Signed by Kaplan: Michael Jordan: All Star Gambler?

Michael Kaplan mickap June 25, 2020

In a recently released documentary, “The Last Dance,” Michael Jordan stared into the camera’s lens and said, “I don’t have a gambling problem. I have a competition problem.”

Jordan – who is said to love gambling so much that he’s blown millions of dollars on golf courses, at card tables and in casino high-limit rooms – has a point. How else would one account for his soaring over the heads of opposing players to slam basketballs into hoops. The need to compete drives every element of his life. That very drive bleeds over from stellar performances on the court to costly endeavors off of it.

In fact, it’s been widely reported that he endured at least one $6 million swing at a Las Vegas craps table, going from being ahead by $1 million to being down $5 million before throwing in the towel. But it could have been worse: The guy he was high-rolling with that night, Cincinnati Bengals cornerback Adam “Pacman” Jones reportedly left the casino, went to a strip club, got into a fight there and wound up suspended from the NFL.

In the sixth episode of the ESPN doc, one former teammate remembered a reality of life on the road for the then rampaging Chicago Bulls. He recalled that, on the team plane, there were two ongoing card games. One, in the rear, had Jordon and other high-flying teammates gambling for thousands of dollars. Up front, this NBA pro and a few others would kill time in the sky by playing blackjack for $1 per hand.

Passing by one day, Jordan asked if they would deal him in. “Sure, why not?” was the gist of the response.

Afterward, though, the teammate couldn’t help but wonder why Jordan would bother wasting his time in such a penny ante game. “I want to leave this plane with your money in my pocket,” came the reply.

In that point-proving instance, Jordan didn’t care how much money he won. He just wanted to win.

Over the course of Jordan’s 15-seasons in the NBA, his gambling has been called into question. Concerns were aired that he could get in deep with nefarious people and be encouraged to throw games (his record-breaking career shows little sign of that). Others viewed his life of chance as a distraction to the game he loved. There were even unsubstantiated rumors that his retirement was influenced by pressure from the league.

But what is it like to gamble with Michael Jordan, on the golf course or at the casino gaming table? During a conversation a few years ago, poker celebrity Phil Hellmuth gave me an inkling. “The way Michael Jordon rolls [on the course] is that he’s got six golf carts in the group with a lot of guys betting; MJ and I were going to play for $1,000 per day [with, no doubt, lots of side-bets along the way],” said Hellmuth, explaining that he arrived late to meet the group at Shadow Creek, the top golf-course in Vegas, and was disappointed to learn that Jordan’s crew was quitting early because of unrelenting heat. “It would have been fun, but I would have been massacred. He shot a 73 and I was shooting 102; it would have cost me $10,000.”

Hellmuth added that the sum was relatively small for Jordan. “He has unlimited money and lets people play for whatever they are comfortable with. I know of another poker player with whom he plays for insane stakes. That night we had dinner at Aria and played high-stakes blackjack. He was drinking $2,500 shots and was stuck [with losses at the blackjack table].” Hellmuth and others hit a club, Jordan kept playing, trying to dig out. “He doesn’t want to lose at anything.”

His unwillingness to leave the table is legendary. Sometimes, though, that never-say-die attitude may have gotten in the way of his profession. In 1993, as reported in the New York Times, Jordan took advantage of the “home-casino advantage.” He was in New York, for a playoff game against the Knicks and slipped down to Atlantic City for a baccarat binge that lasted past 2:00 in the morning on game day. Though the Bulls lost that night, the mighty Jordan still managed to score a perfectly respectable 36 points. However, people were left to wonder if a well-rested non-distracted Jordan could have racked another five baskets and taken his team to victory.

More troubling to the standard-keepers at the NBA were a pair of checks that Jordan wrote. One was for $57,000 to the convicted cocaine trafficker James “Slim” Bouler. Another check, this one for $108,000, was found in the suitcase of a murdered bond bondsman. In both instances, Jordan maintained that they were to pay off gambling debts. While the sums are obviously high for normal people, considering that Jordan ranked among the highest paid athletes in the world, those amounts didn’t put a dent in his net-worth and – dollar blackjack with teammates aside – may have represented the amounts of money risked that makes gambling worthwhile and exciting for him.

But, under some circumstances, he even liked to gamble just for the hell of it. Footage in “The Last Dance” shows him betting on the most mundane thing imaginable: pitching quarters with the goal of landing closest to a wall that was about 20-feet-away. Jordan was playing against his security guard John Michael Wozniak – the former cop, now deceased, told Complex about going with Jordan to get matching jumping-man logos tattooed on their arms. Wozniak won twice, collected stacks of 20s and strutted around like a boss.

A darker side of Jordan’s habits was detailed in the book “Michael & Me: Our gambling addiction … my cry for help!” The author of the book, Richard Esquinas, did a load of gambling with Jordan. On the golf course they played for $1,000 per hole. Fallout from big-money matches reached the point where Jordan was in the hole for $1.2 million following a series of double-or-nothing rounds. Jordan managed to grind his deficit down to $902,000 and they settled on a payment of $300,000. Jordan paid him $200,000 and presumably intended to hand over the rest. But then Esquinas wrote his book and Jordan reportedly bailed.

Perhaps, this goes to show that there is only one thing Jordan hates more than losing: Having it written about.

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michael kaplan

With four books (and more on the way) plus hundreds articles, Michael Kaplan is one of the most experienced writer in gambling related subjects.

He have covered big stories including famous gamblers such as Phil Ivey and Phil Hellmuth for publications including Wired, Playboy, Cigar Aficionado, New York Post and New York Times. Based in New York, where he regularly writes for the Post.

Read more about Michael Kaplan on his author profile.

About the Casinomir Writer

Michael Kaplan mickap
Author since August 30, 2022