Michael McDonald - Rock & Roll Hall of Fame Singer Songwriter, The Doobie Brothers

Joel Braunold - The Perennially Perplexing Prospects of Peace in the Middle East

A self-described public policy entrepreneur, Chicagoan Joel Braunold has dedicated his life to the pursuit of peace in the Middle East. We cover the war in Iran, what constitutes success for each country involved, and the potential winners and losers depending on the outcome. Joel also discusses the challenges facing Israeli-Palestinian peace efforts, which he says have reached a collapse point. Why has peace in the region been so elusive? How do historic and religious roadblocks, proxies, and non-state actors complicate a peace deal? Joel also lays out his hopeful scenario for the future.

Michael McDonald - Rock & Roll Hall of Fame Singer Songwriter, The Doobie Brothers

A powerful and personal conversation with one of the most successful and recognizable voices in music. Michael talks about his extensive career and humble beginnings, his connections to Chicago, and recalls a wild concert fight downstate. He opens up about his relationship with his father, his battle with addiction, and despite his success - an overwhelming feeling of self doubt he struggles with even today.

Former Mayor Lori Lightfoot & Pat Brady - Politics & the Illinois Primary

Two Illinois political insiders are back to share their thoughts on the bombing campaign in Iran, the Epstein files, and the emerging wedges dividing MAGA. We examine the key Senate and House races in the Illinois primary, and a Cook County race they say could lead to a sea change in local politics. The conversation ends with insights on the midterms, and the curious questions around President Trump’s health. Plus, the hurdles facing Governor JB Pritzker if runs for president, and who they see as the potential democratic nominee in ’28.

Professor Robert Pape - The Escalation Trap of the Iran War

University of Chicago professor Robert Pape is an expert in military strategy and escalation patterns. He shares his insight into the U.S. bombing campaign in Iran, and what he would have told President Trump before launching the attacks. The professor had a warning about what’s ahead, and explains an important frustration when it comes to strategy in a war like this.

Bill Glass - Actor, 'Dr. Rick' from Progressive Insurance

The doctor is in. Born in Arlington Heights, Bill Glass has become a cultural phenomenon as 'Dr. Rick' who helps keep people from becoming their parents. Bill talks about his journey from Kansas University through the lean years performing at Second City. We surprise him with a message from his friend Eric Stonestreet, talk about his love of golf, ask if his mustache is real, and if Joe might need a Dr. Rick intervention.