Conversations with Tyler: Cass Sunstein on Liberalism and Rights in the Age of AI

Podcast: Conversations with Tyler
Host: Tyler Cowen
Guest: Cass Sunstein
Date: November 26, 2025

Episode Overview

In this episode, Tyler Cowen sits down with Cass Sunstein at Harvard Law School to discuss the current state of liberalism, its challenges from both within and without, how it interfaces with immigration policy, “wokeism,” the rise of populism, and the novel challenges AI poses to rights and legal frameworks. Drawing on Sunstein’s prolific output—including new books on liberalism, manipulation, and AI—the conversation explores the philosophical, practical, and emotional underpinnings of modern liberalism and offers insight into how it can adapt and respond to the 21st century.

Key Discussion Points & Insights

1. Liberalism’s Self-Preservation and Challenges

• Is Liberalism Self-Undermining?

  • Sunstein sees low probability of liberalism defeating itself, positing external illiberal forces and the innate human desire for order or repression as greater threats.
    • “Liberalism doesn't create the conditions for its own self-perpetuation. So it's not as if it's self undermining, but it doesn't necessarily maintain itself.” (03:12)

• Freudian Critique & Repression

  • Sunstein is agnostic on the Freudian critique that repression inevitably emerges, undermining civilization; he channels Daniel Kahneman:
    • “It's an empirical question and I don't have the evidence… Let's say the three beautiful words, I don't know.” (03:32)

2. Liberalism, Immigration, & Difficult Trade-offs

• Immigration as a Threat to Liberal Societies?

  • Sunstein acknowledges reasonable worries about immigration’s impact but resists culture- or religion-based restrictions. Advocates individualized screening and upholding human dignity.
    • “There's clearly something that's fair in those concerns.” (06:14)
  • Sunstein recounts a personal story at the border, reflecting on the fundamental moral equivalence and contingency of circumstance:
    • "There but for the grace of God go I. That was the... And that I think is a liberal thought..." (10:59)

• Enforcement and the Necessity of Force

  • Cowen presses on the “inevitable brutality” in immigration enforcement. Sunstein advocates for institutional pathways ("lawful pathways") and believes brutality is not intrinsic, but tragedy is sometimes unavoidable.
    • “Brutality isn't intrinsic to the notion of no unlawful pathways... I think there's a way of doing it that is more in sadness than in anger.” (14:46)

• Technological Optimism

  • Sunstein hopes innovations (physical and procedural) can reduce negative tradeoffs in enforcement—paralleling animal welfare advancements.
    • “As we innovate... the option of overcoming the trade off grows.” (16:23)

3. The Current State and Future of Liberal Thought

• Generational Renewal of Liberalism

  • Today's leading liberal thinkers skew older; younger economists (e.g., Esther Duflo) carry the torch, but philosophy seems less engaged.
    • “We're not seeing a flowering of engagement with liberal thought. That's for sure true.” (19:15)
  • Sunstein cites behavioral economists like Sendhil Mullainathan as doing "path breaking liberal work" on agency and freedom of choice. (19:41)

• Why Economists?

  • Philosophers “rise to prominence less regularly” and past intellectual movements (e.g., Oxford/Harvard in their heyday) may be unique products of intellectual clustering and serendipity. (22:14)

• Parfit and Liberalism

  • Sunstein sees Derek Parfit as seeking liberal synthesis across Kantianism, utilitarianism, and contractarianism; Cowen is more skeptical given Parfit’s abstractness and sometimes anti-individualist leanings.
    • “Parfit was... a very enthusiastic and committed searcher for the commonalities among three very different sets of philosophical commitments.” (23:20)

4. Liberalism, “Wokeism,” and Populism

• Populism’s European Surge

  • Cowen points to the rise of populist parties as evidence that even liberal societies must enforce limits, sometimes harshly.

• Wokeism’s Liberal Roots and Limitations

  • Sunstein traces woke ideology to Mill’s The Subjection of Women, with its critique of subordinate group status.
    • “The idea of the subjection of and then fill in the blank permeates woe. And it is a legitimate liberal insight... but it can lead to illiberalism...” (30:07)
  • Key critique: A turn towards shaming and disrespect undermines liberal commitments to mutual respect.
    • “...the woke left... has gone wrong... is a kind of arrogant... shaming of people who are deserving respect and that is ultimately going to undermine liberal commitments...” (31:45)

• Defending Woke Overreach in Response to Threats

  • Cowen hypothesizes that “impossibly strict standards” might be required to counteract rampant illiberalism; Sunstein is wary, especially where ideological cliches substitute for rigorous analysis (e.g., “the law constructs the body?”). (36:51)

5. Appreciation and Critique of Classical Liberals

• Mises vs. Hayek

  • Sunstein appreciates Mises' “cranky, ill tempered, elbows out enthusiasm for freedom.”
    • “His excitement about capitalism and what it generates for people... has a humanistic quality, notwithstanding the elbows.” (26:53)
  • Hayek’s Road to Serfdom is brilliant but overstated:
    • “The fundamental argument... isn't true... that if the government starts regulating economic matters... then we're on the road to something like Stalin or Hitler, that's not true.” (27:57)
  • Cowen: Hayek may have had a point, just with “a 70 year lag” (28:17). Sunstein agrees mild versions of Hayek's warnings are prescient, but not the extreme. (28:41)

• Popper, Dewey, and Others

  • Sunstein lauds Dewey (“Great, great, great, great…” 38:21) and offers succinct praise (or, in Popper’s case, a jab about his lack of humor) for other liberal philosophers. (37:48–39:28)

6. Liberalism and Indigenous Rights

• Sunstein admits limited knowledge; points to Christine Webb’s The Arrogant Ape for philosophical treatment of animal and indigenous rights, and Will Kymlicka for conceptual frameworks. (42:12)
• Both Cowen and Sunstein reflect on the difficulty and political inertia surrounding the blend of indigenous and liberal rights. (44:52)

7. AI, Free Speech, and Manipulation Rights

• Do AIs Have Free Speech Rights?

