just one shot per side.


They don’t call the bling-loving boxer “Money” Mayweather for nothing. 

According to Bleacher Report, he’ll routinely walk around with $60,000 cash on his person (often in a backpack) and has been known to load $1 million into a duffle bag. That’s probably a good thing, as Mayweather has been said to play the highest stakes blackjack that casinos will allow. But his gambling in the pit pales alongside his sports wagering. It’s alleged that Money bet millions on the Denver Broncos to beat the Seattle Seahawks in the 2014 Super Bowl. Denver lost and so did Mayweather. 

But don’t feel too bad for the multimillionaire pugilist. Via non-Super Bowl bets, Mayweather is said to have cleared $200,000 on the Seahawks and another $626,923 on the Broncos, proving that, for some of us, everything comes out in the wash. 

Daily Mail reports that he had one month that yielded $4.7 million in sports betting profits. Then there was the time that his NBA and boxing smarts resulted in a windfall of $827,000 – and he didn’t even need to enter the ring.      

As Mayweather put it during an appearance on ESPN Radio, “Everyday, you have to find one [game] that you truly believe in … and that’s the one you load up on.”

Even for us nickel-and-dime gamblers, Floyd “Money” Mayweather’s words of wisdom serve as sound  advice.

Michael Kaplan is a journalist based in New York City. He has written extensively on gambling for publications such as Wired, Playboy, Cigar Aficionado, New York Post and New York Times. He is the author of four books including Aces and Kings: Inside Stories and Million-Dollar Strategies from Poker’s Greatest Players.

He’s been known to do a bit of gambling when the timing seems right.