Surprising Facts About the World’s Richest Gamblers

Surprising Facts About the World's Richest Gamblers - Featuring Sean Connery as 007 James Bond in Dr. No (1962)

In the world of gambling, the house usually wins. But if you are already seriously wealthy, then you can afford to put more cash on the line than most people will earn in their lifetimes and still walk away financially solvent, win or lose.

It is no surprise, then, that many of the rich and famous are also big fans of gambling. What may be surprising is the extent to which everything from poker to sports betting can appeal to high flyers, so here is a look at just a few of the most eye-catching facts about these high rollers and their hobby of choice.

50 Cent lets his intuition guide his choices

Rapper 50 Cent, real name Curtis Jackson, has made millions from the music industry as well as a variety of business ventures, and over the years he has spent his cash on various luxurious, including exhibiting a penchant for placing big wagers on major sporting events.

Perhaps his most famous gambling win came back in 2012 when he netted half a million dollars after backing the New York Giants to beat the San Francisco 49ers. Furthermore, he did this after getting inner guidance, according to tweets posted at the time.

Lots of gamblers rely on intuition to steer their decisions, as well as using cold logic to get them the results they want. For example, experts use different types of slot machines to find those with the best odds and payout percentages, rather than choosing blindly. In the case of 50 Cent, following his gut has paid off on at least one occasion.

Tiger Woods has carte blanche at most Vegas casinos

Tiger Woods made over $62 million in 2020 and has a net worth of close to $1 billion, so he certainly qualifies as wealthy, and is also known for being an acolyte of the casino lifestyle.

In fact various sources have suggested over the years that Woods is so well known in Las Vegas that he is able to frequent any casino of his choice and make full use of a $1 million limit extended to him by the owners and operators.

High rollers from all walks of life are treated to a raft of perks at casinos, but the celebrity of this golfing pro gives him even more clout, so it makes sense for these venues to go the extra mile to accommodate his tastes. It is believed to be entirely normal for Woods to wager $25,000 on a single hand of poker, his game of choice.

Tobey Maguire was a master of the underground poker scene

He may be known for his clean cut image and playing superheroes on the silver screen, but Tobey Maguire also has a not-so-secret second life as a poker player.

Of course plenty of rich and well known people play poker, but in many cases this is just a pastime which they expect to cost them money in the long run. This is not the case for Maguire, who has competed in professional tournaments and walked away with more cash than he came in with on several occasions.

More intriguingly still, Maguire was also deeply involved in an underground, high stakes poker scheme which eventually came to light in 2011 as a result of a court case, and was subsequently made into Molly’s Game, a movie written and directed by Aaron Sorkin. While Maguire himself is not directly named in the film, his involvement is included pseudonymously. This is how we know more about what he got up to, including securing major tournament wins, trumping other big names like Leonardo DiCaprio and Ben Affleck in the process.

Sean Connery wasn’t only a lucky gambler as James Bond

Iconic actor Sean Connery was renowned for his portrayal of British superspy James Bond, and that character certainly had his fair share of casino experiences, with gambling forming a key part of several of the original novels, as well as the subsequent movie series.

A famous story involving Connery’s real life gambling exploits dates from 1963, when he rocked up to the roulette table at Italy’s Casino de la Vallee and put money down on 17. The first two spins were a dud, but on the third he struck it lucky, and he kept it up for two more spins, eventually walking away with the equivalent in today’s money of almost $200,000.

17 was Connery’s lucky number, and on this occasion that proved to be the case. It shows that with persistence, sometimes your luck can pay off.