It was a chilly evening in Chicago, the kind where the wind sliced through your clothes and made you wish for the comfort of a warm home. Michael Jordan had just wrapped up a charity event, where he’d spent six hours shaking hands, posing for photos, and thanking donors who had given thousands to his foundation. Usually, he enjoyed these events, but tonight, the endless socializing had drained him. The excitement of the night faded as the cold wind stung his face, and his body felt heavy with exhaustion.
Michael pulled out his phone and opened the Uber app. His driver was five minutes away. Standing outside the Palmer House Hilton, he leaned against the building, his security guard, Pete, standing nearby, scanning the area for overly eager fans.
“Car’s almost here, Pete. You can head home,” Michael said, his breath clouding in the cold air.
Pete frowned. “Are you sure, Mr. Jordan? It’s late.”
Michael nodded. “I’ll be fine. Just a quick ride to the hotel. Go home to your family.”
Reluctantly, Pete walked off, and just as Michael expected, a black Toyota Camry pulled up to the curb. He checked the license plate against the app, confirming the car was his. Without looking up, he slid into the back seat.
“Good evening,” Michael said, his attention still focused on his phone.
“The Palmer House Hilton, please,” he added.
The driver, a man with a deep, yet familiar voice, responded. “Yes, sir. Should take about 15 minutes.”
Something about the voice made Michael pause. It was almost as if he’d heard it before, like an old song on the tip of his tongue.
He looked up, catching a glimpse of the driver’s eyes in the rearview mirror. There was something sharp and observant about them, a calm intelligence that still burned brightly, even in the wear of time.
“Coach Wilkins?” Michael asked, unable to hide the shock in his voice.
The driver stiffened slightly before a small, cautious smile tugged at his lips. “Well, well. Michael Jordan in my back seat. Been a while, hasn’t it?”
Michael stared at the man in disbelief. Lenny Wilkins. The legendary coach who had once led teams to three NBA finals. The coach who had faced Michael’s Bulls in some of their toughest playoff battles. And now, here he was, at 72, driving an Uber.
“What are you doing driving an Uber, Coach?” Michael blurted, before he could stop himself.
Lenny chuckled, but it didn’t quite reach his eyes. “Life takes some funny turns. Need to pay the bills somehow.”
The car merged into late-night traffic, and Michael struggled with what to say next. This was a man whose mind had shaped championship teams, whose basketball IQ had outsmarted some of the greatest coaches in history. To see him reduced to picking up passengers for minimum wage was deeply unsettling.
“How long have you been doing this?” Michael finally asked.
“About 18 months now,” Lenny replied, glancing over at him. “Flexible hours, keeps me busy.”
Michael watched as Lenny drove with a methodical precision that reminded him of his coaching style—nothing flashy, just solid fundamentals.
“I thought you were living in Arizona after retirement,” Michael said, breaking the silence.
Lenny’s eyes stayed fixed on the road. “I was. Things changed after Betty passed. Couldn’t stand the quiet house anymore. Came back to Chicago. Always felt like home.”
Michael nodded. He remembered that Lenny’s wife had died of cancer a few years ago. “I’m sorry about Betty,” he said quietly.
Lenny gave a short, appreciative nod. “She was a wonderful woman. Best person I ever knew.”
The car fell into a comfortable silence as they passed through the glowing city lights. Michael had so many questions, but didn’t want to pry. Lenny broke the silence after a few moments.
“I’m guessing you’re wondering how a guy who coached for 30 years ends up driving an Uber,” Lenny said, his voice laced with quiet resignation.
“Only if you want to tell me,” Michael replied softly.
Lenny sighed, his voice heavy with a mix of bitterness and acceptance. “Bad investments. Trusted the wrong people. Then the divorce took most of what was left. Health insurance costs a fortune at my age, especially with my heart condition.”
Michael’s heart sank. To see a man of Lenny’s stature, known for his brilliance and integrity, struggling like this seemed so wrong.
