AI Tools for Practicing Lawyers · 2026-08-15 · 18 min
SHOW NOTES 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.
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