Digging a Hole: The Legal Theory Podcast

Digging a Hole Podcast
  • 4.8 (69)
  • Social Sciences

Yale Law School professors Samuel Moyn and David Schleicher interview legal scholars and dig into the debates heard inside law school halls.

  1. 1d ago

    David Skeel

    Sam is away this week, dear listeners—presumably offsomewhere arguing with older Americans about why they shouldn’t vote—leaving David to talk bankruptcy with David Skeel. (The two Davids rejoice!) In this week’s episode, we turn to municipal insolvencyand the largest government debt restructuring in American history. David Skeel, the S. Samuel Arsht Professor of Corporate Law at the University of Pennsylvania Law School, joins the pod to discuss his new book: Promise Land: The Inside Story of the Puerto Rico Debt Crisis. Drawing on hisexperience serving on (and chairing) Puerto Rico’s Financial Oversight and Management Board during its bankruptcy-like Title III process, the book combines Skeel’s deep expertise in bankruptcy law with a rich account of the conflicts and compromises among bankruptcy lawyers, judges, local and federal officials, Puerto Rico’s citizens, and bondholders of various stripes. Skeel walks us through the specifics of the crisis: howPuerto Rico got into so much fiscal trouble, the island’s appetite for borrowing, and how federal disaster aid shifted the balance of power between the oversight board and the local government. The two Davids also tackle broader questions about municipal bankruptcy, revisiting Skeel’s support for allowing states to file for bankruptcy, his earlier criticism of how creditors were treated in Detroit, whether pensioners should receive more than bondholders, and how much discretion bankruptcy judges should wield. Finally, Schleicher presses Skeel on the controversial COFINA bonds, the major legal questions left unanswered by settlements, and the struggle to restructure Puerto Rico’s electric utility. They close by considering whether Puerto Rico offers a preview of future American fiscal crises and what the optimal design for municipal bailouts looks like. Referenced Readings Promise Land: The Inside Story of the Puerto Rico DebtCrisis, David Skeel (2026).Debt’s Dominion: A History of Bankruptcy Law in America, David Skeel (2001).In a Bad State: Responding to State and Local BudgetCrises, David Schleicher (2023).      Give States a Way to Go Bankrupt, David Skeel, The Weekly Standard (2010).A Bankruptcy Law—Not Bailouts—for the States, David Skeel, WSJ  (2011).       States of Bankruptcy, David Skeel, University of Chicago Law Review, (2012).Fixing Puerto Rico’s Debt Mess, David Skeel, WSJ (2016).Can Pensions Be Restructured in (Detroit’s) Municipal Bankruptcy?, David Skeel (2013).When Cities Go Broke: A Conceptual Introduction toMunicipal Bankruptcy, Michael McConnell and Randal Picker, University of Chicago Law Review (1993).Governance Reform and the Judicial Role in MunicipalBankruptcy, Clayton Gillette and David Skeel, Yale Law Journal (2016).Junk Cities: Resolving Insolvency Crises in OverlappingMunicipalities, Aurelia Chaudhury, Adam Levitin, and David Schleicher. California Law Review (2019).Against Settlement, Owen Fiss, Yale Law Journal (1984).Brighton Beach Memoirs, Neil Simon (1983).

