AI and the Future of Law
The gold standard for how AI tools intersect with attorney-client privilege and how junior associates are using Claude Code and other tools to solve practice problems.
48 episodes curated
Episodes
Did AI Just Practice Law? The OpenAI Lawsuit + Legalweek 2026
Artificial intelligence is beginning to test the boundaries of legal practice itself. In this episode, Jen Leonard and Bridget McCormack examine Nippon Life v. OpenAI , a lawsuit alleging that a chatbot engaged in the unauthorized practice of law by generating legal advice, drafting filings, and influencing litigation strategy. The case raises foundational questions about liability, regulation, and whether existing legal frameworks can meaningfully apply to AI systems. They also explore practical AI use cases and key takeaways from Legalweek 2026, including rising pressure to demonstrate ROI,
How AI Is Changing Contract Law with Dave Hoffman
Artificial intelligence is beginning to reshape one of the most foundational areas of legal practice: contract law. In this episode, Jen Leonard and Bridget McCormack are joined by Professor Dave Hoffman (University of Pennsylvania Law School) to explore how tools like Claude are influencing contract interpretation, legal research, and legal education. They discuss how AI can help judges interpret ambiguous language, what it means for the value of transactional lawyers, and why defining an “AI-ready” lawyer is harder than it sounds. Topics Discussed Using Claude to analyze law journals’ AI pol
AI Recording Tools and Attorney-Client Privilege in the Age of AI
AI recording tools can make lawyers more efficient—but what are the risks to confidentiality? In this episode, Jen Leonard and Bridget McCormack examine how AI recording tools intersect with attorney–client privilege, professional responsibility rules, and the evolving skill demands of an AI-driven workforce. Topics discussed include: How AI recording platforms may introduce third-party privilege risks State consent laws and the ethical limits of secret recording New York Bar Formal Opinion 2025-6 and deceptive practices Whether recording changes how clients communicate with their lawyers The
AI Agents and the Widening Divide in Legal with Zach Abramowitz
As the legal profession enters 2026, the conversation about AI is shifting. It is no longer about awareness or early adoption. It is about measurable impact. In this episode of AI and the Future of Law , Jen Leonard and Bridget McCormack are joined by Zach Abramowitz for a legal market check-in on AI agents, ROI, competitive pressure, and the widening divide between AI superusers and skeptics. They discuss: The shift from AI assistants to AI agents Why 2026 is about measuring ROI, not experimentation The rise of AI-first firms and competitive pressure on traditional models Venture capital, pri
Claude Code, Vibe Coding, and Creative Lawyers at Work
What happens when lawyers stop waiting for permission and start building with AI? Jen and Bridget explore the rise of creative associates and what tools like Claude Code reveal about the future of legal work. From agentic AI systems that refactor how coding gets done to junior lawyers who “vibe-code” solutions to everyday firm problems, this conversation looks at how innovation is increasingly bottom-up in law firms. Topics covered include: Claude Code and agentic AI for knowledge work Why creative associates are driving real change Vibe coding and lowering the barrier to innovation Cultural s
Should Lawyers Trust AI? Inside Harvey and the Future of Legal Work
Can lawyers really trust AI—and what does “trust” mean in modern legal practice? In this episode of AI and the Future of Law , hosts Jen Leonard and Bridget McCormack are joined by Gabe Pereyra, President and Co-Founder of Harvey AI , to explore how generative AI is moving from a productivity tool to core infrastructure for law firms. Gabe explains how leading firms are deploying AI at scale, why hallucinations are no longer the central concern, and how governance, auditability, and human-in-the-loop systems shape real trust in legal AI. The conversation also dives into the future of the billa
Private Equity and the Future of Law Firms: Investing in AI
Private equity interest in U.S. law firms is accelerating, and AI is a major reason why. In this Season 3 kickoff, Jen Leonard and Bridget McCormack explore how ethics rules collide with the capital demands of AI, and why the real story isn’t short-term profits but long-term investment in legal infrastructure. They unpack Rule 5.4, the rise of the MSO model as a workaround for outside investment, and what “ownership” really means when control over data, technology, and professional judgment is at stake. The conversation also examines emerging judicial approaches to AI disclosure and what they
Predictions for 2026 in AI and the Law
What will AI actually change in law by 2026—and how should firms, courts, and legal institutions prepare? In this season two finale of AI and the Future of Law , hosts Jen Leonard and Bridget McCormack step back from the hype cycle to offer grounded, practical predictions about the next few years. They explore Google’s Gemini 3 and the shift from chatbots to agentic systems, the “platformization” of legal services driven by MSOs, ALSPs, and private equity, and the new talent demands this creates inside law firms. Along the way, they introduce ideas like AI legal twins, AI co-mediators, and opt
Building AI Tools for All: Closing the Justice Gap with Sateesh Nori & Tom Martin
How can AI expand access to justice for the millions who can’t afford a lawyer? In this episode, hosts Jen Leonard and Bridget McCormack speak with Sateesh Nori and Tom Martin about AI tools reshaping legal help, including Depositron for security deposit disputes and Law Answers AI for jurisdiction-specific guidance. They discuss Sateesh’s journey from housing court to AI innovation, Tom’s work building scalable solutions for the public, and the profession’s ongoing debate over “second-tier justice.” What emerges is a compelling vision for AI as a bridge—not a barrier—to legal help. Topics: •
Making Talk Cheap: Are AI Tools Devaluing Legal Writing?
