Michael Jordan is known for his competitive nature on the basketball court, but his gambling addiction was just as intense. In the early 1990s, Jordan began to gamble on golf games with his friends, including Richard Esquinas, a wealthy businessman who was also a big gambler. Esquinas encouraged Jordan to gamble more and more, and the stakes quickly escalated. In the lead-up to the 1992 Barcelona Olympics, according to Roland Lazenby’s book, “Michael Jordan: The Life,” Jordan’s insatiable appetite for competition drove him to force his golfing partner, Richard Esquinas, into an astonishing bet of $1,252,000.
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Jordan was “obsessed” with winning, and he would often gamble on anything, from golf games to card games to even the outcome of sporting events. Esquinas was more than happy to take Jordan’s money, and he reportedly suggested double or nothing bets.
Michael Jordan and Esquinas’ High-Stakes Gambling: A Double-or-Nothing Spiral
Jordan and Esquinas had been indulging in their shared love for golf when their friendly competition began to escalate. It all started innocently enough, with Esquinas losing $98,000 to Jordan. Rather than backing down, the two embarked on a double-or-nothing streak that would ultimately cost Jordan a staggering $1.25 million.
Reflecting on the encounter, Esquinas recalled, “Once again, he went into a long story about his wealth. He could handle $1.2 million, he said, should he happen to lose. ‘Let’s play for it,’ he said. ‘E-Man, I can’t believe you won’t give me this game.’ I was trying to get him to comprehend the magnitude of losing at such a level, to defer this insistence that we engage once again. Not only did he want to continue this chase, he was demanding it.”
“I was so angry that I challenged him to a series of double or nothing bets. He accepted, and we went on a streak of wins and losses that eventually cost him $1.25 million.”
The stakes reached an all-time high in the lead-up to the 1992 Barcelona Olympics. Jordan was determined to win the gold medal, and he was also determined to win back some of the money he had lost to Esquinas. The two men agreed to play a golf game for $1,252,000.
Jordan’s gambling addiction would continue to plague him throughout his career. He would eventually seek help for his addiction, but the damage had already been done. Jordan’s gambling addiction cost him millions of dollars, and it also damaged his reputation.
Refusal to Pay and the Fallout
As fate would have it, Jordan lost the bet, bringing his total debt to an astounding $1.252 million, as claimed by Esquinas. However, the aftermath of this loss would prove to be just as dramatic as the gamble itself. Jordan, known for his competitive spirit, refused to honor the bet and pay his dues. This led to Esquinas relentlessly hounding Jordan for the money he believed was rightfully his.
Esquinas claimed that Jordan owed him $1.25 million in gambling losses from golf matches they played near San Diego. Jordan denied the allegations, but Esquinas produced a $57,000 check that Jordan had written to him to cover part of the debt. Jordan claimed that the check was for a golf business, but Esquinas said that it was for gambling losses.
Michael Jordan refused to pay the remaining $1.2 million, and Esquinas began to hound him. He called Jordan repeatedly, sent him threatening letters, and even showed up at his house unannounced. Jordan eventually hired a lawyer to deal with Esquinas, but the harassment continued.
Esquinas continued to hound Jordan after the book was published. He even sued Jordan for $1.25 million, but the case was eventually dismissed. Jordan never paid Esquinas the money he owed him, and the two men never reconciled.
