On Sept. 19, Emmy Award-winning historian Shermann “Dilla” Thomas led about 50 people on a two-hour bus tour through Chicago’s West Side neighborhoods, highlighting its architecture, businesses and history while sharing stories and historical context along the way.
Thomas is a historian, cultural worker and brand ambassador known for making the city’s history accessible through storytelling and social media. A lifelong South Side resident, his Chicago history videos have received more than 40 million views, and he has built a social media following of more than 300,000 people. He won a Chicago/Midwest Emmy for outstanding achievement for a magazine program for his show “You Don’t Know CHI.”
Under Thomas’s direction, the bus traveled through Austin and Lawndale, giving riders a firsthand look at Chicago’s West Side while learning about the neighborhoods and its landmarks. Thomas explained the history behind these landmarks and community spaces, while monitors on the bus displayed photos and other visuals from the past to help bring the history he discussed to life.
“If you forget everything else I say, if it has a name, it has a history. Anything you go by that has a name has a history. And so, just being curious, too, makes us more informed about the spaces that we’re in,” Thomas said.
Thomas said this just as the bus pulled up in front of BUILD (the non-profit focused on violence intervention) explaining that the organization has a coffee shop, supports small-business incubation, helps students pay for and prepare for the ACT test and teaches residents urban farming. He also explained that during harvest season, neighborhood residents can receive the produce grown there.
“So that’s what’s growing here. They teach folks in this neighborhood how to be urban farmers. Because you’ve been riding around with me now for about an hour, and what haven’t you seen? A grocery store. You have not seen one,” Thomas said.
This was one of many scenes captured during the bus tour, as Thomas pointed out BUILD and explained its role in the Austin community.
Perspective of this reporter
Going on the tour gave me a different perspective on neighborhoods I’ve spent so much time reporting on. It was a unique experience to ride through the same streets and places I’ve written about while hearing the history behind them on the West Side. I’ve talked to residents, business owners and community leaders through my reporting, but the tour helped me connect those individual stories to the bigger history. It also reminded me that there’s so much more to these neighborhoods than the stories that make the news, and I found myself looking at some of the places I regularly cover a little differently afterward.
The ride also served as a fundraiser for The Neighborhood Bridge, a nonprofit founded in 2023 to help West Side residents connect with resources and opportunities. Through partnerships with existing organizations, The Neighborhood Bridge connects residents with services such as health care, housing assistance, financial counseling, job training, computer skills and violence prevention programs.
Thomas also explained the history and significance of Austin Town Hall, pointing out its architecture and discussing what the historic building represents within the Austin community.
“This is a replica of Independence Hall in Philadelphia,” Thomas said, adding that there are two replicas of Independence Hall in Chicago.
Thomas said the other replica is located at the Chicago Union Stockyards.
“Central is called Central because it was the center of Austinville,” Thomas said.
I had heard before that Austin was once called “Austinville,” but I never knew the full story behind the name. During the tour, Thomas explained that real estate developer Henry W. Austin founded the community in 1865 after purchasing 470 acres along the Chicago and Galena Railroad to develop a suburban community. He named it Austinville after himself, and as the community grew, the name was eventually shortened to Austin.
The tour stopped at Michelle Clark High School, where Thomas explained the history of the Clark family. He described how Michelle Clark’s parents faced intense racial hostility after moving into Cicero with their family, including harassment that eventually led to their home being damaged and the family leaving the area. Thomas then explained how Michelle went on to become a pioneering Black broadcast journalist and later a White House correspondent. She and West Side Rep. George Collins were killed in a plane crash while returning to Chicago after working on a story connected to Watergate.
“So this was originally constructed as Austin Elementary School. When she passed away, they changed the name to Michelle Clark. So, I just feel like, as Westsiders and Oak Parkers, you should know that story,” Thompson said.
The tour took residents through North Lawndale, where Thomas discussed the neighborhood’s connection to the civil rights movement and Dr. Martin Luther King Jr. ‘s 1966 Chicago campaign. He pointed out the former Vice Lords’ pool hall at 3720 W. 16th St., explaining how King visited the space to connect with young Black men who were not attending his speeches.
“There’s a guy named John Tweedle. Might have heard his name before. He worked for WTTW, the photographer for the Tribune. He happened to be there the day that the Vice Lords found out that they messed up. King started whooping Vice Lord butt all across the pool hall, left and right. The Vice Lords then brought people to hear his speeches. They brought people that they so-called were at war with,” Thomas said.
Thomas said the history behind a place can change how people understand the space around them. For the passengers on the bus, familiar streets, buildings and neighborhoods became reminders that Chicago’s past is still visible in the city today.
After hearing the stories behind Chicago’s streets, buildings and neighborhoods, I am more curious about the spaces around me and want to understand how the past continues to shape spaces and events today.