New Law Order

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.Guest: CJ Mahoney is the Chief Legal Officer of Meta. Previously, he served in senior legal roles at Microsoft and as Deputy United States Trade Representative, where he played a central role in the renegotiation of NAFTA into the USMCA. Earlier in his career, he was a partner at Williams & Connolly, one of the nation’s leading litigation firms.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 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

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.

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” contractsGuest: 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.

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.

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.