A federal court prices an unchecked AI legal workflow: $3,000 sanctions each for the attorneys behind an AI-drafted brief with nearly thirty defective citations

The problem

Generative AI drafts legal prose that reads like law and cites like law, whether or not the law exists. The failure mode is invisible to a reader who does not check, and in February 2025 it reached a federal courtroom: defense counsel for Michael J. Lindell, FrankSpeech LLC, and My Pillow, Inc. in Eric Coomer’s defamation suit filed an opposition brief that had been run through AI and never citation-checked (source).

This is a verified negative: an independent federal court, in signed public orders, measured what that workflow produced and priced it.

What the court found

At the April 21, 2025 hearing, Judge Nina Y. Wang identified nearly thirty defective citations in the February 25, 2025 opposition brief (source). The defects, in the court’s words, were “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” (source).

The colloquy that followed is the record’s core artifact (source):

THE COURT: Was this motion generated by generative artificial intelligence? MR. KACHOUROFF: Not initially. Initially, I did an outline for myself, and I drafted a motion, and then we ran it through AI. THE COURT: And did you double-check any of these citations once it was run through artificial intelligence? MR. KACHOUROFF: Your Honor, I personally did not check it. I am responsible for it not being checked.

Counsel’s later explanation, that an earlier draft had been filed by mistake, did not persuade the court, which noted the contradictory statements and the lack of corroborating evidence (source).

The outcome

What the brief contained, per the court: nearly thirty defective citations in a single opposition brief, ranging from misquotes to citations of cases that do not exist (source).

The sanction: $3,000 against Kachouroff and his firm jointly and severally, and $3,000 against DeMaster individually, imposed under Rule 11(c)(1) and payable to the court’s Registry by August 4, 2025 (source). The court called the fines “the least severe sanction adequate to deter and punish defense counsel in this instance” and wrote that it “derives no joy from sanctioning attorneys who appear before it” (source).

On July 7, 2025, the court made its Order to Show Cause absolute and found that both attorneys violated Rule 11 because they “were not reasonable in certifying that the claims, defenses, and other legal contentions” in the brief “were warranted by existing law or by a nonfrivolous argument” for changing it (source).

Scope matters: the sanctions landed on counsel only (source). Because Kachouroff confirmed he had not told his clients he uses AI tools in his practice, the court did not extend the sanctions to Lindell, FrankSpeech, or My Pillow (source).

How this was verified

Both court orders, the Order to Show Cause [Doc. 309, 2025-04-23] and the sanctions order [Doc. 383, 2025-07-07] in D. Colo. No. 1:22-cv-01129-NYW-SBP, were read from the public RECAP archive and byte-tied (SHA-1 matching the Wayback CDX digest) to same-day Wayback captures. On 2026-08-13 the quoted colloquy, the “nearly thirty defective citations” language, the “least severe sanction” and “derives no joy” quotes, and the $3,000-each figure were re-checked live against the Volokh Conspiracy (Reason, Eugene Volokh) and Associated Press relays; all held.

Every figure here originates with an independent measurer, a federal judge with no stake in AI vendors or in the litigants’ marketing, which is what makes this one of the rare AI-outcome records whose critical numbers do not come from the party that deployed the system. Two things are deliberately not claimed: the exact underlying jury-verdict figure (the Associated Press reports it as “more than $2 million”), and the separate May 2026 order that added a further $5,000 penalty for repeated mis-citation, which is a later, distinct order and is not folded into the $3,000 figure above (source).

Related case files

The same admission-then-sanction pattern runs through Wadsworth v. Walmart, where attorneys at a large plaintiffs’ firm drew Rule 11 sanctions for AI-hallucinated citations they had not checked. It scales up in Lacey v. State Farm, where a special master imposed far larger sanctions on well-resourced firms for the same failure to verify AI output. And Johnson v. Dunn shows the professional cost climbing past a fine: there the attorneys were disqualified and referred, not merely sanctioned.

Sources

Tiers: Tier 1 primary (court order or docket); Tier 2 strong secondary (independent press naming the parties). Figures re-checked live on 2026-08-13.

1. U.S. District Court for the District of Colorado, Coomer v. Lindell docket and orders (Order to Show Cause [Doc. 309], 2025-04-23; sanctions order [Doc. 383], 2025-07-07), No. 1:22-cv-01129-NYW-SBP (Tier 1, primary court record). https://www.courtlistener.com/docket/63296393/coomer-v-lindell/
2. Reason, The Volokh Conspiracy (Eugene Volokh), “$6K Sanctions for Apparent AI Hallucinations in Coomer v. Lindell / My Pillow Election-Related Libel Suit,” 2025-07-07 (Tier 2, law professor relaying and quoting the primary order). https://reason.com/volokh/2025/07/07/6k-sanctions-for-apparent-ai-hallucinations-in-coomer-v-lindell-my-pillow-election-related-libel-suit/
3. Associated Press (via Yahoo News), “Lawyers for MyPillow CEO fined thousands over error-strewn AI court filing about defamation case,” 2025-07 (Tier 2, independent wire naming the parties and the amounts). https://www.yahoo.com/news/lawyers-mypillow-ceo-fined-thousands-225045130.html
4. Reason, The Volokh Conspiracy, “$5K Sanctions for Repeated Mis-Citation in Coomer v. Lindell / My Pillow Election-Related Libel Suit,” 2026-05-09 (Tier 2, context for the separate later order, not part of the $3,000 figure). https://reason.com/volokh/2026/05/09/5k-sanctions-for-repeated-mis-citation-in-coomer-v-lindell-my-pillow-election-related-libel-suit/