Nat'l Rifle Ass'n of Am. v. Vullo

both cited the strength and growing intensity of the "social backlash" against the NRA and similar gun-promoting organizations. Id. at 183, 186. Both also declared that the "tragic devastation caused by gun violence . . . is a public safety and health issue," and they reminded regulated entities that "engagement in communities they serve is closely tied to the business they do with their clients and customers and its impact on such communities." Id. at 183; see id. at 186 ("The manner by which financial institutions engage in communities they serve is closely tied to the business they do with their clients and customers and its impact on such communities."). Finally, both of the Guidance Letters declared:

In light of the above, and subject to compliance with

applicable laws, the Department encourages [regulated

institutions] to continue evaluating and managing their

risks, including reputational risks, that may arise from their dealings with the NRA or similar gun promotion

organizations, if any, as well as continued assessment of compliance with their own codes of social responsibility. The Department encourages regulated institutions to

review any relationships they have with the NRA or

similar gun promotion organizations, and to take prompt

actions to managing these risks and promote public health and safety.

Id. at 184, 187.

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E. The Consent Decrees

Although the Press Release and Guidance Letters did not refer to any ongoing investigations into -- or enforcement actions against -- any DFS- regulated institutions, the Carry Guard investigation continued into the spring of 2018. And it ended only when Lockton, Chubb, and Lloyd's all entered into consent orders with DFS on May 2, May 7, and December 20, 2018, respectively. Id. at 156 ¶ 54 (Lockton); id. at 159 ¶ 62 (Chubb); id. at 164 ¶ 74 (Lloyd's) (together, the "Consent Decrees").

In the Consent Decrees, all three entities admitted that some of the NRA-endorsed insurance programs they offered violated New York insurance law and that they engaged in other business with the NRA on terms that violated New York insurance law. See id. at 199-200 ¶¶ 34-40 (Lockton); id. at 215 ¶¶ 18- 19 (Chubb); id. at 234-35 ¶¶ 16-17 (Lloyd's). All three agreed to pay penalties and to limit substantially -- although not entirely -- the ways in which they did business with the NRA and similar entities moving forward. See id. at 200-03 ¶¶ 41-47 (Lockton); id. at 215-17 ¶¶ 20-26 (Chubb); id. at 235-38 ¶¶ 18-26 (Lloyd's).

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II. Procedural History

The NRA filed suit on May 11, 2018, asserting that DFS, Cuomo, and Vullo violated several of its statutory and constitutional rights by engaging in the conduct described above.

In its second amended complaint (the "SAC") filed June 2, 2020, the NRA again alleged that DFS, then-current DFS superintendent Linda A. Lacewell, Cuomo, and Vullo waged a "campaign [that] involve[d] selective prosecution, backroom exhortations, and public threats with a singular goal -- to deprive the NRA and its constituents of their First Amendment rights to speak freely about gun-related issues and defend their Second Amendment freedoms against encroachment." Id. at 135-36. The NRA specifically alleged that Vullo's

"concerted efforts to stifle the NRA's freedom of speech and to retaliate against the NRA" caused "financial institutions doing business with the NRA to rethink their mutually beneficial business relationships with the NRA for fear of monetary sanctions or expensive public investigations." Id. at 167 ¶ 80; see also id. at 152 ¶¶ 42, 44; id. at 168 ¶ 84. Defendants moved to dismiss the SAC in motions filed on June 23, 2020. See id. at 40.

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In an order dated March 15, 2021, the district court dismissed all the claims against DFS, Lacewell, and Cuomo as barred by the Eleventh Amendment, Cuomo, 525 F. Supp. 3d at 403-11, and it dismissed the selective enforcement claim against Vullo on the basis of absolute immunity, id. at 392-400. The court left intact, however, the NRA's First Amendment claims against Vullo, after holding that Vullo was not entitled to qualified immunity on those claims at the motion-to-dismiss stage. Id. at 400-03. Vullo timely appealed that decision on March 22, 2021. App'x at 362.

As noted, this Court reversed the district court's judgment and remanded the case for the district court to enter judgment for Vullo. Vullo I, 49 F.4th at 721. We concluded that the SAC "fail[ed] to plausibly allege that Vullo unconstitutionally threatened or coerced Lloyd's or the other entities to stifle the NRA's speech" because the allegations therein "show[ed] that [Vullo] was simply executing her duties as DFS Superintendent and engaging in legitimate enforcement action." Id. at 719. And we concluded that, even assuming that the NRA sufficiently pleaded a First Amendment claim, Vullo was "nonetheless entitled to qualified immunity because the law was not clearly established and

15

any First Amendment violation would not have been apparent to a reasonable official at the time." Id.

