Awards
Jacobson has received several prestigious awards for his commentary, anchoring, and reporting skills. The Chicago Chapter of the National Academy of Television Arts and Sciences recognized his commentaries with Emmy Awards. In fact, Jacobson won Chicago Emmy awards for 10 straight years—1974 until 1983—for his commentaries. In 1985, a Washington Journalism Review poll named Jacobson best local anchor in the United States. In 1988, he received his fifth Peter Lisagor Award, his third for "best commentary." During the 1980s, the duPont-Columbia judges honored him twice for his work at WBBM-TV -- once for his commentaries and once for best local election coverage in the United States. Jacobson's notable WBBM-TV specials and programs included the Emmy Award-winning Walter Jacobson's Journal: China and Studebaker: Less Than They Promised, which received a Peabody Award.
Jacobson's most infamous news story occurred at WBBM-TV in February 1991, just two years before he switched to WFLD-TV. Wearing a fake beard, Jacobson dressed up as a homeless person and lived on the streets of Chicago for 48 hours, visiting Lower Wacker Drive, Clarendon Park, the corner of Halsted and Addison Streets, and the corner across the street from the Lincoln Park townhouse of his former anchor partner, Bill Kurtis. He had a hidden camera and recorded what he experienced in a series he dubbed "Mean Street Diary." Critics at the city's newspapers roundly mocked Jacobson for the stunt. "It was amazing that he was able to transform an issue of such inherent sorrow and desperation into something that could yield so many moments of great, if unintended, humor," wrote Rick Kogan in the Chicago Tribune.
In January 1995 at WFLD, Jacobson reprised his role as a homeless man for the hidden cameras.
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