When your basketball roots trace back to the hardwood battlegrounds of Chicago, there’s little or perhaps no room for mediocrity. The city where street courts and summer leagues aren’t just proving grounds, they’re rites of passage to reach the top. For Craig Robinson, former Ivy League standout and brother to Michelle Obama, that upbringing laid a foundation built not just on talent but on tradition and toughness that was aided by big names that even led him to contribute to the biggest name in the basketball world.

And, while he went on to receive awards at Princeton, become a respected college coach, and even work in the NBA front office, Robinson never lost sight of the important events that took place before he gained national notice. His recent appearance on Gil’s Arena gave people a unique, unfiltered look into the pickup culture that shaped him. It was a story not just about legacy, but also about survival by learning how to keep up with the pros before you even got eligible for even getting a driving license, and this could act as a huge message for the current and upcoming generation if they want to reach the top level.

As a teenager, Robinson found himself thrust into the elite crucible of Chicago’s summer leagues, where experience didn’t earn you time on the bench—it earned you pressure. “I was 15, 16 years old,” he recalled. “I would run down the court, run to the corner and hope they didn’t pass me the ball.” But instead of being pushed to the side, veterans like Mo Cheeks, Mickey Johnson, and most importantly, Tony Parker’s father, helped him. “They would run plays for me to have to do something,” Robinson said those runs were a key part of his growth as a basketball player. He was driven by the fear of failing and the pressure of being surrounded by the top names in the game of that time helped him edge over the difficulties.

And then there’s the part about the GOAT Michael Jordan, of course. Years after those summer league games, Robinson’s basketball path came full circle. He talked about how he was part of MJ’s secret comeback group on The School of Greatness Podcast. This was during Jordan’s post-baseball comeback in 1995. “He wanted some guys to work out with who could play enough, but weren’t like gorillas,” Robinson said. Tim Grover, the trainer, chose Arne Duncan, John Rogers, and Robinson to be in the exclusive group. They were all skilled, trusted sparring partners who could push the GOAT without overwhelming him. “We’d play two-on-two or three-on-three. Then five-on-five. It was a safe game. He never wanted to lose.”

The strangest and best part about sports is that it evolves with time. However, all the masterminds have their unique take on that. Craig Robinson has also commented on this, reflecting the essence of the sports.

Chicago Hoops, Then and Now: A Changing Culture Revealed by Craig Robinson

Craig Robinson’s thoughts also provide us a bigger picture of how basketball culture has changed over the years, or in some ways, regressed. Robinson sees a different level of intensity and a different code when he watches his own teenage sons and other talents play in the AAU. “It’s just like non-aggression pact,” he said. “I’ll let you shoot if you let me shoot. Phantom defense. It’s really nice, but not how we used to ball.”

That difference says a lot about how Chicago basketball used to be: not just competitive, but also combative in the greatest way where the young players were confrontational. It was about putting in a lot of effort to get where you wanted to go, and in Robinson’s case, that meant working with future NBA fathers like Tony Parker Sr. and Sunny Parker. Today’s game is more sportsmanlike, but it doesn’t have that same edge.

Still, Robinson doesn’t diminish this generation. “They’re good kids. They’re not savages like we used to be,” he chuckled. It’s a bittersweet admission from a man who once helped Michael Jordan get his edge back: basketball’s soul may be changing, but its roots are still strong as the game has evolved in its unique ways.

Craig Robinson learned something new from each time period. Every moment, from standing in awe as a youngster among pros to assisting the greatest of all time get ready for his second act, each moment shaped the executive, mentor, and father he is today. In basketball, as in life, the game evolves, but the grit in the sport remains constant.