5 MAY

Richard Sander (UCLA Law): A Mismatch Critique of Affirmative Action

Richard Sander, UCLA law professor and economist, has spent decades advancing one of the most controversial arguments in legal education: that large racial preferences in law school admissions may frequently harm the students they are intended to help. In this episode of New Law Order, Joel Cohen and Yale Law Professor John Morley speak with Sander about affirmative action, the Supreme Court’s decision in Students for Fair Admissions, and what new data may reveal about the future of law school admissions. Sander explains his “mismatch” hypothesis: the claim that students admitted with very large academic preferences may be more likely to struggle academically, land at the bottom of the class, and face lower odds of passing the bar than if they had attended a school where their entering credentials were closer to the median. The discussion is direct, data-heavy, and often uncomfortable, touching on race, merit, institutional secrecy, bar passage, and the incentives that shape elite legal education. Sander also examines what changed after SFFA. He argues that the first post-SFFA admissions cycle produced one of the most dramatic shifts in elite law school admissions in decades, with some schools appearing to reduce racial preferences substantially while others found ways to preserve diversity through different admissions strategies. Joel and John press Sander on the strength of the evidence, the limits of the mismatch theory, and whether the legal academy has been willing to test its own assumptions. The episode then turns from law schools to law firms. If elite employers continue to hire for diversity while drawing heavily from credential-driven pipelines, what obligations do they have to train, support, and retain the lawyers they recruit? Sander argues that real affirmative action cannot stop at admission or hiring; it must include institutional investment after the offer is made. Guest: Richard Sander is a professor at UCLA School of Law and a PhD economist whose work focuses on law, inequality, housing, and affirmative action. He is one of the leading academic critics of racial preferences in higher education and was cited by the Supreme Court in Students for Fair Admissions v. Harvard. For more conversations with the figures reshaping the legal business, subscribe to New Law Order. For a CLE-eligible version of this interview and more legal analysis, visit www.talksonlaw.com. For questions or comments, email newlaworder@talksonlaw.com.

1hr 7min

7 APR

Mike Gerstenzang (Cleary Gottlieb): AI from the Inside

Michael A. Gerstenzang, the longtime managing partner and now senior partner of Cleary Gottlieb Steen & Hamilton, explains how he positioned one of the world's most established law firms to lead in AI adoption — not by outsourcing innovation, but by building it from the inside. The conversation traces a series of structural bets that began before generative AI entered the mainstream, starting with ClearyX, a wholly owned technology subsidiary launched in 2021 to reinvent M&A due diligence. Gerstenzang describes the venture's founding provocation — imagine the business that puts Cleary Gottlieb out of business, and build it — and how A/B testing against traditional associate-led diligence demonstrated equal or superior quality at roughly half the cost. The discussion turns to the firm's acquisition of Springbok AI, a legal technology development company whose team now forms Cleary's internal AI acceleration unit, and what that acqui-hire reveals about a deeper challenge confronting every major firm: how to attract and retain elite technologists who would otherwise choose OpenAI or Anthropic over a law firm. Gerstenzang argues that the profession's relationship to technology must shift from infrastructure maintenance to client-facing partnership, and that partners need not master AI themselves but must stop building walls and start supporting those who build windmills. The episode examines the billable hour's structural misalignment with AI-driven efficiency, the emergence of fixed-fee and subscription billing models, and why firms that resist technological adoption will not preserve their margins but simply lose the work to competitors who embrace it. Throughout, Gerstenzang is unsparing about the limitations of the traditional law firm model but remains deeply optimistic about the future of lawyering — practiced increasingly alongside, and powered by, sophisticated technology. For more conversations with the figures reshaping the legal business, subscribe to New Law Order. For a CLE-eligible version of this interview and more legal analysis, visit www.talksonlaw.com. For questions or comments, email newlaworder@talksonlaw.com. Michael A. Gerstenzang, the longtime managing partner and now senior partner of Cleary Gottlieb Steen & Hamilton, explains how he positioned on

