In this episode, Fran Spielman interviews Craig Dellimore, now retired City Hall reporter for WBBM News Radio 780. Craig reflects on his 25-year career covering Chicago politics, sharing his experiences from growing up in Jamaica, Queens, to his time working as a copy boy at The New York Times. He also recalls his memories of significant events, such as Harold Washington's rise to mayor of Chicago and his harrowing experience during a police shooting in Harlem. Craig discusses his contributions to journalism, his pride in mentoring young reporters, and his thoughts on the changing political landscape.