Michael Jordan Gambling – The Rippling Effect on His Career and Personal Life

Everything about Michael Jordan was of epic proportions and had the capacity to become legendary. Sadly, Michael Jordan's gambling enthusiasm was one of those things. Those lending an ear to conspiracy theories even go as far as to say that it was his passion for gambling that urged the NBA superstar to take a break from basketball. Not implausible at all, but let's not jump into conclusions right from the start. We will cover everything from a to z. We will see how the gambling habits of Air Jordan came to be, how that affected his inner circle of friends and teammates, and what this destructive lifestyle has led to.
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The Early Years of Michael Jordan’s Gambling Problem

It’s tempting to think that a great champion such as Mike gets a ‘get out of jail’ card and cruises through life without so much as a single hurdle along the way. This, however, could not be further than the truth. It is believed that Michael Jordan’s gambling problem dates back to his high school years. In his book Michael Jordan: The Life Roland Lazenby tells the story of how the rising star thanks to his prom date for holding up her end of the bet they had had. Another case would be a bet Jordan lost at the pool table. A jammy ex-classmate of the NBA legend put a $5 check-up for auction in 2019.

Needles to say, it sold for a considerable sum of money, making, the lucky fellow’s provident move to ask for a check instead of cash, pay off big time. The accounts other witnesses point out that Michael Jordan’s gambling problem was already too conspicuous back in the day. He’d use every good opportunity to gamble with his teammates and even coaches. It could be argued that it’s a blessing in disguise he didn’t have the income in his early days as an athlete that he would later have as part of Chicago Bulls’ team.

Michael Jordan and Gambling – Making a Name for Himself

Getting on the Chicago Bull’s team trampolined Michael’s gambling problem to a whole new level. Apparently, he was ready to challenge anyone around him to a card game. As you can probably gather already, that means a whole lot of people. Including teammates, biography writers, bodyguards, the list goes on and on.

And by ‘card game’ we don’t mean the collectable kids’ stuff, but straight up real-money poker. Judging by the accounts of writer Sam Smith, he didn’t shy away from splurging big sums of money. Sometimes, he’d do it driven by his overflowing competitiveness. Then the money didn’t matter. A case in point is the frequent bets Jordan would have with a Bulls guard.

Boy Tying His Shoelaces

Joining Team USA in 1992 was a golden opportunity for Michael Jordan’s gambling genius to shine through. The Dream Team’s training camp was in Monaco, where Jordan would have a field day trying to satisfy his insatiable gambling pangs at the famous Monte Carlo casinos. Later on, in Barcelona, he’d use his position of power to organize a high roller card game with people of his means. The usual suspects sitting at the table with Mike were peers Magic Johnson, Charles Barkley, Scottie Pippen. Whether Michael Jordan’s passion for bets rubbed off on Barkley is debatable, but what we do know is that Charles Barkley’s gambling experience qualifies him as a high stakes cash game regulars.

Michael Jordan Gambling on Golf – Close but No Cigar

Michael Jordan’s gambling addiction and consequent pursuits have led him to the golf field. This time he’d only gamble with elect few – golf partners if you will. He must have felt a bit out of his depth because the records show he was on the losing side most of the time.

A lost bet and a check for $57,000 to James Bouler was enough to get Jordan in a world of trouble. He was summoned in court to tell his side of the story because Bouler was suspected of drug dealing and money laundering at the time. It ended up bad for Bouler who was sentenced to serve 8 months in jail, but the NBA legend got out of the whole mess, clean as a whistle.

Golfers Shaking Hands

Obviously, the affair wasn’t enough to scare Michael Jordan straight because his gambling endeavor continued. However, the book of Richard Esquinas, released in May 1993, is what really made NBA fans raise eyebrows. A serious gambling debt allegedly cost Jordan a dear penny. $300, 000 to be exact or so the story of Esquinas goes. Those were the years when the words Michael Jordan and gambling did, indeed, go hand in hand. For the good or for the bad, this was before the time of the best online betting sites.