  2. Sep 23

    Joshua Specht

    Summer is over, dear listeners. Sam spent his time reading hate mail from older Americans, while David has just moved around the corner from a senior assisted living facility. But more importantly, Digging a Hole is back for another season. In this week’s episode, we turn to the history of America’s obsession with land ownership. Here to take us from the rent wars of the 1840s up to the Great Financial Crisis, we have Joshua Specht, associate professor of history at the University of Notre Dame. He joins us to discuss his new book, Property Values: The Rise and Fall of the American Homeowner, which traces the history of American property ownership from the homestead to the modern suburb. Specht lays out his argument that American history can be understood through two linked ideals: nineteenth-century “landed democracy,” in which widespread land ownership underwrote visions of independence and citizenship, and the twentieth-century “ownership society,” which moved those aspirations to suburban homes. Sam questions whether land ownership and homeownership really belong in a single story and whether Americans might someday manage to untether democracy from owning a piece of land altogether. David, meanwhile, asks whether Specht’s narrative gives too much explanatory power to property ownership and not enough to economic growth and dynamism. He also wonders whether the decisive break in American housing really came with the mortgage revolution of the 1930s or with the rise of anti-growth politics in the 1970s. Referenced Readings Property Values: The Rise and Fall of the American Homeowner, by Joshua Specht Red Meat Republic: A Hoof-to-Table History of How Beef Changed America, by Joshua Specht “The Price of Meat,” by Samuel Moyn “How the Gentry Won: Property Law’s Embrace of Stasis,” by Roderick M. Hills Jr. and David Schleicher “The Significance of the Frontier in American History,” by Frederick Jackson Turner Crabgrass Frontier: The Suburbanization of the United States, by Kenneth T. Jackson Americans Against the City: Anti-Urbanism in the Twentieth Century, by Steven Conn

  3. Jun 8

    Sarath Sanga

    Things are looking up, dear listeners. The semester is over, summer is nearly here, and David’s beloved Knicks are up 2-0 in the NBA Finals.  In this week’s episode, we take a step back and do some introspection. Here to discuss whether you should trust Yale, and other elite universities, more than Jalen Brunson in the fourth quarter is friend and colleague Sarath Sanga, Professor of Law at Yale Law School and Co-Director of the Yale Law School Center for the Study of Corporate Law. Sanga joins us to discuss both his new article, A Theory of Trust in Institutions, co-authored by Yehonatan Givati, and the recent Report by the Yale Committee on Trust in Higher Education, of which Sanga was a member. Sanga kicks off the episode by explaining his view of why higher education is hemorrhaging public trust. Sanga argues that universities, and other institutions, pre-commit to doing specific things, and they lose trust whenever they stray from this initial commitment. Sam questions whether universities are now, and always have been, finishing schools for elites and, if so, whether it makes sense to talk about institutions like Yale having a mandate. And David brings up a variety of counterexamples that call into question whether an institution going against its mandate, such as when a university fields varsity sports teams, actually decreases trust in the real world. We hope you enjoy! Referenced Readings A Theory of Trust in Institutions, by Sarath Sanga and Yehonatan Givati Report of the Yale Committee on Trust in Higher Education, by Yale University "Shut Up and Dribble", by Ian Ayres A Running List of Nominations for the Canon of American Legal Thought (1975-2025) A Matter of Interpretation, by Antonin Scalia [Grove] “A Neo-Federalist View of Article III”, by Akhil Reed Amar [Grove] “The Anticanon”, by Jamal Greene [Grove] The Economic Structure of Corporate Law, by Frank Easterbrook and Daniel Fischel [Macey] “The Costs of Employment Segregation: Evidence from the Federal Government Under Woodrow Wilson”, by Abhay Aneja and Guo Xu [Sanga] This episode is all about how Yale, and other elite institutions, are losing public trust. As Yale Law School insiders, what’s your best solution for making YLS more trustworthy?  Sam: I’m very suspicious of law schools, especially ours-why shouldn’t everyone else be?David:  I’m not sure that there is one quick trick in a polarized country, unless we can ensure that none of our graduates ever have an opinion that anyone of any political party ever disagrees with. That said, the best plan is to focus on what we’re good at, teaching brilliant students (like Daniel Browning, our out-going EP and all-around superstar!) and producing a broad range of excellent and rigorous scholarship.

