Chicago newspaper columnist Mike Royko discusses his book "Boss: Richard J. Daley of Chicago" and its subject, former Chicago mayor Richard J. Daley.

Chicago humorist and newspaper columnist for the Chicago Daily News, the Chicago Sun-Times, and the Chicago Tribune, Mike Royko, goes over his past writings. Reflections include Royko's daily column, which covered race relations, politics, the Chicago Cubs, and life in Chicago. Together, Lois Baum and Studs Terkel read one of Royko's articles aloud.

Interviewing lawyer and alderman, Leon Despres. Depres discusses Richard Daley’s time as mayor of Chicago and political events during his terms. Content Warning: This conversation includes racially and/or culturally derogatory language and/or negative depictions of Black and Indigenous people of color, women, and LGBTQI+ individuals. Rather than remove this content, we present it in the context of twentieth-century social history to acknowledge and learn from its impact and to inspire awareness and discussion.

Dick Simpson, alderman of Chicago, discusses neighborhood governments. He describes the history, explains the uses of wards, and shows how the system can work in light of a recent election in Chicago. Studs reads an article about the recent election by Mike Royko.

Non-fiction author Carl Smith discusses his latest work which focuses on the history of Chicago. Topics covered include labor movements, specifically the Pullman strike and the 1970's case trial with the Chicago Seven.