You’ve probably seen the headlines about Mike Lindell’s legal drama, but the weirdest twist didn't come from a stump speech or a pillow commercial. It came from a computer. Specifically, it came from a legal brief filed by his own attorneys that was so full of "hallucinations" it looked more like a sci-fi script than a court document.
The mypillow defamation case ai-generated motion became a massive cautionary tale for the legal world in 2025. It wasn't just a small typo or a misplaced comma. We are talking about nearly 30 citations for cases that simply do not exist. In the high-stakes world of defamation law, where Lindell was already fighting for his business's life, this was basically like bringing a plastic knife to a gunfight.
The Motion That Wasn't Real
In February 2025, Mike Lindell’s legal team filed an opposition to a motion in limine. The case involved Eric Coomer, a former executive at Dominion Voting Systems, who sued Lindell for defamation. Coomer claimed Lindell’s accusations of election rigging had essentially destroyed his life.
The defense team, led by attorneys Christopher Kachouroff and Jennifer DeMaster, needed to push back. Instead of traditional research, they apparently turned to generative AI tools like Microsoft’s Co-Pilot, Google Gemini, and Grok.
The result? A disaster.
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Judge Nina Y. Wang, presiding over the U.S. District Court in Denver, noticed something fishy pretty fast. She found citations to cases with names that sounded legitimate but weren't in any database. The brief even misquoted real case law, attributing legal principles to judges who never said them.
Honestly, it’s the kind of mistake that makes every first-year law student wake up in a cold sweat.
Why the Judge Wasn't Buying the Excuses
When the court initially flagged these "defective citations," the lawyers tried to play it off as a clerical error. Their story was that they had a "final" version and a "draft" version, and—oops—someone clicked the wrong file.
Kachouroff even claimed he was on vacation in Mexico when the filing happened. He told the court he hadn't even heard the term "generative artificial intelligence" before.
Judge Wang wasn't having it.
She looked at the metadata. She looked at the internal emails. She found that the "corrected" version they tried to submit later only seemed to exist after she had already pointed out the errors. The judge called their explanations "troubling" and "contradictory." Basically, she felt they weren't being straight with the court.
The $6,000 Price Tag for a Chatbot
On July 7, 2025, the hammer finally dropped. Judge Wang sanctioned Kachouroff and DeMaster, ordering them to pay $3,000 each. While that might not sound like a lot compared to the $2.3 million defamation verdict Lindell eventually faced in the Coomer case, the reputational damage to the lawyers was way worse.
- Rule 11 Violations: The judge ruled they violated Federal Rule of Civil Procedure 11, which requires lawyers to certify that their legal contentions are "warranted by existing law."
- The Hallucination Problem: The "hallucinations" included fake case names like Timothy Leary v. Sgt. Pepper (an illustrative example of how wild these things can get) and references to courts that don't have jurisdiction over the matters discussed.
- Lack of Oversight: The biggest issue wasn't using the AI; it was the fact that nobody checked the work. Kachouroff admitted he hadn't verified the citations before they were filed.
It’s a classic case of "trust but verify," except they skipped the "verify" part entirely.
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What This Means for the Future of Law
The mypillow defamation case ai-generated motion isn't just a funny anecdote. It highlights a massive shift in how courts handle technology.
A lot of people think AI is going to replace lawyers. Maybe. But right now, it’s mostly just making them look bad if they get lazy. Judges across the country are now requiring "AI disclosure" forms where lawyers have to swear they didn't use a chatbot to invent their arguments.
The legal world is kind of split on this. Some say AI is an incredible tool for organizing thoughts. Others, like Judge Wang, see it as a minefield of "gross carelessness."
Actionable Insights for Using AI in High-Stakes Work
If you’re using AI for anything where the facts actually matter—like a legal filing, a medical report, or even a big business proposal—you've got to be smart about it.
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- Never trust a citation. If an AI gives you a link or a case name, assume it's fake until you see it on a government website or a trusted database like Westlaw.
- Check the "Logic Gap." AI often writes sentences that sound perfect but mean nothing. Read your work out loud to see if it actually makes sense.
- Disclose when necessary. If you’re in a field with strict ethics (like law or journalism), being upfront about using AI is always better than being caught in a lie later.
- Metadata matters. Remember that every digital file has a history. If you claim you wrote something in February but the file was created in April, the "clerical error" excuse isn't going to fly.
The Lindell case proved that while "the dog ate my homework" didn't work in third grade, "the AI wrote my brief" doesn't work in federal court either.
Ultimately, Mike Lindell’s legal troubles continue, but his lawyers’ run-in with AI will be cited in law school textbooks for years to come. It’s a reminder that no matter how fast the tech moves, the person signing the document is the one who pays the price when things go sideways.
To avoid similar pitfalls in your own professional documentation, always cross-reference AI-generated citations against primary sources and maintain a clear version-control log for all legal or official filings.