Cass Sunstein on Liberalism and Rights in the Age of AI
Release Date: 11/26/2025
Paul Gillingham on Why Mexico Stays Together
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for the live Conversations with Tyler recording with Craig Newmark at 92NY! Tyler calls Paul Gillingham’s new book, Mexico: A 500-Year History, the single best introduction to the country's past—and one of the best nonfiction books of 2026. Paul brings both an outsider's eye and ground-level knowledge to Mexican history, having grown up in Cork — a place he'd argue gave him an instinctive feel for fierce local autonomy and land hunger —earning his doctorate on the Mexican Revolution under Alan Knight at Oxford, and doing his fieldwork in the pueblos of Guerrero. He and Tyler...
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Harvey Mansfield on Machiavelli, Straussianism, and the Character of Liberal Democracy
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for the live Conversations with Tyler recording with Craig Newmark at 92NY! Few living scholars can claim to have shaped how we read Machiavelli as decisively as Harvey Mansfield. His new book, The Rise and Fall of Rational Control, argues that Machiavelli didn't just write about politics—he invented the intellectual machinery of the modern world, starting with the concept of "effectual truth," which Mansfield credits as the seed of modern empiricism. At 93, after 61 years of teaching at Harvard, Mansfield remains cheerfully unimpressed by most of contemporary philosophy, convinced...
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Henry Oliver on Measure for Measure, Late Bloomers, and the Smartest Writers in English
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for the Chicago CWT Listener Meetup. Henry Oliver is the preeminent literary critic for non-literary nerds. His Substack, The Common Reader, has thousands of subscribers drawn in by Henry’s conviction that great literature is where ideas "walk and talk amongst the mess of the real world" in a way no other discipline can match. Tyler, who has called Henry's book Second Act "one of the very best books written on talent," sat down with him to compare readings of Measure for Measure and range across English literature more broadly. Tyler and Henry trade rival readings of the play, debate...
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Joe Studwell on Africa, Asia, and What Development Actually Requires
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When Tyler called Joe Studwell's How Asia Works "perhaps my favorite economics book of the year" back in 2013, he wasn't alone: it became one of the most influential treatments of industrial policy ever written. Now Studwell has turned his attention to Africa with How Africa Works. Tyler calls it excellent, extremely well-researched, and essential reading, but does Studwell's optimism about the continent hold up under scrutiny? Tyler and Joe explore whether population density actually solves development, which African countries are likely to achieve stable growth, whether Africa has a...
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Andrew Ross Sorkin on Market Bubbles, Banking Rules, and the Real Lessons of 1929
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Andrew Ross Sorkin sees the crash of 1929 as a tale of excessive leverage and irrational speculation, but Tyler wonders: maybe those sky-high 1929 prices were actually justified given America's remarkable century ahead. Maybe the real problem was the "Negative Nellies" who panicked afterward rather than the speculators everyone blamed. For that matter, isn't 2008 looking less and less like a bubble with each passing year? Tyler and Andrew debate whether those 1929 stock prices were justified, what Fed and policy choices might have prevented the Depression, whether Glass-Steagall was built on...
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Diarmaid MacCulloch on Christianity, Sex, and Unsettling Settled Facts
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Tyler considers Diarmaid MacCulloch one of those rare historians whose entire body of work rewards reading. This work includes his award-winning Cranmer biography, his sweeping histories of Christianity and the Reformation, and his latest on sex and the church, which demonstrates what MacCulloch calls the historian's true vocation: unsettling settled facts to keep humanity sane. Tyler and Diarmaid explore whether monotheism correlates with monogamy, Christianity's early instinct towards egalitarianism, what the Eucharistic revolution reveals about the cathedral building boom, the role of Mary...
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Brendan Foody on Teaching AI and the Future of Knowledge Work
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At 22, Brendan Foody is both the youngest Conversations with Tyler guest ever and the youngest unicorn founder on record. His company Mercor hires the experts who train frontier AI models—from poets grading verse to economists building evaluation frameworks—and has become one of the fastest-growing startups in history. Tyler and Brendan discuss why Mercor pays poets $150 an hour, why AI labs need rubrics more than raw text, whether we should enshrine the aesthetic standards of past eras rather than current ones, how quickly models are improving at economically valuable tasks, how long...
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Conversations with Tyler 2025 Retrospective
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Help us keep the conversations going in 2026. to Conversations with Tyler today. On this special year-in-review episode, Tyler and producer Jeff Holmes look back on the past year on CWT and more, including covering the most popular and underrated episodes, why single-subject deep dives made for some of the best conversations this year, the biggest AI surprises and how LLMs changed the show's production function, what happened with the Magnus Carlsen episode, listener questions on everything from hotel selection to AI x-risk discourse, Tyler's serene acknowledgment that uncontrollable laughter...
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Gaurav Kapadia on New York City, Investing, and Contemporary Art
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Help us keep the conversations going in 2026. to Conversations with Tyler today. Gaurav Kapadia has deliberately avoided publicity throughout his career in investing, which makes this conversation a rare window into how he thinks. He now runs XN, a firm built around concentrated bets on a small number of companies with long holding periods. However, his education in judgment began much earlier, in a two-family house in Flushing that his parents converted into a four-family house. It was there where a young Gaurav served as de facto landlord, collecting rent and negotiating late payments at...
info_outlineCass Sunstein is one of the most widely cited legal scholars of all time and among the most prolific writers working today. This year alone he has five books out, including Imperfect Oracle on the strengths and limits of AI and On Liberalism: In Defense of Freedom. In his second appearance on the show, he brings his characteristic intellectual range to exploring liberalism’s present precariousness and AI's implications for law and speech.
Tyler and Cass discuss whether liberalism is self-undermining or simply vulnerable to illiberal forces, the tensions in how a liberal immigration regime would work, whether new generations of liberal thinkers are emerging, if Derek Parfit counts as a liberal, Mill's liberal wokeism, the allure of Mises' "cranky enthusiasm for freedom," whether the central claim of The Road to Serfdom holds up, how to blend indigenous rights with liberal thought, whether AIs should have First Amendment protections, the argument for establishing a right not to be manipulated, better remedies for low-grade libel, whether we should have trials run by AI, how Bob Dylan embodies liberal freedom, Cass' next book about animal rights, and more.
Read a full transcript enhanced with helpful links, or watch the full video on the new dedicated Conversations with Tyler channel.
Recorded October 10th, 2025.
This episode was made possible through the support of the John Templeton Foundation.
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