Fran Spielman reunites with longtime City Hall rival and friend John Kass to discuss his latest health crisis and rehabilitation after what she describes as his third stroke. He reviews earlier medical emergencies including a stroke during open-heart surgery and a near-fatal diabetes episode, and reflects on how smoking, weight, stress, and conflict at the Chicago Tribune may have contributed to his decline. The conversation also covers Chicago politics, crime, the decline of legacy media, and Kass’s staunch support for Donald Trump.

Fran Spielman interviews retiring Chicago Inspector General Deborah Witzburg, who explains why she chose not to seek a second term, arguing watchdog credibility requires independence and that new legislation strengthening OIG protections made it the right time to pass the baton; she plans to remain in public service but won’t disclose her next role yet.

Fran Spielman interviews Steve Mahr, Chicago’s newly appointed acting Chief Financial Officer, who shares his background in public service and public finance investment banking. They discuss Chicago’s recent budget stalemates, the rejection of Mayor Brandon Johnson’s corporate head tax, and warnings of a possible $160 million midyear shortfall, as well as the city’s decision to split the advanced pension payment due to delayed Cook County property taxes.