People often hold celebrities in high esteem due to their fame and fortune. But the truth is that celebrities enjoy many of the same things as average people, including gambling.

The only difference is that famous people have usually much larger bankrolls. These huge bankrolls allow them to play for larger stakes and win big.

Therefore, it should be no surprise that a number of Hollywood celebrities and pro athletes have won fortunes through gambling.Keep reading as I discuss seven of the largest wins in celebrity gambling history.

1 – Ben Affleck Proves to be an Expert Card Counter

Ben Affleck has been an A-list Hollywood star since he and Matt Damon co-wrote and co-starred in Good Will Hunting. Affleck has continued building his profile by starring in movies like Chasing Amy, Armageddon, Reindeer Games, Pearl Harbor, and Daredevil.

Considering his busy acting career, you wouldn’t think the 46-year-old would have time to become an advantage gambler. But Affleck did just this by developing expert card counting skills.

He put his skills on display at Las Vegas’ Hard Rock Casino, making more than $1 million over two sessions. Hard Rock management eventually saw enough and politely asked him to leave the table. Affleck didn’t receive the usual treatment of being banned from the casino like many other card counters. This would create bad publicity for Hard Rock, which has plenty of celebrity clientele.

Instead, the staff simply told Affleck that he was too good for their blackjack tables and invited him to try any of their other games.

Aside from being an excellent card counter, he’s also an astute poker player. Affleck won the 2004 California State Poker Championship and a $365,400 prize.

The Batman v. Superman actor was even involved in a celebrity filled poker ring that included his buddy Damon along with a number of other famous people.

The only downside to Affleck’s love of gambling is that it reportedly played a role in his 2017 separation from Jennifer Garner. The two have remained close by raising their kids together, but it still looks like they’re moving towards divorce.

2 – Sean Connery Pulls Off Incredible Roulette Feat

The iconic film character James Bond has long been known for his gambling acumen. And Sean Connery, who’s the original James Bond, lived up to 007’s legend by pulling off a near-impossible roulette feat.

In 1963, the Scottish actor was in Italy filming From Russia with Love. While there, he gambled at Saint-Vincent’s Casino de la Vallee.

He walked up to the European roulette wheel and began placing single number bets on 17. A single number wager has the longest odds of winning at 36:1.

Not surprisingly, Connery lost his first two spins with this risky strategy. But he defied the odds on the third spin by winning a single number wager. Many players might’ve adopted a more-conservative strategy from this point on. But Connery let his money ride on 17 a second time.

He won yet again and could’ve walked away from the table with a handsome profit. However, the acting legend put his money on 17 yet again.

Miraculously, he won the bet and left with $27,000 in overall profits. Considering that the odds of winning three straight single number wagers are 50,000:1, Connery definitely got lucky.

But he never had to rely on luck in his acting career, which has seen him star in many blockbusters over the years. Some of the movies that he’s played a leading role in include The Hunt for Red October, The Name of the Rose,The Rock,The League of Extraordinary Gentlemen, Indiana Jones and the Last Crusade, Finding Forrester, Highlander, and Dragonheart.

3 – Dana White Wins $5 Million in Blackjack

Dana White’s day job involves running the Ultimate Fighting Championship (UFC). But when he’s not heading the world’s top MMA promotion, he likes to relax by playing high stakes blackjack.

White is well known for betting up to $25,000 per hand. With a net worth of more than $500 million, the UFC President can afford his high-roller lifestyle.

White is more than just your average whale, though, because he’s won so much in blackjack that the Palms casino has banned him.

This story began in 2001, when White first started frequenting the Palms. He once won $2 million, to which the casino responded by cutting his credit limit in half and reducing his max wager to $5,000.

The 49-year-old wasn’t happy about the Palms’ decision and pulled all future UFC fights from the property. He took his business to Caesars and commended them for not “messing around with limits.”

Apparently, the Palms regretted the decision two years later and sent White an expensive bottle of champagne to win him back. The $5,000 bottle of Domaine de la Romanee-Conti Montrachet did the trick, and Dana both started playing at the casino again and hosting UFC events there.

If the Palms was hoping for a different result this time around, they were disappointed. Not long after being invited back, White won $5 million in a single session.

The Palms paid him in cash and refused to loan him a sack to carry the money with. White would later say that this was a safety issue, because he’d have to carry the cash through the casino and out to the parking lot.

Dana called some friends and had them bring black garbage bags to help him get the money home safely.

Aside from refusing to loan him a money sack, the Palms’ also banned White from their blackjack tables. But they did soften the blow by the sending him a championship belt that read “Palms Undisputed Blackjack Champion.”

4 – Tobey Maguire Dominates High Stakes Poker Ring

No official statistics exist on the biggest celebrity gambling winner of all time. But my best guess is that Tobey Maguire is the biggest celebrity winner.

Maguire participated in a 2011 underground poker ring that included other actors, businessmen, and pro athletes. Notable names in this game include Affleck, Damon, Leonardo DiCaprio, baseball’s Alex Rodriguez, and Instagram star Dan Bilzerian.

