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.