Photo courtesy of Chicago Mahogany

How Shermann “Dilla” Thomas is Championing Chicago’s Neighborhoods by Shining a Light on Underappreciated History April 24, 2024

In a Nutshell

What: With a mission to preserve and disseminate the rich history of Chicago by shining a light on places and spaces on the city’s south and west sides that have helped shape American culture, Shermann “Dilla” Thomas has leveraged a robust social media presence to become one of Chicago’s most important cultural ambassadors.   
Sector: Arts and Culture  
Location: Chicago, IL 
Funding Sources: Chicago Mahogany’s work has been supported by the Greater Auburn-Gresham Development Corporation, The Chicago Community Trust, Enjoy Illinois/Illinois Office of Tourism, 360 Chicago, Chicago White Sox Charities, Cubs Charities, Bears Care, Blackhawks Foundation, and The DuSable Black History Museum and Education Center 
IFF Support: $317,00 equipment loan closed in October 2022 for the purchase of Chicago Mahogany’s tour bus; $50,000 flex loan closed in April 2023 that enabled Chicago Mahogany to preserve cash on hand while fulfilling its first merchandise order by Hudson News 
IFF Staff Lead: Brett Mueller, Director of Lending – Chicago and Northwest Indiana 

Like many Americans, Shermann “Dilla” Thomas picked up a new hobby during the pandemic. Unlike those who are no longer baking bread or trying their hand at home improvement, however, Thomas’ hobby continues to be a large part of his life and is providing once unimaginable opportunities to share his love of Chicago with the world.  

For his efforts to shine a positive light on neighborhoods that are often recognized only for their challenges, Thomas was named Chicago’s Tourism Ambassador of the Year in 2022. It’s just one of many accolades he has received as he’s transitioned from a husband and father of seven with a full-time job at ComEd who made TikTok videos about underappreciated Chicago history as a way to connect with his pre-teen daughter into a highly sought-after historian who’s meaningfully changing perceptions about Chicago and its influence on American culture.  

Thomas is doing so with a robust presence on social media, where his videos have garnered tens of millions of views (@6figga_dilla); through myriad speaking engagements at local schools, the country’s largest corporations, and everywhere in between; via a ubiquitous media presence that has included an appearance on The Today Show, stories in national newspapers like The Washington Post, and countless interviews with Chicago media; and by leading tours of historic neighborhoods on Chicago’s south and west sides on a customized bus to show participants firsthand why he believes that “everything dope about America comes from Chicago.” 

Tours are offered through Chicago Mahogany, an offshoot of the nonprofit Chicago Mahogany Foundation (CMF) that was established by Thomas in 2021 with a mission to preserve and disseminate the rich history of Chicago. Grounded in Thomas’ belief that knowing the history of a place creates respect for it, CMF offers neighborhood tours at discounted rates or free of charge to schools and nonprofits by subsidizing the cost of zigzagging the city in a massive bus that requires fuel, tire changes, and commercial insurance.  

With his encyclopedic knowledge of Chicago history and geography, a two-hour neighborhood tour with Thomas is filled with dozens of historical sites and anecdotes that change from one tour to the next as he tailors the content to each group. Questions are also highly encouraged, creating an entertaining and interactive experience. And while Thomas doesn’t shy away from Chicago history that’s more well known – like the origins of the Great Chicago Fire – his focus on neighborhood history in predominantly BIPOC communities provides a more nuanced understanding of Chicago than can be gained learning only about the city’s downtown. 

By highlighting houses where cultural icons like Louis Armstrong and Bessie Coleman once lived, public art installations like the Victory Monument that honors Black Chicagoans who fought in World War I, locations where Dr. Martin Luther King, Jr. spent time organizing during the Civil Rights Movement, blocks that demonstrate the impact of redlining, and more, Thomas offers plenty of examples of what makes Chicago a complicated yet exceptional place.   