  4. Jun 5

    Lawrence Douglas

    As gas reaches stratospheric prices and the cost of living continues to climb, war seems to be on everyone’s mind these days. What better time, then, to be joined by Lawrence Douglas, the James J. Grosfeld Professor of Law, Jurisprudence and Social Thought at Amherst College, to discuss his brand new book, The Criminal State: War, Atrocity, and the Dream of International Justice?  The episode begins with an overview of two paradigms in international criminal law. Douglas argues that international law has replaced the “aggression paradigm,” which emerged out of the Nuremberg trials, in favor of an “atrocity paradigm,” which focuses on sanctioning grievous acts of violence, especially towards civilians. However, Douglas suggests that both the atrocity paradigm and the now-defunct aggression paradigm suffer from serious deficiencies. Sam asks whether there really has been an aggression-atrocity shift or, instead, whether the aggression paradigm utterly failed, with a long delay before the separate construction of an atrocity paradigm — which itself proved short-lived. David queries whether Douglas’s story is too formalistic and already out of date. And, fortunately for everyone, we resist the urge to do the entire episode in Seinfeld voices. Referenced Readings Humane, by Samuel Moyn From Aggression to Atrocity: Rethinking the History of International Criminal Law,” by Samuel Moyn  The Internationalists, by Oona Hathaway and Scott Shapiro A Running List of Nominations for the Canon of American Legal Thought (1975-2025) A Matter of Interpretation, by Antonin Scalia [Grove] “A Neo-Federalist View of Article III”, by Akhil Reed Amar [Grove] “The Anticanon”, by Jamal Greene [Grove] The Economic Structure of Corporate Law, by Frank Easterbrook and Daniel Fischel [Macey] In this episode, Douglas proposed co-teaching an international law seminar with Sam. If you could teach a seminar on anything, unencumbered by ABA requirements or Yale Law School bureaucracy, what would you teach? David:  Hmmm… Stoicism: From Marcus Aurelius to O.G. Anunoby.  Or perhaps Art History 601: The Art of Walt “Clyde” Frazier’s suits.  Or maybe Negotiation 401: How Jalen Brunson Won By Taking Less Sam: “French Pastry”? I would have listed “Why I Dropped Out of Law School and You Should Too” but then I realized I manage to include the material in most of my classes…

  5. May 12

    Anton Jäger

    Now that classes are over and the end of the semester is near, we’re back for several weeks of podcastmaxxing. So stay tuned for some great episodes in the coming weeks, dear listeners!  Here to help us understand our current political moment and to diversify David’s reading list is Anton Jäger, a Departmental Lecturer in the History of Political Thought and Political Theory at University College, Oxford. Jäger joins the pod this week to discuss his new book, Hyperpolitics: Extreme Politicization without Political Consequences, where he offers a European’s perspective on the American political moment.  This episode begins with an explanation of what, exactly, hyperpolitics is and how it differs from other, older forms of politics. Jäger suggests that hyperpolitics is characterized by a high degree of political involvement but a corresponding deinstitutionalization of politics. Sam queries whether our current moment might be more continuous with the past, with both characterized by a quiescent politics. And David asks about the degree to which our politics has been causally determined by economic forces. Along the way, we also discuss whether it’s helpful to label the Trump movement as fascist, whether hyperpolitics is the product of liberalism’s failure, and whether the smartphones are really to blame for everything. We hope you enjoy! Referenced Readings The Hollow Parties, by Daniel Schlozman and Sam Rosenfeld  Bowling Alone, by Robert Putnam The Dark Side of Democracy, by Michael Mann The Project-State and its Rivals, by Charles Maier A Running List of Nominations for the Canon of American Legal Thought (1975-2025) A Matter of Interpretation, by Antonin Scalia [Grove] “A Neo-Federalist View of Article III”, by Akhil Reed Amar [Grove] “The Anticanon”, by Jamal Greene [Grove] The Economic Structure of Corporate Law, by Frank Easterbrook and Daniel Fischel [Macey] On this week’s episode, Jäger offered a European outsider’s take on American politics. Flipping the script, what’s your best outsider’s take on European politics? Sam: The first wave of right-wing victory is over, and now it is coming for France and Germany. Get ready. David: I can’t believe that British politics is not full of people with their hair on fire about why the country’s economic growth has been so slow – Poland is likely to catch up in per capita GDP in a few years! And, if anything, de-growther forces, on both the right and left, are rising.  It’s like the frogs in slowly boiling water croaking requests to turn up the temperature.