The NRA petitioned the Supreme Court for a writ of certiorari on February 7, 2023, seeking review of our First Amendment and qualified immunity holdings. The Supreme Court granted the NRA's petition on a limited basis, agreeing to hear only its challenge to our First Amendment holding. See Vullo, 144 S. Ct. at 375. And on May 30, 2024, the Supreme Court vacated our judgment and remanded the case, concluding that the NRA plausibly alleged a First Amendment violation. Vullo II, 602 U.S. at 191, 199. The Supreme Court held that any other conclusion was foreclosed by its decision in Bantam Books, Inc.

v. Sullivan, 372 U.S. 58 (1963), which "stands for the principle that a government official cannot do indirectly what she is barred from doing directly: A government official cannot coerce a private party to punish or suppress disfavored speech on her behalf." Vullo II, 602 U.S. at 190. Yet, in reviving the NRA's First Amendment claim, the Supreme Court noted that, on remand, this Court was "free to reconsider whether Vullo is entitled to qualified immunity."

Id. at 199 n.7.

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On remand, we ordered the parties to submit supplemental briefs bearing on the issue of qualified immunity. The parties did so on July 29, 2024. In addition, between October 1 and November 4, 2024, the NRA and Vullo submitted letters citing supplemental authorities pursuant to Federal Rule of Appellate Procedure 28(j). We heard oral argument on November 13, 2024.

D ISCUSSION

Vullo contends on remand that she is entitled to qualified immunity for her challenged conduct notwithstanding the Supreme Court's holding that the NRA plausibly alleged a First Amendment violation. We agree and proceed in two steps. First, although the Supreme Court has held that the NRA plausibly alleged a First Amendment claim, we take up Justice Jackson's invitation to consider separately the NRA's two distinct First Amendment theories:

censorship and retaliation. See Vullo II, 602 U.S. at 203 (Jackson, J., concurring) ("[T]he complaint in this case alleges both censorship and retaliation theories for how Vullo violated the First Amendment."). Second, we consider whether Vullo is entitled to qualified immunity, and we conclude that she is because the law did not clearly establish that her conduct -- which was directed at the nonexpressive conduct of third-party entities within her regulatory sphere --

17

constituted impermissible coercion or retaliation in a manner violative of the First Amendment.

I. The First Amendment

Although the SAC does not clearly set forth separate impermissible coercion and retaliation theories, and the NRA did not argue them as such, it contains sufficient factual allegations to support claims based on both. Compare App'x at 168 (Count One for the "Establishment Of An Implicit Censorship Regime"), with id. at 171 (Count Two for "Retaliat[ion] Against The NRA Based On Its Speech"). We differentiate between First Amendment claims based on impermissible coercion and retaliation theories because the two rest on temporally distinct factual allegations. Coercion involves an attempt to induce or prevent conduct before the fact, and it is unlawful when an official attempts to suppress or compel speech by conveying a threat of adverse action if the target does not comply. See generally Bantam Books, Inc. v. Sullivan, 372 U.S. 58 (1963). Retaliation, by contrast, involves punishment for conduct after the fact, and it is unlawful when an official takes adverse action against an entity merely because it engaged in speech that the official does not agree with. See generally Mt.

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Healthy City Sch. Dist. Bd. of Educ. v. Doyle, 429 U.S. 274 (1977). Given these differences, we evaluate the two theories separately.

A. Impermissible Coercion

As discussed further below, coercion violative of the First Amendment operates on two planes: who is being coerced and what conduct is being targeted. On the first plane, coercion can target the speaker itself (i.e., the person (or entity) engaging in expression), a conduit for the speaker (i.e., a person who disseminates the speech for the speaker), or a third-party associate of the speaker (i.e., a person with whom the speaker interacts or does business). On the second plane, coercion can be directed at expressive or nonexpressive conduct. But no matter the permutation, "[t]o state a claim that the government violated the First Amendment through coercion of a third party, a plaintiff must plausibly allege conduct that, viewed in context, could be reasonably understood to convey a threat of adverse government action in order to punish or suppress the plaintiff's speech." Vullo II, 602 U.S. at 191 (majority opinion). In Zieper v. Metzinger, 474 F.3d 60 (2d Cir. 2007), for example, we found that a reasonable juror could conclude that the police unlawfully coerced a speaker into removing his dystopian film from the internet. Id. at 66-67.

