Podcast Summary

Podcast: Emerging Litigation Podcast

Episode: Artificial Intelligence on Your Trial Team with Adam Massaro
Host: Tom Hagy
Guest: Adam Massaro, Partner at Reed Smith (Denver, CO)
Date: November 19, 2025

Episode Overview

This episode explores the rapidly evolving role of artificial intelligence (AI) in trial preparation and courtroom strategy. Host Tom Hagy welcomes Adam Massaro, an experienced intellectual property and commercial disputes litigator, to discuss how AI tools are reshaping evidence review, expert cross-examination, trial visuals, witness preparation, and even judicial outcome predictions. Drawing on recent high-stakes cases, Massaro shares practical methods, emerging best practices, and his vision for the future of AI in litigation.

Key Discussion Points & Insights

1. AI Adoption in the Legal Sector

• Tom Hagy sets the stage with recent adoption statistics:
  • AI adoption by law firms increased from 11% (2023) to 30% (2024), with over half of attorneys reportedly using AI tools in some capacity ([00:03]).
  • Efficiency gains are being reported: AI helps automate compliance checks, document review, legal summarization, and more.
• Many firms remain cautious due to ethical concerns and accuracy issues, as illustrated by high-profile cases with fake AI-generated citations ([05:00]).

2. How AI Factored into a Complex Neurological Research Case

• Adam Massaro describes leveraging AI at multiple stages ([06:23]):
  • Ran both sides’ expert reports through Large Language Models (LLMs) to synthesize expected testimony and positions.
  • Used proprietary AI to develop complex and unexpected hypotheticals for cross-examination.
  • AI prompts are critical—Massaro advises, “The prompt is key, laying out a clear directive… if you’re just doing remedial searches or remedial asks, I think you get back remedial outputs.” ([08:10])

3. AI as a Tool for Expert Cross-Examination

• Detailed the value of prompting AI to simulate opposing experts.
  • Massaro: “Developing a well-crafted set of hypotheticals is very, very powerful against an expert… some of the hypotheticals we used at trial were ones that I hadn’t thought of. Once AI gave me feedback, it gave me a path that the expert wasn’t expecting.” ([09:21])

4. Predictive Use of AI in Judge vs. Jury Trials

• AI tools were used to analyze judges’ backgrounds and produce outcome predictions, especially useful given public access to federal judicial records ([12:41]).
• Massaro explains, “We have tons of information on how judges rule… predictive outcomes for judge trials is probably going to be stronger and faster before we get to the jury piece on large language models.” ([10:58])

5. AI for Argument Refinement and Brief Preparation

• Massaro uses AI as an “objective third party” to test whether drafts effectively communicate arguments ([14:13]):

  • By summarizing and critiquing written briefs, AI highlights gaps or weaknesses before filing.
  • Favors leveraging AI for logical reasoning over case law, which might be prone to hallucination.

  “If it’s logical, then a judge is going to understand it. If a judge understands my argument and I have a simpler path to victory, I’ve already increased my chances of success.” — Adam Massaro ([15:47])

6. Trade Secret Litigation: Digital Forensics and AI

• In trade secret cases, digital forensics paired with AI streamline pretrial tasks and trial prep:
  • AI is used to organize evidence, prep checklists, and synthesize findings ("repository for that first draft," [16:01]).

7. Teamwork and AI: Enhancing Collaboration

• Massaro shares the importance of team familiarity (with partner Joyce Williams) in integrating AI into trial workflow ([17:33]). AI’s objectivity helps evaluate witness credibility and performance, complementing human insights in high-stress litigation.

