The Man, the Myth, the Gambler: A Collection of Michael Jordan Betting Stories

ESPN delivered sweet relief to socially-distanced sports fans in the form of "The Last Dance," its 10-part 30-for-30 documentary on Michael Jordan and the 1997-98 Chicago Bulls.

Any real examination of Jordan has to include a discussion of his gambling exploits. Jordan is (arguably) the Greatest Player of All Time. But the sheer breadth and intensity of Jordan's gambling exploits are jaw-dropping in their own right.

Anyone. Anywhere. Any time. Any stakes.

It is not hard to find Jordan-related gambling stories. And an image begins to appear of the gambler Jordan was when he wasn't ruling the court. Today, I present an attempt at collecting the stories shared around the world.

These stories are a compilation of internet archives, sourced from searches, Reddit posts, references in bigger stories, first-hand, second-hand, and, at times, third-hand accounts (and noted as such when presented).

THE CONSPIRACY THEORY

It is impossible to cover Jordan's gambling exploits without discussing his 1993 retirement from basketball and the gambling-related conspiracy theories that flowed from it. Former Bulls guard and broadcaster Norm Van Lier is most often sourced as the initiator of that discussion, though it's likely the idea would have arisen somewhere.

After the death of Michael's father, James Jordan, in the summer of 1993, Van Lier began discussing on Chicago sports radio a possible connection between the elder Jordan's murder and his son's gambling exploits. The league had conducted two internal investigations of Jordan's gambling in 1992 centered around checks found during criminal investigations — one during a crime scene investigation at the home of a murdered bail bondsman — and neither had resulted in any public discipline.

According to Roland Lazenby's prolific book on Jordan, "The Life," "[NBA commissioner David] Stern told reporters that the league's latest investigation of Jordan was now closed, emphasizing that he was certain Jordan had never bet on NBA games and was not suffering from gambling addiction."

But when Jordan retired later that summer in '93, Chicago columnist Dave Kindred speculated in print that Jordan's retirement was tied to his gambling exploits. Jordan himself said regarding a possible return to the league at his retirement announcement: "if David Stern lets me back in," which only fed the conspiracy talk.

Stern, when directly asked, was always emphatic that the conspiracy talk was absurd — but Jordan, according to multiple points of record, felt he didn't go far enough. Stern, on the other hand, felt that if he went further it would only fuel the discussion.

The best reasoning for putting that conversation to bed comes from Lazenby, who noted both in his book and in an excerpt for HoopsHype, that for Jordan to become the majority owner of the Charlotte Bobcats/Hornets, he would have to clear the investigation process and have Stern's approval:

The greatest proof that Jordan never, ever did such a thing?

Already a minority owner of the Bobcats in 2007, he would become the majority owner just a few short years after his bummer night in Vegas.

Somehow overlooked in the process of Jordan becoming an owner is the closest thing the public will probably ever get to an answer about the "conspiracy theory." NBA commissioner David Stern and Jordan had never been close, but Stern worked very hard behind the scenes to make Jordan’s ownership happen. And once it happened, the commissioner continued to help in the adjustment.

That's pretty airtight.

No one denies that Jordan gambled, and at times gambled compulsively. But every biography and major piece of text makes it clear that the problems it caused Jordan were embarrassment and risk to the careful public image he had cultivated for marketing success.

GAMBLING IN HIS DNA

Let's go all the way back to Jordan's junior year of high school. Before text messages and Snapchat, before the internet, folks smitten would write each other letters. Jordan wrote the young woman whom he would take to junior-senior prom, and, according to "The Life," penned "I was really happy when you gave me my honest coin money I won off the bet."

In college, the story was much the same. From David Halberstam's "Playing For Keeps: Michael Jordan & the World He Made:"

A year ago, a check for $5 from "Mike Jordan" was auctioned off. TMZ told the tale from the auctioneer:

It was February 27, 1984 and Jordan — in the mood to play pool — went to the basement of the Granville Towers on UNC's campus … and proceeded to dominate on the table.

The guys were betting money … and MJ was up $25.

