“Gambling is legal and betting is legal, for what I bet,” said Michael Jordan once regarding his habits. His legacy extends far beyond the basketball court. Moreover, his off-court activities sparked fascination, from his successful ventures as an NBA team owner to his reported love of high-stakes gambling. And now, a new story regarding his latter habit has been revealed.

Recently, former NBA player and dunk sensation Nate Robinson shed new light on Jordan’s notorious gambling habits. In the recent episode of ‘All Hoops‘ podcast, the 40-year-old claimed that Jordan once questioned his failure to win a dunk contest because he had a bet riding on his performance.

“I was like man, I don’t know what to call you Mr. Jordan. Mr Air, Mr. Heirness, I was calling him everything. Mike, MJ I was like ‘Bro, you’re the reason I play basketball. You made me believe, you know what I’m saying, I want to be like Mike. I believe.’ I told him I said ‘I believe that’ and he was like ‘Man, it’s all good’. Bro like, he was like a regular dude. He was like come here you little, f—-ing like, talking like regular s–t to me. He was like ‘Why didn’t you win the dunk contest? I was betting on you’. I was like damn, my bad,” said Robinson during the podcast.

In the 90’s, Jordan’s gambling habits were as famous as his athletic prowess.  When he was younger, he used to place wagers on friendly card games. When he entered the league, he used to bet on any sporting event, especially in golf. But the habit brought many obstacles.

Jordan gained notoriety for his numerous trips to the Monte Carlo Casino during the 1992 Olympics in Monaco. He played some late-night card games with other well-known players, like Charles Barkley and Magic Johnson. One of the biggest controversies took place when gambling habits linked him to a convicted drug dealer.

A cheque for $57,000 was discovered for James ‘Slim’ Bouler from Jordan. At first, the basketball player claimed it was a loan for a driving range. But in court, Jordan testified that the money was for a gambling loss.

“I always will. I just feel that, at this particular time in my career, I have reached the pinnacle of my career. I have achieved a lot in that short amount of time if you want to call it short. But I just feel that I don’t have anything else for myself to prove,” said Jordan while trying to justify why he moved to gambling.

Now coming to Nate Robinson. He spent very little time with the Chicago Bulls but his time was memorable. Robinson made a name for himself as a fan favorite for his fearless style of play during the 2012-2013 season, averaging 13.1 points and 4.4 assists per game. His best performance for sure came in a triple overtime win against the Brooklyn Nets where he scored 34 points and was the man to carry the team through pivotal moments.

“It was unbelievable. It was for me like breathtaking like damn, like everytime I put on that jersey I felt you know Michael’s presence, that aura, that you know when being a part of the Chicago legacy. I felt that s–t and everytime I came to, I couldn’t wait to get to the gym, when I played, when I was in Chicago,” said Robinson about his stint with the Chicago Bulls.

The story Nate Robinson recently shared reflects both the influence and the mystique of Michael Jordan. It reveals that even after his showcasing elite skills, Jordan’s love of gambling left an impression on the players who looked up to him. However, this isn’t the only insight given by the Seattle native during the podcast.

Nate Robinson shares Team Jordan story

It’s a dream come true for many basketball players to wear the Jumpman logo and to be Team Jordan. And it’s not just about the shoes, it’s a position of elite status, skill, and dedication to the game. It came true for Robinson during the later stages of his career.

In the same podcast, Nate recounted his excitement at being welcomed into the Jordan family. He said, “I was like man, what I gotta do to be on Team Jordan? He was like ‘You got to keep playing and do what you do bro. We’ll get you on it’. And I was on it for my last year, when I was in the league. I was in Denver in my last couple of years. He put me on Team Jordan for like a year.”

Interestingly, being part of the Airness family was not the only thing the 3x NBA Slam Dunk champion liked. In fact, he asked them for a unique way to pay him. “I think I was in for a year or two and they sent me so many Js and I was like, ‘I don’t need no money, just send me gear bro. I just want the merch,’” said Robinson during the podcast.

Robinson has been a true Jordan enthusiast for years. During an ESPN interview, the former point guard revealed that he had approximately 150 pairs of Jordans. For fans, Nate Robinson’s experience is a reminder of how powerful the Jordan legacy is—not just as a brand, but as a symbol of excellence and inspiration.