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born March 2, 1961

I met James in the late 1990s. He used to always come and attend the shows I was performing in. He’s a very nice, supportive, down-to-earth person. A old school diva. And baby, he has very expensive taste. Loves his Mercedes. When he used to come to the club he was always a big tipper, especially for the girls performing. James used to perform a little but give it up because he was serious about his teaching.

James was a school teacher for 20 plus years, teaching Kindergarten to Eighth Grade. He was a good teacher, a good role model. One of his students was Mya Regina Allen, who was in SHEBA a long time and a lot of the girls looked up to. It was hard when she got killed. But she helped catch her murderer. She stayed alive long enough in the ambulance to tell them about him, and they got him. Anyway, James helped Mya and all of his kids. He loves to give back and always believed in paying it forward. 

James got where he did by playing tennis. He was a championship-winning tennis player. This was before Serena and Venus Williams–before Black people played tennis lol. He played in high school and got a scholarship to play tennis in college. Then he did Teach for America and come here to Milwaukee in 1992. Before that he was in Memphis, Tennessee, and before that Indianapolis. Now he’s retired but taking care of a little boy he adopted whose mama asked James to take and raise because she couldn’t with the drugs.

James Simmons

Illustration by Sebastian Penn

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