19

Concerned about the content of the film and afraid that it "was going to incite a riot," id. at 64, law enforcement officials repeatedly called the filmmaker and sent FBI agents and three police officers to his home over his lawyers' objections, id. at

67. We found that those actions, and the accompanying comments, might constitute impermissible coercion because they suggested that "there might be legal consequences if he failed to accede to the government's request that he remove his video." Id. Zieper thus stands as a straightforward example of impermissible coercion: it involved coercing a speaker (the filmmaker) into ceasing his expressive conduct (by removing a film from the internet). If Zieper provides a straightforward example of impermissible coercion against a speaker targeting his or her expressive activity, Bantam Books,

372 U.S. at 58, further instructs that a First Amendment claim may exist even where the coercion targets expressive activity but is more indirect because it targets a conduit of speech rather than the speaker. In that case, the Supreme Court found to be impermissibly coercive a state commission's letter to a book distributor notifying it that certain publications were deemed to be morally objectionable, requesting that they be removed from circulation, and threatening criminal referral to the state attorney general if the distributor failed to comply.

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Id. at 59-64. It did not matter that the plaintiffs in that case were the publishers of the books (i.e., the speakers) rather than the distributors themselves, because it was clear that the commission's actions constituted impermissible attempts to coerce the distributors into refusing to serve as a conduit for the publishers' expression. In other words, "Bantam Books stands for the principle that a government official cannot do indirectly what she is barred from doing directly:

A government official cannot coerce a private party to punish or suppress disfavored speech on her behalf." Vullo II, 602 U.S. at 190. Similarly, in Rattner v. Netburn, 930 F.2d 204 (2d Cir. 1991), we found to be impermissibly coercive a town official's letter to chamber of commerce members because it suggested that a town-wide boycott of their businesses would ensue unless the chamber removed a businessman's advertisement -- critical of town leadership -- from its periodic newspaper. Id. at 209-10. Unlike Zieper but like Bantam Books, Rattner involved coercion against a conduit of speech (the chamber and its newspaper) and targeted expressive activity (the ad in the newspaper). That the chamber removed the advertisement and ceased operations entirely showed that "a threat was perceived and its impact was demonstrable." Id. at 210.

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Next, in Okwedy v. Molinari, 333 F.3d 339 (2d Cir. 2003) (per curiam), we also found to be impermissibly coercive a New York City borough president's letter to a billboard company because -- although the letter did not explicitly threaten enforcement action -- its form and content nevertheless contained "an implicit threat" that retaliation would follow if the company "failed to accede" to the borough president's request to take down a controversial billboard paid for by a local church and its pastor. Id. at 344. Crucial to that holding were the facts that the letter was written on official city letterhead, its author "invoked his official authority" as borough president, it directed the billboard company to contact the borough president's "legal counsel" and chair of an "Anti-Bias Task Force," and it highlighted the author's awareness of the "substantial economic benefits" that the company derived from its billboards in the borough. Id. We concluded that these facts, taken together, plausibly alleged a claim of impermissible direct coercion because the challenged conduct exceeded mere attempts to convince. Id.; see also Zieper, 474 F.3d at 66 ("In determining whether a particular request to suppress speech is constitutional, what matters is the 'distinction between attempts to convince and attempts to coerce.'" (quoting Okwedy, 333 F.3d at 344)). Like Bantam Books and Rattner, Okwedy involved

22

impermissible coercion against a conduit of speech (the billboard company) and targeted patently expressive activity (the billboard display). Finally, while Zieper, Bantam Books, Rattner, and Okwedy all stand for the proposition that pushing speakers or conduits of speech to suppress their expressive activity may be unlawful if it becomes impermissible coercion or, indeed, censorship, Vullo II further instructs that a First Amendment claim may lie even when the challenged conduct targets a third-party business associate that does not itself engage in expressive activity. Vullo II, 602 U.S. at 196. Here, Vullo is not alleged to have targeted a speaker (the NRA) or a conduit for the NRA's speech (for example, a publisher) but third-party, regulated entities. Moreover, the coercive conduct alleged was not directed at speech or expressive conduct but at nonexpressive activity, i.e., underwriting insurance policies. Based on those allegations, Vullo II held that "the NRA plausibly alleged that Vullo violated the First Amendment by coercing DFS-regulated entities into disassociating with the NRA in order to punish or suppress the NRA's gun- promotion advocacy." Id. at 191.

Vullo II thus instructs that Vullo's conduct -- which targeted only the nonexpressive activity of the NRA's third-party business associates -- could form

23

the basis for a viable First Amendment coercion claim. As the Supreme Court concluded, the NRA plausibly alleged that Vullo violated its First Amendment rights by coercing DFS-regulated entities into disassociating with the NRA with the aim of suppressing the latter's gun-promotion advocacy. See, e.g., App'x at 150-51 ¶¶ 36-37 (alleging that Vullo's goal "was to disrupt any and all business arrangements between the NRA and any insurance administrator, broker, or underwriter" and "undermine [its] ability to conduct its affairs in New York").

