The Legendary Gambling Background of Michael Jordan

Michael Jordan is arguably the greatest basketball player of all-time. There are legendary stories about the things he’s done on the court during his career. In 2024, Michael Jordan is becoming just as well-known for his penchant to throw a big wager on just about anything.

It has been 26 years since Michael Jordan played his last basketball game. Decades and billions of dollars later, Jordan is still garnering discussion. Some of it still has to do with his legacy on the court. Some of it has to do with the juggernaut Jordan brand. And then there is a little bit that centers around his legendary gambling.

Whether it be a hand of high-stakes blackjack or friendly competition with some money added in, Jordan is known for his gambling. What much of the public may not realize is just how deep his gambling ties run.

Gambling Early

Jordan has always been a hyper-competitive individual. Some would argue that you have to be to excel at the level that he did. Read Michael Jordan: The Life by Roland Lazenby and you will see that the gambling bug bit MJ early.

Some think it started in high school, but the real evidence starts during his collegiate career at North Carolina. He wrote a $5 check to fellow student after losing a game of pool. There are stories of him betting during practices with both coaches and players alike. Those amounts were small, and the stories never surfaced.

Gambling During His Career

By the time he got to the NBA, Jordan was making serious money. It turns out he was betting serious money first. Sometimes, it was just boredom. He would bet $100 with teammates that his bag would come out first at luggage claim.

Even some of the most famous moments of Jordan’s career have gambling connotations to them. For instance, he famously shrugged after hitting his sixth three-pointer in the first quarter of Game 1 of the 1992 NBA Finals. It turns out he was shrugging at Magic Johnson, seated in the crowd, after being beaten by the legend at cards the previous night.

Major Controversies

The controversies soon followed. In 1993, MJ was forced to testify because of a $57,000 check he wrote to James “Slim” Boulder. Boulder was not only a known gambler but an alleged drug dealer who got nine years in prison for money laundering.

A golfing partner claimed that Jordano owed him $1.3 million, later settling. Other stories started to build. But it was following the death of his father in 1993 that rumors really started flying. Jordan retired in 1993 citing a desire to play baseball, but others were wary.

The conspiracy theory at the time was that Jordan had gotten into deep water with the wrong crowd. Then-NBA commissioner David Stern, as the rumor goes, had suspended Jordan for a year so that he could cool his heels and get himself together. That has never been proven and likely never will be even if it is true.

Biggest Losses

When you have the resources and competitive streak that Jordan has, losing big sums is only natural. The aforementioned $1.3 million claim was settled down for $300,000. Writing the $57,000 check also had to do with gambling on golf.

Perhaps the most ridiculous story came from former teammate Jay Williams. “Think about gambling to the next degree. Rock, paper, scissors – you bet $20,000 all day long. Why wouldn’t you? You get bored. And don’t get yourself down in a dice game. Don’t be in the corner and let some dude keep fading you out and all of a sudden you’re down $100,000 and he’s like, ‘Yo, bet it back – rock, paper, scissors for $100,000.’”

A Gambler to the End

Though “His Airness” is unlikely to ever develop an issue with online slots, it doesn’t mean that he isn’t still an active gambler. His pursuits are more competitively driven than sitting down at a slot machine and pulling a lever.

For a competitor like Jordan, perhaps the ultimate competitor, there is no letting off the pedal. He will try his very best to win at anything he does. If he can turn it into a wager, even better. When you’re Michael Jordan, you can kind of do what you want.