Celebrity Gamblers: High Rollers from the World of Fame

High rollers already draw lots of attention at casinos due to their big stakes. But high rollers are an even bigger deal when they're also celebrities. Certain celebrities have become well known for their gambling prowess. You can read about these celebrity gamblers below and their top betting feats.

Dana White

Dana White spends the majority of his time working as CEO and president of the UFC. But when he's not at his day job, White enjoys playing high stakes blackjack. The 54-year-old doesn't just play blackjack-he dominates the tables. The blackjack high roller bets up to $75,000 per hand and has won as much as $7 million in one night. White is so good that some Las Vegas casinos have actually banned him from playing blackjack with them. Even still, he's able to find games and continue his winning ways.

Charles Barkley

Former All-NBA Pro and current TNT basketball analyst Charles Barkley hasn't had quite the success that Dana White had enjoyed with gambling. In fact, Barkley estimates that he's lost more than $10 million through casino games. The lowest point of his gambling career saw him punt $2.5 million in only two hours. The 1993 NBA Most Valuable Player eventually admitted that he had a problem and has since curbed his betting ways into a healthier hobby.

Tobey Maguire

Poker legend Amarillo Slim once said, "If you don't see a sucker at the table, you're it," Apparently there were a lot of people poker playing with Tobey Maguire who didn't get this concept. The Spider Man star set up a Hollywood poker ring with a gambler/TV executive named Houston Curtis for the sole purpose of hand-picking fish. Their plan worked out well since both made lots of money off the weak competition, with Maguire netting an estimated $30-$40 million in the high stakes poker games. This Hollywood poker ring would inspire the movie "Molly's Game" as well as Curtis' book "Billion Dollar Hollywood Heist."

Bet Affleck

Coincidentally, actor and director Ben Affleck was part of the underground poker games mentioned above. We doubt that Affleck was one of the game's big losers because he has a pretty good gambling background. Besides having $365,000 in poker tournament winnings to his credit, Affleck has mastered blackjack card counting. In fact, he's been kicked out of multiple casinos for counting cards. The Hard Rock Casino in Vegas even felt the need to ban the "Justice League" star and "Argo" director for life.

John Daly

Pro golfer John Daly is no doubt the worst celebrity gambler on this list. The PGA Championship and British Open winner estimates that he's lost between $55 million and $57 million through gambling. These losses include a streak that would rival Barkley, where Daly blew $1.65 million in five hours on high stakes Las Vegas slot machines. The bad part is that Daly didn't even realize he had lost this much until running the numbers with his accountant. Daly admits that his gambling habits haven't been smart, but he doesn't hold a lot of regrets. "I moved on from it," he said. "I had a lot of fun doing it."

Floyd Mayweather Jr.

Retired boxer Floyd Mayweather Jr. is one of the greatest fighters ever, amassing a perfect 50-0 record and winning 15 world championships. He would like to think that his sports betting skills are about as sharp as hits boxing acumen. Mayweather has frequently showed off multmillion-dollar betting wins through Twitter and Instagram. In one case, he won $3 million on a college football wager. Mayweather even bet on himself during his fighting career since there are no such restrictions in boxing. At one point, he placed a successful $750,000 wager on himself.


Hip-hop star Drake is a newer entry to the world of high stakes celebrity gambling. Although Drake has been rapping since the mid-2000s, he didn't really start gambling until the past few years. The Canadian rapper is making up for lost time with a flurry of big sports bets. It's almost hard to keep track of his wagering recently, but in one case, he won $1.4 million by betting on the LA Rams to win Super Bowl LVI. Drake also wagered around $1 million on Super Bowl LVII, spread across a moneyline bet and six prop bets. His $700,000 moneyline wager (+110) came through when the Kansas City Chiefs won the Super Bowl.

Michael Jordan

Chicago Bulls legend Michael Jordan won six NBA Championships and is widely regarded as the greatest NBA player ever. But his gambling skills have never quite matched what he's been able to do on the basketball court. Case in point, Jordan once lost $5 million in a Las Vegas craps session. Losses like these haven't stopped MJ from betting, though, as he wagers on everything from golf to who will get their luggage first coming off an airplane. Sometimes Jordan is successful with his gambling, like the time he was down $500,000 in a casino and made a comeback to end with $600,000 in profits.