Conversations with Tyler

Cass Sunstein on Liberalism and Rights in the Age of AI

November 26, 2025

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  • Cass Sunstein believes liberalism is primarily vulnerable to external illiberal forces and inherent human tendencies toward cruelty or excessive order, rather than being self-undermining. 
  • A liberal immigration regime requires balancing the Kantian/Millian recognition of moral equivalence with practical concerns about social sustainability and the potential for illiberal forces among immigrants, suggesting lawful pathways are key. 
  • Younger liberal thinkers may currently be more prominent in the social sciences (like economics) than in traditional philosophy departments, though figures like Sendhil Mullainathan show a focus on agency that aligns with liberal thought. 
  • Bob Dylan's liberalism is fundamentally characterized by the theme of self-invention and freedom, exemplified by his refusal to remain static, as captured in the lyric "he not busy being born, is busy dying." 
  • Cass Sunstein views Bob Dylan's music, including "Like a Rolling Stone" and songs from *Blood on the Tracks*, as anthems of liberty, disconnection, and smiling at impermanence, which are core liberal themes. 
  • Cass Sunstein is currently writing a book titled *Animals Matter*, proposing a Bill of Rights for animals, a topic he previously self-silenced due to past ridicule and threats, and he is also planning a book on the principles of constructive disagreement titled *How to Disagree*. 

