HoopsHype looks back at Michael Jordan's Gambling Days

For decades, professional athletes have had a close relationship with gambling. And nowhere has this relationship ever been more obvious than that of Michael Jordan and the casinos.

The six-time NBA champion has been involved in some legendary gambling stories, such as the time when Jordan allegedly spent all night playing craps in a Vegas casino, ultimately losing $5 million when it was all over.

HoopsHype.com recently revisited this story and others regarding Jordan’s betting days. Some of the stories and issues that HoopsHype covered included the conspiracy that the NBA suspended Jordan for gambling, the time he lost over $1.25 million in a 10-day golf excursion, and how the Chicago Bulls once scheduled a preseason game in Vegas so players had time to gamble.

The golf story is particularly noteworthy because Jordan kept pushing the stakes to double or nothing against his opponent, Richard Esquinas, part owner of the San Diego Sports Arena. Esquinas lost the first game and owed Jordan $98k. However, they kept going double or nothing and Esquinas kept beating Jordan over the course of 10 days. When everything was said and done, he was sitting at $626k in losses. Here’s how Esquinas describes the story:

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 do not want this game,’ I said, ‘but I must be honest with you. You lose and you pay. That’s the only way I’ll give you a shot. And, if I beat you, that’s it. No more of this double or nothing.

Jordan lost once again and ended up owing Esquinas $1.252 million total. HoopsHype suggests that Esquinas later had trouble collecting on the debt because MJ is known for welshing on lost wagers.

There are plenty more tales like this from Jordan’s gambling days, prompting some to wonder if he had a problem. But if Jordan did have a major gambling problem, it never affected him buying the Charlotte Bobcats or amassing a fortune worth $650 million (according to Forbes).