The sports world has been aware of Michael Jordan’s penchant for gambling for quite some time. Beyond his prowess on the basketball court, Jordan has always harbored a deep affection for golf, a passion that endures to this day. While it appears he has curbed his gambling activities, golf remains one of his preferred pastimes.

Yet, during the late 1980s and early 1990s, Jordan frequently intertwined his two passions. His gambling fervor was such that he found himself in debt to the tune of over $1.2 million to a former businessman turned author.

In August of 1989, Michael Jordan crossed paths with Richard Esquinas at a summer exhibition game featuring NBA stars. The event, held at the San Diego Sports Arena which Esquinas co-owned, facilitated their introduction, courtesy of former basketball coach Smokey Gains. Their shared interests in golf and gambling quickly sparked a rapport.

Their affinity led to a prompt arrangement for a golf match, with the duo teeing off the very next day. In a display of their competitive spirits, they wagered $2,500 on their inaugural game, a contest reportedly won by Jordan.

Their golfing escapades continued unabated for three years, during which they logged approximately 100 rounds, as recounted by Esquinas. While their typical outing comprised 36 holes, on one occasion, they extended the challenge to 45. With a stake of $1,000 per hole and the provision for side bets if one lagged behind, the stage was set for intense competition. This particular match unfolded in September 1991 in North Carolina.

Following the game, Esquinas found himself indebted to “His Airness” to the tune of $98,000. Undeterred, at their subsequent encounter, they agreed to a double-or-nothing wager for the same amount. In a twist of fate, Esquinas emerged victorious, setting off a series of losses for Jordan in subsequent games. As the defeats mounted, so did the debt, ultimately ballooning to $1.252 million.

However, their relationship soured when Esquinas chose to publish a controversial book, straining the once-amicable bond between them.

In 1993, Richard Esquinas stirred controversy by releasing a book titled “Michael & Me: Our gambling addiction … my cry for help!” This memoir provided an intimate account of Esquinas’ golfing encounters with Michael Jordan, including meticulous documentation of the substantial debt owed to him by the former Chicago Bulls star. Jordan, displeased by the revelations in the book, opted to withhold payment for the remaining portion of the debt, exacerbating the rift between them.

Tom Cruise backs up 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 support of the NBA legend, Hollywood actor Tom Cruise too condemned Esquinas’ action. Cruise sent him a letter where he expressed his displeasure with Esquinas for violating 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 chiseled away at the formidable debt, dwindling it from $1.2 million to $902,000, then further down to $300,000. Their agreement stipulated that Jordan would settle the remaining balance in installments spread over three years. However, after honoring 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.