The Deep Dive podcast by Milwaukee Independent takes a closer look at the stories that matter most, uncovering the layers of complexity behind today’s pressing issues.

From groundbreaking research to critical social movements and the intersection of local and global events, the podcast goes beyond surface-level coverage. Each episode connects the dots, explores nuances, and offers fresh perspectives on the issues influencing Milwaukee and the world. With a commitment to thoughtful analysis and meaningful storytelling, Deep Dive invites listeners to engage with the deeper truths behind the headlines.

  • This episode explores how the 1942 classic “The Screwtape Letters” by C.S. Lewis offers a strikingly relevant lens for understanding the moral atmosphere of Milwaukee under Donald Trump’s second term. As detailed in the piece The Screwtape Letters: Applying what C.S. Lewis said about absolute power to Milwaukee’s moral landscape, the episode traces how Lewis’ satirical exploration of temptation, pride, and self-deception illuminates the city’s contemporary struggles with authoritarian politics, misinformation, and community fatigue. It examines how Screwtape’s strategies — sowing division, feeding anxiety, distorting truth, and exploiting complacency — resonate amid Project 2025, escalating political polarization, and the pressures placed on Milwaukee’s civic and faith communities. By connecting Lewis’ insights to present-day questions of media discernment, moral agency, and the temptations of outrage or apathy, the episode considers how an eighty-year-old work continues to speak to residents navigating corrosive power, fractured public discourse, and the need for humility and empathy in a volatile political climate.

Deep Dive is a Milwaukee Independent podcast

“Borealis” by Apple Inc.

This podcast series is available on iTunes and Soundcloud.