The sports world has long been aware of Michael Jordan’s love for gambling, a passion that has accompanied his basketball prowess for years. Despite this, Jordan has also maintained a deep affinity for golf, a hobby he continues to enjoy today. While it seems he has scaled back his gambling habits, golf remains one of his favored leisure activities.

However, in the late 1980s and early 1990s, Jordan’s two passions often intersected. His enthusiasm for gambling led him to accumulate debts exceeding $1.2 million to a former businessman turned author.

In August of 1989, Michael Jordan and Richard Esquinas crossed paths at a summer exhibition game featuring NBA stars. The event, hosted at the San Diego Sports Arena which Esquinas co-owned, provided the perfect setting for their introduction, facilitated by former basketball coach Smokey Gains. Their mutual interests in golf and gambling quickly forged a connection.

Their shared passion for golf prompted them to arrange a match swiftly, teeing off the very next day. In a testament to their competitive nature, they wagered $2,500 on their inaugural game, with Jordan reportedly emerging as the victor.

Over the course of three years, they indulged in approximately 100 rounds of golf, often playing 36 holes per outing. On one occasion, they even extended the challenge to 45 holes. With stakes of $1,000 per hole and room for side bets if one fell behind, each match was intense and fiercely contested. One such memorable encounter took place in September 1991 in North Carolina.

After one game, Esquinas found himself owing “His Airness” a hefty sum of $98,000. Unfazed, they agreed to a double-or-nothing wager at their next meeting, with the same amount at stake. In a surprising turn of events, Esquinas emerged victorious, initiating a streak of losses for Jordan in subsequent matches. As the defeats piled up, so did the debt, eventually reaching a staggering $1.252 million.

Their once-amicable relationship took a turn for the worse when Esquinas decided to publish a controversial book, leading to strained ties between them.

Tom Cruise was there for Michael Jordan

“I was in the process of finishing off all the payments, but when he pulled this stunt — we never had a written agreement, I was more or less going off my honor — I felt he dishonored me, so I don’t owe him any more honor. What’s the balance? Zero, in my book,” said MJ.

In a show of solidarity with the NBA legend, Hollywood actor Tom Cruise also condemned Esquinas’ actions. Cruise penned a letter expressing his disappointment with Esquinas for breaching Jordan’s privacy.

“I, for one, hope that I never have a friend or confidant who betrays my trust the way you have betrayed that of Michael Jordan,” wrote Cruise.

Following several additional gaming sessions, Michael Jordan successfully reduced the significant debt from $1.2 million to $902,000, and then further down to $300,000. Their agreement stipulated that Jordan would settle the remaining balance in installments spread over three years. However, after making an initial payment of $200,000, Jordan abruptly reneged on the agreement. The catalyst for this reversal was Esquinas’ contentious book, which evidently soured their financial arrangement.