Celebrities known for indulging in gambling

Celebrities and gambling have gone together like peanut butter and jelly for a long time. Th glitz and glamor of resort casinos are a huge draw for everyone, and especially for A-list celebrities. Before the rise of online casinos made gambling a more personal activity, certain celebrities were well-known for spending lots of time at casinos.

The most popular types of gambling among celebrities tend to be poker (high stakes of course!) and sports betting. Both of these have been associated with the rich and the famous for decades, if not centuries. Some celebrities also enjoying playing slots. For celebrities — and the rest of us — the best online casinos closely mimic the feeling of being at a real casino.

Here are some of the most famous gambling celebrities:

Organized crime and celebrities

The early days of Las Vegas were a heyday for organized crime. Most of the big casinos were financed with mob money. This added an extra layer of danger and excitement to an already exciting pastime.

Frank Sinatra was one of the most famous celebrity gamblers of his era. He even owned his own casino at one point! The connection between Vegas celebrities and the Mafia was so strong, it should be no surprise that he was the inspiration for the Johnny Fontane character in The Godfather (1972).

Some celebrities are more infamous than famous. The Kray Twins would certainly fall into that category. Ronnie and Reggie Kray were the kings of the London underworld during the 1960s. They maintained control through violence. Much of their fortune came from the casinos they ran that were popular with celebrities of the day, including Frank Sinatra. The Kray Twins were the subject of the 2015 biopic Legend starring Tom Hardy as both Ronnie and Reggie Kray.

The Viper Room players

In the early 2000s, an underground poker ring for celebrities was established in Los Angeles, with the first game held in the basement of the infamous Viper Room nightclub. For years, stars and wealthy gamblers met up in secret locations to play high stakes poker, sometimes losing hundreds of thousands of dollars on a single hand.

Among the most famous participants were Tobey Maguire (who eventually would run the games), Matt Damon, Ben Affleck, Leonardo DiCaprio and the Olsen twins. Ben Affleck is one of the players who lost big, including losing $400,000 on just one poker hand.

The story of Molly Bloom, has also been turned into a film. She is the woman who hosted the first game in the Viper Room and who managed to create a very successful poker tournament event company. That came crashing down when she was busted by the Federal government as part of a massive money laundering investigation. Molly’s Game (2017) starred Jessica Chastain and accurately captured how the world of underground celebrity poker worked.


Professional athletes make their living by pushing themselves to their limits in order to win. It should be no surprise that so many of them also love gambling. The competitiveness of games like poker is a huge draw, while the intense adrenaline rush of taking a big risk when placing a huge bet on a sports event has to be addictive.

Floyd Mayweather Jr is a flashy dresser and a flashy gambler. The former heavyweight champion loves to place huge bets on sports events but doesn’t have the best luck with picking a winner. His biggest successful bet won him nearly $3m. He has also successfully bet on himself, which is a very confident move. The majority of the bets he places are between $25,000 and $400,000. Whether or not this constant betting is a sign of a gambling addiction or just a very expensive hobby is hard to tell.

Some athletes have admitted that their gambling has crossed the line into problem territory. One of these is Charles Barkley who estimates that he’s lost more than $10m due to his gambling. While many people have problems with gambling, having so much to lose makes it much more noticeable.

Some sports organizations, like the MLB management, try to prevent their athletes from gambling because they worry that there are drugs present or that incurring too much debt could make a player susceptible to being blackmailed into throwing a game. Alex Rodriguez is one of the players that they have tried — and failed — to keep away from the poker table. A-Rod actually attended some of the Viper Room poker games.

Written by Monella