“You don’t think the league could help you?” Michael suggested. “There must be programs for retired coaches.”
Lenny shook his head. “Asking for handouts isn’t my style. Never has been.”
They drove in silence for a few more blocks before Michael’s eyes caught a small notebook tucked in the center console.
“Still drawing up plays, Coach?” Michael asked, nodding toward the notebook.
Lenny’s face lit up for the first time since the start of the ride, his passion momentarily breaking through his reserved demeanor. “Can’t help myself. Basketball gets in your blood. I still watch every game I can. These young coaches today—rely too much on analytics. They’re missing the human element. Some things you can’t measure with numbers.”
Michael smiled, remembering the way Lenny’s teams always played with discipline and grit. They might not have had the most talent, but they made you work for every point.
As they approached the hotel, Michael couldn’t shake the feeling that something was wrong about this—Lenny’s genius being wasted like this.
“Here we are, Mr. Jordan,” Lenny announced as they pulled up to the entrance of the Palmer House Hilton.
Michael reached for his wallet. “Let me give you something extra for the ride.”
Lenny’s expression hardened. “The app handles the payment. I don’t take charity.”
“It’s not charity, Coach,” Michael insisted, holding out $200. “It’s respect.”
Lenny shook his head. “I appreciate the gesture, but no thank you. I’ve still got my pride.”
Michael reluctantly put the money away and instead handed Lenny a business card. “Let’s grab coffee sometime, Coach. I’d love to hear what you think about the current state of the game.”
Lenny hesitated before accepting the card. “I’d like that, Michael. Though, I’m not sure what an old-timer like me has to offer a legend like you.”
“More than you know, Coach,” Michael said with a smile as he stepped out of the car. “Take care of yourself, Lenny.”
“You too, Michael,” Lenny replied with a small, genuine smile.
As Michael walked into the hotel, the image of Coach Wilkins behind the wheel stayed with him. He couldn’t just let this go. Something had to change. He made a decision right then and there. Tomorrow, he would reach out again, and this time, he wouldn’t let the opportunity slip by.
It was clear: Lenny Wilkins still had a lot to offer. It was time someone noticed.
“Rookie Michael Jordan Made Me Retire From the NBA!”: George Gervin Explains Hilarious Story Behind His Retirement
George Gervin and Michael Jordan
Credits: USA Today
Michael Jordan was famously one of the most competitive players to ever take the court. Heck, there were occasions where he was so competitive with even his own teammates, that it could’ve been considered outright disrespectful.
There are countless stories of his from his championship years pushing any and every player around, whether it was to get inside their head or push them to do better. But what about a story from when he was a rookie?
Well, we have one right here for you. And suffice it to say, you’re going to want to see it.
Michael Jordan retired George Gervin with just his trash-talk
Michael Jordan came into the NBA in the 1984 draft. And from the get-go, he was one of the best in the league. And apparently, so was his confidence.
Despite being surrounded by veterans, it appears that the man wouldn’t hesitate to trash-talk anyone in practice.
And as George Gervin admitted in 2017 as per The Post Game, he had to find that out in the hardest way possible, in his first-ever practice with MJ.
“The son of a b*tch (Michael Jordan) is crazy. He played just as hard at practice as he did in the game. I’ll never forget it, I’m at practice with him one time, I’m lackadaisical going through it and stuff. I say, “Dang, young fella.” He said, “Hey, old man, go sit down over there.” I sat down. I was done. He helped me understand I was done. You’ve only got so long to be on top. I was on top for about 12 years. You only have your turn. My turn was pretty much up. I retired after that.”
While the lesson may have been a hard pill to swallow, it’s hard not to chuckle at least a little at the way the incident went down. And we don’t think that was lost on George Gervin either.
What do Michael Jordan’s former teammates think of his competitive leadership?
Michael Jordan was famous for treating his teammates pretty harshly during his hay day.
But, do they hold it against him?
Just take a look at the YouTube clip below.
Perhaps the treatment wasn’t harsher than it needed to be.
