
Dilemma Podcast
Solving the problems of what to do next with some of today's top thinkers and writers. Hosted by Jay Shapiro.
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In this video, I explore the growing clash between “America First” and “Israel First”—a fracture exposing deeper contradictions in U.S. politics and global power. As figures like Tucker Carlson, Dave Smith, Candace Owens start asking tough questions, many find themselves at the edge of a worldview built on a myth of li
I'm still waiting for a debate partner—so I've decided to start without one. In this video, I deliver my opening statement.Plus, I'm announcing a short break to focus on finishing my upcoming book about moral progress and technology.My essay "Be Careful In The Dark" is available here https://whatjaythinks.com/essays/20
Capitalist Libertarianism sells itself as the champion of freedom and personal choice—but what happens when the very systems we’ve unleashed are shaping our desires, not responding to them? In this video, I dig into the fundamental blind spots that libertarians (especially the free-market capitalist kind) tend to ignor
In this conversation, Sophie Scott-Brown, historian and political philosopher, joins me to explore how anarchism isn’t just a theory, but a way of seeing, organizing, and acting in the world. We unpack the illusion of democracy, the dangers of temporary power, and what freedom actually means through an anarchist lens.

Who's Afraid of Anarchy? The Russian Revolution, Spanish Anarchy, Punks, and Today with Ruth Kinna
In Part 2, Ruth Kinna and I trace anarchism’s turbulent path through the 20th century—from early revolutionary violence to its erasure under Lenin, the Spanish Civil War, and the Red Scare in America. As anarchism was eclipsed by state communism and crushed by authoritarian forces, its ideas never disappeared. Instead,
In this conversation, I sit down with Ruth Kinna, historian of anarchism and professor of political theory, to explore the roots of anarchist thought—from Proudhon’s challenge to property to Bakunin’s clash with Marx to Kropotkin’s vision of anarchist communism. But first, we confront the towering figure of Thomas Hobb