What Does It Mean? with John Dempsey cover art

What Does It Mean? with John Dempsey

What Does It Mean? with John Dempsey

Written by: John Dempsey
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About this listen

 John Dempsey brings in experts and newsmakers for curious conversations exploring the stories shaping our world and lives

Hosted on Acast. See acast.com/privacy for more information.

News Sidequest Politics & Government
Episodes
  • Inside Operation Greylord: The Undercover Mission That Shook Cook County

    Inside Operation Greylord: The Undercover Mission That Shook Cook County
    Sep 14 2025
    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.

    Hosted on Acast. See acast.com/privacy for more information.
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    44 mins
  • Tariffs, Rates, and Reckoning: George Lucaci on the Trump Economy

    Tariffs, Rates, and Reckoning: George Lucaci on the Trump Economy
    Aug 1 2025
    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.

    Hosted on Acast. See acast.com/privacy for more information.
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    30 mins
  • Andy Shaw on Trump, Media, and the Future of Politics

    Andy Shaw on Trump, Media, and the Future of Politics
    Jul 14 2025
    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.

    Hosted on Acast. See acast.com/privacy for more information.
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    1 hr
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