B. Retaliation

In addition to coercing the NRA's business partners into cutting business ties with the NRA, Vullo is alleged to have unlawfully retaliated against the NRA for its advocacy regarding the Second Amendment. To plead a First Amendment claim under a theory of unlawful retaliation, a plaintiff must allege that the defendant "took an adverse action in response to his speech that would not have been taken absent the retaliatory motive." Houston Cmty. Coll. Sys. v. Wilson, 595 U.S. 468, 477 (2022) (internal quotation marks omitted). But "[i]t is not enough to show that an official acted with a retaliatory motive and that the plaintiff was injured" -- a plaintiff must allege some "causal connection" between the alleged retaliatory animus and subsequent injury. Nieves v. Bartlett, 587 U.S.

24

391, 398-99 (2019). The retaliation inquiry therefore proceeds in three steps: the plaintiff must first show that (1) its conduct was constitutionally protected and

(2) that same conduct was a substantial or motivating factor in the defendant's decision to undertake the challenged actions, after which (3) the defendant may rebut those allegations by showing that "it would have reached the same decision . . . even in the absence of the protected conduct." Mt. Healthy, 429 U.S. at 287; accord Vullo II, 602 U.S. at 204 (Jackson, J., concurring). That final step establishes what is known as a Mt. Healthy defense, see, e.g., Anemone v. Metro. Trans. Auth., 629 F.3d 97, 117-18 (2d Cir. 2011), the availability of which is important because it balances the interest in legitimate regulatory enforcement against the need to uphold robust constitutional protections. So, although the First Amendment prohibits retaliation for speech generally, see Royal Crown Day Care LLC v. Dep't of Health & Mental Hygiene of N.Y., 746 F.3d 538, 544 (2d Cir. 2014), that prohibition does not impose an absolute bar against legitimate law enforcement. As the Supreme Court noted in Bantam Books:

We do not hold that law enforcement officers must

renounce all informal contacts with persons suspected of violating valid laws . . . . Where such consultation is genuinely undertaken with the purpose of aiding the

25

[plaintiff] to comply with such laws and avoid prosecution under them, it need not retard the full enjoyment of First Amendment freedoms.

372 U.S. at 71-72. And here, "much of Vullo's alleged conduct, if not done for retaliatory reasons, might otherwise be legitimate enforcement of New York's insurance regulations." Vullo II, 602 U.S. at 203 (Jackson, J., concurring).¹ At this motion-to-dismiss stage, however, we need not -- and do not -- consider the viability of any Mt. Healthy defense.²Here, as the Supreme Court concluded, the NRA sufficiently alleged that it engaged in constitutionally protected conduct, see, e.g., App'x at 140 ¶¶ 12-13, and that Vullo targeted its insurance providers in retaliation for that conduct, see, e.g., id. at 143 ¶ 19, 154 ¶ 48, 167-68 ¶¶ 80-85.

II. Qualified Immunity

Although the NRA plausibly alleged a First Amendment claim, we conclude that Vullo is entitled to qualified immunity because the First

26

Amendment rights asserted were not clearly established at the time of the challenged conduct. True, the cases cited above clearly established that coercion amounting to censorship and retaliation violate the First Amendment as a general matter, but they did not sufficiently define the contours of that right such that it would have been clear to every reasonable official in 2017 or 2018 that Vullo's conduct with respect to a third party -- not a speaker or a speaker's conduit -- violated that right.

We make two procedural observations before proceeding. First, we note that the Supreme Court explicitly left that question for this Court to

"reconsider" on remand. Vullo II, 602 U.S. at 199 n.7. After all, the question of whether a plaintiff has adequately alleged a First Amendment violation is distinct from the question of whether the defendant is entitled to qualified immunity based on existing precedent. See Farid v. Ellen, 593 F.3d 233, 245 (2d Cir. 2010) ("For qualified immunity purposes, however, there is a separate question, which is whether the right violated by this conduct was clearly established."); see also McCullough v. Wyandanch Union Free Sch. Dist., 187 F.3d 272, 277 (2d Cir. 1999) ("[I]t is not necessary for a district court to determine whether in fact the First Amendment was violated before deciding whether a

27

defendant is entitled to qualified immunity."). We answer only the latter question here.

