The Volokh Conspiracy

Mostly law professors | Sometimes contrarian | Often libertarian | Always independent

AI in Court

"As Colossal a Collection of Excuses and Projection as the Court Has Seen in 25 Years on the Bench," Says Court About Lawyer's Response in Fabricated Citation Dispute

|The Volokh Conspiracy |


From The Doc App, Inc. v. Leafwell, Inc., decided Nov. 26 by Judge Sheri Polster Chappell (M.D. Fla.):

The Court finds that Mr. Castro violated Rule 11(b) in filing the Motion for TRO and imposes sanctions. His motion contained fabricated citations, citations that do not contain quoted language, and citations that do not relate to the purported proposition. While Mr. Castro purports to "own" his mistakes and uses words like "respectfully," his defiant tone and condescending communications with and about his opposing counsel, Jody A. Stafford, undermine any supposed respectful sentiment. Rather than take responsibility for the legal inaccuracies permeating his Motion for TRO, Mr. Castro's response to the Order to Show Cause is as colossal a collection of excuses and projection as the Court has seen in 25 years on the bench.

Here are a few examples. He claims that Henson v. Allison Transmission, Inc. exists. The Court checked his original citation in the Motion for TRO. The Henson citation in the original motion—No. 6:16-cv-1223-Orl-41DCI, 2017 WL 59085 (M.D. Fla. Jan. 5, 2017)—does not exist. Sidestepping the issue, Mr. Castro explains that he intended to cite Henson v. Allison Transmission, No. 07-80382-CIV, 2008 WL 239153 (S.D. Fla. Jan. 28, 2008). That case does exist. But it does not matter what counsel intended to cite. It is neither the Court's nor opposing counsel's job to identify his fake citations and intuit what he meant.

Anyway, the Court read the version of Henson that Mr. Castro claims stands for the proposition that a party may pursue injunctive relief when continued harm to its business and customer base is likely without court intervention. It discusses the court's authority to act where equity demands it, even in early stages of litigation. The citation error was clerical—not substantive….

Defendant argues that this version "does not concern injunctive relief whatsoever." Yet again, Defendant is correct. Mr. Castro's inaccurate characterization of Henson is beyond perplexing. The Henson he intended to cite does not stand for the proposition in his original explanatory parenthetical: "conduct violating established regulations is unfair under FDUTPA." Rather, Henson concerns a plaintiff's request to review his lemon law case and involves breach of warranty-based claims, the Magnuson-Moss Warranty Act, and the Uniform Commercial Code. See Henson, 2008 WL 239153, at *2. The word "injunction" does not appear once. Nor do the terms "unfair," "deceptive," "FDUTPA," or "regulation." Ultimately, Mr. Castro misrepresents Henson to the Court not once, but twice.

Next, the Court observed that Plaintiff's citation to State Farm Mut. Auto. Ins. Co. v. Pressley, 727 So. 2d 1019, 1020 (Fla. 3d DCA 1999), yields nothing in a Westlaw search. In response, Mr. Castro says that the case does exist, but he meant to cite 28 So. 3d 105 (Fla. 1st DCA 2010). Again, he attaches the case to his response and claims the "citation error was clerical, not substantive." The Court disagrees.

The citation to 727 So. 2d 1019, 1020 (Fla. 3d DCA 1999) and not 28 So. 3d 105 (Fla. 1st DCA 2010) is no mere clerical error. Mr. Castro cited the wrong reporter, court, and year, and the supposedly correct case does not contain the phrase that he quoted ("any form whatsoever") or mention the statute he claims the case concerns (Fla. Stat. § 817.505). This goes well beyond a clerical error. Thus, his assertion that "Pressley supports the proposition for which it was cited" is another misrepresentation to the Court.

Third, the Court confirmed that Mr. Castro quoted language that did not appear in at least two cases cited. Mr. Castro attempts to explain this away, saying he "inadvertently" filed an early draft of the motion and did not remove the quotation marks after converting the quotations to paraphrases. But these are not—as Mr. Castro describes—mere "formatting" or "drafting error[s]." Rather, they are repeated representations by a lawyer to the Court that cases contain specific language when they do not. If these were the only issues with the motion, perhaps the Court might be more lenient. But in the context of the litany of misrepresented authority, leniency is not the order of the day.

Mr. Castro blames the serious issues in his motion on mistakes, inadvertent filings, and clerical errors, among other things. In his response to the Court, he doubles down, concluding "[t]here is no misconduct to explain or address." For all the reasons discussed above, the Court is unconvinced. So what really happened?

Defendant posits he used artificial intelligence ("AI") to draft his filings, but Mr. Castro remains silent on his use of AI to litigate this case in his response to the Order to Show Cause. This silence particularly troubles the Court, as Mr. Castro's excuses about how the Motion for TRO could possibly contain so many misrepresentations simply make no sense. His reckless use of AI, however, would explain things.

Mr. Castro conceded in an email to opposing counsel that he uses "AI tools only to assist with drafting and document organization … but all legal analysis and final language are human-authored and attorney-verified." Further, he stated that he checks his work by pulling every case from Westlaw, opens it in full text, reviews it for context, accuracy, and proper pin cites. He adds that "[e]ach quoted passage is compared word-for-word to the official reporter," and he "then run[s] Quick Check/KeyCite to confirm that every authority is valid and correctly characterized." Given the volume and nature of the misrepresentations in the Motion for TRO and his response to the Court, these statements made to opposing counsel lack any credibility. The Court finds that he has taken no responsibility for his actions.

