MyPillow CEO's Lawyers Face Scrutiny for AI-Generated Legal Brief with Numerous Errors

AI-Generated Legal Brief Sparks Controversy in MyPillow CEO's Defamation Case

In a startling development in the ongoing defamation case against MyPillow CEO Mike Lindell, his lawyers have come under scrutiny for submitting a legal brief generated by artificial intelligence (AI) that contained numerous errors. U.S. District Judge Nina Wang identified nearly 30 defective citations in the document, including misquotes, misrepresentations of legal principles, and even citations to non-existent cases 1

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Admission of AI Usage and Judicial Response

Christopher Kachouroff, the lead counsel representing Lindell, admitted to using generative AI to prepare the brief when directly questioned by Judge Wang during a hearing on April 21, 2025. The judge expressed skepticism about Kachouroff's claim that he had personally outlined and written a draft before utilizing AI, given the pervasiveness of errors in the legal authorities provided 1

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Errors and Misrepresentations

The defects in the brief were extensive and varied:

1. Misquotes of cited cases
2. Misrepresentations of legal principles
3. Incorrect attributions of case law origins
4. Citations to non-existent cases 1

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These errors raised serious concerns about the integrity of the legal process and the potential misuse of AI in legal proceedings.

Lawyers' Response and Explanation

In response to the judge's order to show cause, Kachouroff and his co-counsel Jennifer DeMaster claimed that the submitted document was an earlier draft filed by mistake. They presented alternate versions of the brief and email exchanges to support their argument 2

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Kachouroff stated that he "routinely" uses AI tools such as Microsoft's Co-Pilot, Google, and X to analyze legal arguments, but maintained that he is the only person at his law firm to do so. He also claimed to be unfamiliar with the term "generative artificial intelligence" 2

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Broader Implications for AI in Legal Practice

This incident is not isolated, as it follows a growing trend of legal professionals inappropriately using AI in their work:

1. In June 2023, two attorneys were fined for citing non-existent legal cases after using ChatGPT for research.
2. Later in 2023, a lawyer for Michael Cohen cited fake cases generated by Google Bard.
3. In February 2025, another attorney appeared to cite cases fabricated by ChatGPT 2

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These occurrences have prompted some law firms, such as Morgan & Morgan, to warn employees against blindly trusting AI 2

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The Underlying Defamation Case

The legal brief in question was filed as part of a defamation lawsuit brought by Eric Coomer, a former Dominion Voting Systems employee, against Lindell, his company MyPillow, and his media platform FrankSpeech. Coomer alleges that Lindell and his companies have been prolific vectors of baseless conspiracy theories about the 2020 election, falsely claiming that Coomer committed treason 1

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Potential Consequences

Judge Wang has ordered Kachouroff and DeMaster to explain why they should not face disciplinary proceedings for violating professional conduct rules. The court is also considering sanctions against Lindell, his companies, and the law firm 1

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This case highlights the growing challenges and ethical considerations surrounding the use of AI in legal practice, emphasizing the need for clear guidelines and rigorous verification processes when employing such technologies in the courtroom.