1 sec

26 MAR

Judge Paul Grimm: Deep Fakes in the Courtroom

This week, we’re sharing a timely episode from a related TalksOnLaw podcast, AI Lawyer. In this episode, host Joel Cohen is joined by Judge Paul Grimm for a conversation about one of the most unsettling problems facing the legal system: what happens when audio, video, and other forms of evidence can be generated, manipulated, or challenged by artificial intelligence? Judge Grimm explains how AI is already affecting the justice system long before trial, from predictive policing and facial recognition to risk-assessment tools like COMPAS. The episode explores how these systems can influence investigations, charging decisions, sentencing, and the presentation of evidence in court, often with serious consequences and imperfect transparency. The conversation then turns to deepfakes and synthetic evidence: the growing reality that highly convincing fake audio and video can distort proceedings, while the mere existence of deepfakes makes it easier to deny real evidence too. Joel and Judge Grimm unpack the evidentiary challenges this creates for judges, lawyers, and juries, including questions of authentication, reliability, prejudice, and whether existing evidence rules are equipped to handle these technologies. At bottom, this is a conversation about trust, proof, and the future of adjudication. As courts confront black-box systems and increasingly sophisticated digital deception, Judge Grimm offers a sober but practical look at how judges can use existing legal frameworks while the law struggles to catch up. Guest: Judge Paul Grimm is a former federal district court judge and a professor of law at Duke Law School who has written extensively on evidence, technology, and artificial intelligence. For more conversations with top thinkers at the intersection of law and technology, subscribe to New Law Order. For more legal analysis and CLE-eligible content, visit TalksOnLaw. To listen to more episodes of AI Lawyer, search for AI Lawyer wherever you get your podcasts.

1hr 1min

10 MAR

Jason Boehmig (Ironclad): The Rise of the Legal Technologist

Artificial intelligence is beginning to change not just how lawyers work, but what parts of the job remain distinctly human. In this episode of New Law Order, we speak with Jason Boehmig, founder and CEO of Ironclad, about how AI and legal technology are reshaping the structure of the legal profession. Boehmig explains to hosts Joel and John that software is increasingly taking over the mechanical work of law—document manipulation, contract routing, approvals, and data extraction—freeing lawyers to focus on judgment, strategy, and legal reasoning. While this promises massive benifits to lawyers and their clients, the shift raises uncomfortable questions: if AI tools can dramatically increase speed and accuracy, at what point does failing to use them begin to look like malpractice? And as contracts and legal documents become structured datasets, where is the line between practicing law and analyzing legal data? Drawing on his experience building technology for legal teams, Boehmig explains why many important innovations in legal tech have emerged outside traditional law firms. When legal work is decoupled from the billable hour—as it is inside corporate legal departments—the incentives shift toward efficiency, automation, and system design. That environment has become a laboratory for new ways of organizing legal work. The conversation also explores what these changes may mean for the profession itself. Boehmig predicts fewer traditional junior lawyers performing repetitive work and the emergence of new roles—“legal engineers,” technologists, and data specialists—working alongside attorneys. Much like finance evolved from human traders to a hybrid world of traders and quantitative engineers, the legal industry may be heading toward a similar transformation. Guest: Jason Boehmig is the founder and CEO of Ironclad, an AI contracting company used by legal teams at many of the world’s leading technology companies. A former lawyer at Fenwick, he founded Ironclad after teaching himself to code and becoming convinced that software could fundamentally reshape the way legal work is performed. For more conversations with the figures reshaping the legal business, subscribe to New Law Order. For a CLE-eligible version of this interview and more legal analysis, visit www.talksonlaw.com. For questions or comments, email newlaworder@talksonlaw.com.

1hr 18min

24 FEB

Gretta Rusanow (Citi): The New Math of Law Firm Profitability

Law firms like to describe themselves as simple partnerships. Economically, they behave more like highly tuned performance machines balancing profit, talent, leverage, and now — technological disruption. In this episode of New Law Order, Joel Cohen and Yale Law Professor John Morley are joined by Gretta Rusanow, Managing Director and Head of Advisory Services at Citi’s Law Firm Group, to examine what the numbers actually say about the modern legal industry, (conversation taped in September 2025). Drawing on an uniquely broad dataset spanning roughly 200 firms, Gretta offers a rare, industry-wide perspective on revenue growth, headcount expansion, market concentration, and the shifting structure of the partnership model. The post-pandemic story, she explains, is not one of fragility but resilience: steady revenue growth, rising profits per equity partner, and increasing competitive pressure among the largest firms. The conversation explores why the Am Law elite continue to outpace the broader market, how firms reconcile modest demand growth with aggressive expansion strategies, and why leverage — long treated as a quiet driver of profitability — is being rethought in the age of generative AI. Gretta also unpacks one of the most consequential structural shifts in Big Law: the rise of the income partner tier, its logic, and its economic tradeoffs. In this conversation: The Resilience Paradox: Despite volatility, industry revenues and profits have climbed, challenging long-standing narratives of structural vulnerability.Market Concentration Dynamics: Why the largest firms continue capturing disproportionate growth in a slow-growth demand environment.Leverage Under Pressure: How firms are reassessing the traditional pyramid model amid rising costs and generative AI adoption.The Income Partner Equation: Talent retention tool, economic compromise, or both?The Cost of Technological Arms Races: Why generative AI may accelerate consolidation rather than flatten competition. Guest: Gretta Rusanow is a Managing Director and Head of Advisory Services in Citi’s Law Firm Group. A former practicing lawyer, she advises law firm leaders on strategy, performance, and market trends, drawing on one of the most comprehensive financial datasets in the legal industry. For more conversations with the figures reshaping the legal business, subscribe to New Law Order. For a CLE-eligible version of this interview and more legal analysis, visit www.talksonlaw.com. For questions or comments, email newlaworder@talksonlaw.com.

