Michael Jordan's unquenchable thirst for competition, for "action," and an unshakable belief in his ability to prevail in any form of it created the most serious blemish on his carefully crafted image as a wholesome, genuine role model.
In October 1992, Jordan's name surfaced in the North Carolina drug and money-laundering trial of convicted cocaine dealer James "Slim" Bouler. A personal check from Jordan for $57,000 was part of the evidence seized in an investigation of Bouler.
Jordan had told reporters the check was a business loan to Bouler for a driving range he planned to open. Under oath at trial, he acknowledged the check was payment to Bouler for gambling losses sustained in poker and golf.
The next spring, the Bulls were on their way to a third straight NBA title, and in the early-morning hours before Game 2 of the Eastern Conference finals against the New York Knicks, Jordan was spotted in a high-rollers room at an Atlantic City casino. The New York City tabloids bore in on the story.
Jordan denied that he had a gambling problem. He said he never bet sums he couldn't cover, that it wasn't like he was playing with the rent or the grocery money. He told reporters he'd gone out that night because he was often too wound up to sleep during the playoffs.
Later that year, a San Diego businessman and high-stakes golf gambler named Richard Esquinas wrote a book in which he claimed he'd taken more than $1 million from Jordan on the golf course. Esquinas said he wrote the book to help him get over his gambling addiction and he advised Jordan to seek help as well.
The NBA investigated and said Jordan had not violated any league rules. James Jordan, his father, said Michael "doesn't have a gambling problem; he has a competition problem."
That summer, James Jordan was shot to death during a roadside robbery in North Carolina. Michael's decision to walk away from the NBA two months later, at 30 and at the peak of his game, prompted several conspiracy theories. The most prominent: that his retirement was actually a suspension for gambling, that Commissioner David Stern ordered him to go away and get help.
Daniel Green and Larry Demery, both 19, were small-time miscreants with no ties to any sort of organized crime and were subsequently convicted of James Jordan's murder. But a darker theory held that he'd been killed in retribution for Michael's unpaid gambling debts.
Many news organizations, including the Chicago Tribune, investigated and reported no links between Jordan's retirement and his gambling.
NBA spokesman Brian McIntyre called the theories "complete fabrications."
David Falk, Jordan's longtime agent, acknowledged talking to his client about the people he was associating with lest he jeopardize his status as the world's most successful athlete/endorser.
"It wasn't easy for Michael, but he realized he'd made some poor decisions, and he apologized to the people affected and he moved on," Falk said.
"It took a lot of guts to retire when he did. It took a lot of guts to go play baseball and run the risk of failure after being incredibly successful at something else. But Michael is fearless."
Blemish on Jordan's career: gambling Jordan gambled with his image
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