Judge Nina Wang sanctions MyPillow’s Mike Lindell, Trump ally, over alleged AI-generated legal brief

In a stunning rebuke shaking both political and legal circles, U.S. District Judge Nina Wang sanctioned MyPillow CEO and loyal Donald Trump supporter Mike Lindell on Friday April, 23, 2025 for submitting a sloppy, allegedly AI-generated legal brief riddled with falsehoods and fabricated citations. Critics say it highlights the growing recklessness among Donald Trump’s inner circle.

Lindell, one of Donald Trump’s loudest defenders after the 2020 election, aggressively pushed conspiracy theories claiming widespread election fraud. His crusade to overturn the results has now triggered serious consequences. In the latest Smartmatic defamation lawsuit, Lindell’s legal team filed a bizarre and error-filled brief that Judge Wang described as “frivolous” and “inaccurate.”

Wang’s brief: ‘Citations of cases that do not exist’

Wang’s ruling states, “These defects include but are not limited to misquotes of cited cases; misrepresentations of principles of law associated with cited cases, including discussions of legal principles that simply do not appear within such decisions; misstatements regarding whether case law originated from a binding authority such as the United States Court of Appeals for the Tenth Circuit; misattributions of case law to this District; and most egregiously, citation of cases that do not exist.”

Wang added, “Despite having every opportunity to do so, Mr. Kachouroff declined to explain to the Court how the Opposition became replete with such fundamental errors.”

Judge Wang directly ordered Lindell to pay Smartmatic’s legal fees, marking a major financial setback for the embattled MyPillow founder. Legal experts say the ruling sends a clear message to Trump’s allies: reckless claims and sloppy lawyering will cost dearly.

Lindell’s attorney, Christopher Kachouroff, says it was a mistake

Was about to tweet this—weird how they’re both GOP & not smart.😂

When the hearing on the motion to disqualify DA #FaniWillis resumed today, atty Christopher Kachouroff, who reps Harrison Floyd, was caught on camera w/no pants on right b4 sitting down for his cross examination. pic.twitter.com/DkhKs9nbaX

— M E L L Y med (@mel_med_larson) February 28, 2024

Responding to Wang, Lindell’s attorney Christopher Kachouroff said the brief was an early draft and submitted by mistake, NewsNation reported.  

The AI controversy is not the first Kachouroff trouble. ​During a virtual court session on February 27, 2024, attorney Christopher Kachouroff, representing Harrison Floyd in the Georgia election interference case, appeared on Zoom wearing only a white shirt and light blue boxer shorts. The incident occurred just before his cross-examination, revealing a notably casual approach to courtroom decorum.

Earlier that month, Kachouroff exclaimed “Hate ’em!” during District Attorney Fani Willis’s father’s testimony, forgetting to mute his microphone. Additionally, witnesses saw him use his teeth to open a water bottle cap during the same session.

While permitted in court, legal filings generated — or heavily assisted — by artificial intelligence tools like ChatGPT have created major concerns across the legal community. In Lindell’s case, the alleged use of AI appeared to produce a brief full of made-up case law and factual errors.

In Lindell’s situation, the sanctions add yet another headache to his mounting legal troubles, including previous orders to pay millions in damages related to his election fraud claims. Financially, however, the strain grows heavier. According to Reuters, MyPillow has already lost millions due to Lindell’s political activities and mounting lawsuits.