  6. Mar 26

    Joshua Macey

    Spring has sprung, dear listeners. Now that this dreadfully cold winter seems to be behind us, our power bills might finally come back down to Earth. Here to explain why your electricity bill is so expensive – and what to do about it – is Joshua Macey, a Professor of Law at Yale Law School. Macey’s research and teaching interests are wide-ranging, from energy and environmental law to bankruptcy and legal theory. In this episode of the pod, we get into the nitty gritty on energy, utilities, and governance strategies. The episode begins with a discussion of whether, and under what circumstances, centralized government regulation is (and is not) better than competition among private energy providers. We then tackle several big theoretical questions, such as the best methodology for analyzing regulatory policy, whether a carbon tax could be effective, and whether there should be an Abundance agenda for energy. And we also talk practical solutions: Why don’t we create a vast inter-state energy network? Should every state adopt the Texas approach of “surge pricing” during times of increased electricity demand? And more.  The episode concludes with another excellent nomination for the Canon of American Legal Thought (1975-2025). Referenced Readings “Behavior of the Firm under Regulatory Constraint”, by Harvey Averch and Leland Johnson The Economic Structure of Corporate Law, by Frank Easterbrook and Daniel Fischel  “The Corporate Governance of Public Utilities”, by Aneil Kovvali and Joshua Macey “In Defense of Chapter 11 for Mass Torts”, by Anthony Casey and Joshua Macey “Inside or Outside the System?”, by Eric Posner and Adrian Vermeule  A Running List of Nominations for the Canon of American Legal Thought (1975-2025) A Matter of Interpretation, by Antonin Scalia [Grove] “A Neo-Federalist View of Article III”, by Akhil Reed Amar [Grove] “The Anticanon”, by Jamal Greene [Grove] The Economic Structure of Corporate Law, by Frank Easterbrook and Daniel Fischel [Macey] This episode features a discussion of whether a carbon tax could effectively curb climate change. And David has recently called attention to the new property tax revolt. In this spirit, what’s something you think should be taxed, but currently is not? Sam: In my new book, I argue for a new suite of tax laws that attack the nexus of age and wealth - for example, by incentivizing departure from homes for those who have means to leave and, because they are older, often occupy more square footage than they need. David: Lots of possibilities – low taxes on different tax bases can be very attractive, as the deadweight loss of taxation gets increasingly worse as a single tax gets higher.  A serious answer is congestion. Driving downtown during busy periods creates huge externalities, and once passed, as NYC’s experience shows, congestion charges become popular because they reduce traffic.  A less serious but equally strongly-felt answer: a progressive tax on the length of meetings, particularly Zooms.  How happy would the world be if the person who said “one more thing” at the end of meeting faced a stiff penalty! Also, of course, seconds of speeches during faculty meetings!!! Finally, my wife would also say there should be a tax on exclamation points in emails, as it would encourage people to sound less deranged!!! And by people, she definitely means me :)

