Digging a Hole: The Legal Theory Podcast

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 JohnsonThe 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 :)

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 ReadingsAbundance, 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 KleinLiberalism Against Itself, by Samuel MoynIn 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.

This week, we descend from the ivory tower onto the beaches of Martha’s Vineyard for a discussion of the historical significance – and contemporary relevance – of the Garland Fund, the million dollar fund at the epicenter of the early Civil Rights movement. We’re thrilled to welcome our colleague John Witt, the Allen H. Duffy Class of 1960 Professor of Law at Yale Law School, to join us for a celebration of his new book, The Radical Fund: How a Band of Visionaries and a Million Dollars Upended America. We begin the pod by exploring the causal impact of the Garland Fund. Witt argues that the Fund is both a window that provides a new angle with which to view the left liberal social movements of the 1920s and 30s and a workshop that created the conditions under which civil libertarians, civil rights organizations, and union leaders were forced to come together to have conversations about how to spend the Fund’s limited resources. Sam then asks Witt to explain the extent to which his book aims to offer a revisionary account of liberal progress in the early 20th century. After a brief detour to discuss the heroes and villains of the book, David and Sam both press Witt to opine on the contemporary relevance of the story of the Garland Fund. The show concludes with reflections on Abundance bros, the Debt Collective, philanthro-capitalism, and nonprofit tax exemptions. We hope you enjoy!This podcast is generously supported by Themis Bar Review.Referenced ReadingsSimple Justice by Richard KlugerThe NAACP's Legal Strategy against Segregated Education, 1925-1950 by Mark TushnetThe Lost Promise of Civil Rights by Risa GoluboffCivil Rights and the Making of the Modern American State by Megan Ming FrancisThe Taming of Free Speech by Laura WeinribWinners Take All by Anand GiridharadasWhat are Sam & David’s favorite restaurants in New Haven?Sam: It’s pretty slim pickings tbh - I guess there’s a case for Pasta Eataliana (which should definitely change its name)?David: I assume we’re skipping the classic apizza joints? If we leave Pepe’s, Sally’s, Modern and Zuppardi’s to the side, my favorites are the terrific Fair Haven Oyster Co. and Tavern on State. Also, I recommend encouraging Sam to bake for you! Best desserts in town!

We’ve had a lot of fun this spring, but a sweet summer scent is on the wind, and so we’re going to have to wrap up another successful season of Digging a Hole with today’s episode—it’s a real clambake. Courts have paid a lot of attention in recent years to what the executive branch can and can’t do: non-delegation, major questions, student loans, DOGE. The question of what the federal government as a whole can and can’t do, on the other hand, has been settled for a while. Settled, but wrongly, says our guest. Arguing against the weight of constitutional law, history, and memory, we’re delighted to welcome to the pod Richard Primus, the Theodore J. St. Antoine Collegiate Professor of Law at the University of Michigan, to discuss his Straussian reading of the Constitution and new book, The Oldest Constitutional Question: Enumeration and Federal Power.We start off the episode by defining enumerationism, what it is as a theory, and whether or not it works as a matter of practice. Primus tells us about how Congress’s enumerated powers are important to both federalism and the separation of powers, but shouldn’t actually limit the authority of the federal government. Sam and David jump in with questions about whether a legal theory taught to first-year constitutional law students actually does the work in constraining the exercise of power by the federal government. In response, Primus dives into the structural and historical underpinnings of his pro-federal government argument and ends with his hope for constitutional change. We hope you enjoy.This podcast is generously supported by Themis Bar Review.Referenced Readings“A Question Perpetually Arising: Implied Powers, Capable Federalism, and the Limits of Enumerationism” by David A. Schwartz

