When AI Becomes Your Lawyer: The CEO Who Lost $250 Million Trusting ChatGPT Over His Legal Team

When AI Becomes Your Lawyer: The CEO Who Lost $250 Million Trusting ChatGPT Over His Legal Team TL;DR A CEO reportedly asked ChatGPT for advice on how to void a $250 million contract, followed that advice instead of listening to his own lawyers, and ended up losing badly in court. The story went viral on Reddit with nearly 500 upvotes and sparked a fierce debate about the risks of using AI chatbots as a substitute for professional legal counsel. It’s a cautionary tale that’s equal parts jaw-dropping and entirely predictable — and it’s the kind of story the AI industry probably doesn’t want you sharing at the dinner table. ...

March 20, 2026 · 6 min · 1164 words · Viko Editorial