Second, resolving the defense at the motion-to-dismiss stage is appropriate in this case because our conclusion is based on the law, and only after consideration of the facts as pleaded by the NRA and construed in its favor. See, e.g., Matzell v. Annucci, 64 F.4th 425, 436 (2d Cir. 2023); Smith v. Garretto, 147 F.3d 91, 95 (2d Cir. 1998); Molinelli v. Tucker, 901 F.2d 13, 15-17 (2d Cir. 1990); Vega v. Miller, 273 F.3d 460, 466-71 (2d Cir. 2001).³We see no need to postpone ruling on Vullo's qualified immunity defense because this is not a case where discovery into the claims and allegations would make a difference in the analysis

28

of the asserted defense.⁴In short, the defense is properly asserted and decided at this stage here because "the facts supporting [it] appeared on the face of the complaint." McKenna v. Wright, 386 F.3d 432, 435 (2d Cir. 2004).

A. Applicable Law

Qualified immunity protects "all but the plainly incompetent or those who knowingly violate the law," and it generally attaches to conduct that

"does not violate clearly established statutory or constitutional rights of which a reasonable person would have known." White v. Pauly, 580 U.S. 73, 78-79 (2017) (per curiam) (quoting Mullenix v. Luna, 577 U.S. 7, 11-12 (2015) (per curiam)). In this Circuit, officials are generally entitled to qualified immunity for their official acts unless the plaintiff "pleads facts showing (1) that the official violated a statutory or constitutional right, and (2) that the right was 'clearly established' at the time of the challenged conduct." Tanvir v. Tanzin, 120 F.4th 1049, 1060 (2d Cir. 2024) (quoting Ashcroft v. al-Kidd, 563 U.S. 731, 735 (2011)). Courts need not

29

address these two prongs in a particular order and may "exercise their sound discretion in deciding which of the two prongs of the qualified immunity analysis should be addressed first in light of the circumstances in the particular case at hand." Id. (quoting Sabir v. Williams, 52 F.4th 51, 58 (2d Cir. 2022)); see also Pearson v. Callahan, 555 U.S. 223, 236-37 (2009) (stating that this process prevents

"a substantial expenditure of scarce judicial resources on difficult questions that have no effect on the outcome of the case"). Accordingly, qualified immunity is defeated only if both requirements are met and applies so long as one is not met. As the NRA has plausibly alleged that Vullo violated its First Amendment rights, she is entitled to qualified immunity only if the rights at issue in this case were not "clearly established" at the time of her challenged conduct. Tanvir, 120 F.4th at 1060; see, e.g., Montero v. City of Yonkers, 890 F.3d 386, 402-03 (2d Cir. 2018); Smith, 147 F.3d at 94-95; Bacon v. Phelps, 961 F.3d 533, 545 (2d Cir. 2020).

For a right to be clearly established, "existing precedent must have placed the statutory or constitutional question beyond debate," al-Kidd, 563 U.S. at 741 (emphasis added), such that the ensuing rules declare with a "high degree of specificity" which conduct is permitted and not, Liberian Cmty. Ass'n v. Lamont,

30

970 F.3d 174, 186 (2d Cir. 2020) (internal quotation marks omitted). In other words, a right alleged to have been violated is clearly established only if it is

"sufficiently clear" to "every reasonable official" that the challenged conduct, in the "specific context of the case," violates that right. Radwan v. Manuel, 55 F.4th 101, 114 (2d Cir. 2022) (first quoting Reichle v. Howards, 566 U.S. 658, 664 (2012); and then quoting Mullenix, 577 U.S. at 12).⁵"In determining if a right is clearly established, this Court looks to whether (1) it was defined with reasonable clarity, (2) the Supreme Court or the Second Circuit has confirmed the existence of the right, and (3) a reasonable defendant would have understood that his conduct was unlawful." Id. (quoting Doninger v. Niehoff, 642 F.3d 334, 345 (2d Cir. 2011)). Absent controlling authority from the Supreme Court or this Circuit, a plaintiff may still show that a right is clearly established if "a robust consensus of cases of persuasive authority" says so. Id. (quoting De La Rosa v. White, 852 F.3d 740, 746 (8th Cir. 2017)).