In the face of what is inarguably bad governance and fake—but spectacular!—technocracy (the list goes on and on, but we’ll stop at AI-generated tariffs), we thought we’d take a moment to join the conversation about what good governance looks like. A couple of weeks ago, one of us reviewed Ezra Klein and Derek Thompson’s new book, Abundance, for the New York Times, and then the other one of us reviewed the review. So we figured: let’s work it out on the pod? No guests on this episode, just the two of us in a brass-tacks, brass-knuckles discussion of the abundance agenda and the goals of twenty-first century economic policy.We dive right into what the abundance agenda is and who its enemies are: innovators and builders against NIMBYs and environmentalists on David’s account; techno-utopians who discount the environment and politics on Sam’s. We agree that housing policy, at least, has helped the better-off create a cycle of entrenching their position through stymieing construction and production. We find another point of agreement on how Klein and Thomson’s abundance agenda attempts to harness the power of the state to build, and that certain left-wing critiques are off base, but disagree about whether their proposal is a break from the neoliberal era of governance and what that even was. In some ways, we end up right where we started, disagreeing about whether the abundance agenda seeks to unleash a dammed-up tide that can lift all boats, or whether the abundance agenda leaves behind everyone but a vanguard of “innovators” in the technology and finance sectors. Let us know if you’ve got a convincing answer.This podcast is generously supported by Themis Bar Review.Referenced ReadingsWhy Nothing Works: Who Killed Progress―and How to Bring It Back by Marc DunkelmanStuck: How the Privileged and the Propertied Broke the Engine of American Opportunity by Yoni AppelbaumOn the Housing Crisis: Land, Development, Democracy by Jerusalem DemsasOne Billion Americans: The Case for Thinking Bigger by Matthew Yglesias“Kludgeocracy: The American Way of Policy” by Steven TelesThe Rise and Fall of American Growth: The U.S. Standard of Living since the Civil War by Robert GordonThe Rise and Fall of the Neoliberal Order: America and the World in the Free Market Era by Gary GerstlePublic Citizens: The Attack on Big Government and the Remaking of American Liberalism by Paul Sabin“The State Capacity Crisis” by Nicholas Bagley and David SchleicherRed State Blues: How the Conservative Revolution Stalled in the States by Matt GrossmannThe Captured Economy: How the Powerful Enrich Themselves, Slow Down Growth, and Increase Inequality by Brink Lindsey and Steven Teles“Why has Regional Income Convergence in the U.S. Declined?” by Peter Ganong and Daniel Shoag“Exclusionary Zoning’s Confused Defenders” by David Schleicher“Cost Disease Socialism: How Subsidizing Costs While Restricting Supply Drives America’s Fiscal Imbalance” by Steven Teles, Samuel Hammond, and Daniel Takash”On Productivism” by Dani Rodrik

The start of a new year, the slouch towards the first days of the new semester, the last episode of yet another season of the pod: we’re feeling sentimental here at Digging a Hole HQ. As you take down your old calendars and put up the new, we’re going to take some time to engage in a tradition of ours at the pod and discuss the 2024 Harvard Law Review Supreme Court foreword, “Curation, Narration, Erasure: Power and Possibility at the U.S. Supreme Court,” with its indomitable author and the Seaman Family University Professor at Penn Carey Law, Karen M. Tani. We begin by discussing the genre of the Harvard Law Review foreword, and how Tani’s approach differs from forewords of yore. Next, we dive deeply into each prong of Tani’s framework of curation, narration, and erasure. We turn to familiar themes of the law-politics divide and the relationship between law and history, with Tani clarifying how this past Supreme Court term adds to our understanding of these big ideas. Finally, we conclude the pod with a discussion of prophecy (and here’s one: you’re going to have a ball with this episode, so hurry up and hit play!). This podcast is generously supported by Themis Bar Review. Referenced Readings “A Century-Old Law’s Aftershocks Are Still Felt at the Supreme Court” by Adam Liptak “Nomos and Narrative” by Robert M. Cover “Selling Originalism” by Jamal Greene The Prophetic Imagination by Walter Brueggemann “Demosprudence Through Dissent” by Lani Guinier “A Plea to Liberals on the Supreme Court: Dissent With Democracy in Mind” by Ryan D. Doerfler and Samuel Moyn

The year is 2025. Department of Government Efficiency dons Elon Musk and Vivek Ramaswamy have broken ground on their new taxpayer-funded palace, the architectural plans of which look suspiciously like a Cybertruck. HHS Secretary RFK Jr. has received a standing ovation from Congress after announcing that children will be given brain worms at birth instead of vaccines. Attorney General Matt Gaetz has just announced that people who successfully stand their ground will be mailed a sticker from DOJ. How did we get here? To help us break down the results of last week’s elections, and to offer a sounding board to Sam and David’s hot takes, joining the pod is New Yorker staff writer and political reporter Benjamin Wallace-Wells. We start off by discussing swing voters, the failures of the Democrats and the Harris campaign, and what the election results hint about the future of the Republican party. (FWIW, we recorded before the Hegseth/Gabbard/Gaetz nominations.) We work through how the election was shaped by local concerns including perceptions of crime and disorder all the way to big international topics like the Russia-Ukraine war. Putting their heads together, Sam, David, and Wallace-Wells come up with a grand unified theory of local, national, and cultural politics in America today. Listen to find out everything you need to know about the election—and let us know if we got it right. This podcast is generously supported by Themis Bar Review. Referenced Readings Grand New Party: How Republicans Can Win the Working Class and Save the American Dream by Ross Douthat and Reihan Salam “The Future Is Faction” by Steven M. Teles and Robert P. Saldin “Trump Is About to Face the Choice That Dooms Many Presidencies” by Oren Cass “The Improbable Rise of J. D. Vance” by Benjamin Wallace-Wells “This Is All Biden’s Fault” by Josh Barro “The Failures of Urban Governance” by David Schleicher

