Preservation Chicago's Ward Miller talks with Elliot and Paul about the challenges facing architectural preservation in the midst of the coronavirus pandemic, and 25th Ward Alderman Byron Sigcho-Lopez shares his thoughts on a proposed landmark district in the Pilsen neighborhood.

Elliot and Paul explore corruption on the ballfield and in the city council with author Bill Savage and journalist Paul Dailing.

Graffiti artist Gloria Talamantes and historian Carl Smith help Elliot and Paul understand what Chicago's built environment reveals about our shared past.

Elliot and Paul discuss the centennial of women's suffrage and its legacy with the Chicago League of Women Voters' Anne Jamieson and learn about the Parkway Community House and the Vivian G. Harsh Collection with Chicago Public Library's Beverly Cook.

Paul talks with Ward Miller, executive director of Preservation Chicago, about the nonprofit's annual list of the seven most endangered structures and spaces in Chicago.

Paul talks with Elliot about efforts the find the earliest references to Al Capone and then with John Corbett and Julia Klein about a “lost” encyclopedia of the Chicago underworld, Bullets for Dead Hoods.

Elliot and Paul talk about Chicago zine history and culture with zinesters Eric Bartholomew of Junk Drawer, Joe Mason of Chicago Gets 4 Stars, and Liz Mason of caboose and Quimby's bookstore.

Journalist Sam Cholke joins Elliot and Paul to talk about the first synthesizer, created here in Chicago, while Cultural Historian emeritus Tim Samuelson suggests that the city’s most significant musical contribution isn’t what you might think.

Button Power authors Christen Carter and Ted Hake talk with Paul and Elliot about the history of button-making in Chicago and the role these small objects play in preserving our past, while Nance Klem gets our hosts thinking about the past beneath our feet and how close study of the soil itself helps us understand our city and communities.

The Illinois Labor History Society's Larry Spivack and Alma Washington talk with Elliot and Paul about the legacy of activist Lucy Parsons and the significance of the 1886 bombing in Haymarket Square, while in the second half of the episode journalist Aimee Levitt lays out the history of the Fraternal Order of Police Lodge #7 and how its past is impacting our present.