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An official is thus qualifiedly "immune from liability unless, under the particular circumstances the official faced, any 'reasonable official' would have 'known for certain that the conduct was unlawful' under then-existing precedent." Lamont, 970 F.3d at 187 (alteration adopted) (quoting Ziglar v. Abbasi,

582 U.S. 120, 152 (2017)). We have observed that this is generally the case in any of the following three circumstances: First, that right may not be clearly established because the conduct challenged in a case simply predates any and all judicial opinions announcing that the specific conduct violated a statutory or constitutional right.⁶Second, the asserted right may not be clearly established because there is no controlling law on the issue.⁷Or third, that right may not be clearly established because the relevant caselaw, persuasive as it may be, does not clearly bar the challenged conduct.⁸We list these circumstances in order of

32

theoretical difficulty; that is, it is generally most difficult to establish a qualified immunity defense under the third circumstance, because the Supreme Court has made it clear that "officials can still be on notice that their conduct violates established law even in novel factual circumstances." Vega v. Semple, 963 F.3d 259, 277 (2d Cir. 2020) (quoting Hope v. Pelzer, 536 U.S. 730, 741 (2002)) (rejecting a defense seeking qualified immunity "absent binding precedent that addresses the very same carcinogen in this case"). In those cases, courts must grapple with the difficult question of whether the relevant factual circumstances are truly

"novel" under existing precedent. Compare, e.g., Zieper, 474 F.3d at 70 (granting qualified immunity on a First Amendment coercion claim because the threats at issue were not as "thinly veiled" as those in Bantam Books), with Semple, 963 F.3d at 277 (declining to find that qualified immunity was proper on the basis that "no binding decision discusses the constitutional implications of radon exposure to inmates," because it was sufficient that precedent had addressed the implications of toxic environmental substances more generally).

immunity because the authorities cited by the parties created a "conflict of opinion" and at best "express uncertainty as to the state of the law on this issue"); Miller, 273 F.3d at 467 (applying qualified immunity because "the available precedents that might usefully have guided the [d]efendants leave the unlawfulness of their action at least unclear").

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B. Application

Vullo is entitled to qualified immunity on the NRA's impermissible coercion and retaliation claims because the First Amendment rights at issue were not clearly established at the time of the challenged conduct. See Tanvir, 120 F.4th at 1060. Reasonable officials in Vullo's position "would [not] have known for certain," Lamont, 970 F.3d at 187 (internal quotation marks omitted), based on the cases cited above, that her conduct crossed the line from forceful but permissible persuasion to impermissible coercion and retaliation. We start with the premise that a state official may "share her views freely and criticize particular beliefs, and she can do so forcefully in the hopes of persuading others to follow her lead," as long as she does not "use the power of the State to punish or suppress disfavored expression." Vullo II, 602 U.S. at 188. The NRA alleges that Vullo crossed that line when she purportedly pressured insurance companies and banks into cutting certain business ties with the NRA and pursued investigations and enforcement actions against its business partners.⁹

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To be clear, we do not hold that an official may infringe the statutory or constitutional rights of any person or entity if she can find some sufficiently novel way to use her office and powers to do so. Rather, we hold here that qualified immunity is proper only because no case (or set of cases) had clearly established, by the time of Vullo's conduct, that exercising regulatory power to pressure third-party regulated entities into refraining from nonexpressive activity and disassociating from a plaintiff crossed the line from persuasion into impermissible coercion and retaliation. In other words, Vullo is entitled to qualified immunity because the effect of her alleged coercion of and retaliation against these regulated entities on the NRA's speech is significantly more attenuated here than in the cases cited above. We proceed by applying the defense separately to the NRA's impermissible coercion and retaliation theories.

1. Impermissible Coercion

The NRA alleges that Vullo engaged in unlawful coercion when she used her regulatory power to pressure insurance companies and banks into cutting business ties with the NRA. Vullo, however, allegedly targeted only entities over which she had regulatory oversight and pursued only concededly mandate does not include setting gun-control policy," App'x at 146 ¶ 27, it does include enforcing state insurance law, see id. at 145-46 ¶¶ 24-27.

35

illegal, nonexpressive activity. We find that Vullo is entitled to qualified immunity on this theory because, until Vullo II, no case had clearly established that a regulator could indirectly infringe the First Amendment rights of one entity (the NRA) by coercing third-party associates (the insurers) into refraining from nonexpressive, nonspeech activity (writing certain NRA-endorsed policies). At best, the existing case law before Vullo II addressed only coercive conduct aimed at expressive activity, either through the speaker or some conduit for the speaker. Bantam Books was literally about banning books -- the regulator in that case unlawfully coerced a publisher's distributors into removing certain books and publications from circulation. 372 U.S. at 62-64. Similarly, in Rattner, the village trustee's letter unlawfully coerced a local newspaper into removing a local man's advertisement critical of the local government. 930 F.2d at 209-10. And in Okwedy, the borough president's letter unlawfully coerced a billboard company into taking down a controversial billboard paid for by a local church and its pastor. 333 F.3d at 341-44. In each of these cases, the nexus between the defendant's coercive conduct and the eventual infringement of the plaintiff's First Amendment rights was clear -- because the third party was at least a conduit for the expression sponsored or requested by the plaintiff, coercing the third party

