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Michael Jordan: The GOAT’s Great Gambling Tales

Sports fans across the world have hailed The Last Dance, the documentary series about Chicago Bulls’ dominance of the 1990s, as an entertainment saviour in these tough times. Michael Jordan’s gambling exploits are touched on, but how hard did (or does) Jordan actually go on the punt?

Jordan’s attraction to gambling is acknowledged by most – including the man himself – as being a by-product of his legendary competitiveness. Jordan was obviously blessed with extreme physical gifts but for many, what set him apart on the court was a drive to win that seemed almost psychopathic. Those same traits would pop up off the court – and still do!

As frequently seen on The Last Dance, Jordan was happy to bet on anything with anyone – and it was often his teammates and others around him who were the targets. The documentary shows Jordan betting with his personal security guards on simple coin-toss games. But the most common game was cards. NBA players are constantly travelling, and the endless bus and plane trips were the scene of blackjack and poker games between Jordan and those teammates willing to take him on.

And that’s before you get to the golf course. Jordan is a fanatical golfer but according to some who’ve played with him, the game can often take a back seat to the betting. A round of golf with Jordan can mean betting on everything – outright results, individual holes, individual strokes… you name it, it’s fair game.

Fellow NBA legend Charles Barkley described it in 2017.

“We’d be playing golf with certain people, and we’d be playing a couple hundred dollars a hole. And he’d be playing some guy for $100,000,” said Barkley.

“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 said, ‘Well how much is that putt for?’ He’s like, ‘$300,000.’ I said, ‘Let me get out of your line.’

“It was crazy, man. They were playing for hundreds of thousands of dollars.”

Gambling baggage

Jordan had been known to bet on anything. Sportswriter Bill Simmons tells a story from early in Jordan’s career, before NBA teams used charter flights. They were waiting for their bags in the terminal when Jordan suggested a bet on whose bags would come out first. He bet his own versus everybody else’s – nine teammates. $100, head-to-head. With the true odds at 9-to-1, several teammates took what looked like a great bet – only to lose when Jordan’s bags rolled off first.

The story continues with a theory that Jordan had actually bribed a baggage handler. Jordan himself denied this.

Refuse to lose

Former ice-hockey player Jeremey Roenick once found himself on the other end of a wager with Jordan, which showed the superstar’s complete refusal to accept he couldn’t win. The pair played a round of golf on the day of a Bulls game against Cleveland, with Jordan set to suit up that night. Betting a few hundred dollars per hole – tiny amounts for Jordan – Roenick got on top and finished the round $3,000 ahead of Jordan.

Jordan’s solution was simple: “Let’s go again. We got time.”

He dragged Roenick around the course for another 18 holes in order to win his money back.

But Roenick won again.

Knowing the day was done, Roenick (stupidly) started trash-talking.

“I’m messing around and I said ‘I’m gonna call my bookie… and all of the money you just lost to me? I’m putting it on Cleveland tonight.’” recalls Roenick.

Jordan spied a chance to get the money back, and said he’d offer him far better odds than his bookie.

“He said ‘I tell you what, I’ll bet you that we win by 20 points and that I have more than 40.’”

It should also be mentioned that Roenick and Jordan had been drinking beers all afternoon during their golf game.

Roenick took the bet and, predictably, lost the money as Jordan delivered a couple of hours later.

“Let’s bet our cars”

Age didn’t slow Jordan down… it just meant there was a new wave of youngsters silly enough to take him on. At 38 years old, Jordan was challenged to a three-point shooting contest at practice by 21-year-old rookie teammate Jamal Crawford. Five shots each, head-to-head, $1000 stake. Jordan won but Crawford was undeterred, challenging the legend to a second round for $5,000. The rookie won that, which obviously displeased Jordan.

So he took aim at Crawford’s brand-new Mercedes, his pride-and-joy that he’d just bought and showed off to teammates. Jordan demanded a third round, and put up his own Ferrari against the new Merc. Perhaps bullied into it, Crawford accepted. Famously, Jordan went 5-for-5 from three-point range, immediately had a security guard remove Crawford’s personalised number plates, and burned out of the car park in his new Mercedes.

Lesson learned, Jamal.

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Mark Haywood

By:
Mark Haywood

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