Discussing Mayor Daley and nepotism in government with Alderman Dick Simpson, and author-journalist Mike Royko. Includes clips of Mayor Daley defending his appointment of Thomas P. Keane, son of Alderman Tommy E. Keane. Also includes Mike Royko reading his column from the "Chicago Daily News" July 22, 1971.

Discussing the biography, "Unrepentant Radical: An American Activist's Account of Five Turbulent Decades," with the author Sidney Lens.

Author Sidney Blumenthal discusses his book "The Permanent Campaign," touching on topics including political consultants, modern campaigning, and the election process.

Robert Caro, journalist, discusses his book, "The Power Broker: Robert Moses and the Fall of New York." Caro talks about Robert Moses and the power he had over New York for 44 years. He talks about parks, bridges, highways, and housing that Moses built as he challenged mayors, governors, and the working class. 

Rita Buscari interviews inner-city youth in Chicago in the aftermath of the 1968 riots. Several pre-teen and teenaged African American youth are featured, discussing their experiences during the Chicago riots of April 1968. Topics include: Relationships between children and adults, relationships between police and civilians, relationships between blacks and whites, and the impact that Martin Luther King Jr.

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.

Jane Kennedy (part of the group Beaver 55) went to prison for the scrambling of magnetic tapes at the Dow Chemical napalm producing plant in Midland, Michigan, and, a week later, the destruction of draft files in Indianapolis, Indiana. Both companies were profited from the Vietnam War.

Herman and Rick Kogan give a brief overview of the history of Chicago (1816-1955) by discussing their book "Yesterday's Chicago".

The early influences of his father, his time in prison, and a bomb being sent to his home are among the topics covered in Dellinger’s book, “From Yale to Jail: The Story of a Moral Dissenter”. Dellinger is best known for being one of the Chicago Eight. He recalls a time in Lincoln Park, IL when he was warned to get out of there quickly because the police were told to attack Dellinger and his group.

Discussing "Jesse Jackson, the Man, the Movement, the Myth" and interviewing the author Barbara Reynolds.