MyPillow Lawyers - “Fiction in the Court”
Nominee: Christopher Kachouroff and Jennifer DeMaster (Legal counsel for Mike Lindell/MyPillow) for filing a legal brief featuring almost 30 defective citations and fictional court cases.
Reported by: Jaclyn Diaz, NPR - July 10, 2025.
The Innovation
In a legal case involving MyPillow CEO Mike Lindell's defamation lawsuit, attorneys Christopher Kachouroff and Jennifer DeMaster discovered the efficiency of AI-assisted legal writing. Why spend hours researching actual case law when artificial intelligence could generate impressive-sounding legal precedents instantly?
The Catastrophe
Their AI-generated brief featured almost 30 defective citations, misquotes, and references to completely fictional court cases - creating what legal experts might call “a legal document from an alternate universe.” The brief was filed in a case where Lindell was ultimately ordered to pay $2 million to Eric Coomer of Dominion Voting Systems.
The Aftermath
Federal Judge Nina Y. Wang fined each attorney $3,000, noting that she “derives no joy from sanctioning attorneys” but found their violations of basic legal standards egregious. The judge was particularly unimpressed by their initial attempts to cover up the AI usage, stating that Kachouroff only admitted to using AI when directly questioned under oath.
Why They're Nominated
This represents a spectacular collision of AI overconfidence with legal incompetence: lawyers who trusted AI to generate case law without verification, then compounded the error by attempting to hide their AI usage from the court.
Sources: NPR: A recent high-profile case of AI hallucination serves as a stark warning