Good news, listeners! Our rational and responsive representatives in Washington have agreed to keep the federal government running through December 20. (As far as we know, anyway.) You might be tired of the all the backroom dealing it seems to take to keep national parks open and the wheels of our country turning. Get it together, you grumble. But as realists in the world of legal theory, we wanted to ask: what would it mean to take legislative dealmaking seriously, and is it possible for deals to be good and just? (Shoot for the moon.) And here to help with that question, hitting our pod is an expert in democratic theory and the law, a former editor of NOMOS, and the Silver Professor of Politics at New York University, Melissa Schwartzberg. On this episode, we discuss Schwartzberg and co-author Jack Knight’s doozy of a new book, Democratic Deals: A Defense of Political Bargaining. To help with orienting our readers, Sam asks Schwartzberg to explain how political theorists and political scientists think of legislative dealmaking—and what’s missing. Schwartzberg introduces the book’s main conceptual yardstick, the equitable treatment of interests, and how looking to contract and constitutional law helps illuminate what a well-functioning legislature looks like. David, realest of the realists, pushes Schwartzberg on how her theory applies to state and local legislative bodies like the Los Angeles County Commission, before we end with a democratic-theory-inflected discussion on the role of courts in a legislative democracy. This podcast is generously supported by Themis Bar Review. Referenced Readings On Compromise and Rotten Compromises by Avishai Margalit Democracy and Legal Change by Melissa Schwartzberg Counting the Many: The Origins and Limits of Supermajority Rule by Melissa Schwartzberg “Worthwhile Canadian Initiative” by Flora Lewis

With the long weekend in the books, summer’s officially here. School’s out, and we can’t imagine why people would be thinking about American universities – has anything interesting or controversial been happening on campus recently? (Our field correspondent David Pozen reports.) Anyway, today’s episode is the last episode of the season, and we’re excited to let this one linger in your minds for the next few months. Today’s very special guest is the MacArthur “Genius” Award-winning Dylan C. Penningroth, Professor of Law and Alexander F. and May T. Morrison Professor of History at the University of California, Berkeley, here to discuss his wonderful new book Before the Movement: The Hidden History of Black Civil Rights. Penningroth begins by showing how his research expands the scope of African American history to everyday legal relations between Black individuals and discusses his great-great-great-uncle as a great example. After Sam and Penningroth frame the conversation as one about Black people using private rights in support of the southern economy, David follows up with a question about the inevitability of capitalism. Next, Penningroth makes the case that his account complements, instead of contradicts, the politically-focused work of W.E.B. DuBois and historians like Risa Goluboff and Eric Foner. We end this semester with some advice for social movements. See you on the other side, listeners. This podcast is generously supported by Themis Bar Review. Referenced Readings “The Privilege of Family History” by Kendra T. Field “Race in Contract Law” by Dylan C. Penningroth “Why the Constitution was Written Down” by Nikolas Bowie Nothing But Freedom: Emancipation and Its Legacy by Eric Foner Saving the Neighborhood: Racially Restrictive Covenants, Law, and Social Norms by Richard R. W. Brooks and Carol M. Rose The Lost Promise of Civil Rights by Risa L. Goluboff Simple Justice: The History of Brown v. Board of Education and Black America’s Struggle for Equality by Richard Kluger

Dear listeners, this season has been riveting, and it’s been a little controversial. Some of you have written in (if you listen to this episode, you’ll see we’ve graced certain aggrieved parties with a response). We see you, we hear you, and boy, do we have a classic legal theory podcast for you. Today’s guest is Kunal Parker, Professor and Dean's Distinguished Scholar at the University of Miami School of Law, here to talk about his fabulous new book The Turn to Process: American Legal, Political, and Economic Thought, 1870–1970. If you liked his first book–and if you didn’t, you’re probably a wretched anti-foundationalist–you’ll love this spiritual sequel. We begin by asking Parker to lay out his thesis, which is, surprise, surprise, that there was a turn from substance to process in economic, political, and most saliently for us, legal thought in the twentieth century. Next, we discuss how much the phenomenon Parker describes is its own thing versus concomitant with American pragmatism and the disciplinification of the modern research university. We make sure everything gets filtered through big important legal thinkers–Holmes and Fortas, Frankfurter and Bickel–before turning to today’s neo-formalistic approaches to the law: neo-Aristotelians, the new private law theorists, et al. (and if we’ve missed anyone, we can guarantee that our listeners will let us know). This podcast is generously supported by Themis Bar Review. Referenced Readings “Radical Mismatch” by Stephen Holmes Rules for the Direction of the Mind by René Descartes “Mr. Justice Black and the Living Constitution” by Charles Reich Tocqueville's Nightmare: The Administrative State Emerges in America, 1900-1940 by Daniel Ernst On Democracy by Robert Dahl The Public and its Problems by John Dewey Age of Fracture by Daniel Rodgers

