Dilla standing in front of tour bus

Dilla's tour bus - "Everything dope about America comes from Chicago" (Photo credit: Chicago Mahogany)

Dilla outside leading tour

Dilla leads a tour with United Way in Pilsen and Little Village.

Lemar Johnson loved telling stories. Luckily for Shermann “Dilla” Thomas’ father, his son enjoyed listening.

A drive through Chicago’s neighborhoods was Lemar’s stage. From their home on 81st Street in Auburn Gresham, Lemar and his family would drive north for Bulls games at the Chicago Stadium (demolished and replaced by the United Center in 1994). Sitting in the backseat, a young Dilla would listen as his father talked about each passing neighborhood. Black entrepreneurs in Englewood. Irish stockyard and steel workers in McKinley Park. The vibrant Chinatown along Cermak. The bustling Mexican commercial corridor in Pilsen. Innovation and opportunity in the medical district. A journey around the world within a 10-mile drive.

Lemar, a Chicago police officer for more than 30 years, knew the city’s streets well – and shared his knowledge before he passed. “He had a story for every neighborhood,” Dilla said. “That’s how we bonded, and a lot of it stuck with me.”

Today, Dilla is carrying on his father’s legacy, telling Lemar’s neighborhood stories – and adding his own.

While working for a utility company, Dilla pursued his passion for history and storytelling by leading walking tours and posting videos on TikTok. In his signature candid style, Dilla’s content highlights often overlooked history, including the rich culture and contributions of historically disinvested neighborhoods on the South and West Sides of Chicago.

The urban historian gained a following and before long, launched his own tour company, Chicago Mahogany. Today, he leads tours on his own bus, from Roseland to Little Village. Dilla’s renowned tagline, “Everything dope about America comes from Chicago,” is printed in bold lettering along the side of the 50-passenger vehicle.

Dilla’s stories are rooted in pride for his city, lifting up narratives of community changemakers, which is why a partnership with United Way of Metro Chicago was meant to be. Now, the historian and United Way are teaming up to share the ways history has inspired the present by highlighting the exciting work – and tangible impact – happening in our Neighborhood Networks.

Through a series of jointly hosted tours, United Way and Dilla will be taking audiences directly to our local neighborhoods to see our work in action. And in January, Dilla will talk about Martin Luther King Jr.’s legacy in Chicago at an exclusive virtual MLK Day conversation hosted by United Way.

At United Way, we believe that community change is best led by residents and trusted neighborhood organizations. We come alongside in partnership with these local agencies as they set community goals, drive the work, and create thriving neighborhoods. It’s important to United Way that the vibrant histories and cultures of our Neighborhood Networks are maintained – and not replaced. We know we have another partner for this effort in Dilla.

“The partnership between Chicago Mahogany and United Way is not only special but important for our work together. Our stories are being erased in a lot of spaces, and history is being retold. United Way supporting organic history and storytelling is a way for these stories to live on,” Dilla said.

He also notes that it provides important inspiration for the changemakers of today – and tomorrow. “If you know what’s possible, if you know the adversities and the triumphs of what other people have experienced, it empowers you to keep working and moving forward,” he said.

Blending those stories of the past into a vision forward is what this partnership is all about. We are both committed to telling our city’s story. Because storytelling builds awareness, and awareness leads to action – and, ultimately, transformation.

Along the way, we hope we’re helping create new stories and giving Dilla more fodder, more ways to honor his father’s legacy. Following Lemar Johnson’s example, Dilla is committed to the work of telling Chicago’s stories because he recognizes the power of stories to connect us.

“I knew it would bring a circle around me,” he says of his storytelling pursuit. United Way is proud to stand in that circle.

Join United Way for an exclusive virtual Martin Luther King Jr. Day conversation with Shermann “Dilla” Thomas. RSVP for free.