Michael Jordan Gambling: The Good, the Bad, and the Ugly

Michael Jordan is one of the most star-studded players in the National Basketball Association, a high performer who never accepted defeat, and orchestrated staggering comebacks on his own.

He has long been a cast of elite athletes known for their soft spot for gambling, the likes of whom include Charles Barkley, Floyd Mayweather, Wayne Rooney, Phil Mickelson, and others.

Yet, how big is Michael Jordan’s gambling controversy?

The truth is much of what has transpired around the former Chicago Bulls player and his gambling has been largely speculative, although there have been several well-documented cases of his antics that have brought him a bit of infamy.

Today, we take a deeper look into Michael Jordan’s casino gambling and how gambling has been a part of his life from his earliest years and from before his claim to fame and glory.

Michael Jordan’s Gambling Started Early

Gambling has been a part of Michael Jordan’s life long before he became a basketball prodigy or made any televised appearances to discuss what the media has frivolously labeled a “problem,” a statement that MJ has vehemently denied over the years.

However, in his biography written by award-winning journalist Roland Lazenby, the author acknowledges that MJ got exposed to gambling in his school years, betting on pools, and partaking in various games of chance.

He also tended to honor his debts, an even more admirable trait. Aversion to risk has never been one of Michael Jordan’s character traits, which would ultimately propel him to six titles with the Chicago Bulls and immortalize his name in the sports world.

Yet, one thing that MJ learned from his school years was that fate can be manipulated, not so much when it matters in high stakes competitions, but when it came to gambling – you could have a laugh at the expense of others.

When he joined the Chicago Bulls, he brought with him the tantalizing energy of his personality, a sort of let’s-do-it-and-see-what-happens attitude. Quickly, he found a number of teammates who were happy to do high-stakes gambling.

At this age, Michael Jordan found out that stilting the rules a little to win was not a bad thing after all.

Once again, he seemed to show remarkable pragmatism when it came to his court performance where he only relied on his prowess and training. When it came to gambling, however, it was not past him to give fate a little nudge.

On one occasion in his early days, the Bulls were going to Portland for a game, when MJ said that he would bet anyone $100 that his bag would roll first off the luggage line. Several teammates immediately took him up on this offer. MJ’s bag did come out first.

He beamed.

However, what remained unbeknownst to his fellow players was that Michael Jordan had tipped the baggage handler to set it up. This was an early precursor to the larger controversies that would dot MJ’s career and his relationship with gambling later on.

In 1992, MJ would fly to Monaco for the Summer Olympics, and naturally, he would quickly draw the rest of the players out to the Monte Carlo Casino, one of Europe’s oldest.

As you can imagine, Michael Jordan has been able to involve many of his teammates in gambling on the floor and organizing private high-stakes games off the property.

The Media Sensationalized Michael Jordan’s Gambling

A person of MJ’s stature would naturally attract the limelight onto himself, and this is understandable. Yet, for all his faults in gambling, Michael Jordan has been called out on his gambling by opportunistic media outlets on more than one occasion and most often – in speculative and unjust characterizations.

Back in 1993, Michael Jordan’s dad was murdered. By the time the murder took place, MJ himself had to appear in court and testify against James “Slim” Boulder, a fellow gambler and suspected drug dealer to whom he owed the gambling debt.

Eventually, Slim was sentenced to nine years in prison over money-laundering, whereas MJ walked, but the media started paying attention to him and the size of his gambling debt, which remained shrouded in mystery.

The tragic event in his personal life was not beyond the media’s reach, and Orange County Register, a media outlet, brashly suggested that “not much was known” about the murder, but it was “a fact” that the son – meaning Michael Jordan – had a gambling debt.

This statement, even from someone who chronicles events rather than passes judgment such as a journalist, sounded infuriatingly suggestive. It was even uglier in the broader context of MJ’s life during that time, with the player withdrawing from the Bulls amidst wide speculation of the player’s gambling problems finally catching up to him.

It was very true that Jordan would plunge into gambling as a way to distract himself, but it was also true that the death of his father distraught him deeply. Asked if he would consider returning to the Bulls at a later date, MJ said that he would gladly rejoin his old team – and only his old team – if they would have him.

This statement was immediately overexposed and interpreted to mean that Michael Jordan never really stepped away because he wanted to, but because his gambling had caught up with him. There is no evidence to support this claim. The association’s then-commissioner, David Sterner, refuted those claims.

Michael Jordan Gambling Controversies as They Happened

Around the time of his father’s murder, a lot was happening in MJ’s life. Gambling had indeed caught up to him, but not in the unflattering and salacious way that many media outlets seemed to suggest.

Michael Jordan did have a reckoning – more than one – with his gambling habits, and deservedly so. There were many such cases surrounding the height of his career and culminating in his decision to leave the Bulls on October 6, 1993.

MJ’s claim to infamy came in 1993 when a businessman called Richard Esquinas published a sort of autobiography in which he said that Michael Jordan owed him the eye-watering $1.25 million from golf bets.

“Michael & Me: Our Gambling Addiction… My Cry for Help!” was seen as rather opportunistic. Esquinas was trying to get his money back, but he didn’t mind publicizing the matter to see if it would fetch him an extra profit. The book did not do particularly well at all, and most people got the synopsis from media outlets anyway.

Jordan acknowledged that he had owed Esquinas money but said that his gambling debt was $300,000. That same year MJ got publicly lambasted by fans and the media again, as he was seen gambling in Atlantic City late at night ahead of an important game in the Eastern Conference Finals.

Throughout the 1990s, MJ also became known for doing something he had been known for doing from his school years – betting against fellow players in all sorts of situations. We mentioned Charles Barkley at the beginning. Well, Barkley and MJ were good friends, and they got a visceral pleasure out of placing wagers on their golf games.

Sometimes, these bets are said to have reached six figures, and both athletes have got their fair share of bad press over their behavior.

Let’s Stop Speculating about Michael Jordan’s Gambling

The truth is that a lot of the same things have been written about Michael Jordan and his gambling habits. His notoriety is somewhat deserved, and thinking of MJ setting up the baggage scam is perhaps a little off-putting until you realize that he was having a good time and thought it was a good trick to play on his teammates.

Most of his controversial gambling is now long gone, and dates back to the 1990s, and even if Michael Jordan is probably still a sly and avid gambler, painting him as a scheming person who was out to cheat everyone out of their money is unjust.

MJ is a titan and a legend, whose character flaws are part of what made him exceptionally good at his lifelong passion – basketball. He never mixed his gambling with his basketball and took pride in attaching his name and his name alone to his trophies and titles. For better or for worse, what drove Micahel Jordan to gamble almost recklessly also made him the legend he would go down in history as…