That Time Michael Jordan Allegedly Ran Up a Million-Dollar Golf Debt

The second part, the testy be-shaded interview with Ahmad Rashad that was teased in the pre-game introduction and aired at length at halftime, was about everything else.

Jordan was explaining, but pointedly not apologizing, for a visit to Atlantic City the night before Game 2 of the Eastern Conference Finals that either ended fairly late or very late, depending on whether you took the word of the best basketball player in the world or New York's tabloid sources. At halftime of a game in which he would lead all scorers, viewers saw Jordan expand upon this theme without quite changing his tune. Jordan was responding to a self-published book titled Michael & Me: Our Gambling Addiction…My Cry For Help! that had been released that week, and which had been excerpted in newspapers for weeks before.

"I felt I was betrayed by this individual," Jordan said of the book's author, a 38-year-old San Diego sports executive named Richard Esquinas. "I don't consider him a friend, because friends don't do this to other friends."

Over the previous two years, the things that Jordan did with his friends had become public in a new and decidedly unflattering way. Esquinas, a self-described "street kid" from Columbus, Ohio who had become the general manager of the San Diego Sports Arena, was merely the most recent and most ambitious of Jordan's friends to come to the attention of both the NBA and basketball fans. The story that Esquinas sold about his peripatetic life of golf and gambling with Jordan, which allegedly involved Jordan running up a $1.2 million debt over a ten-day golf binge in San Diego—a debt Jordan supposedly played down to $908,000, negotiated down to $300,000, and ultimately paid $200,000 of—was bigger than the ones that had come before. But it wasn't new.

When basketball fans were introduced Esquinas, they had already met James "Slim" Bouler, a golf hustler who was either a drug dealer or drug dealer-adjacent. In December of 1991, the feds seized a $57,000 check from Jordan to Bouler which the two first spun as a loan; later, as a witness in the federal case that would eventually earn Bouler a nine-year sentence, Jordan admitted that the check was repaying a gambling debt.

Bouler was easy to confuse with Eddie Dow, but he was different. Both were from North Carolina and both were golf hustlers and gamblers, but Dow was a bail bondsman from Gastonia; Dow had three checks from Jordan totaling $108,000 in his possession when he was murdered in a home invasion robbery in February of 1992. This was all old enough news that when the NBA turned to investigating the allegations that Esquinas made in his book, the league simply brought back Frederick Lacey, the former federal judge who had investigated Jordan's gambling in 1992.

In 1993, the circumstances were different. The league was satisfied that Jordan had not bet on NBA games, and got to work rationalizing the fact that he'd bet on virtually everything else. But Lacey's investigation did reveal that, while Jordan had not violated any league rule—"nor has he violated any rule we plan to enact," NBA commissioner David Stern would add—he was also pretty plainly balling out of control off the court. Jordan was big enough that his problem was also the league's problem, which explains why Stern's rationalization by proxy echoed the usual addict's handwaving. "Gambling is actually encouraged by virtually all state governments," Stern told the Chicago Tribune in June of 1993. "Gambling is good, they say, it supports higher education, lower education, senior citizens, you name it."

"I gambled and played golf with Michael for six summers," Bouler told the Washington Post in August of 1993, months after he began a nine-year federal sentence on gun and money laundering charges. "The NBA hasn't even called me. What kind of investigation is that?" Robert Costello, Esquinas' lawyer and a former U.S. Attorney, further criticized the league for not talking to Jordan as part of its investigation.

"The league is stuck between a rock and a hard place," an anonymous NBA GM told the Post. "I sense that Michael has gotten preferential treatment because the league needs Michael to participate in many activities that promote the NBA. So they can't afford to get him angry. I wonder if another player had this problem if there wouldn't be a more ardent pursuit of the facts."

It's hard to say what discipline would even look like in a case like this, had the NBA been moved to act. It's forbidden for league players to gamble on games, but despite Esquinas telling Lacey that he seemed to hear Jordan placing a bet on a college game, there were never serious allegations that Jordan bet on the NBA. Beyond that, the standard for discipline is a vague and subjective standard that hinges on the commissioner's assessment of whether a player has brought disrepute upon the league. There are no formal rules against gambling, and while betting on golf is technically a misdemeanor in South Carolina, where Jordan did a lot of his gambling on the courses of Hilton Head, that law is not enforced.

NBA deputy commissioner Russ Granik made clear that the league was primarily concerned with the creepy company that Jordan kept, and the effect that all that ambient sketchiness might have on the league. If anything about Esquinas' assertion that Jordan might have placed a bet on a college game would have rankled the league, it was the timing. Esquinas said the bet was placed on March 29, 1992, two days before Jordan met with league officials and said that he'd stop hanging around sketchy gambler types like Bouler, Dow, and Richard Esquinas.

By the time Lacey announced in 1993 that he once again found no reason for disciplinary action, Jordan had retired.

In the interview with Rashad that aired at halftime of Game 1 of the 1993 NBA Finals, Jordan echoed that assessment with barely concealed exasperation. "Gambling is legal," he said, smiling mirthlessly, "betting is legal."

"My wife, if I had a problem, would have left me," Jordan said. Rashad laughed lightly. Jordan picked up the pace: if he had a problem, he said, his family would have told him, his wife would have told him. "If I had a problem, I'd be starving, I'd be hocking this watch, my championship rings, I would sell my house," Jordan said. "My wife would have left me, my kids would be starving. I do not have a problem. I enjoy gambling."

