10 Celebrities That Are Known to Bet Big – Rolling the Dice


Sports betting is an exciting and fun way to earn a bit online and to make the games you otherwise follow that much more interesting. When it comes to betting celebrities are just like us. They love to bet and occasionally they win big. In this article, we’ll talk about some of the celebrities who are known for gambling and winning big.

10. Michael Jordan

Michael Jordan is the GOAT not only on the basketball court but also when it comes to sports betting. Many claim that Jordan’s 1993 retirement was actually a suspension because of his betting habits. More sinister rumors have claimed that Jordan’s father was killed because of his gambling debts.

In 1997 Jordan wrote a check to James Slim Boulder, a known gambler and a drug dealer sentenced to 9 years in prison. At the same time, several golf players claimed Jordan owes them over $1.3 in golf gambling debts. These days there’s less of a stigma when it comes to the ties between the NBA and sports booking and now when Jordan is an NBA owner he also invests in DraftsKing, a sports booking site.

9. Charles Barkley

Charles Barkley is another Hall of Famer who was known to place high-roller bets and lose a few of them as well. Barkley famously said he lost over $30 million on sports betting over the years, but also that he won million-dollar bets “a few times”.

A few of the biggest bets Chuck made include:

  • Bet $100,000 on the Portland Trail Blazers winning the 2020-21 NBA Western Conference.
  • Bet $500,000 on New England against the spread (+14) and $50,000 on NE moneyline, against the St. Louis Rams in Super Bowl XXXVI – won a payout of $800,000.

Barkley is now also an ambassador for a betting site and often talks publicly about the importance of responsible betting. For those who want to follow the steps of Barkley, online review sites such as WeGamble provide players with a wide array of betting sites to choose from and find the one that suits their bets and interests.

8. Ashton Kutcher

Ashton Kutcher

Ashton Kutcher is best known for his roles in That 70s Show and Two and a Half Man, but he also has a reputation for betting on sports events and often winning big. Kutcher often talked about his approach to sports betting. He claims that he sees it as a business investment and takes a long and calculated look into bets, instead of looking for quick thrills.

Most of Kutcher’s bets were on college football and he’s known to win about $ 750,000 bets in four weeks.

7. 50 Cent

50 Cent

50 Cent was never shy about his lavish lifestyle and that included making large bets on numerous sports events over the years. Most of his bets are made on college football and NFL games. Famously, 50 said that he followed a voice in his head when he made $500K on football bets in 2012. He made $500,000 profit on the New York Giants to defeat the San Francisco 49ers in the 2012 NFC Championship Game.

50 Cent also promised to share a nude photo if the NY Giants lost the Super Bowl XLVI, but he lucked out on that one.

6. Drake

Drake is probably the most famous Toronto Raptors fan. He also spoke about his love for sports and is known to be seen in public in many different jerseys. The love for the game also translates into the love for betting as well.

When it comes to the public bets, things aren’t going that well for Drake, since the media mostly reported about his many losses. These include: the loss of $60,000 after betting Golden State would defeat the Cavs in the 2016 NBA Finals and the loss of $6,000 after he wagered the Kentucky moneyline against Wisconsin in the 2015 NCAA Basketball Final Four.

5. Charlie Sheen

Charlie Sheen

Given what we know about Charlie Sheen’s personal life it’s of little surprise that he enjoys betting a bit too much. It was alleged by the actor’s ex-wife that Sheen used to bet on boxing matches every night and that he often lost as well. This is somewhat ironic as Sheen’s latest project is on HBO’s show about bookmakers.

During Sheen’s divorce, his second wife Denise Richards claimed that Sheen lost as much as $200K per week. In 2012 Sheen claimed that he stopped betting since it was no longer thrilling, regardless of how large the bets were.

4. Birdman

Birdman And Slim

Another rapper on our list, and another celebrity that was very vocal about their bets and losses. Everyone familiar with Birdman’s career is also familiar with his love for sports and the New Orleans Saints in particular.

Birdman famously lost $2 million wagering on LeBron James’ Miami Heat to defeat the Dallas Mavericks in the 2010 NBA Finals. He also bet $4 million on Floyd Mayweather Jr. to defeat Shane Mosley back in 2010. Birdman came out with $1 million in profits.

3. Ben Affleck

Ben Affleck is known as a Hollywood celebrity who frequented Las Vegas and loved to gamble in high-roller tournaments. In recent years, Affleck has changed his image, and that included giving up on betting. In fact, Affleck was at one point banned from playing blackjack at the Rock Casino in Vegas.

Affleck was caught counting cards which is not technically illegal but it’s not allowed by most gambling establishments. He was also a part of a private poker game that turned out to be a scam that lost Affleck a lot of money, but the exact amount was never disclosed.

2. Ray Romano

Ray Romano

Given Ray Romano’s on-screen persona few thought that he had a gambling streak in him, but those in the know claim otherwise. Romano also played a character that had a gambling problem years later, long after he stopped betting himself.

Compared to the others on our list Romano’s bets were fairly modest. Sums of $ 10,000 per bet were mentioned in some interviews, which would be huge compared to an average player out there, but in Hollywood, it’s even modest. Romano bets on sports booking as well as on casino games.

1. Pamela Anderson

Pamela Anderson

Pamela Anderson was one of the biggest stars of the 90s known for her exciting private life as much as her iconic roles. Famously Anderson met her future husband Rick Salamon at a poker game. In an interview with Ellen, Anderson said that she was $ 250,000 in debt to Salamon when they started dating.

Over the years Anderson moved away from the world of high-roller poker and dedicated her time to political and animal rights activism.

What You Need to Know About Online Betting

All the stories about celebrities winning big can be inspiring to those who are just getting into the world of online gambling. It’s important, however, to keep in mind that celebrities are usually getting into the game with deep pockets already.

It’s important to practice safe gambling when betting online. This means that the player needs to study the odds of different casinos and different games, as well as set up safe betting practices such as creating a stop loss and sticking to it after a few bad turns. Practices such as these prevent players from chasing their losses and it limits the risks involved.