A friend of the guy Jordan was beating thought Michael was hustling his buddy, so he stepped in to play MJ … and win back some of the money he'd lost.

MJ lost a few games in a row — which the consignor says irritated Jordan — so he decided to cash out and take the 5 bucks he was owed.

The friend — realizing Jordan was likely going to be an NBA superstar — asked Michael if he could pay him with a personal check.

Michael accepted … and the UNC student wrote the check to "Mike Jordan" — the name the basketball phenom went by on campus.

Here's a good precursor to the kind of gambler that Jordan would become and one that foreshadowed his obsessive golf gambling. From "The Life": Fellow UNC student David Mann, who used to hang out with Jordan and introduced him to film review, was putting into a cup in the hallway.

"He wants to do it too, and he wants to bet on putting the ball into the cup," Mann recalled. "It was only like a quarter or a dime, but anyway we did this for like thirty minutes and I was beating him. I had to go to class, and he wouldn't let me stop. So he's making me stay there, but I didn't want to lose so I kept putting it into the cup."

Finally, in exasperation, Jordan threw down the putter and walked off. "He ended up owing me about seventy-five cents," Mann remembered, "and he never paid."

This would not be the last time he welched.

[Chad Millman talks Michael Jordan stories with Wright Thompson on The Favorites Podcast]

THE SHARK ON THE PLANE

Jordan's reputation was never one of a sterling teammate. It wasn't just punching Steve Kerr or constantly undermining Toni Kukoc. He would belittle and trash teammates relentlessly, from his rookie season on.

The story that best illuminates how Jordan sought to hustle even his teammates comes from former Bulls center Will Perdue. From Bleacher Report:

That Chicago Bulls charter flights served as de facto casinos throughout the 1990s was an open secret among NBA fans. There's the famous Sports Illustrated photo of Ron Harper, Scottie Pippen and Michael Jordan playing cards, thrown onto a perfectly folded blanket in the airplane's aisle. The setup prevented the cards from sliding away, its meticulousness indicative of the frequency of such games.

But the back of the plane was the fiercely competitive high rollers' room. That's where you'd most often find Jordan, of course—until he learned of the role players' $1 blackjack games up front.

Jordan wanted in. Will Perdue, the Bulls' 1988 first-rounder, swears by his memory of the following exchange between the Hall of Famer and John Paxson:

Paxson: "Why are you even bothering to play with us?"

Jordan: "So I can say I have your money in my pocket."

LITERALLY ANYTHING

When I say he'd bet on anything, I don't mean "any game" — I mean "anything."

From a Bill Simmons column all the way back when ESPN's "Page 2" existed (and cited originally in Halberstam's "Playing For Keeps:"

Back before NBA teams had grasped the rejuvenating power of chartered airplanes, the Bulls were waiting for their luggage in Portland when Jordan slapped a hunny on the conveyor belt: I bet you my bags come out first. Jumping on the incredibly favorable odds, nine teammates happily accepted the wager. Sure enough, Jordan's bags led the rollout. He cackled with delight as he collected everyone's money.

What none of the suckers knew, and what MJ presumably never told them, was that he had bribed a baggage handler to help him out. He didn't pocket much (a few hundred bucks), and considering his net worth hovered around nine figures at the time, it's safe to say he didn't need the extra cash. But that didn't matter. There was a chance at an easy score, and he took it.

Just to review this, the most popular and profitable athlete of all time:

• Bet $100
• Bet $100 on which bag would come out first
• Cheated to win!

How about Rock, Paper, Scissors? Via Jay Williams (NSFW) on "The Brilliant Idiots:"

How about … of all things … the Dunkin' Donuts scoreboard contest?! From Will Perdue, speaking to the Athletic:

"I played with MJ, the ultimate cheater of all time," said Will Perdue, who played with the Bulls from 1988 to 1995, and now is an analyst for NBC Sports Chicago. "He would always want to wager on the Dunkin’ Donuts race. What we didn’t know is that they rehearsed it. The security guards were here during the rehearsal, so they would see who wins. He’d ask the security guards who would win before he’d be willing to wager."

