Ex-wife of Michael Jordan used to write $50,000 checks to clear her husband's gambling debts

Chicago Bulls legend Michael Jordan has a well-documented history of gambling, with countless stories having been told about his gambling escapades.

These stories include Jordan staying up all night to win back the 500K he lost at a casino, only to win $600K more. They also include him losing $5 million during a game of craps. Moreover, Jordan was known to regularly bet on the golf course, where his gambling would go out of control. So much so that it had a severe financial impact on both him and his ex-wife Juanita Vanoy.

In Roland Lazenby’s book “Michael Jordan: The Life,” Lazenby outlined Jordan’s high-stakes gambling on the golf course with his former friend, businessman Richard Esquinas. Jordan racked up a massive debt to Esquinas before the two had a falling out and began to feud. It was then that Vanoy who had to write off checks to clear her husband's gambling debts:

“Esquinas’ days with Jordan, though, had come to an end. They would continue to wrangle over golfing losses, with various estimates suggesting that Jordan paid somewhere between $200,000 and $300,000, some of it in a series of $50,000 checks written by Juanita Jordan,” Lazenby wrote.

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How much money did Michael Jordan owe Richard Esquinas?

Chicago Bulls legend Michael Jordan (left) and businessman Richard Esquinas

In his own 1993 book titled “Michael & Me: Our Gambling Addiction... My Cry for Help!” Richard Esquinas said that Michael Jordan owed him $1.252 million. That came after Jordan repeatedly doubled down on his bets following losses on the golf course.

The San Diego Union-Tribune recently summarized Esquinas' story as follows:

“Over the ensuing week, he chronicles in his book, the script flipped: Jordan owed him $93,000, then $153,000, then $313,000 … then double that … then double that again for $1.252 million following a round at Aviara Golf Club in Carlsbad,” the Tribune wrote.

However, Jordan refused to pay his full debt to Esquinas:

“They ultimately agreed to $300,000, paid in installments over three years. Esquinas says he received $200,000,” the Tribune wrote.

In a 1993 ABC interview, Jordan explained that he refused to pay his full debt to Esquinas due to him publishing a book to damage his reputation:

“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," Jordan said. "What’s the balance? Zero, in my book."

However, 30 years later, Esquinas is still confused as to why Jordan hasn’t paid his full debt, despite now having a $2 billion net worth. Esquinas told The San Diego Union-Tribune that it's likely because the ultra-competitive Jordan doesn’t want to accept his loss:

“For whatever reason, I think a lot of this is just the fact that he did not want the loss,” Esquinas said. “He didn’t want to give me a W. Maybe he was embarrassed. Writing me a check was an L to him.

“I’ve sought advice and read and this and that — only speak the sweet truth, these kind of things — and somebody not wanting to pay versus can’t is what I really couldn’t accept. That’s one of the things that’s hung with me, my inability to reconcile. I understand can’t pay. I don’t understand when a man won’t pay,” Esquinas continued.

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