Court Fines MyPillow CEO’s Lawyers for AI-Generated Brief Filled with Errors

A Colorado federal court has fined two attorneys for MyPillow CEO Mike Lindell for submitting a legal brief riddled with errors generated by artificial intelligence.

Amanda Yeo reports in Mashable that the brief, intended to defend Lindell in the defamation lawsuit Coomer v. Lindell, contained nearly 30 inaccuracies, including fictitious case citations and legal misrepresentations.

The court found that the attorneys’ conduct violated procedural rules and imposed financial sanctions.

This issue arose from a brief filed by attorneys Christopher Kachouroff and Jennifer DeMaster of the law firm McSweeney Cynkar and Kachouroff in February 2025.

They utilized generative AI platforms, including Microsoft Copilot, Google Gemini, and X’s Grok, to draft the filing. The court was alerted to problems in April, when it questioned Kachouroff about the document’s credibility.

The attorneys later admitted to using AI and claimed the erroneous brief was an unintentional submission of an earlier draft. They sought to submit a corrected version and avoid disciplinary measures.

Judge Nina Wang rejected the attorneys’ explanation, finding their claim unsupported by the evidence. Despite email exchanges referencing a “final” version, the court determined the brief submitted was essentially identical to what was shared internally, errors and all.

The revised document appeared to be created only after the court’s inquiry, raising doubts about the credibility of the lawyers’ defense. Ultimately, the judge fined Kachouroff and his firm $3,000, and DeMaster another $3,000. Lindell and MyPillow were not sanctioned.

Lawyers take heed. Generative AI can streamline research and drafting, but human oversight is required. Courts expect attorneys to verify citations and uphold ethical standards regardless of the tools used. Failure can result in financial penalties and adverse publicity.