Since October 2022, when Chicago Mahogany purchased the tour bus with the help of a $317,000 equipment loan from IFF and funding from a handful of Chicago area institutions (see the “In a Nutshell” sidebar for details), Thomas has taken more than 30,000 people on tours of neighborhoods like North Lawndale, Bronzeville, Pullman, and Roseland, among others. During this year’s Black History Month alone, Thomas led 47 tours that were a mix of ticketed rides, chartered corporate outings, and free/subsidized trips.  

“That’s 30,000 people who have probably heard at some point that, if you go to those neighborhoods, somebody is going to carjack you,” says Thomas. “Being able to take people there to connect the past to the present by lifting up the places and spaces that make those neighborhoods unique helps to change the perception. And when people say, ‘I gotta come back’ after taking a tour, that brings opportunity to those areas and helps local businesses.” 

Chicago Mahogany Tours

Chicago Mahogany currently offers public, ticketed tours of six community areas on a semi-regular basis, including Bridgeport, Bronzeville, Chatham, Englewood, North Lawndale, and Pullman/Roseland. More information about the tours and tickets are available on the Chicago Mahagony website.

Among the beneficiaries of Thomas’ tours are Go Green Community Fresh Market in Englewood, Old Fashioned Donuts in Roseland, and The Soul Food Lounge in North Lawndale. With consistent foot traffic from Thomas’ tours, these small, locally owned businesses are consistently being exposed to new customers. So much so, in fact, that the owner of The Soul Food Lounge can no longer take new reservations in the week after a tour group visit because so many participants are immediately booking tables to return to the restaurant on their own. At Old Fashioned Donuts, no employees’ hours have been cut during the typically slow summer months in the last two years because of the new business generated by Thomas’ tours.  

In addition to using the tours as a means of economic empowerment in neighborhoods that have experienced long-term disinvestment and to instill a sense of civic pride about communities on the south and west sides, Thomas is leveraging the bus to influence those with the power to help change the narrative about Chicago through action. In the past year, he’s taken an advance delegation for the upcoming Democratic National Convention (DNC) and a slew of politicians and their staffs on tours to demonstrate the impact of their policy decisions on communities outside of downtown.  

“Owning the bus has allowed me to be a defender of Chicago and to challenge folks in a way that I couldn’t when I was paying $1,300 per tour to rent a bus…[It’s] been an awesome vehicle in both manners of speaking to lift up communities.”

Owning the bus has allowed me to be a defender of Chicago and to challenge folks in a way that I couldn’t when I was paying $1,300 per tour to rent a bus,” says Thomas. “When I call a politician’s office and tell them I need to do some neighborhood tours when the DNC gets here so that folks can see their policies in action, and they tell me they don’t have the budget for that, I’m able to provide those tours on the house to make sure they happen. The bus has been an awesome vehicle in both manners of speaking to lift up communities. 

As Thomas has leaned into tours as a form of advocacy, he has also focused on laying the groundwork for Chicago Mahogany’s sustained success. To create another source of revenue for the organization, Thomas launched a merchandise line that’s sold online, on the bus, and at Hudson News locations at Chicago’s O’Hare and Midway Airports. IFF provided a $50,000 “flex loan” in April 2023 that enabled Chicago Mahogany to fulfill Hudson News’ first order while preserving cash on hand for other needs. That initial order of 5,000 t-shirts for a single store has since led to an expansion of Chicago Mahogany’s relationship with the company, which now sells the merchandise at multiple locations at each airport. 

After a whirlwind few years that also included plans for a Netflix show and daily content creation for his social media accounts and ComEd – all while managing the day-to-day demands of family life alongside his wife, Lynette – Thomas is now turning his attention to creating a permanent home base for Chicago Mahogany in his South Side neighborhood. Currently leasing the building, Chicago Mahogany is planning to purchase the facility and renovate it to serve as a content creation hub that will also be open to young people to stoke their interest in the history of the city and neighborhoods they call home.    

“My dad instilled the love of Chicago history in me, and I hope I’m passing that on,” says Thomas. “Everything dope in America either came from or was improved on by Chicago. It’s the greatest city on Earth.” 

Read about additional community changemakers in Illinois supported by IFF