Michael Jordan‘s on-court image only tells part of the story.
The Chicago Bulls legend gambled on nearly everything. Golf rounds, card games during flights, random moments that most people wouldn’t think to bet on.
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It started in high school, with Jordan reportedly placing bets on prom dates. College did not change anything — pool tables, pickup games, you name it, Jordan bet on it.
By the time he reached the NBA, the habit was fully baked in. Even the Dunkin’ Donuts race at the United Center became a fair game.
The animated Jumbotron race features Dashing Donut, Cuppy Coffee and Biggie Bagel. Fans picked winners through game cards or, now, the Bulls app. Winners receive their prize, covered by Dunkin’, the next day as a complimentary cup of coffee.
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Jordan used to bet on it with teammates. Was free coffee the draw? No. It was about winning, and apparently, he did not play by the rules.
Perdue says Jordan cheated the system
Jordan’s gambling wasn’t hidden, and the media scrutinized him for it, painting him as someone addicted to the thrill, not just the outcome. But rigging bets on a Jumbotron race? That’s where his former Bulls teammate Will Perdue comes in.
Perdue played alongside Jordan from 1988 to 1995. In 2019, he shared a story that now sounds almost ridiculously funny.
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“I played with MJ, the ultimate cheater of all time,” Perdue said.
Turns out the Dunkin’ Donuts races were rehearsed the day before, and Jordan figured that out. He began gathering information on which character would win before placing his bets. Perdue did not catch on right away, but by the time he did, Jordan had already cleaned him up a few times.
“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. 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 added.
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That was Jordan. Winning mattered more than how he got there. He would throw teammates under the bus to gain an extra edge. He wouldn’t just stop there, though. He would back it up and run them over again.
Jordan bet on luggage at the airport
Close wins did not satisfy Jordan’s competitive fire. He wanted blowouts. That mentality bled into everything, not just basketball. Even the airport luggage claim would turn into a contest.
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Before charter flights became standard, NBA teams flew commercial. The Bulls landed in Portland once, waiting for their bags at the conveyor belt. Jordan saw an opening and bet nine teammates that his luggage would come out first. They took the bet. His bags rolled out ahead of everyone else’s. He laughed, collected their cash, and moved on.
“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,” Bill Simmons wrote in ESPN The Magazine.
It was not a large sum of money, as Simmons suggested — a few hundred dollars. On top of that, Jordan was already worth millions by then. So, the amount did not matter. There was a bet to win, and he came out on top.
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Gambling suited Jordan. But winning? It meant more. The same edge that made him unstoppable on the court made moments like that feel routine.
Related: Horace Grant recalls Michael Jordan’s bribe to win bets against him and Scottie Pippen
This story was originally published by Basketball Network on Jan 11, 2026, where it first appeared in the Off The Court section. Add Basketball Network as a Preferred Source by clicking here.