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“I have a competition problem,Michael Jordan once said. Thanks to this one problem, MJ went on to win 6 championship titles. And we saw the Chicago Bulls‘ historic run! However, this one problem has created even more problems. Not just for MJ’s opponents but for the NBA legend himself. His gambling stories are no surprise to fans. There’s even an insane story about Jordan gambling during his college days! But nothing comes close to this one story that a former Boston Celtics player once shared. 

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The story resurfaced again. This happened the night before MJ announced that he would be returning to the NBA. And he was more competitive than ever. While enjoying a good time eating and partying with friends and fellow players, he got involved in a game of Spades with two strangers who weren’t players. And the game got quite intense. As Jordan’s partner for that game, Antoine Walker remembered, they played for a straight 36 hours.

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The two unknown men had the two NBA players almost locked. They were behind $100K and then $200K, and Jordan even brought in more money from home. “They got me and Michael stuck, $100,000. Then they got the $200,000. Then he called home, and MJ called home and got a half a million. This is all cash, too. This is a true story. All cash. And next thing you know, we got a million dollars cash,” Walker said.

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Despite that, MJ and Walker were still down $900K. That’s when Jordan’s competitive fire kicked in, and he finally managed to recover much of the money, with only $300K left to lose. “We get all the money back except like $30,000. Michael Jordan is such a competitor. He was like, I don’t want to see him with that,” he recalled on Run It Back. By this time, the Chicago Bulls legend was completely exhausted. Not to mention, he had a very important announcement to make. 

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This is almost unbelievable. But there are even wilder stories that MJ’s frenemy Charles Barkley once shared.

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Charles Barkley spoke about gambling during a golf session

It’s well known that the two former best friends often had golfing sessions together. They also had company. During his appearance on The Dan Patrick Show, Chuck shared that they did a bit of betting during golf too. Chuck himself is known for his habit of gambling. They bet against each other and other members as well. Cedric the Entertainer too mentioned it once during his appearance at All the Smoke by Matt Barnes and Stephen Jackson

The TNT analyst shared that he used to bet a hundred dollars on each hole. However, MJ’s game was different, as Chuck recalled. “Back when I would play, it was pretty much even [between Chuck and MJ]. But I tell you what, and I apologize to Michael for saying this … we’d be playing golf with certain people, and we’d be playing a couple of hundred dollars a hole. But he’d be playing some for guy for $100,000,” Barkley said.

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He shared that once, Jordan took a putt for $300,000. He never understood why Jordan placed such large bets. The answer is likely his competitive urge! There are both wins and losses in gambling. And just as mentioned before, these just fueled Jordan’s competitive fire to do better than before.

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Pritha Debroy

3,476 Articles

Pritha Debroy works with the NFL Lifestyle Desk at EssentiallySports, where she explores the league beyond the sidelines and focuses on the cultural nuances of football. Bringing a fresh perspective shaped by her background in basketball lifestyle stories and cross-sport expertise, she highlights how NFL athletes build influence off the field. A graduate of the EssentiallySports Journalistic Excellence Program, our in-house initiative that trains writers under industry experts, Pritha specializes in long-form features and player-driven stories that capture the evolving identity of today’s NFL stars. Pritha combines her passion for storytelling with a thoughtful approach to sports culture and lifestyle. With strong communication skills and an eye for detail, she brings a distinctive voice to NFL journalism, delivering engaging and insightful content that resonates with readers.

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Oajaswini S Prabhu

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