Conversations with Tyler Cass Sunstein on Liberalism and Rights in the Age of AI
Cass Sunstein, a leading legal scholar and author, captivates with insights on liberalism's challenges in the age of AI. He discusses the vulnerability of liberalism to illiberal forces and the risks posed by human nature. Sunstein dives into immigration, advocating for humane policies while acknowledging integration concerns. He explores the implications of AI on speech rights and proposes a legal right against manipulation. The conversation surprisingly links Bob Dylan to themes of freedom and self-invention, all while anticipating Sunstein’s next projects on animal rights.
01:19:46
Liberalism Needs External Support
- Liberalism is unlikely to self-destruct but can fail to sustain the social norms that support it.
- Illiberal tendencies in human nature and fear can override liberal commitments without active defense.
Border Encounter That Humanized Policy
- Cass Sunstein describes meeting exhausted Russian migrants at the southern border and seeing gratitude in a tiny exchange.
- He used that moment to invoke 'There but for the grace of God go I' as a liberal grounding for humane immigration policy.
Design Practical Immigration Pathways
- Prioritize lawful pathways like work visas to reduce illegal immigration pressures.
- Combine infrastructure, technology, and personnel to deter unlawful entry without brutality.
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Intro
00:00 • 1min
Is liberalism self‑undermining?
01:15 • 57sec
Human impulses that threaten liberalism
02:12 • 1min
Fertility concerns and liberalism's future
03:32 • 1min
Immigration: threats and reasonable concerns
04:38 • 1min
Screening immigrants by individual traits
05:50 • 1min
How to enforce immigration humanely
07:18 • 5min
Lawful pathways and border infrastructure
11:54 • 4min
Tradeoffs, innovation, and reducing brutality
15:26 • 3min
Is liberalism intellectually replenished?
17:57 • 4min
Parfit, utilitarianism, and liberalism
21:57 • 5min
Admiration for Mises's zeal for freedom
26:42 • 1min
Limits of Hayek's Road to Serfdom claim
27:58 • 2min
How Mill fueled woke impulses
29:40 • 5min
Woke excesses and useful critiques
35:00 • 3min
Views on Popper, Dewey, Ullman‑Margalit
37:46 • 2min
Waldron on judicial review: praise and qualms
39:29 • 2min
Indigenous rights and liberalism resources
41:54 • 3min
Do AIs have First Amendment rights?
45:00 • 4min
Co‑authored AI outputs and regulation
49:15 • 4min
Open source, code, and national security limits
53:36 • 1min
Manipulation risks and political misinformation
54:40 • 40sec
Proposal: a right not to be manipulated
55:20 • 1min
Narrow reforms for correcting falsehoods
56:50 • 4min
Could trials be run by AI?
01:00:53 • 3min
Jury values vs AI accuracy
01:04:10 • 2min
Movies and law: Star Wars influence
01:05:44 • 52sec
Bewitched and rules of magic
01:06:37 • 2min
Bob Dylan's reinvention as liberalism
01:08:34 • 5min
Dylan albums as themes of impermanence
01:13:51 • 2min
Upcoming projects: animals and disagreement
01:15:50 • 3min
Outro
01:19:17 • 24sec
#18466
• Mentioned in 2 episodes
Imperfect Oracle
What AI Can and Cannot Do
Cass Sunstein
#40861
Separation of powers
Mary A. Vance
Mary A. Vance's 'Separation of Powers' provides an overview of the theory and practice of separating governmental powers among the legislative, executive, and judicial branches.
The monograph examines the historical development of the doctrine, its application in constitutional systems, and its significance for maintaining checks and balances in democratic governance.
#17119
• Mentioned in 2 episodes
Animals Matter
The Rise and Rise of Animal Welfare Cascades
Cass Sunstein
#52460
Possession
A. S. Byatt
In 'Possession', A. S. Byatt crafts a complex narrative that intertwines the lives of fictional Victorian poets Randolph Henry Ash and Christabel LaMotte with those of modern scholars Roland Michell and Maud Bailey.
The novel delves into themes of love, possession, and the power of words, blending historical fiction with metafiction.
It won the Booker Prize in 1990 and is considered a modern classic.
#2055
• Mentioned in 17 episodes
Scarcity
Why Having Too Little Means So Much
Sendhil Mullainathan
In this book, Sendhil Mullainathan and Eldar Shafir reveal that scarcity, whether of time, money, or social connections, creates a similar psychology for everyone struggling to manage with less than they need.