Perdue admitted he lost to Jordan a few times before he figured out what he was up to.

"Then I found out what was going on, and then I’d only bet with him if he let me pick first. Then he was like, no," Perdue said.

How about … Crazy Eights?! UNC teammate Buzz Peterson relayed a story in Flip Bondy’s book “Tip Off” on the 1984 draft in which he was playing in a card game at a Syracuse hotel with a group that included Jordan and Peterson’s mother.

Buzz caught Michael cheating at the card game Crazy Eights by hiding an eight — while playing against Peterson’s own mother. "There it was, right under his leg,” Peterson said.

You might be asking yourself "Why would anyone want to play with this guy?" Well, friend, that's a really great question. Jordan was such a force, and such an important force, that people were constantly held in his orbit.

And look, this mindset continues, even innocuously, in public. Like that time Jordan took a bet from Chris Paul in front of a bunch of basketball campers with shoes for the kids on the line:

But while it's true that Jordan would bet anyone, anywhere, there's no question that one particular forum brought out his need to gamble: the golf course.

THE GREEN

As a primer for the way Jordan approaches betting on golf, Charles Barkley told The Dan Patrick Show a few years ago that while he and other members of Jordan's circle would play for $100 a hole, Jordan would routinely play for $100,000 a hole, including one memorable hole worth $300,000.

Let's talk about the most famous golfing story for Jordan. Head on back with me to 1992.

Blackhawks legend Jeremy Roenick is in the inner circle and Jordan takes him golfing. Roenick told this story to the McNeil and Parkins Show on Chicago radio, and Golf Digest transcribed:

"Meet me at Sunset Ridge, early. We’re gonna go play 18 holes," Roenick recalled Jordan saying. We played a round, I beat him for a couple thousand and got ready to leave … Now, the Bulls are playing that night. They played Cleveland that night. I’m thinking he’s leaving, it’s 10 o’clock. He goes, "No, let’s go play again."

"So we go and fill up a bag full of ice and Coors Light and walk again. We roll around another 18 and I take him for another couple [thousand dollars]. Now we’ve been drinking all afternoon and he’s going from Sunset Ridge to the stadium, to play a game. I’m messing around. I’m like, 'I’m gonna call my bookie. All the money you just lost to me, I’m putting on Cleveland.'"

"He goes, 'I’ll tell you what. I’ll bet you that we’ll win by 20 points and I have more than 40 [points].' I’m like, 'Done.' Son of a gun goes out and scores 52 and they win by 26 points or something."

Now, that's an on-the-record account from Roenick of Jordan gambling on his own performance and on the Bulls to win. (It's worth noting the details of Roenick's account don't exactly match up with any Bulls games during the Jordan Era. If Cleveland was the opponent, Jordan scored 40 or more points against the Cavaliers at home five different times in his Chicago career and four times in the playoffs. In four of those games, he scored 50 or more, but the Bulls didn’t win any of those games by 20+ points.)

Regardless of some fuzziness on the details from Roenick, Jordan is the last human being maybe in the history of the world who would ever shave points, but bear in mind that he also told reporters "I'm no Pete Rose" back when his gambling was being investigated.

Professional golfer Rickie Fowler told our own Action Network golf writer Jason Sobel about his time facing down Jordan:

"I feel like a lot of those matches, whether you’re with the boys back home playing for big money or playing with MJ and getting those juices going, those are some of the best preps for going out and being ready to play tournament golf.

He’ll play you for whatever you want. Whatever makes you scared."

"Whatever makes you scared" is certainly telling. These bets for Jordan have nothing to do with the money but everything to do with a thirst for competition and getting another chance to dominate, defeat and intimidate an opponent. It's pathological.

Justin Thomas, now a major-championship-winning golfer, has his own Jordan story of gambling on the course — but his is with MJ, rather than against. Jordan, a frequent visitor to Kentucky to watch (and gamble on) the Derby, got to know a young Thomas in his trips to the Bluegrass State.

