Celebrities at the Casino: Top 5 Winners and Losers

Gambling can be a lifestyle, a do-or-die affair, a leisure activity, or even an opportunity to amass generational wealth. Seeing celebrities in casinos keeps them wondering and muttering, ‘Why is this person still here?’ ‘Do they not make enough money from their jobs?’ Even with their seemingly stupendous wealth from their jobs, they still gamble, maybe to make more money or for the thrill. Some celebrities even have juicy offers, like VIP bonuses or the latest no deposit codes for existing players, at the tip of their palms. In this article, we want to highlight the top winners and losers among celebrities familiar with the casino lifestyle.

Below are some of the top celebrity winners to grace the casino floor

  • Tobey Maguire
  • Floyd Mayweather
  • Curtis James Jackson III
  • Ben Affleck
  • Aubrey Graham

Tobey Maguire

Tobias Vincent ‘Tobey’ Maguire is a 48-year-old American actor and producer. He played the title character in the popular Spider-Man: No Way Home in 2021. Tobey also appeared in films like The Great Gatsby, The Good German Brothers, Pawn Sacrifice, and many more. He had learned poker strategies from Daniel Negreanu – a Canadian professional poker player with six world series of poker titles. 

From the skills he learned, Tobey has had huge poker wins in addition to his big earnings and financial freedom as an actor in Hollywood. Many years ago, he was linked to an illicit poker rendezvous that had some other celebrities like Leonardo DiCaprio. He won an average of $30 million against this illegal poker rendezvous.

Floyd Mayweather

Floyd is an American boxing promoter and a former professional boxer who actively competed for 21 years. He retired with an unbeaten record and won major championships across featherweight and light middleweight. He fought 50 times, won all, and won 27 by knockouts. Floyd is not just a multi-millionaire from his career in boxing; he is also a gambler. He specifically gambles in sports, from the NBA to other matches outside the United States. In 2013, Floyd placed $5.6 million on the Miami Heat to defeat the Indiana Pacers in the playoff, and he won. He also greatly benefited from betting on the Indianapolis Colts to beat the Jacksonville Jaguars.

Curtis James Jackson Iii

Curtis James Jackson III – professionally known as 50 Cent – is an American rapper, businessman, actor, producer, etc. Hip-hop enthusiasts recognize him for singing on the Billboard Hot 100, charting singles in Da Club, and other hit records. He has had an impressive music career at unRecordsumbia Records, Shady Records – an imprint of Interscope Records and Dre’s Aftermath Entertainment – and as a label record owner. 

Aside from the wealth he’s amassed from singing into the mics in recording sessions, he has also been gambling, and not just that, he has also been winning big. He won $500,000 from wagering on the New York Giants to beat the San Francisco 49ers. Sometimes, in 2015, he also wagered on Mayweather to win his match against Manny Pacquaio and walked home with over $5 million.

Ben Affleck

Benjamin Affleck is a 51-year-old famous American actor, screenwriter, director, and filmmaker. He also co-founded a grant-making and advocacy-based non-profit organisation, Eastern Congo Initiative. He has received many accolades as an actor, including two Academy Awards. Despite having risen to the peak of his Hollywood career, the actor has been able to manage a gambling career on the side effectively. The Californian has made his mark in the poker game in the United States. 2004 he participated in the California State Poker Championship and won $ 356,400. He has also won millions of dollars from blackjack sessions at the Hard Rock Hotel in Las Vegas, Nevada.

Aubrey Graham

Aubrey Drake Graham is a professional Canadian rapper and singer. The 37-year-old is popularly known as Champagne Papi, 6 God, or Drizzy. Drake has had a successful music career, with each of his LP projects topping the US Billboard Top 200 chart. In music, he has a Guinness-book-worthy record of hitting 1 billion streams with a single song on Spotify, One Dance featuring Wizkid and Kyla. 

Besides his musical mastery, people are also aware of his gambling habits. He is a celebrity who can risk millions of dollars on a single game. He wagers on sports like Formula 1, UFC, NBA, and the NFL. According to a casino blog, Drake has amassed a gross win of $76.4 million and a net win of $46.81 million in a year from gambling.

Tiger Woods

Eldrick ‘Tiger’ Woods is a 47-year-old American professional golfer. He is arguably one of the greatest golfers ever and an inductee into the World Golf Hall of Fame. He is also one of the most famous athletes in history. Aside from sports, Woods has some noteworthy issues in his personal life, including his gambling habit. He has once lost $25,000 when playing blackjack. This is believed to have birthed a self-limit when gambling in Vegas in certain casinos. He may be better off playing at online casinos that offer anonymity, amongst other perks.

Pamela Anderson

Pamela is a Canadian-American actress, media personality, and model. She is popularly known for her role in the Baywatch and C.J. Parker television series and her modelling work in Playboy magazine. As renowned as she is in her work, she is also a fan of gambling. Like many other famous figures, her love for the game grew until it became something serious over the years. However, only some of her adventures resulted in big wins, as she reportedly lost about $250,000 in one sitting in a poker game. She allegedly admitted to covering her debt with a sexual favour.

Charlie Sheen

Carlos Estevez – professionally known as Charlie Sheen – is a 58-year-old American actor and filmmaker. He appeared in blockbusters like The Three Musketeers, Wall Street, Young Guns, Platoon, etc. He is also a recipient of nominations from Golden Globe and Primetime Emmy. According to a Hollywood reporter, his ex-wife reportedly filed for divorce because of his seemingly unhealthy gambling habits. Sheen allegedly spent an average of $250,000 per week on sports betting. She remembered a particular incident when Sheen was trying to place a bet while they were en route to the hospital to give birth to their daughter.

Wayne Rooney

Rooney is an English football manager and a former professional player. He is considered one of the best players of his generation, holding a goalscoring record in Manchester United and an 8-year-old record in the England national team between 2015 and 2023. While he’s made the headlines for some of the most iconic football performances, he has also been in the headlines for other not-so-good reasons. Rooney wagered and lost half a million pounds playing blackjack and roulette in a few hours. While it may not have affected his bank account too much, that’s a considerable amount to lose in hours of gambling.

Akshay Khanna

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