As noted above, Wolf joined WLUP in 1982. In September 1991, the Chicago Sun-Times reported that Wolf was set to join a new all-sports talk radio station (which would eventually become
WSCR) as an afternoon sports talk host. "From time to time, I get offers from stations. But I'm not going to say hello or goodbye to anybody in your (expletive) column," Wolf told the Sun-Times' Robert Feder. Ultimately, Wolf stayed at WLUP. In February 1994, Wolf ceased working as a morning sports anchor for WLUP's
Kevin Matthews to join WLUP's sister station,
WMVP, as the morning sports anchor for
Steve Dahl. "I'm not the new Garry (referring to Dahl's longtime former radio partner
Garry Meier)," Wolf joked to the Chicago Sun-Times in February 1994. "There never will be another Garry. Garry couldn't be Garry again. I'm not Steve's partner. I'm not even his senior associate. I'm merely keeping a seat warm for
Tom Thayer until he retires from the NFL." In 1996, Dahl left WMVP. Nine weeks later, on May 8, 1996, Wolf's gig as fill-in morning host at WMVP ended as well, as the station decided to go with a variety of guest hosts. Between May 1996 and 1998, Wolf largely was off Chicago's radio airwaves, although he performed occasional vacation fill-in work, most notably at
WCKG-FM. In January 1998, Wolf returned to Chicago's radio airwaves as the morning news and sports anchor for host
Jonathon Brandmeier on
WCKG-FM. "I stand on the shoulders of the giants of news broadcasting-
Edward R. Murrow,
Walter Cronkite and (Chicago newsman and past Brandmeier sidekick)
Buzz Kilman," Wolf joked to the Chicago Sun-Times in January 1998. By December 1998, Wolf's contract was not renewed at WCKG after Brandmeier brought back his old colleague, Buzz Kilman. "Radio is a game of musical chairs. I almost worked with Buzz at the Loop last year. And I've known Buzz since he was middle-aged," Wolf joked to the Chicago Sun-Times in December 1998. 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." Wolf rejoined WLUP in November 2003. "It's good to be home again at the Loop," Wolf told the Chicago Sun-Times at the time. "Anybody who considers a radio station as his home is an idiot. I'm an idiot. As for doing the news, I stand on the shoulders of giants:
Walter Cronkite,
John Chancellor, (and the frequently mocked, short-lived Chicago news anchor) Ron Hunter. I do not take this responsibility lightly. In fact, I take no responsibility at all." In December 2004—and while still on the air at WLUP—Wolf auditioned for a job working alongside
Roe Conn at
WLS (AM) radio. The pairing didn't work out, however. On March 5, 2009,
WLUP fired Wolf from his role as a morning radio sidekick, as part of a cost cutting. In May 2010,
WLS radio hired Wolf as a Saturday afternoon talk-show host, co-hosting a two-hour program with political commentator
Dan Proft. In July 2011, WLS-AM announced that starting July 18, 2011, Wolf and Proft would begin airing their show five mornings a week, replacing the weekday morning show of host
Cisco Cotto, who was fired. Wolf was let go from WLS in early 2015. == Blogging and social media ==