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Tiger Woods to Sean Connery: Celebrities who love to gamble

1st March 2018 Print

It's hard to resist the pull of gambling. When it's good, it's great, and an accomplished gambler can get in and out without breaking the bank. In this list, we've compiled a few famous celebrity gamblers and their luck when it comes to the tables. How do you stack up?

Ben Affleck

Before he became the billionaire playboy Bruce Wayne, Affleck had a great string of luck in his casino game of choice – blackjack. He was so successful, in fact, that he was booted from a blackjack table in 2014 for being too good. It's perhaps no surprise that Affleck enjoys '21'; with sites like Casinos Killer making it easier for players to track down deposit bonuses and other promotions, the classic game's popularity is booming.

Tiger Woods

Being a golfer on the level of Tiger Woods means bringing in more money than you could ever hope to spend. The solution to this? Gamble big, and win bigger. Tiger has been said to bet as much as $25,000 per hand in some games and, according to casino executives, has walked home with winnings of over a million dollars on a regular basis. Nice to know he has something to fall back on should he ever tire of golfing.

Jennifer Tilly

Academy Award nominee, actor, voice-over artist and gambler, Jennifer Tilly is a huge gambling enthusiast who spends much of her time hitting the tables. Tilly is no slouch in the world of gambling, having built up considerable skill and reputation with her years of experience. Back in 2005, she won the World Series of Poker Ladies title, taking home a massive $152,625. Often known for playing the role of a ditz, her skill shows her as anything but.

50 Cent

Not just a successful businessman and rapper, 50 Cent has shown himself to know when to place to place a good bet, and how to win big. In a boxing match between Floyd Mayweather and Oscar de la Hoya, 50 brought home a cool million dollars. That’s worth two million times more than his name, and that’s not bad.

Sean Connery

We could never pass up a story on James Bond, or at least one of the actors who played one of the more popular incarnations. Back in 1963, Connery turned heads by playing roulette and coming out with an enormous win. After a few losses, he kept betting on his lucky number – 17 – and ended up winning on it three times in a row. Following this, he left neither shaken nor stirred, and around $160,000 richer (in today's money).

Floyd Mayweather

One of the richest athletes the world has ever seen due to his boxing, Mayweather has the cash to flaunt, and one of the ways he does this is by hitting the casino. Using what he has learned in his own sporting career and applying it to betting on boxing, basketball, and the NFL has enabled Mayweather to net over $10 million. This includes an enormous win in 2013 where he took home $6.49 million from a single NBA bet.