Chicago historian Shermann “Dilla” Thomas launched his Youtube series, “You Don’t Know CHI,” In November 2024. It was initially a digital passion project that began as a series of short neighborhood histories. In less than a year, the show was picked up by FOX 32, where it now airs weekly. The show also recently received a 2025 Chicago/Midwest Emmy Award for “Outstanding Achievement for Magazine Program – Single Program/Series.”
The Auburn Gresham native has long admired the city’s chart-topping stories. “I grew up during the [Michael] Jordan era,” Thomas, 44, told The TRiiBE. “I was here when [baseball Hall of Famer] Frank Thomas first got signed. We had Bo Jackson, so Chicago was popping. When something’s popping, you’re curious about it.”
Winning an Emmy is no easy feat. Usually networks submit the works of creators, but in Thomas’s case, he submitted his own after sifting through what he describes as“hundreds” of categories. He also paid a submission fee. Voters from the National Academy of Television, Arts and Sciences view the content and select finalists and then a winner.
When asked if he thought he had a chance of winning, Thomas was quick with a “Hell no.”
“So right now, the show ‘You Don’t Know Chi’ airs on Fox 32, but we submitted it when it was on YouTube,” Thomas said. “So I’m going against, you know, WTTW and ABC, and these are major networks, so they’re not gonna give me an Emmy off of a YouTube show.”
The father of seven was sitting at the Emmy ceremony with his wife and partners from Chicago production company Digife when the group learned of their win. Wearing his signature Jordans, and an all-white White Sox hat, Thomas held back tears as he walked towards the stage to accept his award.
“I cried later, yeah, but I’m like, ‘don’t cry on the stage,’” Thomas said. “I was literally at a loss for words.”
In the beginning stages of the show, Thomas explained he was in talks with other big networks, but they simply couldn’t see eye-to-eye when it came to ownership and ultimately creative control.
“I felt a lot of vindication,” he said. “ Because one network didn’t let me keep my name. Like, man, we could have worked this out, you know what I’m saying? But I knew [the series] was a good thing, so I felt that vindication.”
Winning the Emmy was more than personal vindication, it’s validation that his platform elevates the voices, histories, and traditions of Chicago’s Black neighborhoods to a wider audience. While self taught, Thomas attributes his knowledge to a love of reading. He also credits the oral history that he learned just from talking to people as a major source.
“What I do is I go to those spaces, and I believe in partnerships,” he told The TRiiBE. “I let them teach me, correct me.“So the finished product always represents that neighborhood that I’m touring, because I’ve gotten a lot of information from that neighborhood.”
During 2020’s pandemic, Thomas started making TikTok videos, teaching his followers fun facts about Chicago. Thomas now has over 120,000 followers on the platform, with his videos gaining traction nationwide.
In 2021, Thomas started his Chicago Mahogany Tours company bringing the city’s Black history to life by guiding visitors through neighborhoods such as Bronzeville, Englewood, and his own Auburn Gresham.
“It’s a ground-up approach to the history of Chicago,” Thomas told The TRiiBE. “Landmarks, hidden gems, and a big part of it also is pointing out the small businesses in these neighborhoods to encourage –you know – local shopping. So it’s a good time. It’s a two hour tour, we cover most neighborhoods except downtown.”
Winning an Emmy, building a TikTok following, and leading bus tours are all part of a larger mission for Thomas: the idea that someone should be preserving the stories of Chicago’s Black communities before they’re lost. Every video, every neighborhood tour, and every conversation he documents is a way to capture history that often doesn’t make it into textbooks or mainstream media.
Thomas also plans to put his pen to work by writing a series of books about Black Chicagoans who have influenced history. He also wants to create a book that lists the 100 Black Chicagoans who are currently making history. It’s important to document these things, he said.
“I just seen Holy Angels Catholic Church get knocked down in Bronzeville with my own two eyes,” he said. “While the wrecking ball was hitting the building and opening the wall, I could see the books and pictures and other things that were left behind.”
The church was a historical landmark. For Thomas, whoever tore the building down simply didn’t think to preserve whatever historical archives, paintings or literature the building had inside.
“So if that’s how people are getting now, more of us got to really be into preserving our stories and our history,” he said. “ I kind of just feel like it’s my duty.”
