From around 1990 until around 1991, Wolf co-hosted "9:30," an informal talk show on WFLD-TV airing right after the station's 9 p.m. newscast. The program fizzled, however. While hosting the show, Wolf created controversy one night when he displayed a photograph of the Cuban revolutionary and leader Fidel Castro and joked, "They never did assassinate that guy, did they?" "I was just being a smart aleck, but I guess I triggered-maybe that's a bad choice of verb-some bad feelings," Wolf told the Chicago Tribune in September 1991.