A Chicagoan during his youth, Jacobson's love for the Chicago Cubs led him to become a batboy for the team in 1952 and 1953, and motivated him to his first journalism job as the sports editor for his grammar school newspaper.
He then joined the reporting staff of the Chicago American newspaper, where he was the legman for legendary columnist Jack Mabley.
[2] In 1963, Jacobson left the Chicago American to join WBBM-TV as a news writer, and was promoted to be a full-time reporter in 1968.
In March 1973, he returned to WBBM as an investigative reporter and anchor, co-anchoring the 10 p.m. news for much of the next 16 years with Bill Kurtis.
[4] In February 1988, another shouting match occurred in the middle of the newsroom between Jacobson and an assignment desk editor, regarding the previous evening's newscast.
At WFLD, Jacobson was the most popular of the station's news personalities, such as Robin Robinson, Tamron Hall, Byron Harlan, Nancy Pender and Corey McPherrin.
The basic concept revolved around Walter's rants, which usually contained either biting social commentary or attacks on great injustices around the Midwest.
He once used at least ten minutes of air time to explain how as a child he lost his baseball glove at Wrigley Field, and how it was recently found and returned to him.
In November 1993, during the key ratings sweeps period, Jacobson showed up on the news wearing a T-shirt, according to a December 19, 1993, article in the Chicago Sun-Times.
During a commentary in January 1995, Jacobson divulged the home telephone number of Illinois Supreme Court Justice James D. Heiple and urged viewers to use the phone number to tell Heiple what they thought of his ruling in the controversial Baby Richard baby custody case.
In April 2006, Jacobson announced that he would be leaving WFLD in order to retire, although his departure ultimately was the result of the station choosing not to renew his contract.
[13] During every 9pm broadcast before April 30, WFLD aired a special segment to honor Walter and his memorable contributions and accomplishments throughout his career.
In September 2013, Jacobson began working as a commentator at WLS-AM radio in Chicago, airing his "Perspective" commentaries every morning at 9:56 a.m. during John Kass' show.
[17] In a landmark case in media law, Jacobson and WBBM's owner, CBS, were found guilty by a federal jury in Chicago in November 1985 of libeling the Brown & Williamson tobacco company in a November 1981 exposé in which Jacobson accused the cigarette manufacturer of marketing cigarettes to children and teens.
[20] In May 2004, Jacobson was arrested in Chicago's Lincoln Park neighborhood and charged with driving under the influence, running a stop sign, invalid registration and obstructing traffic after he allegedly double-parked his 2004 Saab outside a Lincoln Park pizzeria and was seen by police "stumbling" out of the shop.
[21] Jacobson ultimately passed the Breathalyzer test, and the DUI charge was dropped, just four days before his induction into the Chicago Journalism Hall of Fame.
Jacobson ultimately pleaded guilty to negligent driving, obstruction of traffic and running a stop sign, and he was sentenced to four months' supervision and was fined $450.
[22] After the incident, Jacobson responded—with his Perspective commentary—on Fox News, claiming he was pulled over by an unmarked car full of people in baseball caps, not policemen.
[1] Archived 2008-10-10 at the Wayback Machine On June 18, 2008, Jacobson was arrested near his home in Chicago's Lincoln Park neighborhood for DUI charges after failing a field sobriety and Breathalyzer test.
In April 2009, Jacobson pleaded guilty and received supervision, according to Cook County records and local bloggers.
[23] In late January 1993, Jacobson needed stitches from the emergency room at Northwestern Memorial Hospital after a fall during a late-night visit to the China Club nightclub in Chicago, where he was watching the Village People perform, according to a February 8, 1993 article in the Chicago Sun-Times.
Jacobson made a cameo appearance as himself in 1990 in CBS' short-lived sitcom, Uncle Buck, which was based on the movie of the same name.
The Chicago Chapter of the National Academy of Television Arts and Sciences recognized his commentaries with Emmy Awards.
"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.