Leonard arrived to WGN from Boston in 1967, and remained with the station until his retirement in 1998. Throughout most of this duration, Leonard hosted a top-rated midday radio show where he interviewed people from all walks of life: politicians, entertainers, celebrities, athletes, and others. Leonard scaled back his work schedule in 1995; he appeared on the radio station on a weekend-only basis until 1998.
Leonard was also a staunch supporter of the arts, reviewing theater productions on his website, and was also a movie reviewer for both WGN Radio and Television. Leonard succeeded the late Frazier Thomas as host of WGN-TV’s Family Classics from 1985 to 2000 when by that time, it became a series of quarterly specials. He also regularly appeared on WGN-TV’s newscasts in the role of movie and theater critic.
After retiring from WGN Radio in 1998, Leonard hardly slowed down: in addition to writing reviews of local theater productions on his website, Leonard also appeared via phone on Nick Digillo’s weekend show, where the duo would discuss movies (Digillo credited Leonard for helping him break into the radio business.)