Segments

Liberalism’s Self-Undermining Nature
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(00:01:15)
  • Key Takeaway: Liberalism’s flourishing requires external norms of cooperation and charity that it does not inherently create or sustain against illiberal forces.
  • Summary: Liberalism is more likely to be undermined by anti-liberal forces than by self-undermining mechanisms. It does not automatically create the necessary conditions for its own perpetuation, such as norms of mutual support. These necessary societal elements can be eroded by other forces, leaving liberalism without clear resources to respond.
Illiberalism in the Human Heart
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(00:02:20)
  • Key Takeaway: The impulse toward cruelty or insistence on order exists within the human soul, providing a constant internal struggle against liberal commitments.
  • Summary: The human heart contains an inherent tendency toward illiberal traits like cruelty or an insistence on order, which occasionally triumphs over freedom. This internal struggle is illustrated by the dual nature of Orwell’s 1984, which contains both a critique of tyranny and an attraction to it. Fear and security concerns can override liberal commitments.
Immigration and Liberal Tensions
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(00:04:38)
  • Key Takeaway: Concerns about immigration’s impact on pluralism and illiberal forces are reasonable, requiring screens based on individual characteristics rather than national or religious origin.
  • Summary: While some liberals favor open immigration, others worry excessive immigration can undermine self-sustaining pluralism or introduce illiberal elements. Concerns about immigration are not always reducible to hostility, as real issues regarding cultural integration and social cohesion exist. Liberal immigration policy should favor screening based on individual characteristics over group identity.
Liberal Immigration Enforcement Paradox
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(00:07:18)
  • Key Takeaway: Liberal immigration policy must reconcile the dignity of treating all people as ends (Kantian liberalism) with the necessity of enforcing borders, which involves potentially illiberal means.
  • Summary: Enforcing immigration restrictions, including deportations, inherently involves dealing with physical human bodies, raising questions about illiberal means. Kantian liberalism mandates treating everyone as an end with dignity, which should ground policy even when aggressively preventing unlawful entry. The goal is to manage unlawful pathways with sadness rather than anger, using infrastructure and technology to minimize physical confrontation.
Lawful Pathways vs. Brutality
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(00:11:54)
  • Key Takeaway: The solution to rising right-populism driven by immigration fears lies in expanding lawful pathways for labor needs, reducing the reliance on harsh enforcement of unlawful entry.
  • Summary: The concept of ’lawful pathways,’ such as expanding H-2B visas for needed labor, is a bipartisan point of agreement that benefits both the economy and potential immigrants. Effective border control relies on infrastructure, technology, and personnel to make illegal entry difficult, minimizing the need for physical brutality in deterrence or deportation. Deportation itself is not inherently savage but serves deterrence and rule-of-law functions.
Liberal Thinkers and Generational Renewal
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(00:18:14)
  • Key Takeaway: Contemporary liberal thought is currently seeing younger standard-bearers emerge more frequently in economics than in philosophy, where the focus may have shifted away from core liberalism.
  • Summary: Many canonical liberal philosophers like Rawls and Dworkin are from an older generation, and the journal Philosophy and Public Affairs reflects this shift. Younger liberal thinkers are identifiable among economists like John List and Esser DeFlow, who emphasize freedom of choice. This suggests that the philosophical engagement with liberalism might be in a less visible phase for younger academics.
Assessing Parfit’s Liberalism
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(00:23:17)
  • Key Takeaway: While Parfit’s search for common foundations across contractarianism, utilitarianism, and Kantianism is profoundly liberal, his later anti-individualist conclusions raise illiberal concerns.
  • Summary: Parfit is considered liberal for embracing contractarianism and seeking overlapping consensus among different philosophical foundations, mirroring Rawls’ approach. However, his later focus on the self, individualism, and effective altruism is viewed as potentially illiberal and peculiar. His method of relying on intuitions about exotic cases is compared unfavorably to the empirical findings of Kahneman and Tversky.
Mises’ Enthusiasm and Hayek’s Road to Serfdom
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(00:26:41)
  • Key Takeaway: Mises is valued for his fervent, ‘cranky’ defense of freedom, while Hayek’s central thesis in The Road to Serfdom—that mild economic regulation inevitably leads to Stalinism—is deemed untrue.
  • Summary: Mises’ appeal lies in his passionate, humanistic fervor for capitalism and freedom, despite his ill-tempered style. Hayek’s core argument that incremental economic regulation leads directly to totalitarianism is rejected as factually incorrect. However, the concern that government control over private companies (like Trump’s actions) leads toward undesirable state capitalism is acknowledged as valid.
Mill, Wokeism, and Arrogance
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(00:29:38)
  • Key Takeaway: The ‘woke’ movement derives from Mill’s liberal insight on subordination (e.g., The Subjection of Women) but devolves into illiberalism through arrogant shaming and a failure to respect differing views.
  • Summary: Mill’s analysis of subordination and adaptive preferences is a legitimate liberal starting point for social critique. The illiberal turn occurs when this critique manifests as finger-wagging arrogance and constant shaming directed at others. This behavior ultimately undermines liberal commitments because it fails to show basic respect to all individuals, regardless of their perceived status.
Liberal Thinkers and Judicial Review
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(00:37:41)
  • Key Takeaway: Jeremy Waldron’s argument against judicial review, based on self-government concerns, is unconvincing because liberal democracy requires courts to protect liberal rights against democratic excesses.
  • Summary: Karl Popper is valued for his work on falsifiability and freedom of inquiry, while John Dewey is praised for his belief that the American ’experiment is not played out.’ Waldron’s opposition to judicial review is rejected because courts often protect the ’liberal’ aspect of liberal democracy when the ‘democracy’ aspect threatens fundamental rights like free speech.
