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  • Writer's pictureFrederick L Shelton

The Emperor's New Briefs: Yet Another Cautionary AI Tale

In the legal profession, where the pen is mightier than the sword, some of our comrades have recently found themselves in a rather, shall we say, unrobed position.

Two recent instances, one from the hallowed halls of Massachusetts (Judge sanctions attorney misled by AI) and another from the Show-Me State of Missouri (Missouri appeals court fines litigant), have showcased a modern-day rendition of "The Emperor's New Clothes" – only this time, it's "The Lawyer's New Briefs."

You would think that after Avianca Airlines and as recently as last month, Michael Cohen’s debacle in filings briefs that contained hallucinated cases, that attorneys would learn two things:

1. Don’t use general purpose AI, where you should use legal-specific AI

2. Always use HEF as a final step.

If you thought that would be obvious, you would be wrong. They used general purpose AI (again) and failed to use Human Eyes Failsafe as their final step (again!). Brilliant.

Just like the emperor who was convinced he was wearing a magnificent outfit when, in fact, he was parading around in his birthday suit, these attorneys presented briefs they believed were clothed in legal authority and precedent. Instead, they were starkly naked with inaccuracies, fabrications, and, dare I say, AI-generated faux pas.

Now, don't get me wrong. I am nothing short of an AI enthusiast – when it’s done right!  After all, who among us hasn't wished for a magic quill that could draft flawless arguments while we sip on a well-aged Scotch? But herein lies the rub: the magic quill, much like the emperor's new clothes, is an illusion if not wielded with care.

This returns us to a concept I harp about repeatedly: Human Eyes Failsafe (HEF). Just as the emperor needed a truthful mirror (or a candid child, according to the tale), lawyers must employ their own version of HEF – a rigorous, human review process. Before submitting any document, especially those assisted by AI, a lawyer must don their proverbial spectacles and review EVERYTHING generated by AI as if it were written by a first-year associate.

The moral of these modern-day fables? Don’t be an idiot. Don’t use Chat, Gemini (formerly known as Bard) etc. for ANYTHING that will be submitted in court. You don’t want to be the lawyer caught citing the case of Emperor v. Reality.


Frederick Shelton is the CEO of Shelton & Steele, a national legal recruiting and consulting firm. He can be reached at


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