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Conversations with Tyler
Conversations with Tyler•November 26, 2025

Cass Sunstein on Liberalism and Rights in the Age of AI

A wide-ranging conversation with legal scholar Cass Sunstein explores liberalism, AI, immigration, indigenous rights, and Bob Dylan, revealing Sunstein's nuanced perspectives on freedom, manipulation, and the evolving challenges of liberal thought.
Immigration
Tech Policy & Ethics
Government Surveillance & Privacy
Tyler Cowen
Danny Kahneman
Cass Sunstein
John Rawls
Friedrich Hayek

Summary Sections

  • Podcast Summary
  • Speakers
  • Key Takeaways
  • Statistics & Facts
  • Compelling StoriesPremium
  • Thought-Provoking QuotesPremium
  • Strategies & FrameworksPremium
  • Similar StrategiesPlus
  • Additional ContextPremium
  • Key Takeaways TablePlus
  • Critical AnalysisPlus
  • Books & Articles MentionedPlus
  • Products, Tools & Software MentionedPlus
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Podcast Summary

In this engaging episode of Conversations with Tyler, renowned legal scholar Cass Sunstein discusses his latest works on liberalism, AI, and manipulation while exploring the challenges facing liberal democracy today. (01:19) The conversation delves deep into whether liberalism is self-undermining or simply vulnerable to illiberal forces, with Sunstein arguing that liberalism "doesn't create the conditions for its own self perpetuation" but isn't inherently self-destructive. (01:44) Tyler Cowen and Sunstein examine complex topics ranging from immigration policy and the rise of populism to AI's First Amendment implications and Bob Dylan's embodiment of liberal freedom. (1:13:50)

  • Core themes include the tensions between liberal ideals and practical governance, the relationship between individual freedom and collective security, and how emerging technologies like AI challenge traditional liberal frameworks.

Speakers

Tyler Cowen

Tyler Cowen is an economist at George Mason University and co-founder of the Marginal Revolution blog. He hosts the popular Conversations with Tyler podcast, where he engages leading thinkers across disciplines in wide-ranging intellectual discussions.

Cass Sunstein

Cass Sunstein is one of the most widely cited legal scholars of all time and among the most prolific writers working today. (00:34) This year alone he has five books published, including "On Liberalism: In Defense of Freedom," "Imperfect Oracle" on AI's strengths and limits, and works on manipulation and climate justice. He has served in government roles including at the Department of Homeland Security under the Biden administration, focusing on regulatory policy and resilience.

Key Takeaways

Liberalism Faces Internal and External Threats

Sunstein identifies that liberalism's primary vulnerability isn't self-destruction but rather its inability to create conditions for self-perpetuation. (01:44) The challenge comes from "something illiberal in the human heart" - an attraction to order, control, and sometimes cruelty that can override liberal commitments. (02:29) This insight suggests that maintaining liberal democracy requires constant vigilance and active cultivation of liberal norms, rather than assuming they will naturally persist.

Immigration Policy Must Balance Liberal Values with Practical Enforcement

The discussion reveals the tension between liberal ideals of human dignity and the practical necessity of border enforcement. Sunstein advocates for "lawful pathways" that expand legal immigration while maintaining effective deterrence of illegal entry. (12:03) His experience at the southern border, where he encountered Russian asylum seekers, reinforced his belief that immigration policy should be grounded in recognition of "moral equivalence of everyone on the planet" while still being "appropriately aggressive" in enforcement. (11:01)

Technology Can Reduce Moral Trade-offs in Policy

Drawing parallels between animal welfare and immigration enforcement, Sunstein argues that innovation can make difficult moral trade-offs less painful. (17:04) Better technology at borders - walls, sensors, and personnel - can reduce the need for "brutality" in immigration enforcement, just as meat alternatives reduce animal suffering. This technological optimism suggests that apparent conflicts between humanitarian concerns and policy enforcement may be temporary problems solvable through innovation.

AI Deserves First Amendment Protection Through Human Rights

While AI systems themselves don't have free speech rights, Sunstein argues that government restrictions on AI communication violate the First Amendment rights of human users and creators. (45:15) People have rights to receive information, and content-based restrictions on AI interactions would be presumptively invalid. This framework suggests that AI regulation must be carefully crafted to avoid infringing on fundamental human rights while addressing legitimate concerns about AI-generated content.

A Right Against Manipulation Should Be Legally Recognized

Sunstein proposes establishing a legal right not to be manipulated, similar to how privacy rights developed in the early 20th century. (55:24) This would address situations where people are tricked into decisions without using their reflective capacities, particularly in commercial contexts with hidden terms or deceptive practices. Such a right would focus on "egregious cases where people are losing money or time without getting adequate clarity on what's happening to them," providing legal recourse beyond current fraud protections. (56:13)

Statistics & Facts

  1. Cass Sunstein has five books published in 2025 alone, making him among the most prolific academic writers currently active. (00:55) The books include works on liberalism, AI, manipulation, climate justice, and algorithmic harm, with another on separation of powers coming in February.
  2. There are three distinct walls at the US southern border - one built during the Trump administration, one during the Biden administration, and one during the Obama administration. (13:20) Border officials told Sunstein that walls alone are insufficient and require three components: infrastructure, technology, and personnel.
  3. Many people overstay visas in "great numbers" rather than crossing borders illegally, representing a significant portion of unauthorized immigration. (15:31) This statistic highlights the complexity of immigration enforcement beyond just border security.

Compelling Stories

Available with a Premium subscription

Thought-Provoking Quotes

Available with a Premium subscription

Strategies & Frameworks

Available with a Premium subscription

Similar Strategies

Available with a Plus subscription

Additional Context

Available with a Premium subscription

Key Takeaways Table

Available with a Plus subscription

Critical Analysis

Available with a Plus subscription

Books & Articles Mentioned

Available with a Plus subscription

Products, Tools & Software Mentioned

Available with a Plus subscription

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