To wit, Mr. Castro turns his unconvincing defense into blustering offense, asking the Court to impose sanctions on Defendant under Rule 11(c)(2). He baselessly accuses Ms. Stafford of lacking professionalism, lacking candor toward the Court, and mischaracterizing the record. The Court will not entertain his meritless request any further.

In sum, the Court is unpersuaded that Mr. Castro's misrepresentations of legal authority resulted from mere errors. Every lawyer is an officer of the court and always has a duty of candor to the tribunal. "Citing imprecise, non-existent legal authority breaches [a litigant's] duty of candor." His misrepresentations constitute "repeated, abusive, bad-faith conduct that cannot be recognized as legitimate legal practice and must be deterred."…

Mr. Castro's misrepresentations to the Court and refusal to take responsibility for them require strong sanctions. Accordingly, Mr. Castro must pay Defendant its attorneys' fees and costs incurred in responding to the Motion for TRO and in compiling and submitting any ensuing fee application within 45 days. Additionally, the Court determines that his referral to the Florida Bar for appropriate discipline and other sanctions listed below are appropriate….

The "other sanctions" included (1) a provision that if the lawyer litigates any case in the Middle District of Florida, "he must attach a copy of this Order to his Complaint or Notice of Removal," and (2) a requirement that the lawyer sent a copy of the order to the CEO of his client, and "must file on the docket a notarized affidavit from [the CEO] confirming he has read the Order."

The lawyer has filed a response, which strikes me as having a quite different note from his earlier response to the original Order to Show Cause; an excerpt from this new response:

The Court has imposed serious sanctions on undersigned arising from citation and quotation errors in Plaintiff's motion for temporary restraining order ("TRO"). Those errors were real, serious, and my responsibility alone. I do not minimize them. I accept the Court's finding that my handling of authorities in that filing fell below the standard expected of a member of this bar and warrants sanction.

This motion is not an attempt to relitigate the underlying dispute between The Doc App, Inc. ("Plaintiff") and Leafwell, Inc., nor an attempt to erase the Court's Rule 11 finding. It is a narrow request that the Court reconsider (1) the extent to which the sanctions rest on matters that were not identified in the Court's Order to Show Cause ("OSC"), and (2) the breadth of the sanctions imposed—particularly the two-year requirement to attach the sanctions order to every new case, the compelled client affidavit, and the bar referral—because, with respect, those measures reach beyond what is necessary to deter repetition of the citation misconduct at issue….

In [its] sanctions order, the Court understandably scrutinized the TRO filings. But the order also relied heavily on additional categories of information that were not identified in the OSC:

  1. The tone and content of undersigned's email and conferral communications with defense counsel regarding the citation issues;
  2. Undersigned's purported use of AI tools, which the Court treated as the principal explanation for the errors and as a basis to doubt undersigned's candor; and
  3. Conclusions that undersigned's explanations "lacked credibility" and

reflected a failure to take responsibility….

Undersigned acknowledges that some sanction is warranted. In particular, a fee-shifting award for Defendant's reasonable costs and fees incurred responding to the citation issues in the TRO filing, and a requirement that undersigned complete additional ethics and technology training, are appropriate, direct responses to the conduct at issue and serve clear deterrent and remedial purposes.

By contrast, the combination of: (a) a multi-year requirement to brand every future case in this District with this order, regardless of subject matter; (b) a compelled notarized affidavit from Plaintiff's principal; and (c) a formal bar referral with transmission of the entire record, goes substantially beyond what is necessary to deter future citation errors. These measures are reputational and collateral in nature, with long-term consequences for undersigned's professional standing that are disproportionate to the misconduct found, especially in light of remedial steps already undertaken and the absence of any prior disciplinary history….

[U]ndersigned respectfully asks that [the two-year] branding requirement be stricken as unnecessary to deter and unduly punitive. It also burdens Plaintiff, which has its own reputational and commercial interests and objects to having its business forcibly associated, in future unrelated litigation, with a sanctions order that runs only against counsel….

  • Requirement that undersigned provide the order to his client and file a notarized affidavit from the client—undersigned requests that this be stricken as unnecessary and paternalistic in light of the representations herein that the client has been fully informed, has read the Order, and continues to support counsel's representation. An affidavit has been filed voluntarily out of respect for the Court, notwithstanding undersigned's position that the Court lacks personal jurisdiction to compel such a filing ….
  • Referral of undersigned and the entire record to The Florida Bar—undersigned respectfully requests that this referral be rescinded or, at minimum, narrowly cabined, including by clarifying that any referral is limited to the citation-related conduct described in the OSC and does not rest on disputed inferences regarding email tone or technology use….

[U]ndersigned recognizes the Court's concern that AI tools may have played some role in the flawed citations. To the extent AI-assisted tools were used at any stage, they were used as drafting aids, not as independent sources of law. Undersigned understands that no tool relieves him of his non-delegable duty to personally verify citations and quotations. Regardless of the extent of any AI use, undersigned accepts that his processes in connection with the TRO were inadequate to ensure accurate, court-verifiable citations. In response, undersigned has:

  • Implemented a policy that no case citation or quoted language will be filed unless it has been personally verified against an official reporter or a recognized legal database immediately before filing;
  • Adopted an internal checklist for all dispositive and emergency filings that requires confirmation of every case name, reporter cite, court, year, and quoted passage against the underlying opinion;
  • Prohibited the use of AI tools to generate or edit case citations or quotations in any filing, limiting any AI use to high-level drafting that is then fully vetted against primary sources; and
  • Will enroll in additional continuing legal education focused specifically on legal ethics, candor to the tribunal, and the responsible use of technology in legal practice.