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Field Note: Even Biglaw Gets The AI Hallucination Blues
Even elite firms can get burned by AI hallucinations. In this field note, Ron Drescher breaks down the recent Sullivan & Cromwell filing controversy, where an emergency brief reportedly contained multiple citation and quotation errors that opposing counsel exposed first. The lesson is not that one firm slipped—it’s that polished AI output can create false confidence in any lawyer, especially when they're under severe deadline pressure.
Ron connects the story to his earlier Confession of an AI Hallucinator episode (where he confessed to sending out a memo containing hallucinated cases) and explains why time-stressed emergency filings are fertile ground for hallucination mistakes. He then pivots to a practical alternative: using AI as a research guide, not a research substitute.
Instead of relying on AI to generate authorities directly, Ron proposes using AI to create multiple Boolean search strategies, help navigate Westlaw/Lexis/Bloomberg features, and improve the research process while keeping lawyers anchored to real databases, real cases, and real citations.
The episode also introduces Ron’s “airport metaphor” for after-the-fact AI verification: if the promised shortcut requires hours of extra checking after the brief is drafted, maybe the traditional route would have been faster all along.
Key Topics Covered
- Why AI hallucinations are not just a solo/small-firm problem
- What happened in the Sullivan & Cromwell filing controversy
- Why emergency motions and deadline pressure increase hallucination risk
- The danger of polished but false AI output
- Why Ron is skeptical of AI-as-research-substitute workflows
- Using AI to generate smarter Boolean searches
- Using AI to help master legal research tools you already pay for
- Building briefs from verified authority rather than unverifiable AI citations
- The airport metaphor for inefficient AI verification workflows
Featured Insight
“This is what using the after the fact AI verification technique is like; if you have to go through this whole verification process after writing your brief, maybe you would have been better off using the old fashioned research tools instead.”
Resources & Deliverables
- Sullivan & Cromwell apology letter with Schedule A of disclosed citation errors: https://lawyeraitoolkit.com/deliverables
About the Show
AI Tools for Practicing Lawyers delivers practical, no-nonsense guidance to help attorneys use AI safely, effectively, and profitably in the modern practice of law.
View all episodes
By Ron DrescherEven elite firms can get burned by AI hallucinations. In this field note, Ron Drescher breaks down the recent Sullivan & Cromwell filing controversy, where an emergency brief reportedly contained multiple citation and quotation errors that opposing counsel exposed first. The lesson is not that one firm slipped—it’s that polished AI output can create false confidence in any lawyer, especially when they're under severe deadline pressure.
Ron connects the story to his earlier Confession of an AI Hallucinator episode (where he confessed to sending out a memo containing hallucinated cases) and explains why time-stressed emergency filings are fertile ground for hallucination mistakes. He then pivots to a practical alternative: using AI as a research guide, not a research substitute.
Instead of relying on AI to generate authorities directly, Ron proposes using AI to create multiple Boolean search strategies, help navigate Westlaw/Lexis/Bloomberg features, and improve the research process while keeping lawyers anchored to real databases, real cases, and real citations.
The episode also introduces Ron’s “airport metaphor” for after-the-fact AI verification: if the promised shortcut requires hours of extra checking after the brief is drafted, maybe the traditional route would have been faster all along.
Key Topics Covered
- Why AI hallucinations are not just a solo/small-firm problem
- What happened in the Sullivan & Cromwell filing controversy
- Why emergency motions and deadline pressure increase hallucination risk
- The danger of polished but false AI output
- Why Ron is skeptical of AI-as-research-substitute workflows
- Using AI to generate smarter Boolean searches
- Using AI to help master legal research tools you already pay for
- Building briefs from verified authority rather than unverifiable AI citations
- The airport metaphor for inefficient AI verification workflows
Featured Insight
“This is what using the after the fact AI verification technique is like; if you have to go through this whole verification process after writing your brief, maybe you would have been better off using the old fashioned research tools instead.”
Resources & Deliverables
- Sullivan & Cromwell apology letter with Schedule A of disclosed citation errors: https://lawyeraitoolkit.com/deliverables
About the Show
AI Tools for Practicing Lawyers delivers practical, no-nonsense guidance to help attorneys use AI safely, effectively, and profitably in the modern practice of law.