Have you ever wondered about the legal history of the war on drugs? Even if you haven’t, we won’t mollycoddle you – this episode’s a trip. Our guest on today’s podcast is a scholar of constitutional law and information law known for really getting in the weeds and dunking what we think we know in an acid bath. We’re delighted to have joining us today the radical David Pozen, Charles Keller Beekman Professor at Columbia Law School, here to talk about his far out new book, The Constitution of the War on Drugs. In this episode, we dive into the law, politics, and history of drug legalization and criminalization in the United States. We begin by Pozen giving an impassioned plea for how the war on drugs implicates racial justice, equal protection, federalism, and cruel and unusual punishment. Next, Sam dunks on history. Throughout the episode, we discuss the political economy of drugs (New York’s botched marijuana rollout) and generational divides (Clinton’s “I didn’t inhale”). We end by contemplating the brain-bending, otherworldly potential of the First Amendment to protect heightened brain states. Pour yourself a Coke and enjoy. This podcast is generously supported by Themis Bar Review. Referenced Readings “Silver Blaze” by Arthur Conan Doyle “Beyond Carolene Products” by Bruce Ackerman The American Disease: Origins Of Narcotic Control by David Musto “The Crisis in Teaching Constitutional Law” by Jesse Wegman The Age of Addiction: How Bad Habits Became Big Business by David Courtwright How to Change Your Mind by Michael Pollan

Welcome back, devoted listeners, and say hello to season eight of Digging a Hole, where we’ve got an extraordinarily stacked lineup just waiting in the wings. To make up for the cold, cold months where you had to get your legal theory fix from reading articles (boring) or attending faculty workshops (ugh), we’re kicking off the season with a mammoth episode about a mammoth book. Today’s guest is the former dean and current Sterling Professor of Law at Yale Law School, and Co-Reporter for the American Law Institute, Robert Post, here to talk about Volume 10 of the Oliver Wendell Holmes Devise History of the Supreme Court of the United States (aka the official biography of SCOTUS), The Taft Court: Making Law for a Divided Nation, 1921 to 1930. From the outset, Post sets the stage for his argument that the Taft Court and the 1920s are an important but underappreciated time in American legal history. We discuss how the Taft Court grows out of and evolves according to two social questions wrenching the nation – the First World War and Prohibition. Next, we talk about the different theories of sovereignty and democracy as represented by the different wings of the court, with Taft playing counterpoint to lionized jurists Brandeis and Holmes. Sam, angling for his dream job of author of Volume 14 of the Devise, peppers Post with questions about formalism, realism, and consequentialism. We’re not kidding when we say that’s only half the episode – but, listeners, the second half is a can’t-miss if you care about Taft the master administrator, judicial politics, and the power of the Supreme Court. We hope you enjoy. This podcast is generously supported by Themis Bar Review. Referenced Readings A Muted Fury: Populists, Progressives, and Labor Unions Confront the Courts, 1890-1937 by William G. Ross

It’s the last month of the year and soon (but not yet!), it’ll be the last podcast of the season. We had a lot of people write in about our last episode and so this Christmas, on behalf of all of you, we’ll ask Santa for more Digging a Hole. But before we leave out some milk and cookies, we’ve still got some great episodes for you. Today, we’ve got a pre-recorded episode that – can you believe it – couldn’t be aired for contracts (?!) reasons. But the embargo has been lifted! And here on the pod to talk about no less than a prince of free trade is Jennifer Burns, Associate Professor of History at Stanford University, discussing her new book, Milton Friedman: The Last Conservative. David and Sam start off by making Burns defend the subtitle of the book – was Friedman really the last conservative? Then we discuss the breadth of Friedman’s life and the breadth of Burns’s book, which travels the terrain of the intellectual history of economics to the study of Friedman as libertarian and television celebrity. We get deep into the debate between Keynesianism and monetarism – no math required, but make sure you’ve done your macro readings. Sam wants to know if the book is too easy on Friedman, especially his involvement in Chile. David wants to know if Friedman surrounded himself by sycophants to duck debates. And amidst all of that, Burns makes the case for Friedman as an underappreciated economic thinker who might be right about charter schools. Yes, we know that’s a lot. We hope you enjoy. This podcast is generously supported by Themis Bar Review. Referenced Readings “The Mighty Wurlitzer Plays On” by Tim Barker