Some Communications by Rabbi Shmuley with AI Platforms May Be Discovered in Order to Determine Punitive Damages

From Wednesday's decision in Fontainebleau Florida Hotel, LLC v. Botach [Rabbi Shmuley], decided by Magistrate Judge Marty Fulgueira Elfenbein:

Plaintiff's four subpoenas to the AI Providers and its Seventh RFP seek the same information, specifically Defendant's communications with AI platforms since December 3, 2024, concerning various categories of subjects:

1. All of Defendant's AI Communications with AI since December 3, 2024, concerning or relating to the Fontainebleau Hotel.
2. All of Defendant's AI Communications with AI since December 3, 2024, concerning or relating to this litigation.
3. All of Defendant's AI Communications with AI since December 3, 2024, concerning or relating to counsel for Plaintiff.
4. All of Defendant's AI Communications with AI since December 3, 2024, concerning or relating to any employee, owner, or representative of the Fontainebleau Hotel.
5. All of Defendant's AI Communications with AI since December 3, 2024, concerning or relating to any Court Order entered during this litigation.
6. All of Defendant's AI Communications with AI since December 3, 2024, concerning or relating to Judge K. Michael Moore or the undersigned.

In addition, to these six categories, Plaintiff seeks one more category of documents in the subpoenas to the AI providers (but not in the Seventh RFP), consisting of:

7. All of Defendant's AI Communications regarding Requests 1 through [6] that have, since their creation, been deleted….

Plaintiff [argued] that Defendant's AI communications may reveal the extent of his alleged malice toward Plaintiff, the intentionality underlying his conduct, and evidence relevant to the determination of punitive damages, including whether an exception to Florida's statutory cap applies….

Federal Rule of Civil Procedure 26(b)(1) permits discovery of nonprivileged matters relevant to a party's claims or defenses and proportional to the needs of the case. The Rule expressly recognizes that information within the permissible scope of discovery need not be admissible in evidence to be discoverable…. The District Court's Order at ECF No. [261], which authorized the Parties to conduct "discovery limited to damages," also governs the scope of discovery at this juncture…. Thus, the relevant inquiry is whether the particular AI communications sought by Plaintiff bear a sufficient relationship to the damages issues remaining in this action….

The degree of reprehensibility, the defendant's intent, and the circumstances surrounding the wrongful conduct are … relevant to determining an appropriate punitive-damages award…. To the extent Defendant used AI platforms to generate, revise, or refine statements concerning Plaintiff, its counsel, or its representatives, those communications may reveal not merely the final content of Defendant's statements but also the purpose for which the statements were created, the instructions Defendant supplied, and the effects he sought to achieve. Such information may provide evidence of the intent underlying Defendant's conduct that cannot necessarily be discerned from the resulting public statements alone. The Court does not determine that those communications will establish malice or specific intent to harm; it determines only that they bear a sufficient relationship to those disputed damages issues to warrant discovery….

According[] to Defendant, his alleged hostility does not necessarily prove constitutional actual malice, and it therefore should not be considered when deciding whether punitive damages are appropriate. Constitutional actual malice in a defamation action concerns knowledge of falsity or reckless disregard for truth. By contrast, the reprehensibility inquiry and the specific-intent exception under section 768.73(1)(c) require consideration of the defendant's culpability and intent to harm the claimant. Evidence of hostility, planning, or deliberate efforts to inflict or amplify injury to Plaintiff may be relevant to those questions when sufficiently connected to the alleged wrongful conduct here.

Plaintiff seeks evidence not simply to establish that Defendant disliked the Hotel, but to determine whether Defendant deliberately engaged in conduct intended to cause injury and whether that intent bears on the reprehensibility and statutory treatment of the punitive damages sought. The Court therefore rejects Defendant's argument that because hostility does not necessarily prove constitutional actual malice, it should not be considered when deciding whether punitive damages are appropriate.

Nor does the fact that some requested communications postdate the original publications render them categorically undiscoverable. Subsequent statements and conduct may, depending on their content and context, provide circumstantial evidence of a defendant's earlier intent or reveal a continuing course of conduct relevant to the injury. The temporal relationship between a communication and the alleged injury may affect its probative value, but it does not create an absolute bar to discovery….

The Court does not hold that every subsequent statement by Defendant may support an award of punitive damages. The Supreme Court has cautioned that punitive damages may not be used to punish a defendant for unrelated or dissimilar conduct merely because that conduct reflects poorly on the defendant's character. But the permissible scope of discovery is broader than the scope of evidence that may be ultimately admitted at trial. The present inquiry is whether the requested information is relevant and proportional under Rule 26(b)(1) to the damages issues remaining in this case.

