

Winning 6 championships isn’t everyone’s cup of tea. Keep Bill Russell’s name aside from the conversation, because the legend has 11 of them. An extra ring, maybe for his toe! But Michael Jordan? Not just six titles, but two retirements in the entire span. Now, if you keep aside the GOAT debate for once and just focus on the force and those insane dunks in the games, you’ll realize that His Airness came with a no-mercy mentality.
In fact, people who have experienced this first-hand can tell tales about how relentless the Chicago Bulls legend was. Take, former First Lady Michelle Obama’s older brother, Craig Robinson. In the 1980s, Jordan turned the Schlitz Malt Liquor Summer League into Chicago’s hottest ticket for seven straight years. Held at Chicago State University, the games pulsed with energy, packed with fans hungry for high-level showdowns. Playing for the Playboy squad, Jordan’s arrival demanded extra security, yet every entrance felt like a rock star storming his own court.
Now, Robinson and Mrs. Obama joined Matt Barnes and Stephen Jackson on the All The Smoke podcast. There, the 63-year-old Craig shared his experience against Jordan. “My first encounter in playing in the Chicago Summer League, now I held my own, and we weren’t always guarding each other, but that was five on five. Held my own. It was fine. But then, once he retired and he was coming back, he needed some guys who kind of knew the game that he could sort of quietly start working out with,” he shared.
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Switching lanes from the NBA and then coming back to the court? That required some added hours in training, so Tim Grover, MJ’s trainer, called Craig, John Rogers, and Arie Duncan. “The three of us would go do workouts with him. That’s when he cooked me, I mean cooked me,” Robinson confessed without hesitation. “It was so funny because he was very serious about what he was doing. Where you would think that somebody who is the greatest of all time would be taking it easy on some guys who are trying to help him get in shape.” That’s why he’s the greatest!

via Imago
Credit: NBA
Michelle Obama’s brother also added, “I mean, he was working on stuff and elbow right to the ribs. Okay, all right, let me be prepared next time. Elbow to the neck. And then finally, I got one on him where he fouled me and I made it, and I fell down, and he was like, ‘Craig, you okay?’ I said, ‘Yeah, appreciate.’ He’s like, ‘Then get up.'”
On January 13, 1999, with Phil Jackson’s contract expiring, Scottie Pippen and Dennis Rodman likely leaving, and an owner-induced lockout in play, Michael Jordan walked away from the NBA for the second time. He swore he was 99.9 percent certain to stay gone. Yet by summer 2001, fueled by Mario Lemieux’s comeback, he was training like a man rewriting his own prophecy. And once he returned, he made sure Craig Robinson and two others felt his wrath on the floor during training! Yes, that’s His Airness for you!
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Now, coming back to the present, Jordan’s daughter, Jasmine Jordan, revealed something exciting to Forbes. Nearly 30 years ago, Michael Jordan handpicked rising NBA stars to form Team Jordan. A team of 5 men. Despite launching women’s kicks in 1998, it wasn’t until 2011 that women’s basketball was embraced by the brand. But now, things are shifting towards the bigger picture, and that’s the change you never knew you needed.
What’s your perspective on:
Is Jasmine Jordan's bold move the game-changer women's sports have been waiting for?
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Michael Jordan’s daughter makes a big announcement for the Jordan brand
In a Forbes interview, Jasmine Jordan, the powerhouse driving Jordan Brand’s early NIL leap for women athletes, dropped a mic-worthy truth: “We stopped looking for the validation, we stopped looking for the approval. I’m going to stand here. I want to play this game because I want to. And if you watch me, good for you.” Just like WNBA stars in “Pay Us What You Owe Us” tees, she’s turning defiance into opportunity.
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Jasmine, fresh off stepping in for Michael Jordan at a NASCAR race, dropped the kind of line that makes the ground shake: “You either have to allow us to pave the way or you got to move out of our way,” she said. “[And] that’s going to continue to grow.” She sees this fire fueling women’s sports, drawing fans in, and giving athletes control of their future.
Michael Jordan never walked into a room. He owned it. From cooking Craig Robinson in secret workouts to storming the Schlitz Malt Liquor Summer League like a rock star, His Airness thrived on domination. Now, decades later, Jasmine Jordan is carrying that fire, flipping boundaries into runways for women’s sports. The legacy is alive, louder, and still rewriting the rules.
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Is Jasmine Jordan's bold move the game-changer women's sports have been waiting for?