Michael Jordan insisted that he didn't have a gambling problem in 1993. "I have a competition problem," Jordan claimed in an interview with Ahmad Rashad. As true as that statement was, it doesn't take away from Jordan's well-known history as a gambler. As long as he has been in the public eye, he has been known to bet on everything from golf and cards to minor competitions with teammates (and even security guards).

Episode 6 of "The Last Dance" shined a light on Jordan's gambling habits, though it didn't tell the entire story. So let's dive into Jordan's history as a bettor, starting before he even reached the NBA. 

Early Life

The exact origins of Jordan's gambling habits are unknown, but they date back at least to his high school days. In a letter written to his high school prom date, according to Roland Lazenby's book, Michael Jordan: The Life, he said that he was happy that she'd paid off a bet that he'd won against her. 

Similar evidence exists that substantiates his gambling in college. In 2019, a $5 check written in 1982 by Jordan to a fellow North Carolina student went up for auction. That money was won at the pool table, and the student, sensing Jordan's future fame, asked for a check rather than cash. He gambled with teammates and even college coaches during drills, according to David Halberstam's book, Playing For Keeps: Michael Jordan & the World He Made.

It should be noted that in all cases, the amounts that Jordan bet were substantially smaller than the gargantuan totals he would risk in the NBA. As he described early in "The Last Dance," Jordan didn't have income in college, and needed to ask his mother to send him money just to get by. 

Reaching the NBA

By the time Jordan arrived in the NBA, he had more than enough money to satisfy even his wildest gambling urges, and he did so with practically anyone that would indulge him. He'd play cards with Bulls beat writers Sam Smith and Lacy Banks on the road, Smith revealed in the introduction to The Jordan Rules. He wasn't above rigging contests, either. As Scottie Pippen explained on ESPN's "The Jump," Jordan would often bet on Jumbotron cartoon races with a Bulls security guard during games, but nearly always won because he got the winners from arena staffers in advance. 

His most frequent victims, as detailed by "The Last Dance," were his teammates. Jordan was a relentless card shark on team charters, and while he usually played with the high rollers, he was willing to play for almost any stakes merely for the competition. Jordan hardly cared who he targeted, either. In his book on Jordan's comeback with the Washington Wizards, When Nothing Else Matters, Michael Leahy revealed that Jordan even played with teenaged rookie Kwame Brown, though assistant coach Johnny Bach advised against it. Anyone's money was good for Jordan. 

And he was willing to take it anytime, anywhere. Jordan's time with Team USA amounted to a gambler's paradise. The Dream Team prepared for the 1992 Olympics in Monaco, giving Jordan access to the legendary Monte Carlo casino. When the team arrived in Barcelona, he built a consistent late-night card game with some of the best players in the world. According to Jack McCallum's book on the Dream Team, his most common opponents were Magic Johnson, Charles Barkley, Patrick Ewing, and his own teammate, Pippen. Finally, a crowd that could keep up with him financially. As it soon came out, the numbers he was willing to bet were simply too substantial for the overwhelming majority of the population. 

Slim Bouler and Richard Esquinas

While cards may have been Jordan's most frequent form of gambling, golf was his most expensive. In February 1993, gambler and suspected drug dealer James "Slim" Bouler was sentenced to nine years in prison for money laundering and conspiracy. Jordan was forced to testify over a $57,000 check that he had previously written Bouler. While he initially told the government that it was a business loan, he admitted on the stand that it was a gambling debt accumulated on the golf course. 

And that wasn't even the biggest one he racked up. In May 1993, another frequent golfing partner of Jordan's named Richard Esquinas released a book entitled Michael and Me: Our Gambling Addiction... My Cry for Help. Within it, he claimed that Jordan owed him a staggering $1.25 million from golf bets. Jordan quickly denied those claims, and Esquinas later revealed that he had settled with Jordan for a much smaller amount, only $300,000. 

To make matters worse, much of this golfing took place in Hilton Head, South Carolina, where it was technically illegal to gamble. Jordan was never charged for anything, and it would only have been a misdemeanor, but breaking the law hardly fit Jordan's squeaky clean image. That reputation would take its biggest hit in the 1993 Eastern Conference finals. 

On the eve of Game 2 of Chicago's series against the New York Knicks, Jordan was spotted gambling in Atlantic City. It actually was not the first time he had made the trip during the postseason. Not only did he venture north to Atlantic City during a 1991 playoff series against the Philadelphia 76ers, but he even took reporter Mark Vancil with him. That trip and the others Jordan took during his regular road trips to the East Coast never caused a fervor, but with Bouler's conviction and Esquinas' book still in the public consciousness, this one proved extremely controversial. 

It also undoubtedly impacted Jordan's play. The Bulls lost Game 2 in New York, and while they won Game 3 on their home floor, Jordan shot just 3 of 18 from the field. The Bulls obviously recovered and won the championship, but the rumors surrounding Jordan's gambling habits took on a life of their own. 

The first retirement, and subsequent conspiracies

The NBA investigated Jordan's gambling habits and ultimately cleared him of any wrongdoing, but that didn't stop the conspiracy theories. When Jordan retired unexpectedly in 1993, many to this day take it as a secret suspension for his gambling habits. They stemmed from a story written by Mark Whicker of the Orange County Register that suggested a connection between Jordan's gambling debts and the death of his father, James Jordan, who was murdered in 1993. 

"For now, we just know that there is evidence of the son's gambling problem, and there is suspicion of a son's paying problem," Whicker wrote. "The father of that son has been murdered. Coincidence, anyone?"

That connection has since been debunked, but a sentence uttered by Jordan during his retirement press conference still lingers in the minds of conspiracy theorists. When asked if he would consider returning, he responded by saying yes, "if David Stern lets me back in." 

As damning as that quote might appear in the wrong light, no evidence has been presented in the past 27 years to further substantiate the idea of a suspension. Jordan had to be vetted by the league before purchasing the Charlotte Hornets, and his approval suggests that nothing was found. 

The aftermath

Despite the damage his reputation took upon the string of 1993 gambling controversies, Jordan didn't quit gambling afterward. While he managed to avoid the limelight in doing so, numerous stories have surfaced from his second Chicago three-peat and beyond. Frequent gambling partner Ron Harper, who both golfed and played cards with Jordan on the team plane as depicted in "The Last Dance," did not join the Bulls until 1994. 

This even continued beyond his playing career. Bill Simmons detailed a card game that took place at All-Star Weekend in 2006 that involved Jordan, Charles Oakley and others in The Book of Basketball. In 2019, Chris Paul wagered free sneakers with Jordan at his basketball camp. 

Some of the stories featured insane stakes. Former MTV personality Kennedy told TMZ in 2013 that Jordan tried to make a bet with her over a dice game in 1995 in which she would have to sleep with him if she lost. Jordan, for obvious reasons, has not commented. 

Though Jordan claimed he could stop gambling, there is no public evidence suggesting that he ever did. In fairness, he never needed to. His career flourished in spite of everything that happened in the time leading up to his first retirement, and he is so wealthy through his basketball and endorsement earnings that he could never realistically lose it all betting. Whether he ever truly had a problem is ultimately irrelevant. Even if he did, it was just a speed bump. Jordan's rise to the top of the basketball world was hardly interrupted, and as a result, he can enjoy his hobby unimpeded.