Here, Plaintiff alleges a continuing course of conduct directed toward the Hotel, its personnel, and its representatives, including conduct involving AI-generated content. Plaintiff has also identified testimony from its damages expert concerning the alleged cumulative effect of Defendant's continuing online activity on the Hotel's reputation and business. As such, Defendant's communications with AI platforms concerning the Hotel and the Hotel's employees, owners, or representatives, including Plaintiff's counsel, may reveal information relevant to Defendant's alleged intent to harm Plaintiff, the nature and persistence of the challenged conduct, and the extent to which that conduct allegedly amplified Plaintiff's injuries. The Court therefore concludes that Request Nos. 1 (seeking AI communications about the Hotel), 3 (seeking AI communications about Plaintiff's counsel), and 4 (seeking AI communications about any employee, owner, or representative of the Hotel) in the subpoenas to the AI providers and the Seventh RFP fall within the scope of damages discovery authorized by the District Court….

Further, to the extent Request No. 7 in the subpoenas to the AI providers … seeks Defendant's AI communications regarding Requests Nos. 1 through [6] that have been deleted since their creation, the Court concludes that this Request is authorized by the District Court's Order only to the extent it seeks any deleted AI communications regarding Request Nos. 1, 3, and 4….

But the court rejected the other requests, which dealt with AI communications "concerning or relating to this litigation" (2), "concerning or relating to any Court Order entered during this litigation" (5), and "concerning or relating to Judge K. Michael Moore or the [Magistrate Judge]" (6):

Starting with Request No. 2 in the subpoenas and the Seventh RFP, it seeks all AI communications concerning or relating to "this litigation." That formulation is exceptionally broad. It encompasses potentially every AI exchange on matters having no meaningful connection to the amount of damages or Defendant's alleged intent to harm Plaintiff. Plaintiff has not established that every communication relating to this litigation bears on an issue remaining for the damages trial….

Turning to Request No. 5 in the subpoenas and the Seventh RFP, it seeks all AI communications concerning or relating to any Court Order entered during this litigation. Such communications may include Defendant's attempts to understand an Order, research its consequences, consider procedural options, or evaluate the litigation. The fact that Defendant may have expressed disagreement with, frustration about, or hostility toward a Court Order does not, without a sufficient connection to the alleged injury, make the communication relevant to Plaintiff's damages. Although Plaintiff contends that Defendant's reactions to Court Orders reflect the depth of his hostility and the reprehensibility of his conduct, that theory is too attenuated to justify discovery of every AI exchange concerning every Order entered in this case. The Court therefore finds that Request No. 5 exceeds the permissible scope of damages discovery.

Finally, Request No. 6 in the subpoenas and the Seventh RFP seeks all AI communications concerning or relating to District Judge K. Michael Moore or the undersigned Magistrate Judge. The Court likewise finds that Defendant's private communications with AI platforms concerning judicial officers, without more, do not bear a sufficient relationship to the damages Plaintiff seeks for the alleged harm to the Hotel. The discovery inquiry is not whether Defendant has criticized the judiciary; it is whether the requested information is relevant and proportional to the damages issues remaining in this action. A request encompassing every AI communication about the judges presiding over this litigation exceeds that scope. The Court thus finds that Request No. 6 exceeds the permissible scope of damages discovery.

The Court recognizes Plaintiff's argument that Defendant's criticism of the judicial process may demonstrate the persistence of his alleged hostility. But the Supreme Court has cautioned against using dissimilar conduct as a basis for punishing a defendant for being an objectionable person rather than for the conduct that injured the plaintiff….

And the court rejected the argument that the communications were categorically "protected work product":

Federal Rule of Civil Procedure 26(b)(3)(A) generally protects "documents and tangible things that are prepared in anticipation of litigation or for trial by or for another party or its representative." The doctrine is designed to protect the adversarial process by preserving the privacy necessary for litigation preparation….

The Eleventh Circuit's interpretation of Rule 26(b)(3)(A) confirms that work-product protection is not limited to materials prepared by counsel but extends to materials prepared by or for a party or its representative in anticipation of litigation….

