The Most Notorious Basketball-playing Gamblers of All Time
By: Brian 
September 5, 2023

The Most Notorious Basketball-playing Gamblers of All Time

Gambling is deeply ingrained in American culture. Ever since the days of the mafia running the scene in New York, punters and speculators have long wanted to test their luck in the Land of the Free. In modern times, the pastime has never been more popular, with Las Vegas raking in record-breaking income year after year.


As such then, it's unsurprising that numerous sports figures have engaged and continue to engage in betting. Over in England, Premier League striker Ivan Toney has landed himself in hot water by breaching the FA's gambling provisions. He had hundreds of breaches against the governing body's gambling code and is now suspended until January, but it isn't just English football stars that like to have a dabble now and then.


The relationship between sports and gambling has evolved over time, and in recent years, the two have become more interlinked than ever before. From the early days of baseball to today's NBA, sporting sensations have reshaped the landscape of not just sports betting, but also high-end casino action as well. Traditional methods like sportsbooks persist, but the emergence of online casino table games have added a new dynamic to the world of gambling, making it more accessible than ever, with players able to now place wagers from the comfort of their own home or even in the locker room after practice or on game day.


Understanding the historical context and customs surrounding gambling in sports and particularly in basketball has become more crucial as prominent athletes participate in online gambling. With that being said, let's take a look at some of the most notorious basketball-playing gamblers on the planet today.

Michael Jordan

One prominent figure worth exploring is Michael Jordan. His basketball prowess is second to none and his legacy as the greatest player in history is already secured. However, his love for high-stakes betting earned him quite the reputation as that of a high roller. Engaging in golf matches for substantial sums, he challenged fellow players, celebrities, and casino owners to a few rounds on the links, betting huge sums of money against his opponents in the process. His gambling habit supposedly strained his relationships, leading to allegations of unpaid debts and questionable connections however, MJ once famously stated in an infamous interview-turned-meme that "It's not a problem, it's a hobby, I enjoy it."


While the Chicago Bulls star’s on-court exploits were second to none as demonstrated by both his dominance on the court and the dominance of the United Center side as a whole. The Bulls won six championships throughout the 1990s including two three-peats, with Jordan and his double act partner Scottie Pippen front and center to the team’s success. However, despite that, his gambling "hobby" would continue to make both domestic and international headlines, despite how he was performing on the court.


Opinions differ on whether his wagers impacted his performance, but there's no denying that the controversies surrounding his gambling add another layer to his complex legacy. And the less said about the conspiracy theory that his father was killed, and Jordan shipped off to the MLB, the better.

Charles Barkley

Another notable sports figure with a penchant for gambling is Charles Barkley. Once a professional basketball player turned sports analyst, Barkley has never hidden his passion for the world's oldest pastime. Throughout his career, this enthusiasm has periodically created financial troubles.


Despite his current standing as a respected commentator, Barkley has not been immune to scandals related to his gambling habits. In 2006, the NBA handed out one of their biggest ever sanctions when they imposed a substantial $400,000 fine on the former Phoenix Suns star for his gambling losses. We're not sure how much difference that will have made to his antics however, with many speculating that he went to the casino in an attempt to win the money back shortly thereafter.

Shaquille O'Neal

Shaquille O'Neal had a long, successful career at the summit of professional basketball. He was drafted as the number one overall pick by the Orlando Magic in the 1992 NBA Draft however, it wasn't until a decade later that he would truly take his game to another level. Paired up with Kobe Bryant in California, the duo led the Los Angeles Lakers to a historic threepeat of Larry O'Brien Championship trophies at the turn of the millennium, before switching to the Miami Heat and adding one last NBA Finals victory in 2006.


The seven-footer has been known to have indulged in gambling with his vast sums of cash over the years, a habit that has cost him a considerable amount of his fortune. While he has since addressed and sought help for his addiction to gambling, it's clear that dealing with money is not always easy, even for the rich and famous.


The New Jersey-born giant however has had a much more sensible approach to money when it comes to his children and he has made it clear that he’s not just going to hand them everything they want. He’s said that he wants his children to learn the value of a dollar, and to develop a strong work ethic.

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