AI Rights and First Amendment Limits
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(00:45:04)
  • Key Takeaway: AI itself lacks First Amendment rights; however, government regulation of AI output is constrained by the human users’ and producers’ rights to receive and generate information.
  • Summary: Objects like toasters or AI lack free speech rights, but the human interaction with AI is protected by the First Amendment, particularly against content-based restrictions on receiving information. Co-authored human-AI speech is generally protected unless it falls into established regulable categories like commercial fraud or criminal conspiracy. University policies banning AI use in student papers are likely permissible as they address plagiarism, not viewpoint suppression.
Need for Right Not to Be Manipulated
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(00:55:21)
  • Key Takeaway: Modern society requires establishing a legal ‘right not to be manipulated,’ especially in commercial contexts where trickery impedes deliberative capacities, similar to the historical development of privacy rights.
  • Summary: No current legal system explicitly recognizes a right not to be manipulated, though incipient movements exist, including a US government statement supporting this concept. This right should initially target egregious cases where people lose money or time due to hidden terms or trickery that undermines their ability to exercise deliberation. This is distinct from fraud, focusing on the mechanism of deception itself.
Libel Law Weakness and Remedies
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(00:57:46)
  • Key Takeaway: While the high bar for libel suits (requiring actual malice) correctly deters over-regulation of speech, a better remedy for negligent falsehoods would be a small monetary sum plus a mandatory correction.
  • Summary: The New York Times v. Sullivan standard protects speech by making libel suits costly, which is beneficial for public discourse. However, this leaves victims without recourse for damaging falsehoods spread through mere negligence. A proposed adjustment would allow suits for a minimal sum and a required retraction when negligence, but not actual malice, is present.
AI in Legal Trials
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(00:58:54)
  • Key Takeaway: AI running trials is conceivable but faces constitutional hurdles (Sixth Amendment right to a jury) and public aversion, as juries are meant to incorporate community moral conscience, not just accuracy.
  • Summary: AI trials are becoming thinkable, but the constitutional right to a jury trial currently supersedes technological advances in this area. Juries serve the function of bringing the community’s moral views to bear, which is accuracy-independent. Public aversion to AI in decision-making is partly based on the belief that humans possess context or moral insight that algorithms lack.
Bob Dylan’s Liberalism and Genius
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(01:08:27)
  • Key Takeaway: Bob Dylan embodies liberalism through his commitment to self-invention and freedom, exemplified by his refusal to repeat past successes and his transformation of traditional songs.
  • Summary: Dylan’s genius is evident in how he takes classic songs, like ‘Chimes of Freedom,’ and twists their meaning through musical and lyrical innovation. His core liberalism is captured by the idea that ‘he not busy being born is busy dying,’ emphasizing constant self-reinvention. His refusal to perpetually sing his hits demonstrates a commitment to freedom over commercial repetition.
Bob Dylan’s Liberalism
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(01:10:26)
  • Key Takeaway: Bob Dylan embodies liberalism through his commitment to self-invention and freedom, symbolized by his refusal to repeat songs.
  • Summary: Dylan’s liberalism is encapsulated by the line, “he not busy being born, is busy dying,” emphasizing continuous self-reinvention. His refusal to keep singing the same song demonstrates a core commitment to freedom and change. “Like a Rolling Stone” is identified as an anthem of liberty, exhilarating audiences with its theme of being unattached and unknown.
Dylan’s Song Themes
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(01:11:52)
  • Key Takeaway: Dylan’s angry songs and love songs both express facets of liberal freedom, including uninhibited expression and freedom found in disconnection.
  • Summary: Even songs initially described as ‘vomit, hatred’ like “Like a Rolling Stone” are interpreted as songs of liberty when performed, making listeners feel exhilarated. Angry songs like “Positively Fourth Street” reflect freedom in being uninhibited and disconnected. The song “You’re Gonna Make Me Lonesome When You Go” from Blood on the Tracks is cited as a liberal song of freedom and separation, smiling at impermanence.
Personal Intellectual Shifts
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(01:14:45)
  • Key Takeaway: Cass Sunstein shares his personal alignment with Dylan’s spirit of reinvention, evidenced by his enthusiastic shift toward embracing Austrian economists like Hayek.
  • Summary: Sunstein identifies with Dylan’s tendency toward reinventing oneself and not wanting to be pinned down, wishing he had a more dramatic equivalent to Dylan going electric. He expresses excitement over realizing he was previously wrong about Austrian economists like Hayek and now feels he has joined their intellectual team. This shift is viewed not as shame, but as an exciting process of becoming less wrong.
Upcoming Work on Animal Rights
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(01:15:49)
  • Key Takeaway: Sunstein is writing a new book, Animals Matter, proposing a Bill of Rights for animals, overcoming past self-censorship due to political backlash.
  • Summary: Sunstein’s next major project is a book on animal rights, Animals Matter, which he finds more engaging than his work on the Star Wars book. He previously self-silenced on animal welfare topics for 15-20 years after facing ridicule and death threats during a government job confirmation process. The book involves proposing a Bill of Rights for animals and exploring the incredible learning involved in studying creatures like octopuses and dogs.
Book on Disagreement
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(01:17:20)
  • Key Takeaway: Sunstein is developing a book, How to Disagree, focusing on formalizing principles for constructive disagreement that fosters friendship and truth rather than rage.
  • Summary: A potential book, How to Disagree, aims to clarify disagreement principles, drawing on game theorist Rapoport’s formalized rules. Key principles include characterizing opponents’ arguments accurately and gratefully, and highlighting points of agreement, especially non-obvious ones. Sunstein is concerned about avoiding the appearance of being a ‘scold’ while writing about how to disagree constructively to achieve clarity, friendship, and truth.