When determining whether a document is protected under the work-product doctrine, "litigation need not necessarily be imminent … as long as the primary motivating purpose behind the creation of the document was to aid in possible litigation." The document must have been "created principally or exclusively to assist in anticipated or ongoing litigation." "Just because a document may have been used later to assist in litigation … does not mean it was principally prepared for such purpose." …

Here, communications independently generated by Defendant to create, revise, or disseminate content concerning the Hotel, its personnel, or Plaintiff's counsel are not transformed into attorney work product merely because Defendant is a litigant or because the resulting content may bear on this action. To the extent such communications were created for the purpose of producing public-facing statements or pursuing Defendant's independent activities, rather than preparing the defense of this litigation, they ordinarily would not satisfy Rule 26(b)(3)(A). The Court therefore rejects Defendant's blanket work-product objection to Request Nos. 1, 3, 4, and 7.

However, that conclusion does not foreclose a properly supported, document-specific claim of protection. If a particular communication was prepared because of this litigation and otherwise satisfies Rule 26(b)(3), Defendant may assert the protection in accordance with the Federal Rules. Defendant must, however, identify the withheld material and describe the nature of the asserted protection sufficiently to permit Plaintiff to assess the claim without revealing the protected information itself….

[I]f Plaintiff serves the subpoenas on the AI providers and requires them to produce the document directly to Plaintiff's counsel, Defendant will be deprived of the opportunity to determine whether there are any work-product protected documents within the production that should otherwise be withheld and identified on a privilege log. For that reason, the Parties are DIRECTED to meet and confer to discuss the logistics of how the AI providers, to the extent they have responsive materials, will be instructed to produce such materials….

Some backstory on the lawsuit from an earlier post, Magistrate Judge Recommends Massive Sanctions on Rabbi Shmuley Boteach for Violating Court Order in Anti-Semitism Lawsuit (District Judge K. Michael Moore had since adopted the Magistrate Judge's Report):

This case arises from an incident that occurred at the Fontainebleau Florida Hotel …. Plaintiff alleges that the following events occurred:

After more than an hour of loitering, Defendant Boteach engaged in an uneventful conversation with a registered guest of the Hotel and the two parted ways. More than an hour later (after midnight on Sunday, December 2, 2024), Defendant Boteach engaged in a verbal altercation with the same registered guest wherein the guest and Defendant Boteach exchanged hateful words at each other.

The guest used language that was heinous and accused Defendant Boteach of being a "baby killer" and other words that are easily interpreted as antisemitic. Defendant Boteach, in turn, hurled anti-Islamic words at the registered guest and repeatedly shouted, "Allahu Akbar? Are you going to blow yourself up or something? … he uses the expressions of, like, suicide bombers." Within hours, Defendant Boteach posted an edited video of the exchange on Instagram and began his campaign of threats against the Hotel, its ownership, its outside lawyer, and its employees—who had nothing to do with the altercation except that Hotel security de-escalated and ended it.

Plaintiff alleges that following the altercation, the Defendant, who the FAC [First Amendment Complaint] describes as a "social media influencer and rabbi" with "hundreds of thousands of social media followers[,]" went on a "multi-week assault on the [Hotel], its personnel, and representatives—creating AI videos purporting to show them celebrating antisemitism, comparing them to Nazi collaborators, falsely accusing them of banning Jews from the property, and fabricating statements that they embraced a policy of Judenrein, i.e., the extermination of six million Jews." The FAC alleges that Defendant falsely stated that he was denied entry to the Hotel because he is "too Jewish," that the Hotel refused to cooperate with law enforcement's investigation of the incident, and that he "was trespassed from the Hotel for being 'too Jewish[.]'"

Plaintiff further alleges that "Defendant Boteach published a statement that, in part, called for guests 'who have booked' at the Hotel to 'cancel your reservations'" and to "'be smart and cancel and give your hard-earned money to a hotel that doesn't abide antisemites.'" Moreover, Plaintiff alleges:

At all hours of the day and night, Defendant Boteach proceeded to harass the Hotel and its representatives. For example, he posted a "headshot" photograph of the head of the Hotel's outside counsel with the words "DIGITALLY DECAPITATED" and later, at 3:49 am, menacingly threatened that counsel was "about to have a really interesting Shabbat" when he arrived at his synagogue, which Defendant Boteach identified by name and location. Defendant Boteach directly contacted counsel's clergy and posted harassing images of them.

That post also explains the Magistrate Judge's conclusion that the defendant had repeatedly and willfully violated a court order, and therefore ought to have default judgment entered against him as to liability (with further proceedings to take place as to damages).

Sean Alexander Burstyn (Burstyn Law PLLC), Christopher Ara Ajizian (Christopher Ajizian P.A.) and Todd Rapp Friedman represent the hotel.

The post Some Communications by Rabbi Shmuley with AI Platforms May Be Discovered in Order to Determine Punitive Damages appeared first on Reason Magazine.