Michael Jordan 's competitive nature is the stuff of legend. His desire to win was so strong that he needed an outlet for it beyond the basketball court. That's where gambling came in.
While Jordan has never publicly admitted to having a gambling problem, he was known to bet on just about anything, anywhere. From casinos to the fairways of golf courses, he was always looking for a way to satisfy his competitive drive.
One of the most frequently repeated stories dates back to the early 1990s, when a San Diego businessman, Richard Esquinas, claimed that Jordan owed him $1.25 million from a series of golf bets they played together. The allegation became part of the broader conversation about Jordan's gambling during that era, though it remains just one of the many stories that have followed his career over the years.
Esquinas, a former general manager of the San Diego Sports Arena, wrote about his travails with Jordan in his book entitled, " Michael & Me: Our Gambling Addiction . . . My Cry For Help! " There, he claimed that Jordan owed him over a million in gambling debts throughout their four-year relationship, wherein they played more than 110 rounds of golf.
Esquinas singled out one bad day in particular for Jordan, who lost $1.25 million during a golf match that happened on September 20, 1991, at the Aviara Golf Course. However, that amount was whittled down to $902,000 when they played together for the last time during a three-day golf escapade across San Diego County.
While beating Jordan at golf was one thing, collecting on the winnings from him was another, as Esquinas claimed the Chicago Bulls icon was noncommittal about paying up. It wasn't until Esquinas lowered the amount to $300,000 that Jordan agreed to pay, but only after asking that the payments be spread over time.
By that time, Esquinas admitted he just wanted the whole thing over with, having felt exasperated by the ordeal.
"I took a ($602,000) hit just to get the hell out," Esquinas said . "I just wanted out. I knew it was a quick fix, that he could afford it. I figured that it was a number he could afford. I wanted out of this whole process."
Esquinas and Jordan met in 1989 and began playing high-stakes golf. As they spent more time playing, they became more comfortable keeping tabs on how much they owed each other and being flexible with payments.
There was even a time when Esquinas allegedly could not pay Jordan $98,000 on a bet during a match in 1991 in North Carolina. However, he turned things around in September of that same year, going from owing Jordan $98,000 to having the latter owe him $1.25 million. According to Esquinas, while the sum might have been pocket change for Jordan, it was staggering to someone like him.
"I feared that I'd be perceived as a threat to Jordan, and the things that come with those fears," he revealed.
Esquinas' fears were most certainly not unfounded, as he claimed that Jordan told him over the phone: "Rich, I just might as well shoot you as to give you a check for $1.2 million. "
"I played it off but he was definitely drawing the line that he wasn't going to pay the full amount," he added. "What he was saying was, 'I'm not paying the full amount.' And right there, I knew I had trouble collecting."
After a media boycott following reports of his Atlantic City trip the night before Game 2 of the 1993 Eastern Conference finals against the New York Knicks, Jordan decided to address the allegations made by Esquinas.
"I have played golf with Richard Esquinas with wagers made between us. Because I did not keep records, I cannot verify how much I won or lost. I can assure you that the level of our wagers was substantially less than the preposterous amounts that have been reported," he said in a faxed statement released through his agent, David Falk's office.
"It is extremely disappointing to me that an individual whom I caused no harm and who held himself out as my friend would shamelessly exploit my name for selfish gain. It is equally disappointing that my off-the-court activities are receiving more attention in the midst of the NBA Championship than my on-court activities."
"I want to publicly apologize to my family, my teammates, Jerry Reinsdorf, the NBA and fans for the distraction this story has caused. I also want to thank those members of the media who had the courage and independence to report the incident and the coverage it received for what is an embarrassment for all of us."
Ultimately, Esquinas said he only received $200,000 from the NBA legend.
The allegations Esquinas made against Jordan were hardly the first, as he had also gotten involved with a convicted money launderer, James "Slim" Bouler, in the early 1990s. During Bouler's federal trial, a $57,000 check written by Jordan surfaced as evidence. He later testified that the payment was meant to settle a golf bet and denied any involvement in illegal activities, and investigators ultimately found no link between the NBA legend and Bouler's criminal operation.
This story was originally published by Basketball Network on Mar 15, 2026, where it first appeared in the Off The Court section. Add Basketball Network as a Preferred Source by clicking here.