36

into limiting or ceasing those activities also meant limiting or terminating the plaintiff's speech and expression. The conduct sought to stop the speech itself. After all, a book publisher will clearly have trouble disseminating its speech if a regulator has coerced its distributor into stopping the circulation of its books. See Bantam Books, 372 U.S. at 62-64. Private citizens and public entities, too, would struggle to express their political views if officials used their influence to coerce others into refusing to publish those views. See Rattner, 930 F.2d at 206- 07; Okwedy, 333 F.3d at 344. That precedent thus made clear that "[a]lthough an individual has no right to force a private publication to air his political views, a government does not have license to forbid the publication to air those views."

Rattner, 930 F.2d at 208 (citations omitted) (emphasis added). This case falls decidedly outside that line of precedent. Here, although Vullo is alleged to have coerced third parties who dealt with the NRA, those third parties were not disseminating speech on the NRA's behalf or otherwise engaging in expressive activity. As Justice Jackson pointed out, "[t]he NRA does not contend that its (concededly unlawful) insurance products offered through those business relationships were themselves 'speech,' akin to a billboard [(as in Okwedy)], a television ad, or a book [(as in Bantam Books)]." Vullo

37

II, 602 U.S. at 202 (Jackson, J., concurring). Thus, the nexus between coercion and infringement is not clear here. Unlike the plaintiffs in Bantam Books, Okwedy, and Rattner, the NRA does not allege that Vullo targeted the means through which the NRA was actually engaging in expressive activity. They do not contend, for example, "that Vullo pressured the printer of American Rifleman (a longstanding NRA periodical) to stop printing the magazine, or coerced a convention center into canceling the NRA's annual meeting." Id. Instead, the NRA alleges that Vullo infringed its First Amendment rights in a much more attenuated manner:

Vullo coerced insurance companies into "terminat[ing] longstanding, beneficial business relationships with the NRA," which allegedly had the eventual effect of

"depriv[ing] [it] of basic bank-depository services, corporate insurance coverage, and other financial services," thereby making it difficult for the NRA to maintain its " corporate existence" and pursue "its advocacy mission." App'x at 136. Those extra causal steps between coercion and infringement mean that traditional coercion cases present "an awkward fit with the facts of this case."

Vullo II, 602 U.S. at 202 (Jackson, J., concurring) (emphasis omitted); see also id. ("[T]he effect of Vullo's alleged coercion of regulated entities on the NRA's speech is significantly more attenuated here than in Bantam Books or most decisions

38

applying it." (emphasis added)). In other words, we can surmise only that a reasonable officer in Vullo's position likely would have thought that her conduct -- which targeted regulated entities for concededly illegal, nonexpressive activities and only indirectly affected the NRA -- was permissible.¹⁰Accordingly, the existing precedent did not adequately define the contours of the First Amendment right at issue such that Vullo would have been on notice that her specific conduct violated it. See Semple, 963 F.3d at 274.¹¹

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The NRA correctly notes that the "result [in Vullo II] flowed from Bantam Books." NRA Supp. Br., ECF No. 143, at 4. Indeed, the Supreme Court emphasized that an official may not engage in "conduct that, viewed in context, could be reasonably understood to convey a threat of adverse government action in order to punish or suppress [a] plaintiff's speech." Vullo II, 602 U.S. at 191. But under the qualified immunity analysis, general pronouncements of law are not sufficient to "clearly establish" a right. Although "[a] court need not have passed on the identical course of conduct in order for its illegality to be 'clearly established,'" Williams v. Greifinger, 97 F.3d 699, 703 (2d Cir. 1996), the Supreme Court has "repeatedly told courts . . . not to define clearly established law at a high level of generality," al-Kidd, 563 U.S. at 742. Instead, the dispositive question is "whether the violative nature of particular conduct is clearly established" by existing precedent that has "placed the statutory or constitutional question beyond debate." Id. at 741-42.

That is not the case here. A reasonable officer in Vullo's position would not have been on notice, at the time of her conduct, that such conduct since the ads might be for illegal sex-related products or services, such as prostitution."). Backpage thus does not clearly establish the particular right at issue in this case -- although the First Amendment violation against the plaintiff was similarly indirect, the incursion on speech was much more direct.

