CHICAGO – For someone who grew up in the city when the group was at its peak, it’s a very interesting lesson to present to an audience that experienced it or is getting to learn about their impact.

Sherman “Dilla” Thomas’ biggest problem was finding a way to encapsulate the impact of the 1990s Chicago Bulls and Michael Jordan into 60 minutes on October 30 at the Harold Washington Library.

“It was amazingly difficult to try to pack it all in a one-hour program,” said the Chicago historian, who runs Chicago Mahogany tours, who came to fame with his TikTok lessons and now gives guided tours of historical landmarks in the city.

But Thomas was up to the task in front of the audience both in-person and online for the discussion on the Michael Jordan-led team’s legacy in Chicago. It’s multi-faceted, something that he communicated to the audience during his time at the lectern.

One of the more interesting parts of the discussion was the impact that one part of the dynasty that exists through a piece of fashion – footwear. The birth of the “Air Jordan” brand by Nike created not only something popular for fans to wear but also an industry that remains robust to this day.

“It certainly has created its own economy,” said Thomas of the Air Jordan shoes.

Even for the historian, the shoes carry significance, purchasing a number of pairs in his life, even as a reward for delivering a lesson.

“When the Chicago Bulls invite me to come speak to their players or when the Chicago White Sox invite me to take their ACE kids out on a neighborhood tour, when the check comes, I reinvest it into my business, all but whatever it costs to get one pair of shoes, and those shoes are Michael Jordan shoes,” said Thomas.

Of course, there is the physical growth that can be seen when someone drives to the United Center, with the West Loop growing significantly in the 25 years since the dynasty’s conclusion.

“A lot of that comes from (Oprah Winfrey’s) Harpo Studios and Michael Jordan winning six rings with the Chicago Bulls,” said Thomas of the West Loop impact. “We formerly used to call that place ‘Skid Row,’ the stretch of Madison from Wells to, say about, Western. It was full of SROs or single-room occupants.

“It was a place where a lot of Chicagoans wouldn’t have wanted their kids to be traveling alone. Today it’s one of the most swankiest spots in the city.”

Larry Hawley has more on Thomas’ view on the impact of the 1990s Bulls from WGN News Now in the video above.