Tracy McGrady Shares How Michael Jordan Handed Him $20K In A Bag Of Cash After Losing A Boxing Bet

Tracy McGrady received a first-hand experience of gambling with Michael Jordan after winning a bet over a boxing match.

4 Min Read
Mandatory Credit: Fadeaway World

NBA legend Michael Jordan is primarily known for his accomplishments on the basketball court. As one of the most decorated athletes of all time, Jordan is widely regarded as the GOAT. Outside of this, however, Jordan’s vices, specifically his love for gambling, have laid the foundation for some interesting stories.

Former NBA player Tracy McGrady spoke about his experience of gambling with Michael Jordan on the “Cousins” podcast with Vince Carter. While recalling the story of placing a $20,000 bet over a boxing match between Roy Jones Jr. and Antonio Tarver in 1995, McGrady detailed how Jordan eventually paid him after he won.”

“We were at a fight, I’m sitting directly behind MJ in Oak,” McGrady began. “At this time, Roy Jones Jr. is a Jordan athlete. That is why Mike is in the building. They turned around and asked me who I had in the boxing match.”

Earlier in the podcast, Tracy McGrady revealed that Antonio Tarver was a close friend, implying that he would always pick Tarver to win. Needless to say, this laid out the groundwork for a wager.

“Mike was like, ‘Put some money on it.’.. He was like, ‘All right, whatever you want to bet.’ I said, ‘I’ll do 20. I’ll do $20,000,'” McGrady added. “I was talking out of my a–. I was nervous as hell. I got tough boy talk.”

It was clear to McGrady that both Michael Jordan and Charles Oakley would want the money immediately after the fight if they won, which was a problem since he didn’t necessarily have it on him.

“I’m praying, boy, praying to my Lord and Savior. ‘Tarver, please win this fight tonight, dog. Please, because I ain’t got 20,000 on me right now. I don’t want to deal with these dudes.’ Man, Tarver knocked that [man] out.”

With the result in Tracy McGrady’s favor, the former NBA player recalled feeling the pressure lift off his shoulders. But when the time came to collect the money, McGrady wasn’t prepared for Jordan’s reaction.

“We went to the club that night. Me, Oak, MJ, we all went to the club… He [Jordan] called me over, and I sat down. He’s like, ‘You got me, motherf—-r.’ That is what he was saying. You got me. Bro, he handed me a bag of $20,000. Cash. And I was like, ‘I’m glad I won this, because I didn’t have that $20,000 to give you. Not tonight.'”

While McGrady gained an intriguing story from his brief experience with Jordan, this incident is a clear depiction of how competitive Michael Jordan could be. Even with incredibly high stakes, the six-time champion showed virtually no hesitation.

Although his approach to gambling could be perceived as an extension of his competitive nature, this habit caused some controversy during his playing days. With reports insinuating that Michael Jordan’s first retirement was even a product of this, it can be argued that this habit proved detrimental to some extent.

For the most part,  Michael Jordan has denied claims about his retirement being influenced by gambling. However, when considering the sheer number of stories linked with him involving gambling, Jordan’s reputation may have been tarnished if he played in today’s NBA.

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Siddhant Gupta is a basketball columnist at Fadeaway World, based out of Mumbai, India. He combines firsthand playing experience with thoughtful analysis to report on the NBA's ever-evolving world. A lifelong athlete, Siddhant's perspective is rooted in years on the court, giving his work a unique edge that resonates with both casual fans and seasoned ones.Before joining Fadeaway World, he spent two formative years at Sportskeeda, where he sharpened his skills and had the opportunity to interview NBA legend Ray Allen during his time in India. A diehard Los Angeles Lakers fan since 2008, Siddhant doesn't just report on the game—he lives it. Beyond his work, he is a student of the game, constantly learning, debating, and engaging with the local and global basketball communities.
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