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Artificial Intelligence

The machine that guesses

Why AI sounds sure when it's wrong · 13 min

A New York lawyer asked ChatGPT whether the court cases it gave him were real. It said yes. They weren't. Why chatbots invent facts in a confident voice, what OpenAI's own researchers argue, and the one check that would have saved him.

Takeaways

  • A chatbot is built to predict the next word, and, OpenAI's own researchers argued in 2025, the way we test these machines rewards a confident guess over "I don't know".
  • The rarer and more specific the fact, the more the answer is a guess: in one 2023 test, 55% of references from GPT-3.5 and 18% from GPT-4 were invented.
  • This week: sort one question into pattern or fact, and give the fact one check from outside the machine.

Chapters

  1. Six cases that never existed0:17
  2. A super search engine?2:03
  3. Graded like a test-taker4:04
  4. Same question, different stakes7:09
  5. Hear it done8:39
  6. Build yours9:57
  7. The answer11:37

References

  1. United States District Court, S.D.N.Y. (Castel, J.) — Mata v. Avianca, Inc., No. 22-cv-1461 (PKC), Opinion and Order on Sanctions(2023)
  2. ABA Journal — Lawyers who 'doubled down' and defended ChatGPT's fake cases must pay $5K, judge says(2023)
  3. Courthouse News Service — Lawyer who cited bogus legal opinions from ChatGPT pleads AI ignorance(2023)
  4. Shannon, C. E. — Prediction and entropy of printed English(1951)
  5. OpenAI — GPT-4 Technical Report(2023)
  6. Kalai, A. T., Nachum, O., Vempala, S. S., & Zhang, E. — Why language models hallucinate(2025)
  7. Walters, W. H., & Wilder, E. I. — Fabrication and errors in the bibliographic citations generated by ChatGPT(2023)
  8. Magesh, V., Surani, F., Dahl, M., Suzgun, M., Manning, C. D., & Ho, D. E. — Hallucination-free? Assessing the reliability of leading AI legal research tools(2025)
  9. Charlotin, D. — AI Hallucination Cases Database(2026)