In 1987, Wolf joined WFLD FOX News Chicago, where he became the morning sports anchor. While working for FOX he received three local Emmy awards. "I had never been on TV before, other than in a crowd shot during a Cubs game," Wolf told the Chicago Tribune in 1991. "But I'd been on radio and when I heard about Fox opening (August 1987), I sent the news director a tape I made. They were looking for a local guy, someone with a Chicago flavor, but with a different take on sports."