The saga of Mike Lindell, the outspoken MyPillow CEO, took a dramatic turn this week when a Colorado federal judge called out his legal team for submitting an AI-generated brief riddled with errors. On April 27, 2025, reports surfaced that U.S. District Court Judge Nina Wang discovered nearly 30 defective citations in a document filed by Lindell’s attorneys, including references to fictional cases that simply don’t exist. This blunder, tied to a defamation lawsuit from a former Dominion Voting Systems employee, has put Lindell and his lawyers in hot water, with the judge demanding an explanation by May 5 to avoid sanctions or disciplinary action. The incident adds fuel to Lindell’s ongoing legal battles, which have already left him financially strained and his company teetering. Let’s dive into the latest developments shaking up his world.
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Mike Lindell’s AI Brief Debacle
The Colorado court fiasco is the freshest wound for Mike Lindell. His attorney, Christopher Kachouroff, admitted to using generative AI to craft the brief, claiming it was a draft submitted by mistake. Judge Wang wasn’t buying it, noting errors like misquotes and fabricated case law. Kachouroff argued there’s “nothing wrong with using AI when properly used,” but the damage was done. The brief, filed in February, was part of a defense against Eric Coomer, who sued Lindell for defamation over false 2020 election fraud claims. This isn’t Kachouroff’s first embarrassment—last year, he was caught pantsless during a Zoom hearing. The judge’s order for Lindell’s team to justify their actions has sparked debate about AI’s role in legal work and Lindell’s crumbling defense strategy.
Financial Ruin and Mounting Debts
Lindell’s legal troubles are bleeding him dry. In mid-April 2025, he told a Washington, D.C., court he’s “in ruins,” unable to pay a $56,396 sanction to voting software company Smartmatic. Tearfully, he claimed to have “no money,” with only a truck and two houses in liquidation. MyPillow, once a $300 million empire, is now drowning in over $70 million in debt, including $9 million owed to FedEx and nearly $778,000 to DHL. Retailers dropped the brand after Lindell’s election fraud crusade, and a $100 million sales drop forced layoffs and warehouse closures. He even owes the IRS millions from a COVID-era credit. Despite this, Lindell vows to keep fighting, insisting his legal woes are “lawfare” to silence him.
| Lindell’s Financial Woes | Details |
|---|---|
| Total Debt | Over $70 million |
| FedEx Lawsuit | $9 million for unpaid shipping |
| DHL Judgment | $777,729.73 for unpaid bills |
| Smartmatic Sanction | $56,396 (unpaid) |
| IRS Debt | Millions from COVID credit |
Mike Lindell’s Defamation Battles
The defamation lawsuits are at the heart of Lindell’s downfall. Eric Coomer’s case in Colorado accuses Lindell of spreading lies about Dominion’s role in the 2020 election, often paired with MyPillow sales pitches. Smartmatic and Dominion also sued, with Smartmatic’s case leading to contempt rulings for Lindell’s failure to provide financial documents. In March 2025, a Minnesota judge ordered him to turn over website analytics and tax returns, but Lindell claims he’s complied fully. He sees these cases as attempts to muzzle his election fraud narrative, vowing to push for paper ballots and “melt voting machines.” Yet, courts aren’t sympathetic—his “frivolous” counterclaims have only racked up more penalties.
Public Reaction and Political Ties
Public sentiment on X is a mixed bag. Some users mock Lindell’s AI brief blunder, with posts calling it a “hilarious” low point. Others, loyal to his MAGA roots, see him as a victim of political persecution. His ties to Donald Trump, including a 2025 White House appearance, keep him in the spotlight. A Trump appointee even asked the IRS to review Lindell’s audits, raising eyebrows about political favoritism. Despite his claim of living off $1,000 a week, supporters rally behind his defiance, while critics point to his history of false claims, like the debunked Chinese election interference theory that cost him $5 million to a software engineer.
What’s Next for Lindell?
The road ahead looks grim for Mike Lindell. The Colorado court’s May 5 deadline could bring sanctions or even disbarment for his lawyers, weakening his defense. MyPillow’s cash-strapped status makes settling lawsuits unlikely, and Lindell’s refusal to back down suggests more courtroom clashes. He’s hinted at leaving the pillow business for full-time election activism, but with no financial cushion, that’s a risky pivot. The AI brief scandal has also sparked broader questions about technology in law, with experts warning against overreliance on tools prone to “hallucinations.” For now, Lindell’s fighting spirit keeps him in the headlines, but each misstep tightens the noose around his empire.
As the dust settles, Lindell’s story is a cautionary tale of unwavering belief clashing with reality. His supporters see a patriot; detractors, a man undone by his own rhetoric. One thing’s clear: the Mike Lindell saga is far from over, and the world’s watching to see if he can pull off a comeback or sink deeper into the chaos. Stay tuned—his next move could be his boldest yet or his final unraveling.