Howard Shapiro, the chairman of Weigel Broadcasting, died on Thursday from complications of pneumonia. He was 86.

“A larger-than-life figure in Chicago business and broadcasting for decades, Howard guided Weigel Broadcasting from a struggling single UHF television station in Chicago to a company with more than ten stations in three markets as well as involvement in two national broadcast networks,” the company said in a statement.

Weigel Broadcasting owns and operates stations in Chicago, Milwaukee and South Bend, IN.

“Howard had a very gruff exterior, but he was a real softie inside,” Neal Sabin, Weigel Broadcasting’s president of content, told Time Out Chicago’s Robert Feder. “He really cared about people — he just didn’t want you to know it. I’m honored to have spent so much time with him.”