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.


