Michael Jordan. Legendary player, legendary gambler...

By Andrew D

April 05, 2023

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As one of the most famous athletes of all time, in any sport or discipline, Michael Jordan is one of the most recognisable faces on the planet Earth. He changed the face of modern basketball with his extraordinary athleticism and vision. Bringing a new wave of talented youngsters in his wake, some of whom have gone on to match and even surpass his incredible feats. 

But even the greatest are human at the end of the day and not immune from making mistakes or bad decisions. Michael Jordan had some ups and downs along the way and his biggest issues revolved around, you guessed it, gambling.

The clue is in the title to be fair...

Michael makes money

Although the numbers can be a little difficult to pin down exactly, it seems fairly unanimously agreed that Michael Jordan is the single richest sportsman in the world. If not, he’s really, really close with an estimated worth of $1.6 billion. 

Not all of Jordan’s money came from his active basketball career, which ended in 2003. In fact, only a fraction of that staggering fortune was earned during his time with the Chicago Bulls and the Washington Wizards. $94 million of it to be precise…

The key to such an extraordinary accumulation of wealth was, at first, the huge number of brand endorsements that Jordan accepted and where he invested those dollars. From 200 to 2012, Jordan earned $480 million dollars from his association with Nike alone and there are many more. 

A serious bankroll for a serious sports gambler

It is rather obvious to anybody who has ever seen Michael Jordan play, or even watched footage of his athletic exploits, that the guy was driven as a player. He was clearly an apex competitor who cannot bear to lose and did everything within his power on the court to ensure he seldom did. 

It is less obvious unless you are an avid follower of sports news and gossip, that Jordan is a high-rolling gambler who loves betting and has won and lost some unimaginable amounts over the years. There are rumours about Jordan’s gambling being more than just a hobby and that it caused some very serious issues, but more of that later. 

A competitive streak like no other

As with anything involving figures so heavily scrutinised and visible in the public eye, it behoves us to take stories and rumours about them with a pinch of salt. That said, it would not be too outlandish to say that Michael Jordan’s competitiveness and willingness to put his money where his mouth is are legendary. From £100,000 games of rock, paper, scissors, to organising who-can-drink-water-fastest races and sledging president Bill Clinton to try and put him off during a game of golf. NBA legend Charles Barkley, who was close friends with Jordan at the time, described how he would play for a few hundred dollars per hole himself, while Jordan would go much, much further...

"We'd be playing golf with certain people, for a couple hundred dollars a hole, nothing big, and he'd be playing some guy for $100,000," Barkley said of Jordan. "He's like, 'Charles, pick that up.' I'm like, 'This putt is for $200.' He's like, 'Pick that up, Charles, get out of my way, you're in my line.' I'm like, 'How much is that putt for?' He's like, '$300,000.' I said, 'Let me get out of your line.' It was crazy man."

Charles Barkley

Jordan is almost obsessively competitive and it seems that comes with a reputation for being a sore loser. He even refused to stop banging on Chuck Daly’s hotel room door after Daly won a leisurely round of golf the pair played earlier that day. Eventually, Daly acquiesced and they played again. Jordan won.

An over-the-top competitive nature, combined with the inability to let it go and walk away are characteristics that almost certainly drove Michael Jordan to ever bigger and better achievements on the basketball court and in his business affairs. But in the unforgiving world of sports betting and gambling in general, where it is all too easy to lose sight of the situation, that attitude can soon attract trouble.

Losing big

In 1993, successful San Diego businessman, Richard Esquinas wrote a book about four years he spent playing golf and gambling with Michael Jordan. The book was entitled ‘Michael & me: our gambling addiction…my cry for help!’ and tells stories of how they played each other for thousands of dollars at a time.

There was one stage when Jordan had a shocking losing streak, meaning that he owed 1.25 million dollars. With a change of luck, he managed to get back to just under a million, but it serves to illustrate just how serious the situation was at that time.

NBA investigations begin

Jordan’s betting habits were attracting all kinds of unwanted attention and the NBA grew concerned about how it might reflect on the league and the wider brand. In 1992, Jordan testified in the drug/money laundering trial of a convicted drug dealer, to whom he had given thousands of dollars to clear away his gambling debts.

