Ep. 109: Why Libertarianism Fails? The Famous 19 Question Challenge by Jon Stewart, Answered

In this episode, Jacob Winograd takes on Jon Stewart’s infamous “19 Questions for Libertarians” from his 2011 exchange with Judge Napolitano. Stewart’s list of “gotcha” questions—about roads, firemen, safety nets, and “heartless” libertarians—once made waves online. But more than a decade later, Jacob unpacks why those same arguments still miss the mark.

From a distinctly biblical libertarian perspective, Jacob answers each question one by one, exposing the hidden assumptions behind them and showing that true compassion doesn’t come from coercion. He breaks down what liberty really means, why government isn’t the source of rights, and how biblical principles of justice, charity, and personal responsibility offer a better foundation for a free and moral society.

Full Episode Notes at BiblicalAnarchyPodcast.com

The Biblical Anarchy Podcast is part of the Christians For Liberty Network, a project of the Libertarian Christian Institute.

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