Fran Spielman interviews former University of Illinois defensive lineman and current State Representative Kam Buckner. Buckner shares his insights on a variety of topics, including the importance of growing the tax base and fostering local talent in sports. He reflects on his college football career and the lessons it taught him about teamwork and diversity. The conversation also delves into Buckner's views on the challenges facing the University of Illinois' football team, the necessity of transit and infrastructure improvements, and the need for a balanced approach to taxing and funding.

Senior mayoral advisor Jason Lee discusses the various challenges Mayor Brandon Johnson's administration faces in balancing Chicago's budget. Topics include progressive revenue strategies, potential cost-cutting measures, environmental justice initiatives, and affordable housing policies. Lee also addresses the controversy around Aldermanic prerogative, the impact of pension costs, and the contentious proposals to raise the garbage collection fee and introduce video gaming at airports. Additionally, he touches on the mayor's approach to Chicago Public Schools' financial crisis, transit funding, and future development projects such as the proposed stadium for Chicago Fire at the 78.

In this heartfelt episode, Fran Spielman and Pat Hughes commemorate the life and career of legendary Cubs player Ryne Sandberg, who recently passed away from prostate cancer at 65. The episode also features a past interview with Sandberg, offering further glimpses into his philosophy and approach to the game.

Fran Spielman interviews former Illinois Governor Jim Edgar, discussing his views on legacy, his approach to public service, and significant moments from his political career. Edgar reflects on his pardon of Alderman Walter Burnett, his perspective on the death penalty, and his tenure during which he aimed to restore public confidence in state government. Edgar also opens up about his current battle with pancreatic cancer, the challenges of chemotherapy, and his outlook on life and family.

In this episode, Fran Spielman interviews Ald. Walter Burnett (27th), discussing his career highlights and the emotional farewell he received from the Chicago City Council. Burnett shares insights from his 30-year tenure, working with four Chicago mayors, and the challenges faced in political mediation and community development.

In this episode, Fran Spielman interviews David Axelrod, a veteran political consultant turned commentator. The discussion covers a wide range of topics including the struggles of Chicago Mayor Brandon Johnson, the upcoming mayoral race, and the challenges facing the Democratic Party on national and local levels. Axelrod shares his insights on key political figures such as JB Pritzker, Rahm Emanuel, and their potential presidential ambitions.

In this episode, Fran Spielman welcomes Ray Long, a recently retired investigative reporter for the Chicago Tribune with over 45 years in journalism. Long discusses his career journey, including his early days covering City Hall with Spielman, memorable stories from his stint as a reporter, and significant events like the turbulent tenure of Mayor Richard M. Daley. They also touch on Long's moderate upbringing, his transition from aspiring radio personality to print journalism, and his experience writing a book on political heavyweight Mike Madigan without direct interviews.

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.