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New Law Order

TalksOnLaw | Joel Cohen & John Morley

Business

Technology

Frequency: 1 episode/23d. Total Eps: 13

New Law Order is a podcast about the business of Big Law and the technologies remaking it. Hosts Joel Cohen (founder of TalksOnLaw) and Professor John Morley (Yale Law School) interview the lawyers, founders, academics, and judges quietly, and not so quietly, rewiring the legal industry. Each episode is a candid, on-the-record conversation about what is actually happening inside the world's most prestigious law firms, the rise of AI and legal technology in legal practice, the economics of the modern partnership, litigation finance, the future of associate work, and the structural shifts the legal industry would rather not talk about... but must. Recent guests include: - Brad Karp, Former Chairman, Paul, Weiss - John Quinn, founder, Quinn Emanuel - Chris Bogart, co-founder & CEO, Burford Capital - Mike Gerstenzang, former managing partner of Cleary Gottlieb - Jason Boehmig, CEO, Ironclad - Gretta Rusanow, Head of Advisory Services, Citi Law Firm Group - Jeffrey Toobin, legal analyst and bestselling author - Scott Shapiro, professor, Yale Law School - Hon. Paul Grimm, Duke Law - Richard Sander, UCLA Law Topics include: Big Law strategy, AI in law firms, legal tech, ClearyX, litigation finance, law firm profitability, the partnership model, generative AI for lawyers, deep fakes in evidence, affirmative action after SFFA v. Harvard, and how the legal industry is being restructured by software. CLE-eligible interview versions and additional legal analysis are available at TalksOnLaw.com. New Law Order is a TalksOnLaw production, supported by a grant from the Oscar M. Ruebhausen Fund at Yale Law School. For questions or comments, email the show at newlaworder@talksonlaw.com.

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John Morley (Yale Law): The Fall of Weil

Season 2

Thursday, October 29, 2026 • Duration 01:06:42

Weil, Gotshal & Manges wasn't losing money. Its profits per partner were still going up when, on October 28, the 95-year-old firm told its partners it would wind down. Delta and General Motors went through bankruptcy and kept flying planes and building cars. No partner-owned law firm has ever done that. In this episode, recorded the day Weil made its announcement, Joel turns the tables and puts co-host John Morley in the guest chair. Years ago John wrote Why Law Firms Collapse, a study of three dozen law firm failures, and he says Weil followed the pattern “almost uncannily according to script.”

John explains why law firms are “less likely to fall off the table, but more likely to shatter when they hit the ground.” Law firms are owned by their workers, and the workers can walk out the door. When one rainmaker leaves, revenue falls faster than costs, profits per partner drop, and the next partner now has a reason to go. It's a run on the bank. Bankruptcy law speeds it up: partner pay is a distribution on equity, and distributions made while a firm is insolvent can be clawed back, so a partner who sees a 50 percent chance of collapse should value every dollar of pay at fifty cents.

So why Weil? What matters, John argues, isn't absolute profit but profit relative to peers. Weil came out of the financial crisis strong on the back of its debtor-side bankruptcy practice, didn't invest in private equity the way its rivals did, and slid down the rankings for two decades. Then came the classic triggers: business concentrated in a few hands, the departure of corporate chair Mike Aiello and a group of partners for Cravath, a centralized governance culture, a leadership succession that fell through, and a merger search that went nowhere. John compares Wachtell, which held together, and Slater & Gordon, a publicly traded firm that went through bankruptcy and kept operating, and explains how ethics Rules 5.4 and 5.6 make American firms uniquely brittle.

He also walks through what happens now to Weil's partners, associates, and staff, from unfinished-business claims to decades of lease obligations; what every other firm should do before the pattern reaches them; and why Weil's fall shows that the 2025 executive orders against firms like Paul Weiss posed a real, existential risk.

Guest: John Morley is the Augustus E. Lines Professor of Law at Yale Law School, where he teaches Business Organizations, Securities Regulation, and Trusts and Estates, and co-hosts New Law Order with Joel Cohen. His article Why Law Firms Collapse, published in The Business Lawyer, studied three dozen law firm failures.

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.

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David Wilkins (Harvard Law): Bias Without Bigotry

Season 2

Wednesday, September 9, 2026 • Duration 01:08:18

Big Law has spent decades and a fortune on diversity, and the numbers barely moved at the partnership level. The usual explanation is that somewhere in the building (or somewhere in your head) there's racism and misogyny. David Wilkins, Harvard Law professor and possibly the most important scholar on the legal profession, has a less satisfying answer: you don't need bigots to get this result. You just need busy partners.