17 FEB

Scott Shapiro (Yale Law): Law as Code & the AI Power Shift

Artificial intelligence is usually sold as productivity: faster research, faster drafting, faster answers. In this episode of New Law Order, Yale Law professor Scott Shapiro explains that the real story is power. If the law is a system for coordinating human behavior at scale, then tools that can interpret rules, test edge cases, and generate persuasive legal analysis may change who can navigate the system—and who gets steamrolled by it. The conversation also explores a darker symmetry: the same tools that help people comply with legal obligations can help sophisticated actors evade them. Shapiro sketches the emerging role of artificial intelligence as both compliance engine and exploitation engine—and what that means for the balance of justice when the best “legal hacker” is a machine. Shapiro draws a crucial distinction between generative models and rule-based systems. Generative tools can sound authoritative while being intentionally or accidentally wrong, which can present dangers. Rule-based approaches, by contrast, raise a different question: what happens when the logic is correct but the reasoning is no longer human-followable? At that point, “legal reasoning” starts to look more like an appeal to authority—raising uncomfortable issues about legitimacy, transparency, and trust. In this conversation: Law as a Social Technology: why legal systems exist and what they are built to doGenerative Models versus Rule-Based Reasoning: reliability, hallucinations, and explainability in legal workWhen Legal Reasoning Stops Being Human: what legitimacy requires when the logic becomes unreadableArtificial Intelligence as Exploitation: using models to find loopholes, stress-test regulations, and “break” contracts Guest: Scott Shapiro is a Yale Law School professor and legal philosopher whose work explores the structure of legal systems and how technology changes the way law is interpreted and applied. For more conversations with the titans changing the legal business, subscribe to New Law Order. For a lawyer Continuing Legal Education version of this interview and other legal insights, visit www.talksonlaw.com. For questions or comments about the show email us at newlaworder@talksonlaw.com.

10 FEB

Chris Bogart (Burford Capital): Litigation as an Asset Class

What happens when you stop treating litigation as a cost center—and start treating it like capital? In this episode of New Law Order, Joel Cohen and John Morley sit down with Chris Bogart, co-founder and CEO of Burford Capital, to unpack how legal finance emerged—and what it reveals about the structural limits of the modern law firm. Bogart traces the origins of litigation finance to his time as a litigator at Cravath, Swaine & Moore and later as General Counsel of Time Warner, where constant pressure from CFOs exposed a deeper problem: dollars spent on litigation don’t just reduce earnings—they reduce enterprise value by multiples. In that light, litigation finance is about preserving balance-sheet value. The conversation reframes litigation as a financial asset—one that can be underwritten, modeled, and monetized—while also explaining why traditional law-firm partnerships struggle to do this themselves. Bogart lays out how annual partner distributions, high partner mobility, and prohibitions on outside capital make Big Law structurally ill-suited to finance long-dated risk. He also explains how medieval doctrines like champerty lost their force, clearing the way for institutional capital to enter the space. Finally, Bogart pulls back the curtain—carefully—on how Burford evaluates cases, and why litigation finance increasingly functions as a tool for risk management rather than speculation. In this conversation: Litigation as Capital Allocation: Why legal spend can destroy multiples of market value—and how funding changes the equationWhy Law Firms Can’t Be Banks: Partner mobility, annual distributions, and the cash-flow problem baked into Big LawUnderwriting a Lawsuit: How Burford evaluates merits, economics, and collectability—and why most cases don’t qualify Guest: Chris Bogart is the CEO and co-founder of Burford Capital, the world’s largest litigation finance firm. A former partner at Cravath and former General Counsel of Time Warner, he pioneered legal finance and helped bring it into the mainstream of global capital markets. For more conversations with the figures reshaping the legal business, subscribe to New Law Order. For a CLE-eligible version of this interview and more legal analysis, visit www.talksonlaw.com. For questions or comments, email newlaworder@talksonlaw.com .