And as JT told our Jason Sobel, Jordan called on Thomas, then a 16-year-old phenom, to help swindle his buddies out of some cash:

"I was riding with MJ. When we got to the first hole, he said, ‘Go get your clubs.’ He told [his playing partners], ‘Alright, I’ve got the little man. We’ll take whoever wants us.’

There’s eight people. He wouldn’t tell me the game; he said I didn’t need to hear that.

Everyone’s giving me grief, because I was playing the same tees as them. I was tiny when I was 16.

So we played the last seven holes and I made four birdies. We drummed ’em pretty good. That was fun.

He just made me feel comfortable. I’d played in some big national tournaments, but that was the biggest deal I’ve ever played in. It was pretty cool. We had a pretty memorable day that we still talk about.

He always took care of everybody tipping, so let’s just say my tip was a little bigger that year.”

And then, of course, there's the story of Richard Esquinas.

Esquinas was a real estate developer in San Diego. He met Jordan in 1989, and for four years, he and Jordan met regularly to golf and gamble exorbitant amounts of money.

In 1993, Esquinas published a book (through a publisher, it should be noted, he owned) entitled "Michael and Me: Our Gambling Addiction… My Cry For Help!"

In the book, Esquinas details a September 1991 golf trip in San Diego with Jordan, claiming that MJ got down $1.252 million. Esquinas told the Chicago Tribune that Jordan played down his debt to around $900,000 with a game the following June.

And then, in what was again part of a trend established with Jordan, Esquinas says he found it difficult to collect, detailing multiple correspondences asking for the money. The matter was eventually settled for much less, with Esquinas claiming he lowered the amount to $300,000, telling the Chicago Tribune, "I just wanted out. I took a hit just to get out." Esquinas ended up receiving only $200,000, according to a story published by Vice.

Here's what Jordan said about it in an interview with Ahmad Rashad:

"I felt I was betrayed by this individual. He considered himself a friend. I don't consider him a friend, because friends don't do this to other friends."

"I would be sick if I lost $1.2 million," Jordan added. "And he would be sick if he reduced it to $300,000." Jordan didn't deny owing Esquinas $300,000, or paying him $200,000, but dismissed the $1.2 million figure as "preposterous" and overinflated. "He exaggerated to a point, and I've come up with my own conclusion to why he exaggerated … It sells books."

THE CARDS

Golf may have been his main conduit for competition and wagering, but the GOAT loves card games, as well: blackjack, poker and especially a game played on Bulls flights and in hotel rooms all across the world called "Tonk," or by Bicycle's rules, "Tunk."

Some of the best stories revolve around the Dream Team in 1992 . From Jack McCallum's vital account of that wild summer:

But there was Jordan in Monte Carlo, gambling the night away, Horace Balmer, the NBA's security man with him much of the time. (The players called Balmer "Bam" for the exclamation he uttered when he threw down his cards; this was before Emeril Lagasse.) From time to time Jordan even had his own blackjack table reserved and played all five hands. Jordan was breaking no laws, remember, although the casino couldn't have been thrilled that on some occasions a mysterious man stood behind him at the blackjack table. "Michael's personal card counter," someone in the Dream Team party described him.

Jordan has played poker with celebrities of all types and skill levels. T.I. said several years ago he and Jordan discussed poker strategies.

And Phil Hellmuth authored a piece, detailing Jordan's victory at a charity card event, including some play that illustrates both Jordan's poker savvy and his ruthless aggression.

"As I talked a little trash with Jordan about his Hold ’em game, I noticed that he was the chip leader for most of the night. In one hand I saw him call the $4,000 big blind bet (he limped in) in late position with A-A. Limping in with pocket aces is a pretty sophisticated play, and it worked like a charm when the flop came down 8-6-2, and Jordan busted the player in the small blind (who was holding Q-8). Later, I saw Jordan limp in with A-J, whereupon the small blind moved all-in with A-10, and the big blind called all-in with his short stack of chips with 10-3. Jordan called, and he was a huge favorite to win an enormous pot one more time! The flop was J-4-4, Jordan busted two players in this hand, and he was now at the final table with the chip lead.

