Celebrities Who Beat the Odds: The Greatest Gambling Wins in History

Celebrities are never shy of showing off their riches. If they’re not posting their supercars and private jets on Instagram, they are on TV with gold chains and designer outfits.

Some celebrities also visit casino sites to play for real money. But they don’t bet $20 or $50 every now and then. They spend like the higher rollers they are. In this article, we’ll talk more about celebrity gamblers who’ve won a lot of money at casinos.

#1: Ben Affleck

Some know him for his role as Batman. Others know him as JLO’s on-and-off boyfriend. Regardless of where you know him from, there’s no denying that Ben Affleck has had a stellar acting career.

He’s a double Academy Award winner, a Golden Globe Award recipient, and a philanthropist. In his free time, the 50-year-old loves to play poker and blackjack. In fact, he’s so good at blackjack that the Hard Rock Casino in Las Vegas no longer accepts him as a customer.

Of course, casinos don’t ban you for no reason. Affleck was banned from the Hard Rock establishment in 2014 for counting blackjack cards. He was really good at it, though: he once won $800,000 at the same casino.

As we’ve already mentioned, Affleck plays both blackjack and poker. And he’s good at both games. A case in point—the Goodwill Hunting star won the 2004 State Poker Championship in California and walked away with a prize pot of $356,400.

#2: Dana White

Dana White is best known for running the biggest MMA organization in the world: the UFC. He’s worth more than $500 million, a fortune he loves to spend on luxurious items and gambling high-stakes blackjack games.

Similar to Ben Affleck, White hasn’t always had a cordial relationship with Las Vegas casinos. In 2014, the UFC executive won $2 million in two months playing blackjack at the Palms Casino.

The casino wasn’t happy and so it slashed White’s blackjack limits from $25,000 to $5, 000 per hand. Palms also threatened to ban White, to which he responded by pulling out UFC events at the casino. Discover More

In all fairness, White had a good reason for feeling angry. Not only was he a regular player at Palms Casino, but he was a great tipper. Reports say he would often leave $10,000 in tips per night and left a total of $200,000 in tips during the period he won $2m.

#3: Floyd Mayweather Jr.

Floyd Mayweather is nicknamed “Moneyman” both because he’s rich and because he likes to show it off. The undefeated retired boxer made more than $1.1 billion during his two-decade-long career.

And he continues to make more money through exhibition bouts and sports betting. For example, he won $4.7 million betting on NFL games between September and October 2014.

His biggest victory at the time was a two-leg parlay in which he backed the Colts and Seahawks to win their individual matches by over 7.5 points. Additionally, Floyd picked a $1.4 million profit by betting on the Broncos and a further $1.5 million after correctly predicting Arizona would beat Oakland.

Beyond the NFL, the 45-year-old has displayed betting tickets showing his large winnings after betting on college basketball, MMA, and boxing matches.

#4: 50 Cent

Known for hits like ‘Candy Shop,’ ‘Many Men’ and ‘In da Club’, rapper 50 Cent is also a passionate gambler who’s won more than $5 million in sports bets. In 2012, the rapper made $500,000 after backing the Giants to defeat the Broncos in the NFC Championship game.

When asked why he placed the risky bet, Fiddy claimed there were voices in his head instructing him to place the bet. The ‘Power’ TV Show actor credited the same voices for inspiring him to wager on the same year’s Super Bowl Game.

50 Cent bet $1 million the Giants would defeat favorites New England Patriots. New York won, netting the 47-year-old more than $1.5 million in profits. Fiddy has also claimed to have won millions of dollars in boxing.

He allegedly backed Mayweather to beat Manny Pacquaio in 2015. And that was despite him having beef with Moneyman. The issue was hilarious. Mayweather insulted 50 during an ice bucket challenge.

50 Cent responded by challenging Mayweather to read a Harry Potter page. And if he were successful, the rapper would donate $750,000 to a charity of Mayweather’s choosing.

#5: Tobey Maguire

Although he’s best known for his role as Spiderman, actor Tobey Maguire has appeared in more than a dozen films. In his free time, the 47-year-old Golden Globe Award winner plays poker.

Maguire is so good at poker that he’s made more than $200,000 in regulated competitions. To be clear, the Ice Storm Actor has made more than $1 million through illegal poker games, one of which got him into legal trouble.

According to CNN, Maguire was sued for participating in illegal high-stakes poker tournaments. He allegedly won $311,000—the main man behind the Ponzi scheme. Ruderman was sentenced to eight years in prison while Maguire settled his lawsuit with an $80,000 payout.

#6: Phil Ivey

Phil Ivey is famous for being a successful gambler. Poker is Phil’s game of choice. He’s so good at it that he’s won 10 World Series of Poker bracelets and one World Poker Tour title.

To make it clear, a poker bracelet is the most desired prize in any WSOP poker tournament besides money. When it comes to winning money, Phil has appeared in the top 25 of WSOP events for more than 10 years. For perspective, these events attract up to 7000 competitors.

#7: Matt Damon

Matt Damon is one of Ben Affleck’s best friends. They’ve been friends ever since they co-wrote and starred in Goodwill Hunting (1997). Beyond their friendship, the pair loves to play blackjack and poker together.

In 2010, the two friends made it to the WSOP Main Event. But they didn’t win. Damon participated in more poker competitions over the years. But he hasn’t always been as successful as his friend. It’s probably why he doesn’t talk a lot about his poker hobby that much.