Michael Jordan’s Gambling Exemplified America’s Lust for Private Vice from Public Figures

There was a time in America where the press let the private vices of athletes and entertainers — drinking, drugs, carousing, gambling, etc. — exist in a realm nearly completely outside the coverage of them. While it’s presumable the public would’ve eaten up stories about that, the media consisted largely of an oligopoly of newspapers, radio stations (where there are a finite number of spots on the dial), and television (where there were just three networks before the advent of cable). They effectively acted like gatekeepers, and there was an informally collective decision that this wasn’t newsworthy.

Whether Michael Jordan was the first or merely among the early subject of changing tides, he found himself utterly besieged by coverage of his gambling escapades during the 1993 playoffs. This immense scrutiny was ultimately at least part of what drove him away from basketball as a three-peat NBA champion in the prime of his career.

The sixth episode of The Last Dance began with Michael Jordan, with the weight of the world on his shoulders, remarking that people would love to lead his life for a day or even a week, but not for a whole year.

Between Jordan’s basketball success and the careful cultivation of his brand — the enormous Nike sneaker machine, the Be Like Mike campaign for Gatorade — he was irresistible to the public. Thus, when Sam Smith’s Jordan Rules came out in 1992 and painted him as insatiably competitive and as a ruthless teammate, it was like a surprisingly powerful ocean wave that knocks you off your feet.

Then came a wave of gambling stories in 1992 and 1993:

  • Jordan had to testify that he lost $57,000 to golf hustler Slim Bouler, who wound up getting caught up in federal money laundering charges. (The Athletic has covered this story.)
  • In 1993, a golfer named Richard Esquinas wrote a book called Michael & Me that said Jordan lost over a million dollars to him betting on golf.
  • Jordan was spotted out in Atlantic City until 2:30 am, playing blackjack with his father the night before a playoff loss to the Knicks. This was deemed story-worthy by the New York Times.

While the media tone was largely critical of Jordan during this time, he did have some defenders. As we covered on Outkick last week, Peter Vecsey told Bob Costas on NBC’s halftime show during the Eastern Conference Finals that the network embarrassed itself by previously interviewing Esquinas. Vecsey said that Jordan gambled large sums because he was a high earner, that it was already known that Jordan gambles and thus new chapters of the same story were not newsworthy, and that Jordan was not breaking NBA rules. The only thing Jordan was guilty of, Vecsey said, was choosing bad friends. (Costas handled himself with immaculate professionalism in response.)

Michael Wilbon also defended Jordan’s Atlantic City trip in the Washington Post. “What bothers the holier-than-thous is the appearance,” Wilbon wrote. “A role model in a casino before a game? (Shriek!) Jordan is a person, an enormously well-paid athlete, but a person nonetheless. He can’t go to the movies, the mall, or a ballgame as it is because he’d be mobbed in a way no rock star in the world would be mobbed. So now, according to all the perfect people in the world with no obsessions and no eccentricities and no private passions, Jordan shouldn’t go to a casino either, unless we, the public, sanction it. Please stop, this is growing sillier by the minute.”

Jordan at the time did not give an especially convincing explanation that he did not have a gambling problem, but a competition problem. Wearing sunglasses indoors, he explained to Ahmad Rashad that he had not lost the things a gambling addict would lose (i.e. everything):


While it’s impossible to say for sure, I’d bet that if Jordan came along a decade earlier he wouldn’t have had to face nearly the amount of scrutiny for gambling that he did at this time. Of course, he probably also wouldn’t have been as big of a star, either, as David Stern’s global hype machine for the NBA was just cresting into full force at the time when MJ was the centerpiece. Now, we don’t bat an eye about privacy for public figures. Smartphones and tabloids, across all media platforms, have melted through the previously closed gates like molten lava.

It’ll be interesting to see if next week, when they discuss Jordan’s first retirement, if they delve into the conspiracy theory that David Stern asked him to walk away from the game due to gambling issues.

Written by Ryan Glasspiegel

Ryan Glasspiegel grew up in Connecticut, graduated from University of Wisconsin-Madison, and lives in Chicago. Before OutKick, he wrote for Sports Illustrated and The Big Lead. He enjoys expensive bourbon and cheap beer.