Between 1998 and 2003, Wolf largely was off Chicago's radio airwaves, although he performed occasional vacation fill-in work and had his Chet Chitchat character contribute weekly segments on Friday mornings on Kevin Matthews' show on then-ABC Radio-owned WXCD-FM between 2000 and 2001. "I believe the (Monday Night Football) hiring of Dennis Miller was the cornerstone of an ABC plan to distinguish its sports presentation as the most pseudo-intellectual in broadcasting," Wolf joked to the Chicago Sun-Times at the time the Chet Chitchat deal was signed. "The hiring of Chet Chitchat is the masterstroke that completes that plan."