Chicago Bulls legend Michael Jordan’s exploits on the court were on the verge of being tarnished by his gambling controversies in the 1990s. The hype Jordan had garnered in the league and across the nation led to jam-packed arenas and busy streets, just to catch a glance of the great man. But the very same popularity turned into a PR nightmare due to slanderous reports of Jordan’s gambling escapades, which ended up prompting NBA Commissioner David Stern to issue an investigation on Jordan over his ‘gambling issues.’
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Michael Jordan was an avid golfer and loved to play cards. However, what a lot of people did not know initially was MJ’s tendency to bet big amounts of money while competing in these games, leading to questions as to whether Jordan had a gambling problem.

SI.com once questioned Michael Jordan’s known contacts and associates based on the fact that three checks were retrieved from the briefcase of Eddie Dow, a bail bondsman from Gastonia, N.C. after his supposed homicide. The checks were a total of $108,000.
This eventually led to the NBA’s investigation on Michael Jordan and his so-called peers he spent time with, off the court. The investigation revealed Jordan’s ties with James Bouler and a $57,000 payment to him. Initially, MJ had claimed that it was money to build a driving range, however, it was later revealed that it was a gambling debt payment.
By the time the two-week investigation ran its course, then Commissioner David Stern announced, “There appears to be no reason for the NBA to take action against Michael.” While the world may have been satisfied with the results of the NBA’s investigation, Sports Illustrated felt otherwise. According to an archived article by Richard Demak from back then, the NBA did not speak to many people outside of MJ’s entourage when conducting their investigation.
“Apparently the NBA is satisfied that the questions about Jordan have been answered. But who answered them?” the report asked the question.
After being exonerated by the league, Michael Jordan issued an apology to the fans and the media for gambling and getting involved with such personalities. He later admitted to taking precautions going forward.
Michael Jordan was the face of the league at the time that ensured new investment opportunities and a whole new horizon of expansion. And an investigation on his gambling addiction was not an ideal situation for the NBA. The whole situation was a PR nightmare for the NBA. There is no reason to think that the NBA had ever any motivation to go all in to implicate a star like Jordan. Therefore, SI’s hypothesis certainly had some merit behind it.
Michael Jordan’s 27-year-long grudge
Michael Jordan and Sports Illustrated were not always on good terms after a certain point in Jordan’s playing career. While he was the sole superstar on the basketball court, the same could not have been said for his performances on the baseball pitch. This prompted Sports Illustrated to come out with the ‘Bag It Michael’ cover, taking a shot at his baseball aspirations. And after that, Jordan refused to speak to any reporters associated with SI.
In an interview later on, Jordan explained, “If you had a question, ask. This is what I want to do, I’m not doing what they think I should be doing. My father already told me I was doing the right thing, and I did it.”
The ‘Bag It Michael Jordan’ cover was spearheaded by editor Steve Wulf, who admitted in 2020 to making a mistake 27 years ago. He stated that he was skeptical about Michael’s baseball career and did not believe he could make it to the MLB.