Celebrities against Gambling: The History of Gains and Falls

Being a famous person always implies not only fame and glory but also unimaginable amounts of money. Wealth becomes a reason for various extraordinary hobbies and posh activities. Money breaks all existing rules of a boring everyday routine. Do you know where one can also spend big money? Casinos. Gambling is a stupefying mix of a risky atmosphere, absorbing vehemence and considerable bets.

Besides, a casino is a form of entertainment not everyone can afford. That is why playing is so common among famous people from different spheres. Today, we are going to discuss who is the luckiest star and who’s down on his or her luck.

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Biggest Celebrity Gambling Losses

There is no doubt that gambling is always connected with risks and challenges. There is never a stable guarantee that your bet will win. However, when speaking of celebrity gamblers, the losses can sometimes appear to be devastating. We have chosen five star-spangled gamblers.

Show me a gambler and I will show a loser

© Mario Puzo

Gladys Knight

gladys knight casino losesGladys Knight, American singer, and songwriter, who is also known by the name The Empress of Soul, earned fame as an incorrigible player. Though she was busy producing multiple R&B hits after her retirement in 2000, Gladys tried to dissemble her vice. Later, she recounted her struggle and fight against playing addiction in her autobiography. Her total losses never were announced, but they say that Gladys could spend $40,000 per night playing table games (blackjack and baccarat). Sports betting can also be ascribed to her front-runner games of choice.

David Milch

david milch casino losesAnother famous producer also suffers from a venturous habit. David Milch abuses various staking pursuits. It is well known that once he lost $25 million playing in casinos. Milch made an attempt to pay off his debt and was able to pay back about $17 million. However, he failed in paying the total debt and that is the reason why they took possession of $100 million that he had amassed from his working. In addition to that, his wife wanted to get a divorce as she was no longer able to put up with Milch’s addiction.

Ray Romano

ray romano casino losesRay Romano, starred in the popular TV series “Men Of A Certain Age”. In fact, Romano’s character Joe Tranelli was also addicted to playing. One more curious fact is that Ray Romani himself is a celebrity gambler. His passion for playing got so bad that he had to seek help. In the end, he succeeded in overcoming his addiction and it definitely let him feel his character much better.   

Charlie Sheen

cgarlie sheen casino losesCharlie Sheen often takes the lead in a lot of poll numbers concerning stars who love his only problem. Charlie was a fan of staking and he used to spend an enormous amount of money on sports bets. He could spend up to $200,000 per week playing and this was not just on one occasion.   

Leonard Tose

leonard tose gambling losesFinally, Leonard Toe lost approximately $50 million of his trucking-industry profit in casinos. It all ended up with him having $25 million of debt and in order to pay all of it, he had to sell his ownership of the Philadelphia Eagles NFL franchise in 1985. Furthermore, Toe did not manage to solve his problems with staking and it led to the seizure of two of his houses for unpaid taxes.

Celebrity Gamblers Always Have a Chance to Win

As we have already said, gambling is always connected with huge risks and sometimes the risk pays off. Touching on casinos, the risk is usually paid off quite bountifully. Here is our top-5 list of successful celebrities who won the fight against gambling.

Tobey Maguire

tobey maguire casino winsOr, should we call him Peter Parker? Anyway, he happened to take part in an illegal wagering ring in 2011 and he was tried by a court for engaging in these illegal activities. Nevertheless, this fact does not prevent us from saying that he is a professional poker player. There is proof! Toby was reported as winning $10 million in Poker tournaments.

Matt Damon

matt damon casino winsGoes side by side with Toby Maguire. The truth is that Matt is also addicted to gambling and he also took part in an illegal gambling ring that took place in 5-star hotels. Moreover, he is an old friend of Ben Affleck and they often wager together. There is no particular information on his resounding victories but still, there is no grounds to have any doubts concerning Matt’s impressive wagering talent.

Ben Affleck

ben affleck casino winsFun fact detected: He is not only a talented comedian-actor but also a highly-qualified gambler. It cannot be denied that he had to go through therapy due to his playing habit and alcohol addiction. However, Ben has outstanding poker and blackjack skills. He won the online California State Poker Championship and he was forbidden to wager at a Las Vegas casino as he was too good at winning hands.

Victoria Coren-Mitchel

victoria coren mitchel casino winsShe is an indisputably good writer but there is one more thing which she does really well – poker. Victoria is known to have become the first woman to win a European Poker Tour title in 2006. She took leading positions in other tournaments and what is more exciting, she won the European Poker Tour Sanremo as well. Overall her winnings are estimated at over £2 million.

Derren Brown

derren brown casino winsDerren is not distinct in crazy bets but apart from that, he is rather successful in gambling. In casinos, he always bets only small amounts of money and he never loses. Casinos, for their part, are not too pleased with such consequences because Derren was banned from the Broadway Plaza Casino in Birmingham. Places for wagering are frequently careful with all players who win too often. It cannot happen in this world.

Success in losing

However, the winner still cterrance watanabe gambling losesan only be one. The only king among a wide range of superstars who are shaking the arena of betting. Have you got any guesses? Have you heard anything about Terrance Watanabe? Although Terrance is a successful businessman, it would not be a lie to say that he gained real popularity due to his gambling passion.

In fact, he is quite well-known among different world casinos, but his real star shined, in 2007, when it was reported that Terrance lost $127 million in one year. This sum refers to his losses in only two Las Vegas casinos – the Rio and Caesars Palace. One more interesting detail: Terrance hardly has outstanding playing skills – this was pointed out by casino employees. He only has the possibility to lose. Thus, in gambling, it seems that it is not talent, but luck, that determines your success.

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Look at ten Biggest Celebrity Gambling Wins & Losses

① Celebrities Against Gambling ᐉ Ups and Downs【TOP 10】 video preview #celebrity #celebritynews You can find out more about the biggest losses and wins of celebrities in our blog: https://casinocanada.com/blog/10-big-celebrity-gambling-losses/ If you would like to know more about casino games and its variations, visit the #1 CANADIAN GAMBLING GUIDE: https://casinocanada.com/ Gaming comes with risks. If Lady Luck is not on your side, there is not much you can do. Here are some of the toughest battles of celebrities against gambling. In this video, we talk about the biggest celebrity gambling losses and wins. Check out our lists of top celebrity highrollers who went down in gambling history as legends. Some of the famous names are Ray Romano, Charlie Sheen, Tobey Maguire and Ben Affleck. TimeLine. Loses 1. N.1 – Gladys Knight 0:25 2. N.2 - David Milch 0:55 3. N.3 – Ray Romano 1:26 4. N.4 – Charlie Sheen 1:52 5. N.5 – Leonard Tose 2:26 WINS 1. N.1 – Tobey Maguire 3:20 2. N.2 – Matt Damon 4:05 3. N.3 – Ben Affleck 4:36 4. N.4 – Victoria Coren – Mitchel 5:07 5. N.5 – Derren Brown 5:38

Lucas Goldberg
Lucas, a seasoned site editor at CasinoCanada, boasts a decade-long journey in the gambling industry with a focus on providing players with meticulous reviews and insights of online games and casinos.
Site Editor
University of Toronto
Bachelor of Arts in Communications, Digital Media, and Journalism, PlayTech Analytics career, communication with users through high-quality gambling content.
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Reviewed by Head of Content:
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Last updated on: 20.02.2024

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