Anyone who lived through the 90s knows Michael Jordan doesn’t like to lose. He’s one of the most competitive athletes of all time, not only on the basketball court, where he’s often considered the best to ever play the game. In 2020, we truly got a sense of MJ’s competitive nature off the court as well, in the documentary miniseries The Last Dance. Michael Jordan liked to gamble, and he absolutely hated when he lost. To add to what we already know, Nelly has revealed that he once lost a substantial amount of money to the legendary basketball star.

In 2004, Nelly became a minority owner of the Charlotte Bobcats, under majority owner Robert L. Johnson. He purchased his stake in 2044, ahead of the team’s debut season. In 2010, Michael Jordan bought out the other minority owners, but kept Nelly because the basketball star thought the rapper was “funny.”

In a recent interview on the podcast 7 pm In Brooklyn With Carmelo Anthony, Nelly discussed how he lost money to Michael Jordan. In the episode, released on October 30, 2026, Nelly talked about a time he played Spades against Jordan. He recalled, “It was the same way as hoopin’, just don’t wake his a** up. You know what I’m saying? It was me and my little brother, and him and Oakley. I think we were winning the first couple of games, and we got to talkin’ sh*t.” Nelly quickly added, “And he did it in front of my woman; my woman was there. That’s what made it work; that’s why I started talkin’ sh*t.”

He’s referring to R&B singer Ashanti, whom Nelly was famously dating at the time. Though the couple split up in 2013, they later reconnected and secretly married on December 27, 2023.

“I Lost a Lot of Money That Night.”

Nelly was right. It’s exactly like when Michael Jordan is on the basketball court. You don’t want to “wake him up”, and here’s why. Nelly didn’t go into detail about how much, or even when this occurred, but he simply stated: “I lost a lot of money that night.” He also added that he looked to Ashanti, asking, “Babe, what you got in that pocket?” This fueled a round of laughter from Nelly, Anthony, and his co-hosts, Monica McNutt and Kazeem “Kaz” Famuyide.

Nelly appeared on the podcast to promote the upcoming premiere of season two of his reality show. Nelly & Ashanti: We Belong Together first premiered in 2025. Additionally, the married couple has announced their first official joint tour, scheduled for 2027. The tour was officially announced on October 21, 2026, during the couple’s appearance on Good Day New York.

The second season of Nelly & Ahanti: We Belong Together will premiere on November 19, 2026, on Peacock.

Photo by Bob Leverone/Sporting News via Getty Images

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In 2011, Taylor Swift fans got a huge surprise when Nelly joined Taylor Swift on stage in Houston. Nelly himself was surprised enough to receive the phone call, but even more surprised when he received payment. On October 28, 2026, the iconic 2000s hip-hop artist appeared on The Breakfast Club podcast and radio show to promote his new reality show, Nelly & Ashanti: We Belong Together. Aside from promoting his new show, Nelly told this bizarre story about flying from his home city, St. Louis, to join Taylor Swift on stage.

On the episode, Nelly stated, “I’ve known her for a long time. Her pops, her management. I’m gonna tell you what really threw me, right? She called me one night, just out of the blue, and said, ‘Yo, Nelly, listen, me and my friends, we made a routine to ‘Hot in Herre’ last night, and I wanna ask you a really big favor.” Nelly explained, “Now, I’m in St. Louis, and she’s in Houston. She said, ‘I got two shows in Houston tomorrow and the next day. Can you come down to Houston and just perform it? I don’t wanna disrespect you. I don’t really have a budget like that.’

He added, “Now, listen to her. She says she doesn’t really have a budget. But she said, ‘What I will do is send my plane. I’ll get your room and all of that. And we only have like $50,000.’ I said, ‘Can you put that in a McDonald’s bag?’ I said, ‘But I would’ve done it for free.'”

Nelly Joins Taylor Swift In Front of 56,000 Fans

Nelly told The Breakfast Club hosts that the money wasn’t an issue. Taylor Swift kept her word and treated Nelly and his family, while her management handed over a McDonald’s bag of cash. “The plane picked me and the kids up and flew us down to Houston because she was doing three or four nights at the baseball stadium, with 56,000 people. They had them rammed in there! We did it, and she was like, ‘Yo, three minutes, three minutes!’ Her manager, Robert Allen, comes out and tosses me a McDonald’s bag with $50,000 in cash.”

“But she was just like, ‘Yo, the jet is there whenever you’re ready.’ And she got us the presidential suite right there. I think it was the Four Seasons, right there by the stadium. Had the whole top floor. We never even saw the room. We went from the show right back to the airport, or whatever the case may be.”

Nelly joined Taylor Swift for a cover of Nelly’s 2010 hit, “Just A Dream”. It was the rapper’s biggest hit since 2005. This isn’t the only time Nelly joined Taylor Swift on stage. In March 2013, Taylor Swift brought her Red Tour to Nelly’s home city, St. Louis. Nelly joined Swift on stage at the Scottrade Center, which has since been renamed the Enterprise Center, to perform “Hey Porsche”. Nelly once again joined Taylor Swift on stage in 2015, during her 1989 World Tour stop in St. Louis, to perform Nelly’s signature hit, “Hot In Herre”.

Photo by Dilip Vishwanat/LP5/Getty Images for TAS

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