There is a certain congruence that seems to exist between the bright lights of the casino world and the bright lights of Hollywood. Back in the day, Las Vegas was actually considered the favorite adult playground for the “rich and famous.” Given this historical relationship between celebrities and the gambling world, it should come as no surprise that a few celebrities have managed to “break the bank” throughout the years.
Of course, it helps when you have a large sum of money to wager from acting gigs and sponsorships. The rest of us need all the help we can get in the form of no deposit welcome bonuses and other promotional offers. For kicks, let’s take a look a four (4) celebrities that have had significant success as gamblers.
Ben Affleck
Back in the 1950s, it was the “Rat Pack” that ruled the bright lights of Las Vegas. That highly talented group of celebrities included Frank Sinatra, Sammy Davis Jr., Dean Martin, and Joey Bishop. More recently, there has been a new Rat Pack trolling casinos and poker rooms all over the world. The new Rat Pack includes Hollywood’s best in Ben Affleck, Toby Maguire, and Matt Damon among others.
Regarding Affleck, he has managed to make a name for himself as a semi-professional poker player and a rather notorious blackjack player. His gambling success started in 2004 when he won the California State Poker Championship, taking down a number of prominent pros in the process while winning $365K. He has also been a regular participant in the World Series of Poker where he has managed to take down some pretty good prize money.
As good as Ben is as a poker player, his blackjack prowess is even more notable. On one notable blackjack run at the Hard Rock Cafe in Las Vegas, he took down an amazing $800K in a single night. Maybe, his winnings brought too much attention from the casino’s management. Ben would later get banned from a number of U.S. casino properties after being accused of being a card counter.
Floyd Mayweather
During his undefeated career as a professional boxer, Floyd Mayweather spent a good deal of time in Las Vegas. He also wagered huge sums of money in sportsbooks, but what else would you do with your spare time if you have a net worth in excess of $500 million?
Throughout the years, Mayweather has made quite a few sports wagers in excess of seven figures. For the record, one of his biggest wins came in 2013 when he wagered $5.9 million on the NBA’s Miami Heat to beat the Indiana Pacers in Game 6 of a playoff match. The Heat crushed the Pacers, rewarding Mayweather with over $5.0 million in cash.
All the big wins aside, it would be remiss to not mention that the boxing champ did lose $13 million in one day when wagering on the Denver Broncos to win the Super Bowl in 2014.
50 Cent
In gambling circles, it’s never clear who the big winners are unless they decide to boast about their winnings. It’s clear that rapper/hip hop superstar 50 Cent has had more than his fair share of big wins from sports bets over the years. If anyone has any doubt, a quick look at his social media accounts will testify to his prowess as a sports bettor. Then again, who goes on social media to brag about their losses?
As for the big wins, he can boast about collecting millions from betting on high-profile boxing and MMA matches. His one huge sports bet of note came when he wagered $500K on his beloved New York Giants to beat the San Francisco 49ers in a 2011 NFC playoff game. When he won the bet, he famously made and wore a chain that included all of his winnings and posted pictures on social media. That’s how you boast about winning bets.
Tobey Maguire
Top actors are known for their creativity. That certainly would be applicable to our favorite neighborhood “Spiderman” Tobey Maguire. When Tobey isn’t out saving people from the bad guys, he can often be found playing high-stakes poker somewhere in the world. On more than one occasion, Maguire has won thousands in cash in the World Series of Poker.
As for his creativity, Maguire has never been one to sit around looking for a chance to play poker. In fact, he has become quite famous because of his willingness to organize high-stakes underground poker games that include some of the wealthiest people in the world. To be clear, most of these games are illegal.
It is said that the hit movie “Molly’s Game” was taken right out of Maguire’s playbook. The movie tracks an entrepreneurial woman named Molly who shook the poker world by organizing some of the biggest underground poker games in history.
For his part in the underground poker world, it was rumored that he once won between $10 million and $40 in a single poker run. With that kind of money, who needs to be an actor?
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