In his first three years attending Michael Jordan’s Senior Flight School, John Rogers wouldn’t dare raise his hand when Jordan would ask who wanted to challenge him in a game of one-on-one. Instead, Rogers — the founder and CEO of Ariel Capital Management and a minority owner of the Sky — would sit back and watch his fellow campers get brutalized by His Airness.
But in 2003, the summer after Jordan retired from the Wizards, Rogers felt obligated to give it a shot. So after watching Jordan dominate 20 or so campers, he sheepishly raised his hand. Jordan called on him to be his next potential victim.
‘‘Don’t be mad at me, I’m just too good for you,’’ Jordan taunted before they started. ‘‘Do you think I just had this camp so all of y’all could just beat me?’’
Rogers almost blew the biggest game of his life, but his familiarity with Jordan’s mind games prepared him for that moment.
When Jordan was considering his second return to the NBA in 2001 after retiring from the Bulls in 1998, Rogers, a former basketball player at Princeton, was a member of an exclusive group. He, former Bears defensive end Richard Dent and Craig Robinson, Michelle Obama’s brother, were among those invited to play in pickup games at Hoops the Gym in the West Loop.
‘‘We were all great friends, so this idea that we were in this little secret club, it was just so much fun,’’ Rogers said. ‘‘And we would just pinch ourselves and say: ‘We can’t believe we’re here helping get the world’s greatest player prepared to make this secret comeback.’ ’’
Once the sneakers were laced, it was strictly business. Jordan treated every contest like Game 7 of the NBA Finals.
‘‘It was very intimidating,’’ Rogers said of Jordan’s intensity. ‘‘You didn’t want to screw up, you know? You wanted to be helpful, you wanted to have fun, but you were there to help get him prepared, and you didn’t want to make some kind of stupid mistake or rookie mistake and distract him from his mission.’’
Fast-forward to when the two met again on the court at Jordan’s camp. Rogers got off to a 2-0 lead in a game to three. Could he actually shut out the GOAT?
Of course not.
Rogers missed a layup and thought he was done for. He knew Jordan would show him no mercy.
But then MJ missed — twice — and the ball was back in Rogers’ hands. He drove left and created just enough separation where he could get a shot off untouched.
‘‘Oh, no!’’ Jordan yelled as the shot went off the glass and through the hoop.
The gym erupted in cheers. Jordan lost for what was thought to be the first time in the history of the camp.
‘‘I know he’s told people that he wanted to play me again and put me in my place and show me what it was like to play in the NBA,’’ Rogers said. ‘‘So I never went back to the camp.’’
Rogers, 62, knows his victory might have been more luck than skill. Still, it remains the highlight of a lifetime. And he wants to go out saying he’s 1-0 against Jordan.
Rogers’ playing days are long over after hip-replacement surgery, but the game remains a part of his life. He has increased his investment in the Sky several times in the last 15 years and said he thinks women’s basketball has a place in Chicago. He also said the Sky will be profitable one day.
‘‘It’s just a matter of exposure, and then eventually it’ll take hold and [we’ll see] more movement where these corporations can be held accountable for their commitments to diversity and inclusion,’’ he said. ‘‘Once they’re there, they’ll see how great the team is, and there’s no doubt it’s going to grow into a very profitable, successful enterprise.’’