At some point during the poker game, California hedge fund manager Bradly Ruderman was arrested for defrauding his clients. Ruderman’s former clients wanted to recover their money through any means possible, including going after the $35 million that Ruderman lost in the poker ring. This case led to an investigation and the revelation that Maguire won somewhere between “$30 and $40 million” from the game.

I’m not entirely sure that a professional poker player has ever won this much money in lifetime cash game profits. If the estimates on Maguire are correct, he may very well be the winningest poker player of all time.

This poker ring inspired the 2017 movie Molly’s Game. Told from the viewpoint of the game’s hostess, Molly Bloom, this film describes the players without using names.

A report from The Ringer suggests that “Player X” represents Maguire. Played by actor Michael Cera, Player X is a cruel person who enjoys berating the hostess and destroying his poker opponents financially.

Of course, Molly’s Game is all based on the accounts of Bloom herself. So it’s hard telling if Maguire’s alleged character was really this bad.

Nevertheless, it’s interesting that she makes Player X out to be the villain among everybody in the poker game.

5 – Floyd Mayweather Wins $5.9 Million with NBA Bet

Floyd Mayweather has never been shy about his wealth, frequently carrying around wads of cash and celebrating his nickname “Money.” This image extends into Mayweather’s sports betting habits, where he frequently makes six and seven-figure wagers.

Money’s biggest reported sports betting win happened when he risked $5.9 million on a 2013 NBA Playoffs contest between the Indiana Pacers and Miami Heat. Mayweather put his money on Miami to cover the spread in Game 6 of the Heat-Pacers series. They won by 23 points, which earned him a profit worth well over $5 million.

In another instance, Mayweather bragged about how he bet $720,000 on the Indianapolis Colts beating the Jacksonville Jaguars. The Colts won and earned him a $1.4 million payout, to which he quipped “When you’re betting on Andrew, it’s never luck.”

Yet another famous Mayweather betting story is when he tried wagering $400,000 on himself in a 2017 boxing match with Conor McGregor. He wanted to split the money between a bet on himself winning at -200 odds, and the bout ending in under 9.5 rounds.

M Resort took considerable time to figure out whether it was legal for boxers to wager on themselves in Nevada. Mayweather got tired of waiting and eventually left without gambling.

Money continues to be one of the biggest bettors in Las Vegas, which earns him VIP treatment at any sportsbook he visits. He also posts his huge wins on social media sites.

6 – Jennifer Tilly Wins WSOP Bracelet

Jennifer Tilly is in the rare category of a celebrity who tried making a serious career out of gambling.

Acting is still definitely her craft since she’s starred in movies like Let It Ride, Made in America, Bullets over Broadway, Bound, Liar Liar, and Bride of Chucky. But she took a serious chance at poker in the mid-2000s.

Caught up in the Poker Boom, Tilly began playing in tournaments and cash games. She quickly experienced success by winning the 2005 WSOP Ladies No-Limit Hold’em Championship along with $158,625. Just a few months later, she won the World Poker Tour Ladies tourney along with $25,000. In all, Tilly has $992,501 in live poker tournament winnings.

Considering that she’s a movie star, it’s no surprise that Jennifer Tilly has also appeared on poker TV shows, including Bravo’s Celebrity Poker Showdown and GSN’s Poker Royale.

Tilly stated in a 2005 interview that she was more interested in a professional poker career than acting. However, she later changed her mind and now merely treats poker as a hobby.

“I’m not giving up poker entirely – gambling is an addiction after all,” she said.“I’m just going to treat it more like a hobby and less like a career.”

7 – 50 Cent Wins $1 Million Super Bowl Bet

Rapper 50 Cent was formally friends with Floyd Mayweather. Therefore, it makes sense that he too is a high stakes sports bettor who’s netted a few big wins.

50, whose real name is Curtis Jackson, once bet $500,000 on the New York Giants beating the San Francisco 49ers in the 2011 NFC Championship game. Jackson made this bet because he grew up in New York. And his hometown premonition turned out to be correct as the Giants beat the Niners by a score of 20-17.

The following week, rapper Birdman announced that he was going to wager $5 million on the New England Patriots beating the Giants in Super Bowl 46. The Birdman also challenged anybody to place in matching wager on New York.

Jackson wasn’t ready to bet these high of stakes. But he did offer to match Birdman up to $1 million.

The Giants pulled off an upset victory, winning Super Bowl  by a score of 21-17. The victory helped 50 win a $1 million payout, while it’s unclear if Birdman even made a bet.


Celebrities have the fame and wealth to turn their successful gambling sessions into huge profits. This is definitely the case with the celebrities on this list, who experienced huge windfalls through gambling.

Tobey Maguire is the biggest winner, earning an estimated $30-$40 million through poker. It appears that he took advantage of the combination of juicy cash games and subpar opponents to win big.

Ben Affleck is another skilled gambler to make this list. He counted cards so well at Hard Rock that they asked him to leave the tables.

Dana White is in the same boat as Affleck in that he was essentially banned from the Palms blackjack tables. White won millions of dollars, though, before the Palms had enough.

It’s unclear whether Floyd Mayweather and 50 Cent are truly skilled sports bettors, or they just make outlandish wagers. Whatever the case may be, they also make this list with seven-figure sports gambling wins.

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