  7. Mar 5

    Tara Leigh Grove

    Reports of the pod’s death are greatly exaggerated, dear listeners. Despite the lengthy hiatus, we’re finally back with a terrific episode on judicial method, judicial power, and much more. To kick off the Spring installment of the pod, we’re incredibly fortunate to be joined by Tara Leigh Grove, the Vinson & Elkins Chair in Law at the University of Texas at Austin School of Law, who comes on the pod to discuss her article, “The Power to Impose Method,” forthcoming in the Yale Law Journal.  The episode begins with a general discussion about the Supreme Court’s power to impose an interpretive methodology on lower courts, what is often called “methodological stare decisis.”  Grove advocates for something resembling a middle ground—the Supreme Court has a limited, bounded power to impose method on lower courts. We then get into the nitty gritty of the distinction between holding and dictum and of Article III’s case and controversy requirement. David asks why the Supreme Court can’t just do what it wants regarding method, and he queries whether the Supreme Court also has power to narrow the precedential force of its interpretive holdings. Sam asks why we should care whether the Supreme Court could impose method in one fell swoop if it’s clear that it can impose method in a piecemeal, case-by-case fashion. We conclude our discussion of Grove’s article by debating the normative credentials of interpretive pluralism.  Before wrapping up the pod, we launch a brand new featured segment on The Canon of American Legal Thought, where we ask guests for (at least) one nomination for a list of the most important legal scholarship of the last fifty years. Grove offers not one, but three, excellent nominations, and Sam and David resist the urge to nominate their own work. We hope you enjoy! This podcast is generously supported by Themis Bar Review. Referenced Readings “The Power to Impose Method”, by Tara Grove A Running List of Nominations for the Canon of American Legal Thought (1975-2025) A Matter of Interpretation, by Antonin Scalia [Grove] “A Neo-Federalist View of Article III”, by Akhil Reed Amar [Grove] “The Anticanon”, by Jamal Greene [Grove] H.L.A. Hart’s “no vehicles in the park” hypothetical has been described as “the most famous hypothetical in the common law world.” In the spirit of this episode, give us your hottest take on this chestnut of statutory interpretation. Are airplanes vehicles? Tricycles? Sam: Anything is a vehicle that an adequately powerful consensus decides is one. Do the math. David: As is often the case, the fight over legal interpretation missed the big policy change – many parks closing their internal roads to cars, leaving more space for bikes and runners alike.  The closing of Central Park to cars (other than the separated cross-town thoroughfares) is a huge policy success, and far more important than edge cases about motorized scooters.

  8. 11/14/2025

    Jerusalem Demsas

    It’s been quite an eventful month, dear listeners. After a few flight cancellations, Democrats decided it was time to finally reopen the government. The House released a cache of Epstein files that name President Trump. And Zohran Mamdani has officially been named king of New York. In these turbulent times, we’re lucky to be joined by Jerusalem Demsas—journalist, grade A pundit, and Editor & CEO at The Argument magazine—who is here to talk Mamdani, liberalism, and much more. The episode begins with reflections from Demsas and David about what Mamdani’s election means for New York. Will his affordability platform transform New York for the better? Or will his vision be foiled by New York’s entrenched and inefficient bureaucracy? Beyond the Big Apple, Sam asks for predictions on whether Mamdani (or his coalition) can scale to the national level. We then discuss the significance of the elections in Georgia, where Democrats notched a big victory in some less important state-wide elections. Finally, Sam asks Demsas to reflect on the future of liberalism in America. Should liberalism be canned for a progressive alternative, or is it, as Demsas will argue, the only way we can live together in a pluralistic country? Most importantly, this episode gives Sam and David their annual opportunity to play political pundits. We hope you enjoy! This podcast is generously supported by Themis Bar Review. Referenced Readings Abundance, by Ezra Klein and Derek Thompson “How do we live with each other?”, by Jerusalem Demsas “This Is the Way You Beat Trump — and Trumpism”, by Ezra Klein Liberalism Against Itself, by Samuel Moyn In this episode, there was a general skepticism that Mamdani could lead the Democratic party at the national level. So, in this episode’s spirit of hot-take punditry, who is your pick to be on the top of the Democratic ticket in the 2028 election? Sam: No clue. We are in the democratic equivalent of Deuteronomy 18 territory: a prophet will be raised up from among the people, but we don’t know who it is yet. Dan Osborn? David: I’m hoping not for a prophet, but for someone who can fulfill Biden’s promise to make national politics less interesting and, as we suggest in the episode, return a little power to Congress even if it is not in his/her short-run political and policy interests.  A midwestern governor or western senator, perhaps.  But I’m afraid it’s going to a battle of meme lords and discourse makers.

See All (82)

4.8
out of 5
69 Ratings

About

Yale Law School professors Samuel Moyn and David Schleicher interview legal scholars and dig into the debates heard inside law school halls.

Information

You Might Also Like