He finished third in his class and then attended Yale University, where he played football and was in the same Residential College as future movie critic Gene Siskel.
[1] Weigel spent the first two years out of Yale working as an inner-city schoolteacher in New Haven, Connecticut.
After completing his graduate degree at Northwestern, Weigel returned to New Haven to work as a waiter.
While waiting tables, however, he ran into Yale's president, Kingman Brewster, Jr., who knew Weigel and then helped him to get a job as a reporter at the New Haven Register.
In 1975, Weigel began filing reports for WMAQ-AM and several months later became a sports anchor for WMAQ-TV.
[1] Tim enjoyed a side career of playing semi-pro Football for the Chicago Lions in the late '70s into the early '80s.