High school baseball players learn about Negro Leagues on South Side tour ahead of Sox’s Double Duty Classic game

The Double Duty Classic game began in 2007 and showcases the history of the Negro Leagues. A group of top high school players from Chicago and the Midwest play in the game Tuesday after a tour to shore up their baseball and South Side history.

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Chicago historian Shermann “Dilla” Thomas says goodbye to player Sir Jamison Jones after Thomas’ Chicago Mahogany Bus Tour on Monday.

Chicago historian Shermann “Dilla” Thomas says goodbye to player Sir Jamison Jones after Thomas’ Chicago Mahogany Bus Tour on Monday.

Owen Ziliak/Sun-Times

On Monday afternoon, in the safety of his air-conditioned bus, Shermann “Dilla” Thomas, a local historian who runs Chicago Mahogany Tours, has his audience of 29 high school baseball players captivated.

As the bus winds its way around the South Side of the city, its first stop is the spot where Comiskey Park once stood — where the Chicago White Sox played and where Negro Leagues baseball teams played East-West All Star Games.

The high school baseball players will play in the White Sox’s annual Double Duty Classic game Tuesday evening at Guaranteed Rate Field, featuring the future of baseball and honoring its past.

But before they play, the students learned about the Negro Leagues. From 1920 through the 1930s, its teams were the only way for Black baseball players to chase their dreams.

Other tour stops included Louis Armstrong’s home, Emmett Till’s Chicago home, murals and Parkway Gardens.

Sir Jamison Jones, a senior from Blue Island who is going to Illinois State University and hopes to get drafted into Major League Baseball, got some valuable lessons from the tour.

“I learned a lot about the city that I didn’t know and stuff that I should,” Jones said. “(I didn’t) really know much before, because they don’t teach this in school.”

The Double Duty Classic has been a tradition since 2007 that brings talented high school baseball players from around the Midwest to play in Chicago. The students are part of the Amateur City Elite program, created by the Sox to revitalize interest in baseball among young Black players.

The game honors the history and legacy of the Negro Leagues. The Sox have historically highlighted Negro Leagues teams, and in 1992, they held one of the first Negro Leagues reunions and recognition ceremonies.

Top players are selected from the ACE program to play in the annual game and don nostalgic uniforms. Players and families can meet with scouts during a question-and-answer session.

Chicago historian Shermann “Dilla” Thomas speaks to local high schoolers playing in the Double Duty Classic baseball game.

Chicago historian Shermann “Dilla” Thomas speaks to local high schoolers playing in the Double Duty Classic baseball game.

Owen Ziliak/Sun-Times

Thomas wanted to show the teens that playing baseball on the South Side of Chicago comes with more than a retro jersey.

“We celebrate (former Chicago Cubs player) Ernie Banks,” Thomas told the Sun-Times. “He couldn’t live on the North Side; he had to live in Chatham, and it was his friends that played for the White Sox that showed him the ropes. Many of them learn the ropes from the Negro Leagues players that lived here.”

Thomas turned his Chicago history TikTok posts into a career — plus he’s got 1.3 million likes on the app under the name @6figga_dilla. His popular Chicago Mahogany Tours are designed to showcase the beauty, culture and history of the South Side. He took the juniors and seniors from the Double Duty Classic under his wing for the second year to teach them about Black Chicago’s history.

While in bumper-to-bumper traffic on the expressway, Thomas takes the opportunity to let the group ask him questions.

Topics vary. First is favorite food spots in Chicago, broken down by categories. Later, a student asks about Chicago’s response to George Floyd’s death in 2020. Thomas closes the tour with a promise to the young men.

“Anything is possible. I know that’s something adults say, and you say, ‘Get out of here,’” Thomas said. “You sat on my bus for two hours, and I got this bus from TikTok. Anything is possible. Except for getting on the expressway at this time of the day. Don’t do that.”

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