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violated the NRA's First Amendment rights. See Ziglar, 582 U.S. at 152 (qualified immunity applies "if a reasonable officer might not have known for certain that the conduct was unlawful"). Given that even this Court erred in its merits conclusion in Vullo I, it would make little sense to hold that a reasonable officer in Vullo's position should have known -- in 2017 or 2018 -- that her conduct violated the NRA's First Amendment rights. See Terebesi v. Torreso, 764 F.3d 217, 233 (2d Cir. 2014) ("It is difficult to ask that a [defendant] identify clearly established law that three judges of this Court could not find."); cf. Mandala v. NTT Data, Inc., 88 F.4th 353, 360 (2d Cir. 2023) (holding that appellant was entitled to file an amended complaint because dismissal of the original complaint was affirmed over "vigorous dissent," and a petition for rehearing en banc was denied over the objection of five circuit judges). "[A] reasonable officer is not required to foresee judicial decisions that do not yet exist," Kisela v. Hughes, 584 U.S. 100, 107 (2018), and so Vullo was not required to foresee that the Supreme Court would rule as it did in Vullo II.

In summary, qualified immunity on the NRA's coercion theory is proper because, although Bantam Books and the cases applying it made clear that coercion with the aim of suppressing speech is unlawful generally, they did not

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make clear the more particularized application of that principle here -- where the allegedly coerced party was not itself a publisher or conduit of speech. A reasonable officer in Vullo's shoes "might not have known for certain that the [challenged coercive] conduct was unlawful," Ziglar, 582 U.S. at 152 (emphasis added), because Bantam Books and the cases applying it did not put the question

"beyond debate," al-Kidd, 563 U.S. at 741. Vullo is thus entitled to qualified immunity on the NRA's First Amendment coercion claim.

2. Retaliation

The NRA also alleges that Vullo engaged in unlawful retaliation when she pursued investigations and enforcement actions against the NRA's business partners. But again, qualified immunity is proper here because the nexus between the alleged retaliation and the alleged eventual infringement of the NRA's First Amendment rights is too attenuated. Specifically, although the SAC repeatedly alleges that Vullo retaliated against the NRA for its speech activity, see App'x at 136, 143 ¶ 19, 154 ¶ 48, 167 ¶ 80, 169 ¶ 91, 171-72 ¶ 101, the reality is that the SAC alleges only that Vullo punished the NRA's business associates to punish the NRA for its speech. The route from alleged retaliation to

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eventual infringement is thus circuitous and indirect, and insufficient to have put Vullo on notice that her acts would violate First Amendment rights. At the time of Vullo's conduct, no precedent had clearly established that indirect retaliation of the kind at issue in this case was unlawful. At most, our existing retaliation cases had addressed only instances in which a defendant retaliated directly against the plaintiff and for the plaintiff's speech activity, whether by actively punishing or passively refusing to do something for the plaintiff.¹²

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Those cases do not address a sufficiently close analogue to the current situation -- one in which a plaintiff alleges an indirect violation of its First Amendment rights because the defendant exerted pressure relating to the nonexpressive activities of third parties with whom the plaintiff dealt. That distinction is arguably a narrow one, but it is nevertheless determinative, especially here, where a regulator dealt directly with regulated entities, and applicable state laws were undeniably violated.

In sum, the various cases addressing unlawful retaliation did not provide the requisite guidance clearly establishing that Vullo could not engage in the conduct at issue in this case. Because the available cases did not place the question "beyond debate," al-Kidd, 563 U.S. at 741, reasonable officials in Vullo's position likely would not have understood that they were engaging in impermissible law enforcement, nor would they "have 'known for certain that [Vullo's] conduct was unlawful' under then-existing precedent." Lamont, 970 criminally prosecuting him on false charges because he publicly exposed corruption within an agency); Blue v. Koren, 72 F.3d 1075, 1078-80 (2d Cir. 1995) (state agency officials allegedly retaliated against a local nursing home through selective and rigorous enforcement of regulations because the nursing home prevailed in a prior proceeding); Rodriguez v Phillips, 66 F.3d 470, 478 (2d Cir. 1995) (corrections officer allegedly retaliated against plaintiff by reporting him for behavior that led to the plaintiff's placement in administrative segregation because the plaintiff once verbally defended an inmate whom the officer was disciplining).

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F.3d at 187 (quoting Ziglar, 582 U.S. at 152) (emphasis added). Qualified immunity on the NRA's retaliation claim is therefore proper.

C ONCLUSION

We hold that qualified immunity on the NRA's First Amendment coercion and retaliation claims is appropriate in this case because of the markedly attenuated link between facially valid law enforcement against a third- party associate and an infringement of a plaintiff's First Amendment rights.¹³ Accordingly, we REVERSE the district court's order denying Vullo's motion to dismiss on the basis of qualified immunity, and we REMAND the case for the district court to enter judgment dismissing the remaining claims against her.

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