First Retirement and Its Alleged Connection to Gambling

1993 was a very eventful year for the NBA superstar. It is when, among other things, he announced his first retirement. The reasons for that are still unclear, and they probably have to do with the emotional state of Michael Jordan at that time. That, however, didn’t stop backbiters from pointing their fingers at Michael Jordan’s gambling problem, saying that it must be the reason he’s retiring.

In his post-retirement press conference, Air Jordan certainly laid the groundwork for a lot of conspiracy theories. To the question, if he is going to return, he answered ‘if David Stern lets me back in’. Who would have imagined that ‘throwing a bone’ to the press could have such detrimental consequences? To this day people look back at this as a hint at a serious misdemeanor committed by the, now, owner of Charlotte Hornets, Michael Jordan. He had to, however, pass a series of checks before purchasing the team, came out clean, and was approved.

He Would Bet on Anything and Everything

When it comes to Michael Jordan’s colourful personality and gambling tastes, it’s easy to forget something. In order not to miss anything, we made a list of all the things number 23 was interested in, as far as betting goes. Not every single bet he has made has a dramatic punch to it worthy of a Hollywood saga, so you might have a hard time making a connection between Jordan and some of the games on the list.

  • Betting at the craps table
  • He will be first to receive his luggage
  • Betting on rock paper scissors
  • High stakes poker with friends
  • Cartoons

Personal Drama

James Jordan was murdered in 1993. Daniel Green and Larry Martin – teenagers at that time – were accused and found guilty of the murder. They were sentenced to life imprisonment. The case would have been closed at that if it wasn’t for the conspiracy theorists. Actually, it was a story by Mark Whicker that aroused the suspicion of a Michael Jordan gambling – father death connection. In his book, Whicker tries to make the reader think with a very convincing wording: ‘…there is evidence of the son’s gambling problem, and there is suspicion of a son’s paying problem,’ ‘The father of that son has been murdered. Coincidence, anyone?’

Man Holding His Wrist

There is nothing to prove that what Whicker suggested in his book is the truth. To the contrary, the theory of Michael Jordan’s gambling addiction being linked to James Jordan murder has been disproved. After all, even if we never get our hands on hard evidence, it’s highly unlikely that an NBA star of that caliber was ever unable to pay the debt, be it to a gang boss.

Questions and Answers

Let’s not play fast and loose with the truth because this is a very complicated matter that requires unbiased judgement and a lot of answers. Below are the most frequently asked Michael Jordan gambling questions along with short answers. Get to reading if you think there’s a piece of the puzzle that is still missing for you.

🃏 Why did Michael Jordan start gambling?

From the looks of it Mike started gambling in college. Michael Jordan: The Life by Roland Lazenby details how Michael Jordan thanks his prom date for being a good sport and paying him off. Gambling with coaches and teammates was also in Jordan's plans.

✋ What did Michael Jordan get caught gambling on?

During his career in the Chicago Bulls, Michael Jordan was often seen gambling with his teammates. His other gambling adventure includes being caught paying off a lost golf bets Golf and playing blackjack at an Atlantic City table just before an Eastern Conference final.

⛳ Who does Michael Jordan golf with?

Michael Jordan's golf bets made him involved in the James Bouler case back in 1993 when he was called in court to testify. Sometime before, he had paid a $300,000 golf debt to Richard Esquinas whom he owed upward of $1 million, Esquinas claims in his book.

🛑 Why did Michael Jordan retire?

Rumor has it that his main reason to retire might as well be his gambling addiction. His own explanation is none the clearer. If we were to take at face value what was said at the press conference before Michael Jordan retires for the first time, his father's death knocked him off-center.

📈 How much did Michael Jordan lose gambling?

The biggest losses of Michael Jordan that records of existing are his lost golf bets. We don't know exactly what was the usual size of a bet he'd place, but what we know is that Air Jordan paid 57,000 to James Bouler and $300,000 to Richard Esquinas. Both payments were the result of an accumulated golf gambling debt.

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