Soon thereafter, the NBA launched two investigations into Jordan’s betting behaviour

but was careful to claim that the league was only concerned with any potential connections to ‘inappropriate’ individuals who might tarnish the image of the illustrious NBA and bring disrepute to them all.

There was never any evidence that Michael Jordan ever wagered on any NBA games, let alone those that he played in himself and he was soon cleared of any wrongful behaviour. The matter was dropped and no further action was taken but the die was somewhat cast.

The final straw came the following year when Michael Jordan took a limousine to Atlantic City with some friends and his father. He was seen leaving a high-stakes poker game in the wee small hours and it was just hours before he was due to play in a major game. The trip was bang in the middle of the 1993 NBA Playoff series against the New York Knickerbockers and Jordan’s timing could not have been worse. 

Rumours of a gambling addiction swirled in the media just as they had in the locker rooms and behind closed doors of high-ranking meetings. Jordan refused to speak to the media at all for 2 weeks,  finally returning to defend himself against the accusations and speculations of his gambling being an addiction rather than a way to just enjoy himself and blow off steam.

“It’s a hobby. If I had a problem, I would be starving, hawking this watch and my championship rings, selling my house. My wife would have left me, or my kids would be starving. I do not have a problem. I enjoy gambling. The media has taken it far greater than it is. Soon, whenever I walk away from this game, it’s going to be the only bad thing people say about Michael Jordan.”

Michael Jordan

Shock announcement

On October 6th, 1993, seemingly to the total surprise of most people in the industry, Michael Jordan announced his retirement from basketball. He was at the zenith of his playing career, with 3 back-to-back NBA titles, three NBA Finals MVP awards, and seven straight scoring titles. The foundations of the sport were rocked badly and it would not be an exaggeration to say that it caused a crisis and a wave of shock and panic throughout the game.

Here was the poster boy of all time. The best player that any of them had ever seen and, more importantly to many if we’re honest, an absolute nailed-on money-making machine. They stood to lose the biggest asset the sport had ever produced and there must have been quite a few sweaty, clenched meetings and emergency discussions around that time. 

Jordan attributed the decision to having lost his father, who was tragically murdered earlier that same year but, naturally the rumours whipped into a whirlwind of madness and speculation once again.

The most accepted conspiracy that emerged was this:

Jordan had been secretly suspended by the NBA after more stories of wild gambling and out-of-control bets that threatened to sully his image and that of the NBA. We already know that they recently had been investigating this situation to mitigate any damage. It is hardly the biggest leap of imagination to think that they agreed to let him call it retirement and everybody could walk away with their dignity and reputations intact. We shall probably never know. 

A somewhat wilder conspiracy that surfaced was as follows:

Jordan’s father had been murdered as a retaliatory act for unpaid gambling debts to some of the less-than-salubrious characters he seemed to have found himself embroiled with in one way or another. Both rumours were, of course, categorically denied by all involved and we’re not necessarily always in agreement with the old adage that ‘there’s no smoke without fire’ but it certainly was a strange and shocking decision for an athlete who was at the very top of his game and had the world in the palm of his talented hand.

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Jordan was not done shocking fans and onlookers just yet and announced that he would be joining the minor league baseball team the Chicago White Sox in 1994. The fact that the owner of his beloved Chicago Bulls also owned the baseball team cannot have hurt his transition into the team.

In the less than 2 seasons he played the game, it was generally accepted that he was a decent player who might even have been special if he had spent more time focusing on that than basketball as a youngster. Jordan was clearly one of those annoying kids at school who could play any sport better than you. It stands to reason that he could probably have excelled in a great many disciplines. 

Unfinished business

In March 1995, Jordan gave a 2-word press release that set the basketball world alight:

“I’m back”

He went on to play 3 more seasons with the Chicago Bulls. This culminated in a Finals series with the highest Finals television viewing figures in history, and the highest game figures for Game 6. It could not have ended more dramatically for the greatest player who ever lived and his last ever touch of the ball for them on a basketball court won them the trophy. With 5 seconds of the game remaining and the Bulls trailing by 1-point, he snatched his final 2 points of the game, taking him to a total of 45. A quite staggering, remarkable end to his franchise-changing career with the club.

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