Venable learns about invaluable Chicago lore from 'Dilla'

This story was excerpted from Scott Merkin’s White Sox Beat newsletter. To read the full newsletter, click here. And subscribe to get it regularly in your inbox.

GLENDALE, Ariz. -- Will Venable knew a decent amount about Chicago before taking over as White Sox manager, having worked three years for the Cubs (2018-20).

But after being picked as the next White Sox man in charge in the offseason prior to the 2025 campaign, Venable wanted to understand more about the city where he was returning to after coaching with the Rangers from 2023-24. It’s at that point where Venable unofficially met Shermann “Dilla” Thomas.

“Right when I got this job, the first thing I did was get on the Internet. Knowing I was going to have a press conference, I needed to learn about Chicago,” Venable told MLB.com. “And his videos were the first to come up. I was like ‘Oh my gosh. This guy is brilliant. He’s super cool.’

“I’m learning a bunch about Chicago. Then it was into the year and it was SoxFest [Live ‘25], Dilla showed up. I was so excited to meet him.”

Thomas is a Chicago historian, influencer and activist who has carved out quite a niche through social media. He also leads Chicago Mahogany Tours, which really is germane to this story. Thomas took Venable on a 90-minute journey on the Thursday afternoon before SoxFest Live at the end of January, an informative car tour having a little extra meaning before the start of Black History Month in February.

“Just such a brilliant guy,” Venable said. “He makes history cool. And on Black History Month, with all the history that there is, we spent a lot of time in Bronzeville. It was just amazing. I learned a ton.

“My only issue is that I don’t retain information as well as he does. So, I need to go a couple of times to really nail some of this stuff. It was a great experience and what a fun guy to be around.”

Their Bronzeville trip highlighted some of the Negro Leagues history found in that area. It also included some of the cultural gems and small businesses Thomas felt the White Sox coaches, players and staff “should lift up and visit,” as he mentioned during a recent interview with MLB.com.

Venable’s father, Max, and Venable’s family are into jazz, so they visited the Chicago homes of Louis Armstrong and Nat King Cole. Thomas took Venable to Wendell Phillips High School, where the Harlem Globetrotters started. They saw Ted “Double Duty” Radcliffe’s home and talked about Rube Foster’s heritage and legacy in Bronzeville.

There was even a trip to South Side Park’s old location, which is on Princeton and 38th Street.

“It was one of the original ballparks of the Chicago White Sox, and also where the Chicago American Giants played,” Thomas said. “This is the 100th anniversary of Black History Month, so we went by the Wabash YMCA, which is where Carter G. Woodson came up with the idea for Negro Achievement Week.”

A discussion of the White Sox ballpark’s importance to the neighborhood was also part of the excursion.

“Wentworth served as the boundary between the Irish neighborhood of Bridgeport and the Black neighborhood of what we call Bronzeville,” Thomas said. “And because of baseball, people got a free pass in between the Sox Park and De La Salle [High School].

“Kids leaving Bridgeport walking to De La Salle weren’t messed with and Blacks going to see baseball games by and large were not messed with. And in between the space, I’m sure there were some relationships. I’m sure that people broke out of societal norms and talked to each other. So, that was kind of the journey.”

The White Sox Amateur City Elite youth baseball earned high praise from Thomas, as this exceptional program deserves. Thomas also handed out plaudits for Venable, calling his desire to learn more about the city and the Black history connection “amazing for Chicago.”

“Any coach who moves to Chicago doesn’t owe us anything beyond wins,” Thomas said. “I acknowledge that, but I also believe all of us at some point in our life are going to start to think about legacy.”

Being an advocate in this area means something to Venable, thinking back to his father’s MLB career, and then ahead to the future.

“I had coaches in the big leagues when [his dad] was in the Minor Leagues that were not as good as him. However those decisions are made, I just know that he’s one of the best hitting coaches I’ve ever had, and he didn’t have an opportunity,” Venable said. “So, I’m always going to advocate for anybody with talent who deserves a shot in the Major Leagues, regardless of their background or their ethnicity.

“Going out and spending some time with Dilla was a great example of just having the freedom to do those things. Just having the bandwidth to do that during the season, it’s something I expect to have more ability to do [this season].”