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Celebs Who Won Big in Gambling


The reason why celebrities are held in high esteem by ordinary people is that of their good looks, fame, and fortune. But the fact that celebrities enjoy doing the same things as average people including indulging in different forms of gambling. What makes us different is the kind of lifestyle we live. Most celebrities are on a high pay grade, as such, they are can afford to gamble much bigger stakes than the rest of us. Thus, it should be no surprise that a good number of Hollywood celebs, professional athletes and musicians have been big-time winners in gambling. Unfortunately, some of these big celebrities have been struggling with gambling addiction as well. Read on to learn about some of the top celebrities who are also expert gamblers and have won big through gambling.

Ben Affleck

Ben Affleck is a famous Hollywood Director and Screenwriter. He has built his career by starring more than 50 blockbuster movies such as Chasing Amy, Daredevil, Armageddon, Reindeer Games and won two Oscars. Besides his busy career life, Ben is also an accomplished Poker and Blackjack player! Back in 2004, he entered a casino and emerged the winner of California State Poker Championship, walking away with a whopping $356,400. This win earned him a position on the World Poker Tour final tournament. He is also reported to have more than $1 million in two Blackjack sessions among many other huge prizes while playing Blackjack at the Hard Rock Hotel in Las Vegas until the casino management politely asked him to leave the table. The famous Batman and Spiderman actor is rumored to have been involved in a celebrity poker ring together with his close buddy Matt Damon. Unfortunately, his love for gambling has contributed significantly to his divorce with Jennifer Garner.

Sean Connery

James Bond is an iconic movie star that has been known for his gambling acumen. In fact, he lives up to his 007′ legend by winning a roulette feat that is always considered impossible. Sean has featured in other popular movies like The Name of the Rose, Dragonheart, Indiana Jones and Last Crusade, The Hunt for Red October and many others. The Scottish actor was once in Russia for filming and decided to try out his luck at St. Vincent’s Casino de la Valle. It is reported that he joined a European wheel roulette game and placed a single wager on 17. This roulette bet is to know for the most significant odds of winning at 36 to 1. Unfortunately, he lost in his first two spins, before defiling the roulette odd by winning a single number bet. Surprisingly, Sean wagered his wins on the same 17 and finally earned $27,000 in profit.

Victoria Coren Mitchell

If you have ever watched British panel shows, then the name Victoria Coren will quickly ring in your mind. She is married to the Peep Show star, David Mitchel, and besides her excellent presentation and writing work, she is also a talented Poker player. Victoria was the first woman to win in the European Poker Tour and led in several renowned poker challenges. Her total gambling winnings are over $2 million. Victoria is also known for her love for Texas Hold em poker game at Victoria Casino in London.

Dana White

Dana White is a professional in Ultimate Championship (UFC) and big-time fan of Blackjack. He is popularly known for staking up to $25,000 per hand. With a net worth of over $500 million, such a wager is nothing to Dana White. He is reported to have won many times in Blackjack until the management at Palm Casino banned him from the table! The UFC President was not happy at the casino’s treatment and moved to Caesars Casino where he warned them not to interfere with his bet limits. The Palms Casinos realized the mistake they had made two years later and apologized with a very expensive bottle of Domaine de la Romanee-Conti Montrachet worth $5,000. It did not take White long before he hit a $5 million win in a single game round after returning at Palm Casino. The management paid Dana White all the money in cash and denied him a carrying bag! He was also entirely banned from playing at any blackjack table in Palms Casino after awarding him with the champion’s belt labeled, “Palms Undisputed Blackjack Champion.”

Tobey Maguire

Tobey Maguire is considered one of the biggest poker winner in gambling history. He was involved in an underground illegal poker ring back 2011 that involved Hollywood’s celebrities, people in business and pro athletes like Leonardo DiCaprio, Ben Affleck, Damon Matt, Dan Bilzerian, and Alex Rodriguez. The case which involved Bradly Ruderman for defrauding his clients is what revealed that Tobey had won between $30 and $40 million from the Poker ring. This story inspired a 2017 movie dabbed, ‘Molly’s Game,’ where Maguire is portrayed negatively. Maguire learned his skills of playing poker from a six times winner of World Series of Poker, Daniel Negreanu.

Floyd Mayweather

The retired boxer Floyd Mayweather has never been shy of telling the world how wealthy he is. He is frequently seen carrying around bundles of cash as he celebrates his nickname “Money.” He loves betting on sports where he makes nothing less than a six of the seven-figure bet. It is reported that he once wagered $5.6 million on a 2013 NBA Playoffs match between the Indiana Pacers and Miami Heat. He placed his money on Miami Heat who won with 23 points. Well, the bet earned Mayweather a cool profit of over $5 million. Also, he was heard bragging about a bet he placed on a match between Indianapolis Colts vs. Jacksonville Jaguars, where his bet was on the Colts. They won, and he walked away with a payout of $1.4 million. What’s even more interesting is that Mayweather once placed a bet on himself in 2017 when he was fighting Conor McGregor. His prediction was winning at -200 odds and the fight ending in under 9.5 rounds. Unfortunately, the bet never materialized because M Resort took long to consult whether or not a boxer can bet on himself.

Michael Jordan

Michael Jordan is well known as the greatest basketball player in history. He is not only a six-time NBA champ but also a good gambler. Michael has featured in some of the most exciting gambling stories. His fellow NBA player and friend Charles Barkley said that MJ had at one time placed a bet $300000 on a single golf putt. In another story told by Earvin Johnson, MJ would sleep for one hour every night and spend the rest of the time playing poker with Magic, Barkley and Scottie Pippen during the 1992 USA Dream Team Olympics. Surprisingly, he woke up the following day and dominated his the competition and carried home the Dream Team winning gold. Whereas MJ is a big-time winner, his gambling habits have put him in some serious controversies. Jordan was once seen gambling in Atlantic City during the Chicago Bull’s 1993 compete for the NBA title. The game was between the Bulls and the New York Knicks, and MJ was spotted in the gambling binge the night before the match. The NBA launched investigations into Jordan’s gambling life, and the legend retired from gambling four months later.

Deren Brown

Known as the master of illusion and misdirection, it does not come as a surprise to see him practicing gambling too. He was a regular customer in some of London’s best casinos before he moved to host nearly impossible shows and performances. According to casino operators, Deren always played small stakes but what surprises them is that he never lost his bets. In fact, he was banned from playing in several casinos including Birmingham’s Broadway Plaza Casino and others.

50 Cents

Curtis Jackson III alias 50 Cent not only famous for his rap songs but also for surviving nine bullet shots. He is among the first musician to accept bitcoin payments for his fifth album ‘Animal Ambition’ which earned him $500,000 in Bitcoin. This equivalent to more than $7 million when converted. Besides, he is an ardent sports bettor, and it is reported that he once scooped around $500,000 on an NFL match between New York Giants and San Francisco 49ers back in 2012.

The Bottom Line

Celebrities have everything it takes to be successful in their gambling sessions. They can participate in high stake betting without worrying about the size of their bankroll. The names you see above are just but the iceberg of course; there are many others who opt to remain anonymous for personal reasons. The fact is that not all celebrities are successful gamblers. There are cases where big celebs have lost large sums of money while gambling. Additionally, some celebs are struggling with the problem of gambling addiction in their lives.

Written by CelebMix