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AI in Court

"The AI Data Will Provide an Unrivaled View into the Mind of a Defendant …"

"whose [mental state] is itself the measure of Plaintiff’s [punitive] damages."

Eugene Volokh | 10.19.2026 9:42 AM

That's part of libel plaintiff's argument(filed last week) for subpoenaing defendant's AI queries in Fontainebleau Florida Hotel, LLC v. Botach; the defendant is popularly known as Rabbi Shmuley Boteach. From the introduction:

The Court asked whether Botach's communications with AI platforms fall within the scope of "damages" discovery permitted by ECF No. 261, and specifically how those materials relate to malice and the statutory cap on punitive damages. Precedent from the United States Supreme Court and Eleventh Circuit, as well as Florida law, answers that question directly.

Under Fla. Stat. § 768.73(1)(c), the cap on punitive damages lifts entirely where the fact finder determines that "the defendant had a specific intent to harm the claimant" at the time of the injury. As discussed below, legions of cases from trial courts to the Supreme Court hold that post-defamation conduct is probative of whether defamatory statements were made with intent to harm. Specific intent is therefore not background color to the damages trial or damages discovery. Discovery into Botach's intent to harm Plaintiff is damages discovery, and the AI materials are the most direct evidence of that intent.

Botach did not merely publish an errant falsehood on a blog or make a heated statement in a debate. He methodically engineered his attacks—drafting, refining, and iterating for painful effect through the most potent technologies known to humankind. The prompts and chats are his mental state reduced to writing, and they are probative of damages.

And from the defendant's response:

The Court should sustain the objections to the proposed AI-provider subpoenas as drafted and apply the same limits to the overlapping Seventh Request for Production. The issue is whether these demands fall within the scope of "discovery limited to damages." The unresolved punitive amount permits discovery concerning punishment for the adjudicated wrong, not an unrestricted inquiry into Defendant's research or litigation conduct.

The amended complaint already alleges knowing falsity, deliberate fabrication, repeated publication, financial motive, and specific intent to harm. Plaintiff did not pursue AI discovery before the general discovery cutoff. But under the guise of "discovery limited to damages," Plaintiff seeks every responsive AI exchange concerning this litigation, the Hotel, Plaintiff's lawyers, every court order, and the judges. It reaches accounts associated with an expansively defined "Botach," without limiting production to his queries or material used in the actionable publications. The Court should enforce the reopening order before requiring any production and independently preserve substantiated work-product objections.

For more backstory on the case, an excerpt from the long Report and Recommendation issued July 29 by Judge Marty Fulgueira Elfenbein in Fontainebleau Florida Hotel, LLC v. Botach:

This action arises from an encounter between Defendant and then-hotel guest Faiz Akbar … in the lobby of Plaintiff's hotel in December 2024. The Parties sharply dispute the nature of the encounter, who initiated or escalated it, and whether Plaintiff responded appropriately to Defendant's subsequent complaints.

Plaintiff's operative First Amended Complaint alleges that Defendant published false statements concerning the incident and Plaintiff's response to it, including statements that Plaintiff discriminated against Defendant because he is Jewish, knowingly permitted an antisemitic assault to occur on its premises, removed Defendant rather than the alleged aggressor, and refused to cooperate with law enforcement. Based on those allegations, Plaintiff asserts claims against Defendant for defamation and tortious interference with business relationships.

Defendant filed a Counterclaim and Third-Party Complaint asserting claims against Plaintiff and naming Jeffrey Soffer … and Akbar as Third-Party........

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