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If you do a search on social media about Chicago’s history, particularly TikTok, you will most likely discover one of Dilla Thomas’ quick and engaging videos covering everything from Chicago icons and neighborhoods to special Chicago traditions like dying the river green on St. Patrick’s Day or calling dibs on parking spaces with chairs. Thomas originally crafted the videos to teach his seven kids about their hometown. Today, his audience is much larger, as has garnered a following of 150k followers across his social media platforms for his famous 60-second videos.

By Rosalind Cummings-Yeates

If there’s a phrase that sums up both the greatness and the challenges of Chicago, it’s the signature statement of Chicago urban historian, Shermann “Dilla” Thomas; “Everything dope about America comes from Chicago.” That sentence covers the dazzling fact that Chicago is responsible for gifting the world skyscrapers, softball, brownies, house music, jungle gyms, Mortal Kombat, improv comedy, kidney transplants, blood banks, vacuum cleaners, soap operas, car radios, mobile phones, zippers, Twinkies, Chicken Vesuvio, Ferris wheels, the film industry, 8-hour work days, caramels, dishwashers, gospel music, TV remote controls, open-heart surgery and the first gay rights group. That’s just a summary. The list is endless, yet the city’s impact and significance rarely get recognized.

But what does Chicago mostly get acknowledgment for? The answer prompted Thomas to create his statement on X (Twitter) in response to a dismissive but very widely believed comment; “Nothing comes from Chicago but deep dish and gang bangers..." "I've always felt like I needed to defend my city.” 

Statistically, Chicago shouldn’t need defending. In the most recent reports by Forbes and Statista of cities with the most violent crime, Chicago didn’t even rank in the top 10. And for the seventh year in a row, Chicago was voted the Best Big City in the U.S. by Conde Nast Traveler. Clearly, there’s a disconnect between the perception of Chicago and the reality of living in the city. Thomas has been on a mission to bridge the gap and change the narrative about the city with viral videos, TV appearances, speaking engagements, and his own tour company showcasing Chicago’s history.

Thomas grew up during the mid-80s in the Auburn Gresham neighborhood on the South Side with four brothers, a sister, and a godsister. He describes his childhood as idyllic — he had a two-parent household and he rode bikes, played Little League baseball, attended swim meets, and visited museums, White Sox and Bulls games, and Great America. A defining feature of his youth was that he was a “PK” or police officer’s kid. His father, the late Lemar Thomas, was a pivotal member of the Chicago police force, serving for 32 years and working as part of the bodyguard detail for the city’s first Black mayor, Harold Washington. He was also a member of the African American Police Force League, which helped create more diversity in the Chicago police force by suing the city about the cultural bias embedded in the police entrance exam.  

“As a PK, you overdo everything for acceptance from your friends. You want to be cool. If the group decides to leave the block, then you’re the one leading them off the block as far as possible,” he said. “I didn’t want to be looked at as an extension of the police.” To develop a “cool” reputation, Thomas attempted to hang out with a group of friends who were frequently getting into trouble, but it didn’t work out. His father’s moral influence and his own sharp logic worked against him. “I tried to run with the rough crowd for about two years,” he said. “I asked too many questions; ‘do we really want to jump him? Are we sure that’s the right guy? Couldn’t we find a better way?’ After a while, they asked me to stop coming around.” By that point, Thomas realized his dad was the kind of cop who made a difference in the community. “I had the type of father who would check to see if everything was legal if a neighbor got pulled over. When someone was scared, when someone got jumped, they didn’t call 911, they knocked on our door. It drove my mom crazy,” Thomas said.

His father was a role model who fought for justice and fair treatment for citizens at a high cost. “At one point he was fired and had to sue his way back on the force. I was more afraid of disappointing my dad than the gang bangers. All they could do was beat me up. I had his name, and I didn’t want to disrespect it. I learned to be cool in my own way.”Inadvertently, one way Thomas managed to create his own path was through his father’s requirement that all his children had to know specific streets and directions if they wanted to go somewhere in his car. “My dad wanted us to know all the logistics if we wanted to use his car. I couldn’t just say I was going to Stoney Island Ave., I had to know it was 1600 East,” he said. Thomas quickly became an expert in Chicago geography. He could navigate the city’s grid system and side streets better than most city-savvy adults and family and friends started to call him whenever they were lost. Soon, Thomas started wondering about the names of different streets and he researched their history in encyclopedias. (This was before Google.)

Fast forward a few years, Thomas started pouring all of that learning into his role as Chicago’s urban historian, enthralling video viewers with tales of the city’s history and culture, helping audiences discover the real Chicago on national platforms like the “Today Show,” NBC’s “First Look” and the “Kelly Clarkson Show” and presenting Chicago history lessons everywhere from Northwestern University to Microsoft.


After viewers kept asking if the historic sites in his videos were still around, Thomas decided to start Chicago Mahogany Tours in 2021 to show people the history in person. Passengers can hop aboard his state-of-the-art tour bus and take two-hour tours of historic Chicago neighborhoods like Bronzeville, Englewood, Pilsen, Bridgeport, and North Lawndale. He’s even developing a Chicago show for Netflix.

Despite all the attention and accolades, Thomas is most proud of his family. After marrying the love of his life Lynette, Thomas bought a house five blocks away from where he grew up. He and Lynette juggle taking their seven kids to school and activities between tours, work, and speaking engagements. He consciously made the choice to stay in the south side community he grew up in. “Four of the people I grew up with are cops because they saw my dad in his uniform, bringing people McDonald’s. Every neighborhood needs good role models,” he explained.

The children of Auburn Gresham don’t just have a good role model, they have a Chicago historian, a local celebrity, and an advocate. Thomas doesn’t just teach people about Chicago, he has lived through every aspect of the city, both good and bad. When asked what makes Chicago so great, Thomas summed it up very neatly. “Chicago offers the same things and more than New York and LA in a smaller setting. We have world-class cuisine, museums, and culture at a lower cost. We’re the only major city with a free and accessible shoreline that runs the length of the city. That’s 26 miles of lakefront, there’s nothing doper than that.”

It wasn’t long before he accumulated extensive knowledge of Chicago’s geography and history while he was still in high school. Thomas’ training as a future urban historian had just begun. After graduating and attending Eastern Illinois University, where he regularly defended Chicago against the perceptions of clueless suburban kids, Thomas took a summer job this time exploring Chicago’s landscape. He had no idea that a few years later, another job would expose him to even deeper levels of Chicago. “One of my fraternity brothers was a meter supervisor for ComEd and they were hiring,” he said. “It’s a union job, with a decent retirement plan and your day ends between 3 pm – 5 pm because you can’t read meters at night,” he added of the job’s appeal. Thomas figured he was just taking a stable job, but he was really unlocking the last layer of his Chicago history education as he would learn about what happened with the white flight from the city by speaking to retirees who possess "all the history."

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