Five Tips for Fighting Pro Se Litigants Who Use AI

An insurance company just spent $300,000 fighting a pro se litigant who had no lawyer — just ChatGPT. That number should worry every practicing litigator. What happens when the other side has access to an inexhaustible junior associate that never bills, never tires, and never stops drafting the next motion?

In this episode:
- Nippon Life Insurance Company of America's lawsuit against OpenAI over a pro se litigant's AI-generated filings
- How Graciella Della Torre used ChatGPT to try to reopen a case that had already settled and been dismissed with prejudice
- Why the $300,000 in legal fees is the real story here, not who ultimately wins the Nippon v. OpenAI lawsuit
- The new asymmetry AI creates between represented parties and self-represented litigants
- Narrowing the battlefield with procedure instead of trying to out-produce an AI on paper
- Verifying every citation, quotation, and legal proposition in an AI-assisted filing, not just whether the case exists
- The Matthew Elliott case and hidden white-text prompt injection aimed at an AI system that wasn't even part of the court's process
- Judge Walter Spader's sanctions against Elliott, and Spader's own disclosure that he used AI to help draft the sanctions order
- Whether a pro se litigant's ChatGPT prompts and conversations are discoverable
- Warner v. Gilbarco and Tremblay v. OpenAI, and what they say about work product protection for AI use

We also discuss:
- Matt Lafferman and Rick Shearer's writing on the developing case law around AI and discovery
- Why courts are treating AI tools as tools, not persons, for work product purposes
- Judge Sarah Smith's public statement on the limits of her own AI use on the bench
- The distinction between using AI and committing misconduct with AI
- UAE courts' nationwide AI procedures, compared with Connecticut's approach

Key Takeaway:
Lawyers have spent years asking whether AI will replace lawyers. That's not the immediate problem. AI doesn't need to replace opposing counsel — it just needs to give the person without a lawyer the ability to litigate like they have one. The right response isn't more paper. It's narrower issues, verified authorities, documented patterns, and a clear line between AI use and AI misconduct.

This is a Flintstones-lawyer blind spot waiting to happen — the attorney who assumes a pro se opponent's filing quality reflects their legal knowledge, and gets buried in volume. It's also a Simpsons-lawyer governance problem: verification has to become a standing practice, not a one-off gut check. And it's a Jetsons opportunity — a citation-verification workflow built now is the difference between a manageable pro se case and a $300,000 one.

Mentioned in This Episode:
- 21 Ways AI Can Hallucinate in Your Legal Brief

- Nippon Life Insurance Company of America v. OpenAI, (1:26-cv-02448)
District Court, N.D. Illinois
- Graciella Della Torre
- ChatGPT
- Claude
- Gemini
- Matthew Elliott v. New York Bariatric Group
- Judge Walter Spader, Connecticut State Court
- Ars Technica, Suspecting court of using AI, man injected prompts in filings to try to win case
- Reuters
- Matt Lafferman, Dentons, Legal AI Lab
- Rick Shearer
- AI and Privilege: When AI Becomes Evidence
- Warner v. Gilbarco, Inc . (2:24-cv-12333)
District Court, E.D. Michigan
- Tremblay v. OpenAI, Inc. (4:23-cv-03223)
District Court, N.D. California
- Judge Sarah Smith, Third Judicial Circuit, Illinois, Standing Order

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