Phil Gordon announced the final table action while the spectators gathered around seven deep to watch Jordan attempt to win one more championship. Chan, Oakley, Ewing, Raymer and I were standing behind Jordan as he dusted off players. One key hand Jordan had 5-5, with a flop of 7s-7d-2s, and he bet out. The only player at the table that had him covered moved all-in, and Jordan — who had been playing with that particular player all night — studied for almost 80 seconds before he called. It was a great call, and Jordan now took a huge chip lead with three players remaining.

When Jordan made it down to the final two players, he was all-in with A-7 vs. his opponents Q-9. He needed the A-7 to stand up (he was about a 57 percent favorite), and if it did, then he would have a huge chip lead. The flop came down 8-7-6, and now the player with the Q-9 needed a five, a nine, a ten, or a queen. It was a dangerous flop for Jordan, but the next card was a seven, and now he only had to hold off a five or a 10 on the last card. The last card was a jack, and Jordan went on to win the title, the trophy, and the $25,000 first-place prize, which he promptly donated right back to the Trent Tucker Charity, along with the $50,000 he paid for the custom made 'chopper' motorcycle he bought for his friend Mr. Oakley."

You know the whole "Zero Dark 23" bit from LeBron about how he turns off social media to stay focused on the playoffs? Well, let's compare that to this infamous story from 1993 the night before a playoff game vs. the Knicks, via the New York Times News Service:

The Chicago Bulls' Michael Jordan apparently spent the night and early morning before Tuesday night's playoff game gambling in an Atlantic City, N.J., casino.

According to an employee at Bally's Grand, Jordan was at the hotel's casino late Monday night. The employee, who requested anonymity, said Jordan checked into the hotel at 5:07 p.m. and checked out at 11:05 p.m.

A spokesman for Bally's, Michael DiLeva, would only say: "We have to respect the privacy of our guests."

However, two spectators at Tuesday night's New York Knicks-Bulls game said they saw Jordan at Bally's as late as 2:30 Tuesday morning. The spectators, longtime courtside regulars at Madison Square Garden, also asked that their names not be used.

In addition, radio stations in Philadelphia and Atlantic City received calls yesterday from people who said they saw Jordan at the casino.

As he finished his media-room interview after the game Tuesday night, Jordan privately was asked if he had been in Atlantic City Monday night. He smiled, then mumbled something and kept walking.

I've saved the best for last.

Jordan's infamous shrug vs. the Trail Blazers in the 1992 NBA Finals is an iconic moment.

For years, it was thought to be a fun expression from the GOAT amazed by his own ability. Then later, it was thought to be an expression of hatred for Clyde Drexler, whom Jordan held one of his many eternal grudges against.

Nope.

He was shrugging at Magic Johnson, who had busted Jordan the previous night and into the morning at a game of cards.

That's how much gambling is a part of Jordan's story. Even some of his most iconic moments trace back to wagers.

THE MAN, THE MYTH, THE GAMBLER

I never had misconceptions of Jordan's identity. I never fell for the warm smile he put on during McDonalds commercials and Nike advertisements in magazines. The man was ruthless; that wasn't hard to see.

But after reading all these articles and all these books to collect the story of Jordan's gambling life, there was one quote that resonated with me and forced me to view Jordan differently.

It came from James "Slim" Bouler, a drug dealer and golf hustler who had a check from Jordan in the amount of $57,000 seized in an arrest. Per the Washington Post, Bouler said:

"The only people who are saying Michael Jordan is having a gambling problem are the people who don't know Michael. Some people love to eat. Some people love to fish. Some people like to hunt. Some people like to drink beer. And some people love to gamble. Michael Jordan loves to gamble."

For most, gambling is about the thrill of winning.

But for Jordan, even as he lost hundreds of thousands of dollars at a time, it was about one thing — the one thing that drove his career, his personal life, his identity. No matter the stakes, no matter the setting, no matter the game…

It was always about beating you.

And by you, I mean everyone.