In this conversation, Wilkins joins Joel and John to explain how a firm full of well-meaning people still produces lopsided results. Partner time is scarce. Partners hand it out on almost no information, so they bet on associates who look like the last associate who made it, and hesitate over the profiles they've watched walk out the door. That partner isn't a villain, Wilkins says. He's just "a person in a competitive market."

Wilkins also takes apart Big Law's favorite metaphor — the "tournament" where associates compete and the best rise to partner. Partners aren't neutral umpires with time for all. They're busy people rationing training, and the associate with a sponsor or a feel for the unwritten rules draws the good work while an equally capable one drafts the same motion for the ninth time. Money runs through all of it: who gets to Harvard, who graduates without loans, who can survive a lean year. Wilkins describes a loop where family wealth becomes educational capital, then opportunity, then wealth again.

Then there's the post-SFFA landscape, where firms have quietly killed their fellowships and stopped saying the word "diversity" out loud. (Longtime listeners will recall our earlier guest Richard Sander, Episode 10, made the case for the decision.) Wilkins is less impressed with what firms have done since. His point is that the Court reached admissions, not hiring, and much of the retreat traces to political pressure that goes well beyond anything the Court held. The demographics didn't change. Neither did the structural problem. The encouraging part, in Wilkins's telling: a firm that fixes how it hands out training, sponsorship, and real work doesn't just get more diverse. It gets better at finding the talent it's currently wasting.

CJ Mahoney (Meta): Inside Counsel at Scale

Season 1

Tuesday, May 26, 2026 • Duration 01:12:41

In this episode of New Law Order, Joel Cohen and Yale Law Professor John Morley speak with CJ Mahoney, Chief Legal Officer of Meta, about one of the hardest legal questions facing modern technology companies: when a product becomes deeply woven into daily life, how should the law think about harm, responsibility, and regulation? Drawing on a career that has taken him from Williams & Connolly to the Office of the U.S. Trade Representative, Microsoft, and now Meta, Mahoney offers an unusually candid look at what it means to serve as the top lawyer inside a company operating at the center of law, politics, and technological change.

A major focus of the conversation is the growing wave of litigation against Meta alleging that its products are addictive and harmful, particularly for younger users. Mahoney explains how Meta sees those cases, why he believes the underlying social and mental-health issues are more complex than the lawsuits suggest, and why he is skeptical that litigation is the best tool for addressing those concerns. The episode explores the tension between genuine public anxiety about screen time, adolescent well-being, and platform design, on the one hand, and the difficulty of translating those concerns into coherent legal standards on the other.

The discussion also turns to the broader challenge of regulating a company like Meta. Mahoney reflects on defending Meta’s acquisitions of Instagram and WhatsApp, the problem of assigning legal responsibility in fast-moving technological environments, and the way major platforms increasingly face pressure to answer for social problems that may be real, but are not easily reducible to a single product or defendant. It is a conversation not just about Meta, but about the limits of courts, the ambitions of regulators, and the strain placed on legal doctrine when technology changes faster than consensus can form around it.

Finally, the episode turns to AI and the legal profession. Mahoney discusses how Meta’s legal department is already using AI for summarization, drafting, spend management, and workflow support, and why he sees the next phase not as isolated AI tools, but as deeper integration into business processes. He also offers a clear-eyed view of what that means for lawyers and law firms: more pressure on routine work, greater importance for judgment and strategy, and a world in which knowing how to use AI may become part of baseline professional competence.

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

Season 1

Tuesday, May 5, 2026 • Duration 01:06:41

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.

Mike Gerstenzang (Cleary Gottlieb): AI from the Inside

Season 1

Tuesday, April 7, 2026 • Duration 00:01

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

Judge Paul Grimm: Deep Fakes in the Courtroom

Season 1

Thursday, March 26, 2026 • Duration 01:01:11

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.

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

Tuesday, March 10, 2026 • Duration 01:17:48

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.

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

Tuesday, February 24, 2026 • Duration 01:04:28

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.

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

Season 1

Tuesday, February 17, 2026 • Duration 01:25:13

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 do
Generative Models versus Rule-Based Reasoning: reliability, hallucinations, and explainability in legal work
When Legal Reasoning Stops Being Human: what legitimacy requires when the logic becomes unreadable
Artificial 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.

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

Season 1

Tuesday, February 10, 2026 • Duration 01:22:35

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 equation
Why Law Firms Can’t Be Banks: Partner mobility, annual distributions, and the cash-flow problem baked into Big Law
Underwriting 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.

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