Is AI making legal writing too easy—and too cheap? In this episode, Jen Leonard and Bridget McCormack explore how generative AI tools are reshaping writing as a professional skill. They discuss the paper “Making Talk Cheap,” which argues that when anyone can generate polished text, writing loses its value as a signal of skill, effort, or merit. What does this mean for hiring, advancement, and lawyering in the AI era? Plus, they unpack a new Wharton study showing how enterprise AI use is soaring—with real ROI—while sharing personal stories of AI’s practical impact. Topics Covered: Wharton’s 202
AI in LA Courts: David Slayton on Access to Justice
Can AI make the nation’s largest trial court more accessible, trusted, and just? In this episode, LA Superior Court CEO, David Slayton joins hosts Jen Leonard and Bridget Mary McCormack to unpack how generative AI is already reshaping court services—and why “effective” beats “efficient.” We explore Court Help on LACourt.gov, change-management tactics that stick, and the delicate balance between moving too slowly (and getting overwhelmed) and too fast (and losing public trust). Practical, candid, and grounded in real operations, this conversation offers a roadmap for legal leaders navigating AI
Live from MAICON 2025: Building AAA’s First AI Arbitrator
Can an AI fairly decide a dispute—and win party trust? Recorded live at MAICON 2025, this episode dives into the American Arbitration Association’s first AI arbitrator, a documents-only two-party workflow designed for construction cases with a human in the loop. AAA President Bridget McCormack explains the multi-agent architecture, why procedural fairness matters, and how the tool reflects a century of arbitration expertise. We also unpack OpenAI’s Sora 2 rollout, likeness/IP controversies, and the shift from opt-out to permission-first models—and what deepfakes mean for courts and the rule of
How AI Is Changing Legal Education with Dyane O’Leary and Jonah Perlin
How should law schools teach judgment, writing, and readiness in the age of AI? Georgetown’s Jonah Perlin and Suffolk’s Dyane O’Leary join hosts Jen Leonard and Bridget McCormack to explore how generative AI is reshaping legal education—from 1L writing and grading to ethics, policy, and professional judgment. They share real classroom experiments that reveal how professors are using AI to teach reasoning and curiosity, and how schools are balancing innovation with integrity through redesigned assessments and “AI literacy” curricula. The conversation also dives into multimodal and voice-based t
Can Judges Use AI? Inside the Pennsylvania Supreme Court’s Interim Policy
Can state‑court judges safely use generative AI? In this episode, Jen Leonard and Bridget McCormack unpack Pennsylvania’s interim policy for courts—what it allows, what it restricts, and how human review and confidentiality guardrails work in practice. They compare real AI workflows from their own desks—editing a book with Claude and turning a long essay into slides—and dissect the “AI pilots are failing” storyline versus the reality of high adoption and slower ROI. You’ll also hear why court labs, enterprise access, and judge‑focused guidelines matter now. We cover: Pennsylvania Supreme Court
Inside Legal Innovation: AI Adoption with Jae Um & Ilona Logvinova
What does it take to modernize a 100-year-old legal institution and prepare lawyers for the AI era? In this episode, Jen Leonard and Bridget McCormack sit down with Jae Um (Lumio) and Ilona Logvinova (Cleary Gottlieb) to explore how legal organizations move from AI experiments to real impact. From acquisitions and change management to digital agents and legal education reform, this conversation breaks down what actually drives innovation in law. We cover: Practical AI workflows and tools in legal practice Culture, incentives, and strategy in firm innovation Inorganic vs. organic growth (acquis