3 FEB

John Quinn (Quinn Emanuel): Building a World Litigation Empire

John Quinn proved the legal industry orthodoxy wrong. In a world obsessed with the "full-service" law firm model—where litigation can feel like a service arm for lucrative corporate retainers—Quinn bet the house on a radical idea: a global firm dedicated exclusively to legal disputes. Today, Quinn Emanuel is a litigation behemoth with over 1,000 lawyers, generating billions in revenue without closing a single M&A deal. In this conversation, Quinn joins Joel and John to share the unlikely origin story of the firm, which began in 1986 with a business plan that completely failed. He explains the crucial pivot away from trying to be outside general counsel to focusing narrowly on what they did best: trying cases. He reveals how this specialization led to their greatest strategic advantage—a "conflict-free" platform allowing them to sue major global banks and institutions that traditional white-shoe firms couldn't touch. Quinn also opens up about the firm’s aggressive talent strategy, detailing the game-changing hire of superstar Kathleen Sullivan, and explains why they have generally avoided merging with other firms in favor of organic growth. Finally, he offers some skepticism on the AI hype in legal services, arguing why artificial intelligence won't replace human judgment required for high-stakes advocacy anytime soon. Guest: John Quinn is the Founder and Chairman of Quinn Emanuel Urquhart & Sullivan LLP, the largest business litigation firm in the world. For more conversations with the titans changing the legal business, subscribe to New Law Order. For a lawyer CLE version of this interview and other legal insights, visit www.talksonlaw.com. For questions or comments about the show email us at newlaworder@talksonlaw.com.

1hr 15min

27 JAN

Brad Karp (Paul Weiss): Law According to Karp

Brad Karp, Chairman of Paul Weiss, is arguably the most powerful law firm leader in America—and he has had a hell of a year. Eight weeks after suffering a heart attack, Karp faced what he calls the "existential crisis" of his career: a "nuclear" executive order from the Trump administration designed to destabilize his firm. In this exclusive and candid interview, Karp sits down with Joel and John to share what he’s learned at the helm of one of the world's leading and most profitable firms. He opens up about the radical transformation of Paul Weiss from a litigation-focused partnership into a private equity and M&A powerhouse. Brad also shares the inside story of how Paul Weiss survived the White House's bombshell executive order against it. While critics (including our illustrious previous guest, Jeffrey Toobin) have called the firm's settlement a "capitulation," Karp argues it was a necessary duty to protect thousands of employees from a "run on the bank" that would have destroyed the firm. Spoiler– John agrees. Guest: Brad Karp is the Chairman of Paul, Weiss, Rifkind, Wharton & Garrison. For more conversations with the titans changing the legal business, subscribe to New Law Order. For a lawyer CLE version of this interview and other legal insights, visit www.talksonlaw.com. For questions or comments about the show email us at newlaworder@talksonlaw.com.

1hr 14min

20 JAN

Jeffrey Toobin: Bending the Knee – Trump's Executive Orders on Law Firms

What happens when the President of the United States declares war on specific law firms? In a move described as "literally without precedent" , the Trump administration unleashed executive orders targeting major firms like Paul Weiss and Perkins Coie—not for illegal activity, but for perceived political offenses. The sanctions threatened to revoke security clearances, bar lawyers from federal buildings, and cancel government contracts for the firms' clients. In this episode of New Law Order, hosts Joel Cohen and John Morley sit down with legal analyst and author Jeffrey Toobin to dissect this constitutional crisis and the industry’s fractured response. While some firms litigated and won, others "capitulated," agreeing to multi-million dollar settlements to make the problem go away. Was this a necessary move to save their firms from an "existential threat" resembling a run on the bank? Or was it, as Toobin suggests, a sacrifice of principle to protect partner profits? Guest: Jeffrey Toobin is a staff writer for The New Yorker, a senior legal analyst for CNN, and the author of several best-selling books, including The Nine and The Oath. Premium subscribers on Apple Podcasts get early access to upcoming episodes and occasional subscriber-only content. For more conversations with the titans changing the legal business, subscribe to New Law Order. For a lawyer CLE version of this interview and other legal insights, visit www.talksonlaw.com.

1hr 16min

New Law Order

Episodes

Richard Sander (UCLA Law): A Mismatch Critique of Affirmative Action

Mike Gerstenzang (Cleary Gottlieb): AI from the Inside

Judge Paul Grimm: Deep Fakes in the Courtroom

Jason Boehmig (Ironclad): The Rise of the Legal Technologist

Gretta Rusanow (Citi): The New Math of Law Firm Profitability

Scott Shapiro (Yale Law): Law as Code & the AI Power Shift

Chris Bogart (Burford Capital): Litigation as an Asset Class

John Quinn (Quinn Emanuel): Building a World Litigation Empire

Brad Karp (Paul Weiss): Law According to Karp

Jeffrey Toobin: Bending the Knee – Trump's Executive Orders on Law Firms

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