"I would be sick if I lost $1.2 million," Jordan added. "And he would be sick if he reduced it to $300,000." Jordan didn't deny owing Esquinas $300,000, or paying him $200,000, but dismissed the $1.2 million figure as "preposterous" and overinflated. "He exaggerated to a point, and I came up with my own conclusion to why he exaggerated …"

To sell books? Rashad offered.

"It sells books," Jordan said.

Esquinas self-published Michael & Me through a company called Athletic Guidance Center Publishing, and brought in longtime Los Angeles Times editor Dave Distel as a co-writer. It is not what I would call a good book, although its combination of cornball macho grandiosity ("I've always contended that I psychologically beat Jordan") and crocodile-tear smarm—Esquinas said he wrote the book because "it was right for my recovery from my addiction to gambling and the right way to reach out to a friend I perceived had the same problem"—it probably qualifies as ahead of its time. It reads, as it perhaps inevitably would, as a fraught and chaste romance.

It was in August of 1991, as Esquinas tells it, that things got baroque; Jordan was in Southern California for a charity basketball game and some photo shoots. The two played golf wherever and whenever they could during that time, trading wins and losses and debts in the five figures. "We certainly did not have to settle for muni tracks," Esquinas writes in Michael & Me. "We went first class." Esquinas flew into Chicago that month, and then to North Carolina on Jordan's jet, "playing cards all the way," for the rounds of golf that would set in motion every sad and sordid thing that followed.

Esquinas lost big during these games, which took place "from Chapel Hill to Raleigh to Durham to heaven knows where." The two covered the ground between tee times in a Datsun 300ZX Bi-Turbo at 90 miles an hour or above, trailed by Jordan's entourage, "wearing those expensive designer shades." As Esquinas tells it, the two were in a fugue state, bingeing not just on the action—Esquinas said he was up $20,000 on Jordan at the time—but the bulletproof invincibility of the moment. Jordan was a NBA champion and a North Carolina icon; he could drive 120 and get out of a speeding ticket with a smile or an autograph. "We never got stopped," Esquinas writes. "You gamble hard and fast, then you drive hard and fast."

The whole of Esquinas' story with Jordan, until the debts get too big and things get weird, plays out like this. It's a fling, a thing between these two men that exists beyond other distractions. Esquinas talks about bailing early on a party that a member of Jordan's entourage threw before the NBA All-Star Game in 1991, despite the attention of "girls hitting on us strong." Jordan, he writes, quickly followed him back to the suite. "We had to tee off at 8 o'clock the next morning so we had to leave the hotel at 6:30," Esquinas writes. "Once again, we had our priorities."

This wary and disinterested chastity is a recurring theme in Michael & Me, and for all the questions about the narrator's reliability, it all more or less scans. This is the thing about addiction, which is somehow both secret and obvious—a fun vice that other people enjoy in moderation somehow overcomes and overwhelms and overtakes everything else, and the world warps accordingly. Jordan, who could do anything he wanted to do, chooses to bet big on card games and golf games and whatever else can be bet upon with a crew of clammy randos and hangers-on and pro gamblers and anyone else who will take the action. "Any Joe Blow can get in if he throws down the challenge," a veteran of Jordan's "Mike's Week" getaways in Hilton Head told Newsweek in 1993. "Michael was shark meat."

Those big checks and un-denied debts aside, the story of Michael Jordan, Competition Addict is mostly comprised of rumor and legend; in our more wary modern moment, every golf buddy would have been compelled to sign a non-disclosure agreement, and those rumors would be all we'd have. There is no proof that Jordan did anything illegal, or ever made a bet he couldn't cover. "Was I gambling with goons who had bad reputations? Yeah, I was," Jordan told the writer Bob Greene after making his pledge to the league in 1992. There is no law against that, and there is not even an NBA rule against it. But it is the sort of thing that people tend to judge.

"We do not have bad people on this basketball team," Bulls general manager Jerry Krause told the New York Times when Esquinas' allegations first surfaced. "We have class people, we have people with character. We're extremely proud of the way they react to situations. Michael Jordan's personal habits have been outstanding." Krause later allowed that he had no way of knowing if the allegations were true, but it hardly mattered. Esquinas' book, coming as it did after the disclosures of Jordan's debts to sketchy characters like Bouler and Dow, contributed alongside the far superior The Jordan Rules to what looks in retrospect like a breaking point in Jordan's career.

All this dodginess and desperation and headlong joyless competitive thrashing bled in from the edges of the simple, aspirational Jordan fable that had been so successfully sold; the picture darkened, and started to look a little more like what it was. Esquinas' alleged altruistic motivations were impossible to credit, and his integrity was easy to doubt. But the story that he told was, for all that, hard to deny. Jordan would win a lot more before he was finished, but the willful Be Like Mike innocence was lost. There was no denying his greatness, before or after, yet a full and true accounting of the man could never be complete when it only involved effortlessness and will. Eventually, it became clear that Jordan's greatness came at a great personal cost; that's the only way it works. We all pay a price for everything. Still, it was startling to see it itemized in print, one sad and helpless debt at a time.