  • Sunstein: AIs don’t have rights, but users do.
    • “A toaster doesn’t have free speech rights. A vacuum cleaner lacks free speech rights… But there are people in the situation who have rights.” (45:15–45:55)

• Co-authorship: Human + AI Outputs

  • Human-AI collaborative works are generally First Amendment-protected, unless falling into regulable categories (fraud, libel, etc.). (49:21–52:05)
  • Regulating speech simply because of AI authorship would likely fail legally in most composed contexts.

• Open Source AI & The First Amendment

  • The ground for any regulation matters: if regulating open source code involves national security (a “massive threat”), the government may act; otherwise, protections remain robust. (53:45)

• Manipulation and Rights

  • Sunstein advocates new legal rights against manipulation, akin to the right to privacy:
    • “I think we need a right not to be manipulated. We don't have that.” (55:20)

8. Legal Innovations and Algorithmic Judging

• AI Trials & Algorithm Aversion
  • AI could run small-claims/correction trials in future, but algorithm aversion (mistrust) is still strong. Jury rights and moral deliberation stand as bulwarks. (60:59)
    • “We’re not there yet. But... Some of algorithm aversion... is based on just mistakes, but some... [is] on a belief that in some context human beings will know things that algorithms... don't.” (61:53)
  • The constitutional right to jury trial is a major legal obstacle for AI-run proceedings. (62:19)

9. Law, Literature, and Cultural Reflection

• Byatt’s Possession, Star Wars, Bewitched, and Bob Dylan
  • Sunstein’s favorite novel (Possession), formative films (Star Wars), nostalgia for Bewitched, and the liberal spirit in Bob Dylan’s music underscore how non-legal culture shapes his liberalism.
    • “Bob Dylan is a liberal and his liberalism is captured in the lyric: he not busy being born, is busy dying.” (70:31)
    • “Smiling at impermanence... is a big liberal theme, because impermanence makes things not routine and also makes for freedom.” (73:50)

Notable Quotes & Memorable Moments

• On liberalism’s fragility:

  • “In the human soul, the idea of... an insistence on order... is just there. And it occasionally triumphs.” —Cass Sunstein (02:19)

• On the tragedy of immigration policies:

  • “There's tragedy. And to recognize that tragedy is inevitable is a way of keeping an incentive to reduce the number and ferocity [of harms].” —Cass Sunstein (17:44)

• On what’s missing in current liberal discourse:

  • “We're not seeing a flowering of engagement with liberal thought. That's for sure true.” —Cass Sunstein (19:15)

• On ‘woke shaming’:

  • “One thing the woke left has gone wrong with... is a kind of arrogant... shaming of people who are deserving respect and that is ultimately going to undermine liberal commitments.” —Cass Sunstein (31:45)

• On legal rights against manipulation:

  • “I think we need a right not to be manipulated. We don't have that.” —Cass Sunstein (55:20)

• On AI and free speech:

  • “A toaster doesn’t have free speech rights... Let's say chatgpt or Grok is a communicator, but they lack free speech rights.” —Cass Sunstein (45:15)

• On the liberalism of Bob Dylan:

  • “Like a Rolling Stone... was a song of liberty... Everyone felt, you know, like they were flying.” —Cass Sunstein (72:02)

Timestamps for Key Segments

| Section | Timestamp | |-------------------------------------------------|---------------| | Introduction and Sunstein’s Latest Work | 00:04–01:12 | | Threats to Liberalism | 01:15–03:23 | | Freudian Critique and Human Nature | 03:23–04:06 | | Fertility Crisis & Liberalism | 04:06–04:22 | | Immigration: Policy and Personal Reflections | 04:38–11:21 | | Populism and Enforcement Dilemmas | 11:21–16:23 | | The Current Liberal Thinkers | 17:57–20:49 | | Parfit, Wokeism, and the Woke Critique | 23:15–32:15 | | Popper, Dewey, Margalit, Waldron, Indigenous | 37:41–44:57 | | AI and Free Speech Rights | 45:01–49:14 | | Manipulation, Law, and Future Rights | 54:32–56:48 | | Legal Weakening of Libel | 57:46–58:13 | | Algorithmic Judges & Juror Rights | 61:53–64:13 | | Possession, Star Wars, Bewitched, Bob Dylan | 64:13–74:45 | | Closing Projects and Thoughts on Disagreement | 75:44–79:09 |

Additional Highlights

• Sunstein is working on new projects—including animal rights (“Animals Matter”), a book on how to disagree (“How to Disagree”), and an ongoing interest in Star Wars and Bob Dylan.
• Sunstein’s admiration for Edna Ullman-Margalit as a greatly underappreciated modern philosopher is a recurring theme (38:38–39:28).
• Personal anecdotes—Sunstein’s story of seeing Russian asylum seekers at the US border, his jury service, being described by students as a prolific scribbler—enrich the philosophical conversation with human detail.

Final Thoughts

This is a densely packed, engaging conversation that shows Cass Sunstein as a defender of liberalism’s spirit—open-ended, ethical, self-critical—and ready to adapt to novel challenges from AI, societal fracture, and cultural change. The episode is highly recommended for listeners interested in the intersection of law, philosophy, policy, and the new dilemmas posed by technology.