Michael Jordan’s legendary competitiveness is well-documented, but so is his infamous love for high-stakes gambling.
Former NBA center Brendan Haywood recently added another wild chapter to the MJ gambling lore during an appearance on 670 The Score, recalling a surreal moment from his rookie season that perfectly captured just how much money Jordan had—and how little he seemed to care about losing it.
Haywood, who entered the NBA in 2001 with the Washington Wizards, shared a story from a preseason game when the team was in Connecticut. As a rookie, he was still learning the ropes of NBA life, but nothing could have prepared him for what he witnessed in the casino that night.
“I realized right away what type of money Michael Jordan had in the preseason of my rookie year. Because we’re playing a preseason game, I think we’re in Connecticut, Mohegan Sun Casino, and I’m over there and I’m talking to Mike.”
“As I’m walking through the casino, I see Mike and Patrick Ewing—who was one of our assistant coaches. So Pat’s down like 40 grand. He’s over there sweating, he’s nervous, and he’s not having a good time. And I see Mike over there laughing and joking and smoking his cigar.”
“And I said, ‘Man, M, man, you must be killing him. I mean, how many you up?’ He said, ‘Up? Man, I’m down about 800,000.’ And I was just like, ‘Oh my God.’ And he just didn’t even—he was just laughing and joking, didn’t even care.”
“Ended up staying up playing all night long, hitting the casino for like $200,000, came on the team bus with it in his hands. So that’s when I knew how much money he really had—the difference between big bank take little bank.”
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Haywood’s jaw dropped. He couldn’t believe someone could be that relaxed while being down nearly a million dollars. But Jordan wasn’t rattled—he was laughing and living in the moment like he had just won a couple hundred bucks.
Stories like these continue to add to the mythos of Michael Jordan’s off-court persona. While his six championships and unmatched competitive fire define his basketball legacy, tales from teammates and insiders paint a picture of a man who lived life on his terms, whether on the hardwood or in a casino.
Jordan’s gambling has long been a subject of both fascination and controversy. But this story makes one thing clear—win or lose, MJ stayed true to himself, cigar in hand and always betting on his ability to come back. Even down $800K, he walked away with a smile and a fresh stack of $200K, just another night for the legend.
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