Terry Hake joins John Dempsey to share the incredible true story of how he went undercover in Operation Greylord, exposing widespread corruption in Chicago’s court system. As a young assistant state’s attorney turned FBI operative, Hake helped convict dozens of crooked judges, attorneys, and officials, at great personal cost. This gripping conversation explores the emotional toll, the courtroom drama, and the lasting impact of one of America’s biggest corruption busts.

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Wall Street veteran George Lucaci joins John Dempsey to break down the economic volatility of Trump’s second term. From the president’s tariff threats and attacks on Fed Chair Jerome Powell to the long-term dangers of rising national debt, Lucaci explains what’s driving the markets—and what could derail them. It’s a candid, wide-ranging conversation about interest rates, inflation, and whether trickle-down economics was ever more than a myth.

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Legendary Chicago political reporter Andy Shaw joins John Dempsey for a candid conversation about Trump’s rise, the fractured state of American media, and the political future of figures like Brandon Johnson and JB Pritzker. From insider stories at ABC7 to his thoughts on housing, polarization, and what Democrats get wrong, Shaw pulls no punches. Plus: a personal story about marijuana at the 2004 DNC and life in retirement between Michigan and Mexico.

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Political scientist David McLennan joins John Dempsey to unpack why Donald Trump’s base remains loyal—even when his policies hurt them. They discuss emotional politics, the recent Medicaid-cutting “Big Beautiful Bill,” and the future of the GOP after Trump. Plus: Why Senator Thom Tillis bowed out and what it means for 2026.

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In this episode of What Does It Mean?, John Dempsey talks with author, actor, and corporate coach Paul Quinn about the power of asking for what you want in life. Quinn shares insights from his new book, The Big Ask, including why so many people fear asking and how to overcome that resistance with courage and clarity. Packed with real-life stories and practical tools, this conversation offers a roadmap to unlocking personal and professional breakthroughs.

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John Dempsey sits down with former congressman and presidential candidate Joe Walsh for an unflinching conversation about his political transformation from Tea Party firebrand to outspoken critic of Donald Trump. Walsh discusses the personal and professional cost of turning against the MAGA movement, his disillusionment with the Republican Party, and his frustrations with a Democratic Party that he believes has lost touch with working-class voters.

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In this episode of What Does It Mean?, retired NASA astronaut and planetary scientist Tom Jones joins John Dempsey to discuss the James Webb Space Telescope’s detection of possible biosignatures on the distant exoplanet K2-18b. Jones explains what the discovery of certain gases could mean for the search for extraterrestrial life and why it's such a groundbreaking moment in astronomy. He also shares insights from his new book Space Shuttle Stories and reflects on the legacy of human spaceflight.

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John Dempsey stopped by John Howell's podcast "As I Was Saying" to relive Rory McIlroy’s dramatic victory at the 2025 Masters. The two discuss McIlroy’s emotional journey, his long-awaited Grand Slam, and the tournament’s unforgettable moments. They also weigh in on the state of professional golf, the culture at Augusta, and the future of the game.

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John Dempsey speaks with Ted Rossman, Senior Industry Analyst at Bankrate.com, about how rising tariffs and inflation are affecting American consumers. Rossman explains why current market volatility feels different from past crises and offers practical advice for managing personal finances during uncertain times. From credit card debt to side hustles, this episode is packed with insights to help listeners stay financially resilient.

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John Dempsey is joined by veteran Chicago radio host John Howell for an unfiltered conversation about Donald Trump’s return to power, the economic shock of new tariffs, and the fractured state of American media. Howell reflects on the dangers of a presidency unbound by internal checks and explains why January 6th was a turning point in his own career. From Trump’s fixation on Greenland to the future of the Democratic Party, this episode covers the chaos, consequences, and context behind today’s headlines.

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