Legendary Gamblers: George Clooney

Mr. Ocean's Eleven is no stranger to a bit of gambling, whether on or off screen. In fact table games are his favorite type of games in real life too! From playing a role of a casino con-man, to creating plans and investing millions into his own casino, we look at the life of, legendary gambler, George Clooney.

Who is George Clooney?

George Clooney has been an A-list actor and iconic figure in Hollywood throughout the last 20 or so years of his career. While he had a few roles before, he got his big break as Dr. Doug Ross on the hit television show ER where he won two Prime Time Emmys.

After his television success, Clooney transitioned to the big screen with leading roles in The Perfect Storm, O Brother, Where Art Thou?, and of course potentially his most famous role in Ocean’s Eleven. He then went on to direct several hit movies including Syriana and Leatherheads, both of which he also was the lead actor in.

He also “wrote all but two scenes” in Leatherheads. Outside of movies, Clooney is a staunch activist and humanitarian who co-founded Not On Our Watch, a humanitarian organization. Clooney’s acts on, as well as off, the screen have made him one of the most globally respected people on the planet.

What Makes George Clooney’s Gambling So Legendary?

As we mentioned earlier, one of George Clooney’s most famous role was in the Ocean’s movies which include Ocean’s Eleven, Ocean's Twelve, and Ocean's Thirteen.

This series was a remake of the Frank Sinatra-starred film, of the same name, from 1960. Clooney plays a thief who plans to rob three casinos in one night with his crew. However, Clooney himself is no stranger to casinos or the Vegas lifestyle...

Interest From a Young Age

As a teenager, Clooney could often be found playing poker which has followed him into his adult life. The stakes have risen since his youth as he has been known to play in many high-stakes poker games.

The Poker Trio

Clooney, Matt Damon, and Ben Affleck were a well known threesome who enjoyed playing at the casino together. Damon's spark of interest developed from his role in The Hustler where he was even trained by poker pro Johnny Chan. Damon's affinity rubbed off on Affleck and the two began competing in poker tournaments together.

However, Clooney was also involved in the poker fun, just not at a competitive level. The three would regularly be spotted and papped at card tables in Las Vegas casinos. In fact, once a year the trio get together to spend a week gambling in the City of Sin!

Betting He Would Remain Single By 40

Before Clooney was married, to Amal Alamuddin, he was often seen as a Hollywood playboy who would never settle down again; following his divorce in 1993. He seemed so sure that he would be unmarried by the time he turned 40, that he made a wager with both Michelle Pfeiffer and Nicole Kidman. Clooney bet each of the women $10,000, that not only would he stay unmarried by the time he turned 40, but he would also have no kids.

While his name was tied to many women during that period, including actress Lucy Lu and professional wrestler Stacy Keibler, he never officially settled down. When the time came and he hit the age of 40, in 2001, Kidman was willing to pay up her part.

Clooney, however, insisted that they make it a double or nothing bet on the principle that he would stay unmarried by the time he hit 50. In an instance that promotes safe gambling, Clooney chose love over a wager.

George Clooney’s Biggest Gambling Controversies

The wins never come without losses and Clooney has seen a fair few losses within his affinity for gambling. From millions lost, in investment, to an unbelievable lucky streak, we delve into Clooney's most notorious gambling controversies...

Losing Millions After Investing into a Casino

While Clooney played a character in a movie that robs a Las Vegas casino, he was probably feeling a bit robbed when his plans for a Vegas casino fell through. Las Ramblas, the proposed name of the Paradise, Nevada-based resort, was going to be an 11-tower hotel and condo combination right outside of the Vegas strip.

It was announced in 2005, and was planned to be opened around June 2007, with an estimated evaluation of $3 billion. It is reported that Clooney put in around $10 million into this venture, which was eventually sold to Edge Resorts for $202 million. The land has been sold numerous times since Clooney and other investors decided to sell it in 2006.

Losing 25 Straight Hands of Blackjack

Just because Clooney is a celebrity doesn’t mean that he can’t have a cold betting streak like the average everyday person. In a behind-the-scenes interview for Ocean’s Thirteen, co-stars, Damon and Clooney reminisced about a time when Clooney lost 25 straight hands of blackjack.

Damon said that he would not have believed it, if he hadn’t seen it with his own eyes. It got so bad at one point, Damon said, that even the dealer was laughing at Clooney’s misfortunes!

Cursing The Owner of Wynn Resorts

Clooney’s struggles in Vegas, outside of failed business ventures and losing 25 hands of blackjack straight, also include a verbal spat with one of the most prominent figures in Las Vegas history, Wynn Resorts casino mogul, Steve Wynn. While there isn’t a ton known about exactly what went down during the conversation, we know that there were nine other people at the table, according to Clooney.

During this conversation, Wynn called Barack Obama, the president at the time, “an asshole”. Clooney then responded by calling Wynn the “asshole” and stated, "I wasn’t going to sit at his table while he was being such a jackass.” Clooney also mentioned that other adjectives and adverbs were used during the argument. It is unknown if they even reconciled their differences.

Where is George Clooney Now?

Clooney keeps busy by working on many different projects in Hollywood, whether that’s as an actor or as a director. Many fans of Clooney are very excited for him to star in the new movie Wolves alongside former Ocean’s Eleven co-star Brad Pitt which is listed as an American psychological thriller film, written and directed by Jon Watts.

Both Clooney & Pitt are co-producers on the project. Clooney is also heavily involved in his charity and philanthropy work with the The Clooney Foundation for Justice, which is currently in 40 countries.

As of a 2022 IRS filing, the foundation received $10 million in donations, and has spent nearly $4 million on its programs. Clooney doesn’t seem to gamble as much as he used to but he still hosts a charity poker game or two from time to time; with some other A-list celebrities on the guest list. Given his 25-hand cold streak, it’s a safe bet to make that he hasn’t played any blackjack since.