8. Witness Preparation: The Next Frontier

• Applying AI to witness and expert prep:
  • Submitting deposition transcripts and, in the future, video for microexpression analysis ([19:38]).
  • Simulating adversarial cross-examination through AI personas.
  • Massaro notes, “I want them [AI] to adopt the veneer or the personality of that expert on the other side… we don’t actually try it [the cross-exam outline] to make sure it’s going to work. AI gives you reps… cost effective for the client.” ([20:53])

9. AI for Financial Analysis and Legal Visuals

• AI ingests and summarizes complex financial data sets (Excel, AR aging, projections) supporting trial narratives:
  • “I just get the prompts, you know, tell me all the AR that’s 60, 90 days old… bucket in various Excel buckets and columns, what will be the projected financials for this issue or that issue? So I think it’s going to be very, very helpful.” ([23:50])

10. How Adam Massaro Got Started With AI

• Reed Smith’s internal platform enabled his adoption.
• Motivation: “My constant desire is figuring out how can we try more cases at a more cost effective level. To me, this was just the next step.” ([25:58])

11. Future of AI in Litigation

• Near term: Building "avatars" of opposing counsel to inform case strategy and budgeting ([28:25]).

• Long term: Dynamic, milestone-based predictions of case outcomes for clients, quantifying how legal work reduces risk over time.

  “I think we’re going to be able to demonstrate how have we provided actual value to the case because we’ve gotten it better… I think the clients deserve more and I think we can figure out ways to give better quality.” — Adam Massaro ([28:25])

12. Client Attitudes Toward AI

• Many corporate clients are ahead of law firms in AI adoption and expect their firms to use these tools ([32:47]).
  • “We’re seeing it in a lot of RFPs and requests… the clients are going to drive this more than anything else.”

Notable Quotes & Memorable Moments

• On the importance of prompts:

  “The prompt is key, laying out a clear directive… if you’re just doing remedial searches or remedial asks, I think you get back remedial outputs. But the prompt really is the driver.”
  — Adam Massaro ([08:10])

• On cross-exam prep using AI personas:

  “Put my witness in this situation, obviously the AI system as the deponent or the adverse witness, and then tell them I’m going to cross them… I think it gets you reps in a whole different way and… more cost effective for the client and probably gets you a better outcome too.”
  — Adam Massaro ([20:53])

• On aligning AI logic with persuasive advocacy:

  “If it’s logical, then a judge is going to understand it. If a judge understands my argument and I have a simpler path to victory, I’ve already increased my chances of success.”
  — Adam Massaro ([15:47])

• Future vision for litigation AI:

  “Let’s say we’re assuming plaintiffs side in a complex case… predictive AI in the future says when you file this case, you got a 15% chance… [then] evidence gets better… our predictive outcome is more like 40%… and so the point being is, I think we’re going to be able to demonstrate how have we provided actual value to the case because we’ve gotten it better or flip on the defense side… through our work, we’ve cut your risk down. Let us get you to zero percent at trial.”
  — Adam Massaro ([28:25])

Timestamps for Key Segments

• [00:03] — Intro & AI adoption trends in legal industry
• [06:05] — Adam Massaro joins; background and recent case
• [06:23] — How AI factored into complex trial prep and strategy
• [08:10] — Importance of structured data and prompts
• [09:21] — Using AI to craft expert cross-examination hypotheticals
• [10:58] — Predictive use of AI for judge vs. jury trials
• [14:13] — AI for argument refinement and brief communication
• [16:01] — Digital forensics and AI in trade secret litigation
• [17:33] — Team collaboration and leveraging AI for witness prep
• [19:38] — Enhancing witness preparation using AI and future video analysis
• [20:53] — AI for cross-exam simulation and pretrial "reps"
• [23:50] — AI for financial analysis and trial visuals
• [25:58] — Adam’s motivation and pathway to adopting AI
• [28:25] — AI’s near-term (avatars, opposing counsel analysis) and long-term (outcome prediction) future
• [32:47] — Client attitudes: Demand for AI-enabled legal services

Conclusion

This insightful episode demonstrates both the immediate benefits and evolving frontiers of AI in litigation, from cross-exam simulations to client-driven adoption and future outcome prediction. Adam Massaro’s practical examples, paired with Tom Hagy’s probing, make this a must-listen (or read) for litigators, in-house counsel, and legal technologists seeking to harness AI for competitive advantage and client value.