The authors discuss how scarcity leads to tunnel vision, reduces cognitive bandwidth, and affects decision-making.
They provide examples such as why busy people mismanage their time, why dieters struggle with temptation, and why poverty persists.
The book also offers insights into how individuals and organizations can better manage scarcity for greater satisfaction and success.
#15648
• Mentioned in 3 episodes
Climate Justice
Cass Sunstein
#201
• Mentioned in 91 episodes
The road to serfdom
Friedrich Von Hayek
In this influential book, Hayek argues that the abandonment of individualism and classical liberalism leads to a loss of freedom, the creation of an oppressive society, and ultimately, the tyranny of a dictator.
He challenges the view that fascism and Nazism are capitalist reactions against socialism, instead positing that these ideologies share common roots in central economic planning and the empowerment of the state over the individual.
The book emphasizes the dangers of collectivism and the importance of maintaining a free market system to preserve human freedom and dignity.
#61423
Algorithmic Harm
Protecting People in the Age of Artificial Intelligence
Cass Sunstein
Oren Bar-Gill
This book examines how algorithms can both benefit and harm consumers, particularly when they exploit informational gaps or behavioral biases.
It discusses policy and regulatory strategies to mitigate these risks and protect individuals in the age of AI.
#12577
• Mentioned in 3 episodes
On Liberalism
In Defense of Freedom
Cass Sunstein
#5409
• Mentioned in 7 episodes
The Arrogant Ape
The Myth of Human Exceptionalism and Why It Matters
Christine Webb
In 'The Arrogant Ape,' Christine Webb dissects the pervasive myth of human exceptionalism, arguing that this belief is a root cause of the ecological crisis.
The book challenges the notion that humans are inherently superior to other species, examining how this mindset influences our treatment of the environment.
Webb explores how human exceptionalism manifests in various aspects of society, from cultural norms to scientific perspectives.
She investigates the origins of this belief, tracing its development from childhood to adulthood.
By dismantling the foundations of human exceptionalism, Webb encourages readers to reconsider their relationship with the natural world and to embrace a more interconnected and sustainable way of living.
#3497
• Mentioned in 11 episodes
The subjection of women
John Stuart Mill
Published in 1869, 'The Subjection of Women' is an essay by John Stuart Mill that argues against the social and legal inequalities faced by women.
Mill contends that the inferior status of women is not based on natural differences but rather on social customs and historical power dynamics.
He compares the status of women to that of slaves, highlighting the lack of legal rights, including property ownership and suffrage.
Mill advocates for women's education, employment opportunities, and the reform of marriage laws to achieve greater equality.
The essay, influenced significantly by his wife Harriet Taylor Mill, was a groundbreaking call for gender equality and had a significant impact on the women's rights movement despite facing criticism and controversy at the time of its publication.
#270
• Mentioned in 74 episodes
On liberty
John Stuart Mill
Published in 1859, 'On Liberty' is a seminal work by John Stuart Mill that argues for the protection of individual freedoms from the tyranny of the majority and government interference.
Mill uses utilitarian philosophy to justify the value of liberty, emphasizing the importance of freedom of thought, discussion, and action.
He introduces the 'harm principle,' which states that individuals should only be restrained from acting when their conduct may harm others.
The essay is structured into five chapters, each addressing different aspects of liberty, including the liberty of thought and discussion, individual liberty, the limits of authority, and practical applications of his theories.
Mill argues that protecting individual liberties is essential for societal progress and the avoidance of social stagnation.
#13905
• Mentioned in 3 episodes
Manipulation
Cass Sunstein
#1
• Mentioned in 1,365 episodes
1984
George Orwell
Published in 1949, '1984' is a cautionary tale by George Orwell that explores the dangers of totalitarianism.
The novel is set in a dystopian future where the world is divided into three super-states, with the protagonist Winston Smith living in Oceania, ruled by the mysterious and omnipotent leader Big Brother.
Winston works at the Ministry of Truth, where he rewrites historical records to conform to the Party's ever-changing narrative.
He begins an illicit love affair with Julia and starts to rebel against the Party, but they are eventually caught and subjected to brutal torture and indoctrination.
The novel highlights themes of government surveillance, manipulation of language and history, and the suppression of individual freedom and independent thought.
Cass 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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