July 8, 2025

In a turn of events that might make even the most tech-savvy attorney pause, Mike "MyPillow" Lindell's legal team faced sanctions not for the content of their argument, but for how it was prepared. Lawyers Christopher Kachouroff and Jennifer DeMaster were fined $3,000 each after a court determined that their reliance on generative AI led to multiple errors in court filings, including citing non-existent cases.
The issue came to light during a pre-trial motion when Judge Nina Wang pointed out numerous discrepancies in their documents. These included misquotes and misrepresentations of case law, incorrect attributions, and even references to binding authorities that simply did not exist. The errors, according to the court’s findings, stemmed from the lawyers' use of AI in drafting the documents.
This isn't the first instance where reliance on AI in legal proceedings has caused a stir. The legal community has already seen similar cases, such as the 2023 New York case, Mata v. Avianca, where a lawyer faced sanctions for trusting AI-generated, yet fictitious, legal precedents. Despite this, Lindell’s lawyers argued that a "Westlaw Report" had cleared their final brief, which they later admitted was an earlier version filled with the same AI-generated errors.
The fines levied against Lindell's lawyers might seem lenient compared to the potential damage such errors could cause in court decisions. This incident raises significant concerns about the increasing reliance on artificial intelligence in legal documentation and the vital need for thorough human oversight. As technology continues to permeate all aspects of legal work, this case serves as a stark reminder of the importance of traditional verification practices in ensuring accuracy and upholding justice.
This sanction comes amidst other higher-profile penalties for similar AI-related errors, signaling a tougher stance from courts on the need for diligence in legal practice. As we move forward, both the legal profession and AI developers will need to address these challenges to prevent such occurrences from undermining the integrity of legal proceedings.