With sports fans all giddy about the Last Dance, the story of Michael Jordan and the 1996-97 Chicago Bulls, it’s an opportune time to take a look at another side of His Airness. Yes, he was the greatest basketball player in the world and he was competitive. Jordan was so competitive he liked to bet … on himself.

Retirement Theories

Remember when Michael Jordan retired from basketball the first time?

He was tired of his celebrity status and all the non-basketball related stress on his life. He packed it in and went on to play minor league baseball.

There were many that believed that wasn’t the real story. Jordan had admitted he had to pay off $57,000 in gambling losses in 1992, the year before he retired. It was also reported that Jordan was seen in Atlantic City the night before a playoff game against the New York Knicks.

The conspiracy theory was that Jordan’s retirement was really a suspension from the NBA handed down by then-commissioner David Stern.

The commissioner vehemently denied such a thing.

Former Chicago Bull Norm Van Lier, who was a broadcaster at the time, talked on Chicago sports radio about a link between Jordan and his father’s death in 1992. Van Lier intimated that Jordan’s gambling issues may have been the cause of James Jordan’s demise.


Michael Franzese on Michael Jordan's Father Killed Over Jordan's Gambling


Did He Do It?

The best proof available that Jordan never bet on NBA games and did not have a compulsive gambling problem was his foray into NBA ownership.

Jordan became a minority owner of the Charlotte Bobcats in 2006. In 2010, Jordan and his group, MJ Basketball Holdings, bought a majority stake in the franchise.

In order to own an NBA franchise, one must pass an in-depth investigation.

The league commissioner, Stern, would have to approve the deal. He did, of course, laying to rest any question of Jordan gambling on NBA games while a player or owner.

Born to Bet

While Jordan didn’t bet on his Bulls, he wagered on just about everything else.

The stories are legendary and they start young. When Jordan was in high school, he reportedly wrote a note to his prom date. The note said, “I was really happy when you gave me my honest coin money I won off the bet.”

Jordan’s betting continued at North Carolina where it was reported that then UNC assistant Roy Williams owed the Tar Heels star more than one Coke.

Jordan bet on everything from pool to putting contests.

One night in 1984, Jordan was up $25 playing pool. A young man thought Jordan was hustling his friend so he stepped in and began beating Jordan. The young man beat Jordan several games in a row leaving Jordan up $5. The young man, seeing how irritated Jordan was, decided to cash out. He asked if he could write a check and made it out to “Mike Jordan” as he was known then. The check was recently sold at an auction for $12,000.

Air Jordan Flying Casino

Former Bulls center Will Perdue recalls how Jordan would hustle his teammates in card games on the team plane. Chicago’s flights served as a flying casino with cards played in the aisle, $1 blackjack games up front, and the high rollers games in the back.

Jordan primarily played with the high rollers, but when he found out about the $1 blackjack, he had to get in.

Bulls guard John Paxson asked him why he’d want to play with a bunch of low-budget roles players. Jordan simply said, “So I can have your money in my pocket.”

If You Ain’t Cheatin’ You Ain’t Tryin’

Jordan would bet on just about anything.

One story went something like this.

The Bulls flew to Portland, and in the days before private planes, the Bulls actually had to pick up their own luggage. Jordan bets nine of his teammates that his bags would come out first. Jordan won the $100 bet, but that isn’t the whole story.

His Airness had bribed one of the baggage handlers to make sure his bags came out first. Jordan loved to win and would do just about anything to make sure he came out on top.

Perdue laughingly called Jordan the greatest cheater of all-time.

Jordan liked to wager on the Dunkin’ Donuts races held during games. What Perdue didn’t know was that the whole thing was rehearsed prior to the game. Security guards were present during the rehearsal and Jordan would get the winner from them. It took Perdue a few losses before he figured out what Jordan was doing.

How about the time Jordan cheated while playing Crazy 8s?

Yep, Jordan and his college roommate Buzz Peterson were in a Syracuse hotel playing Crazy 8s with a group that included Peterson’s mother. Jordan hides an 8 under his leg and Peterson catches him. Still, Jordan was the best man at Peterson’s wedding.

The Masters

Michael Jordan loves golf.

Combined with his love for wagers, it’s easy to believe that Jordan and his circle of friends would play for $100 a hole. There are some stories of Jordan playing for $100,000 a hole.

One of Jordan’s more famous golf stories goes like this:

Chicago hockey star Jeremy Roenick was one of Jordan’s inner circle, and the two often played golf together. There was a wager on every hole, of course. One morning, they get together and play 18 holes. Roenick gets the best of Jordan and is up a couple thousand dollars. 

The Chicago Bulls have a game that night against Cleveland, so Roenick figures Jordan will pay up and take off. Not a chance. Jordan wants to go again. Roenick fills up the cooler with cold beer and the pair play another 18 holes. Roenick wins again.

After 36 holes and who knows how many beers, Roenick says he’s going to call his bookie and put all the money he just won on Cleveland. In true Jordan fashion, he bets Roenick that the Bulls will win and he will score more than 40 points.

Jordan goes off for 52 as the Bulls beat the Cavs.

The Shrug

Remember Jordan’s shrug in the 1992 NBA Finals?

Jordan hits six 3-pointers in the first half and sets an NBA record for points scored in a half in a championship series. When he hits the final 3-pointer, he looks to the bench and shrugs. It was an iconic moment in NBA history.

For years, the shrug was thought to be Jordan’s way of saying he was amazed at his own ability.

It was not.

He had been up the entire night and early morning before the game losing at cards. The shrug was directed to the person he had lost to the previous night – Magic Johnson.


What made Michael Jordan the greatest of all-time was a willingness to bet on himself. Jordan loved to win and he truly believed he would beat anybody all the time. He believed it so much he was willing to bet on it no matter what the stakes, no matter the game.

For Jordan, there was no difference. Gambling and winning were one in the same.

About the Author

A native of Western Pennsylvania, Rick, a Generation X-er, who now lives just north of the Motor City, Detroit, Michigan. A former high school, college, and professional football player, Rick now spends his time as a high school coach and as a personal quarterback trainer. An all-state high school quarterback, he went on to become an Academic All-American at Division II Indiana University of PA. He later coached at his alma mater helping lead the program to the 1990 NCAA Division II national championship game. Rick has also served as a high school head coach and as an assistant in Pennsylvania, New York, and Michigan.

His passion for sports writing started when he was the sports editor for his high school newspaper and continued when he worked as a sportswriter for the Jamestown (New York) Post-Journal in the early 1990s. A true sports fanatic, Rick enjoys all things Pittsburgh: Steelers, Pirates, and Penguins. The Immaculate Reception, the 1979 We Are Family Pirates, and the ’91-’92 Penguins are among his favorites. After working as an educator and athletic director for several years, he again took up sports writing and has contributed to several websites and publications, including Coach & Player magazine, X & O Labs, American Football Monthly, and many others.

When not consumed with coaching, watching, thinking about, or writing about football and other seasonal sports, he finds himself working out like he was still in college and reading everything from military history to Brad Thor novels. Rick has also been chasing rock god stardom as a drummer who has played with bands that have opened for the likes of Fuel, Days of the New, and Alien Ant Farm. He continues to play with his church worship group. Most importantly, Rick is married to the love of his life, Lisa, and has two beautiful daughters.

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