The Only Kid in Chicago Who Got to Play Pickup Basketball With Michael Jordan

Aaron Watkins believed he found Michael Jordan's weakness after playing in a pickup basketball game with him when he was 14 years old. Here is the inside story on how the game went down.
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The phone rang at Aaron Watkins’s home on the south side of Chicago on a chilly night in January 1994.

“Hurry up, get down here,” Aaron’s father, Jim, said. “Mike is here.”

Watkins, 14, hopped on the bus and rode more than an hour downtown to the gym where his father was working out. What happened next, he’ll remember for the rest of his life.

He got to play basketball with Michael Jordan. 

Afterwards, he was interviewed by SportsChannel Chicago about the pickup game and offered his scouting report on how to guard Jordan. The segment resurfaced this week on Twitter and went mildly viral, thanks to young Aaron’s jab that “Michael’s weakness is his shot.” 

During his first retirement, Jordan used to work out regularly at the Athletic Club at Illinois Center with his trainer, Tim Grover. The upscale gym’s clientele was a who’s who of Chicago’s rich and famous. Ariel Investments CEO John Rogers, who was teammates at Princeton with Barack Obama’s future brother-in-law, Craig Robinson, played hoops at the gym with future Obama education secretary Arne Duncan. Chicago-born NBA players like Tim Hardaway and Kendall Gill were known to drop in on pickup games at the club’s glass-enclosed court, as were some Bears players.

Jim Watkins was also a regular. He’d seen Jordan around the gym and developed a rapport with Grover. Jordan used to call Jim “baby” and “rub his belly,” Aaron says, but Jim had never actually seen MJ on the court until that night, so he called Aaron and told him to get to the gym.

It was a Monday night. Kids were usually only allowed in the gym on Sundays but Jim was tight with the front desk employees so Aaron was able to get inside. He was the only kid in the room. Aaron knew his dad could pull the right strings to get him admitted to the gym, but he was nervous when he walked up and saw the place was packed to the gills with people trying to catch a glimpse of MJ. 

“Whenever there were no NBA players, the court was just empty,” Aaron, now 40 and living in California, says. “When I walked in, I was like, ‘Oh my god, I’m not going to be able to get in.’ It looked like Chicago Stadium. There’s glass all around the gym and there were people who were plastered against the glass to see Mike. Over the top [of the court], there’s a running track, so people were all over there.”

Aaron did get in, though, and had come prepared to play, dressed in his basketball clothes. But after watching Jordan play a few games, Jim thought he and his son should head back to the south side. 

“After like the fourth game, my dad was like, ‘Alright, son. You ready to go?’” Aaron says. “I was still excited to see Mike but I thought it was getting late so I should go home.”

Just in the nick of time, Jordan spotted Aaron and invited him to join his squad. 

“As I was walking off, Mike saw me—I was the only kid in the gym—and Mike said, ‘Hey, little man, you wanna play with me?’ I had on those snap pants and I immediately just ripped them off and hopped in the game.”

Aaron, who stood only about five feet tall at the time, was suddenly living out every Chicago kid’s dream, sharing the court with the greatest of all time. 

“I had three assists and I scored the winning basket in that game and then I played one more game with him,” Aaron says. “One assist was to MJ. I remember that one vividly. I threw it to him on the right elbow. He just did a little turnaround and hit the shot. 

“On the game-winning basket, Mike came up to set a screen on the guy that was guarding me. I had a moment of daylight. I hadn’t taken a shot all game. I didn’t even know what the score was, I was just excited to be in the game with Mike. The rest of the gym just seemed empty. I couldn’t hear anything, it didn’t seem like there were any other people there. I hit the shot and I started running down the court to hit defense and I see my dad run on the court—he was the one in the Scottie Pippen jersey in the video—he ran on the court and gave me a high five. I ran back over to Michael and Michael slapped me on the back of the head and said, ‘Play better defense next time.’”

Aaron Watkins outside the gym where he would play basketball with Michael Jordan

Aaron Watkins outside the gym where he played basketball with Michael Jordan.

Whenever Jim would see Jordan at the court, he’d call home to tell Aaron to get on the bus and come to the gym. Aaron played a few more games alongside MJ, sometimes on the same team, sometimes against him, but never played as well as in that first game. 

While Jordan was gracious enough to let a kid join his team that night in January, his pickup games at the Illinois Center were no charity exhibition. 

“Those runs did get intense,” Aaron says. 

There was one guy in particular whose college career had been derailed by injury (Aaron thinks his name was Tim) and used to go at Jordan hard during those games. 

“He was really, really good and he talked a lot of trash,” Aaron says. “He was there more regularly than Jordan. Whenever Jordan was there, [Tim] would definitely bring his A game. 

“One time, that same day [of the interview], actually, Mike was guarding him and he called a foul on Mike. Mike was like maybe six feet away. Mike grabbed the ball and threw it at him like you would throw a fastball. The guy started to charge back at Mike, but you saw in the video how many people were around—that’s the entire city of Chicago and Michael Jordan is the king of Chicago. Everybody would have jumped on him. I think he thought better of it and calmed down.”

Those runs at Illinois Center were the pinnacle of Aaron’s basketball career—he stands 5'6" these days and didn’t stand a chance of making his high school team, which featured Antoine Walker and Donovan McNabb—and he’s glad he now has video proof.

“I’ve told this story to people and it sucked because there weren’t any iPhones. I couldn’t find the video and forgot that it even existed,” Aaron says. “When I saw it again, it instantly took me back to being 14 years old. I’m just appreciative that the video surfaced so I can show it to my kid one day.”