Gun rights’ advocates often quip “The Second Amendment protects the other nine.” Now, the National Rifle Association is hoping in two separate, but related cases that the First Amendment will protect it from what it claims is the State of New York’s unlawful regulatory and administrative enforcement. 

On March 18 the Supreme Court will hear NRA v. Vullo from the Second Circuit to determine if a New York financial regulator who urged banks and insurance companies against doing business with the NRA engaged in unconstitutional coercion of private actors as part of a government effort to suppress and retaliate speech.  And, last February, a Manhattan jury found the NRA liable for failure to “properly administer charitable funds.” The judge in that case rejected the organizations’ First Amendment claims that the prosecution for a regulatory infraction proceeded from animus towards the NRA’s political positions despite the New York Attorney General Letitia James plainly stating she wanted to pursue the organization for its political advocacy. 

In both cases, New York justified its officials’ alleged political animus in their regulatory enforcements against the NRA by invoking Nieves v. Bartlett, a 2019 case where the Supreme Court created a high- evidentiary bar to allege retaliatory arrests. The Court will hear Gonzalez v. Trevino, on March 20, which could clarify this standard.  Thus, the Supreme Court’s position this term on retaliatory arrests very well may implicate cases involving retaliatory enforcement of regulatory infractions. 

The difficulty with retaliation claims.

In 1949, Judge Learned Hand explained the difficulty courts face in retaliation claims. While “an official, who is in fact guilty of using his powers to vent his spleen upon others, or for any other personal motive not connected with the public good, should not escape liability for the injuries he may so cause.” However, it is “impossible to know whether the claim is well founded until the case has been tried, and that to submit all officials, the innocent as well as the guilty, to the burden of a trial and to the inevitable danger of its outcome, would dampen the ardor of all but the most resolute, or the most irresponsible, in the unflinching discharge of their duties.” Gregoire v. Biddle, 177 F.2d 579, 581 (2d Cir. 1949).

Moreover, an official with malicious motives may have prosecuted a case regardless. Without opining on Former President Trump’s current legal problems, consider his famous quip: “I could stand in the middle of Fifth Avenue and shoot somebody.” Regardless of whether New York prosecutors had it in for him, President Trump could not claim this was selective and political prosecution, as they would have arrested anyone for doing so. However, if he jaywalked across Fifth Avenue and the prosecutors threw the book at him, he would likely be able to claim this was political retaliation. 

Courts have struggled to draw the line between these two extremes for decades. 

For selective civil and regulatory enforcement, the Supreme Court held in Mt. Healthy City Board of Ed. v. Doyle, that the plaintiff had the burden to prove that her constitutionally protected conduct was the “substantial” or “motivating” factor for the government’s action. The burden then shifts to the government to prove by “preponderance of the evidence that it would have reached the same decision” regardless. 429 U.S. 274, 287 (1977).

Nieves created an even higher evidentiary bar—at least for cases involving on-the-spot arrests. It held that independent probable cause to arrest will defeat a retaliation claim, if the plaintiff cannot present objective evidence that similarly situated individuals engaged in the same conduct were not punished. New York hopes to apply this standard in both of its cases with the NRA.  

NRA v. Vullo

In 2018 New York Governor Andrew Cuomo issued a press release stating he would direct the state’s Department of Financial Services to ask “regulated entities” to “determine whether any relationship they may have with the NRA or similar organizations sends the wrong message to their clients and their communities who often look to them for guidance and support.”  His Financial Superintendent Maria Vullo followed up by adding that “DFS urges all insurance companies and banks doing business in New York to join the companies that have already discontinued their arrangements with the NRA,” because of the “reputational risks, that may arise from their dealings with the NRA or similar gun promotion organizations.”

Vullo invokes Nieves to argue that the Department of Financial Services had a non-retaliatory motive to act against the NRA. Specifically, the NRA promoted an insurance program called “Carry Guard” which insured legal fees for self-defense claims in civil and criminal firearms cases. New York claimed that this violated New York’s insurance law. While not denying there was some retaliatory motive, Vullo argued her “enforcement acts were [not] objectively unreasonable, for the straightforward reason that Carry Guard and the NRA’s similar products were unlawful.” 

Even under Nieves’ high standard, the NRA is expected to win as the letters to banks and insurance companies made no reference to Carry Guard. The NRA has received bipartisan support in this case. Both the ACLU, which is representing the NRA, and numerous liberal law professors have filed amici that answer “no.” The Biden Administration even conceded that the NRA pleaded a viable claim that New York “violated the First Amendment by coercing regulated entities to terminate their business relationships,” and is splitting time with the NRA at oral arguments.  

People v. NRA           

While running for office in 2018 and 2020, Attorney General James explicitly stated that she planned to target the NRA because of their political activism calling their lobbying “directly antithetical” to New York’s policies and an “organ of deadly propaganda masquerading as a charity for public good” with a “poisonous agenda.” She saw her efforts as complementing the “pressure upon the banks that finance the NRA” at issue in Vullo. She stated she wished to use her “power as attorney general” to “take down the NRA.”

Speech and lobbying—even it promotes a “poisonous agenda”—is plainly First Amendment protected. In 2020, James sued the NRA for claims related to self-dealing and financial mismanagement. The lawsuit purportedly sought to ensure that the NRA used its funds to lobby effectively. It claimed the organization’s failure of proper administration has had the  “effect . . . to  divert millions of dollars away from the NRA’s charitable mission imposing substantial reductions in its expenditures for core program services, including gun safety, education, training, member services and public affairs.” 

The Attorney General sought dissolution, which it has never done for a large charity. In rejecting this motion, the New York trial judge Judge Cohen noted her “allegations concern primarily private harm to the NRA and its members and donors” and these very members would be harmed by dissolution. 

However, he rejected the NRA’s First Amendment retaliation claim by applying Nieves to civil enforcement proceedings. Because there were media reports about financial mismanagement at the organization, the Attorney General had independent probable cause, and thus her express desire to prosecute the NRA for its political views were irrelevant. 

Gonzalez v. Trevino: Clarifying the Nieves Standard 

On March 20, the Supreme Court will hear Gonzales v. Trevino,  which may make Nieves irrelevant to regulatory and civil enforcement proceedings. The facts behind the case read like a textbook example of First Amendment retaliation. The mayor and police and police chief of Castle Hills, Texas took great pains to arrest a rival city council member for accidentally taking a petition—which she herself delivered and thus would have no reason to steal—under an tampering with official documents charge, which is used to prosecute fake IDs.  

However, applying Nieves, the Fifth Circuit held that there was probable cause and no evidence of similar unprosecuted cases—or any cases at all—with similar conduct, the retaliation claim failed. In his dissent, Judge Andy Oldham argued that “lack of nonexistent comparative evidence” of similar unprosecuted conduct is not the only type of “objective evidence” of improper retaliation. He argued, “there’s zero difficulty or complexity in figuring out whether it was animus or her purportedly criminal conduct that caused her arrest.” Gonzalez v. Trevino, 42 F.4th 487, 504 (5th Cir. 2022) (Oldham, J., diss.), cert. granted, 144 S. Ct. 325 (2023)

The Supreme Court took certiorari on whether it could accept “objective evidence” of animus beyond unprosecuted but similarly-situated cases and whether Nieves is limited officers making “split-second arrests” rather than premeditated enforcement actions.

And there is good reason to limit Nieves officers making “quick decisions in circumstances that are tense, uncertain, and rapidly evolving” situations. It protection of official acts that occur quickly and often under stress and threat of physical harm should not extend to cases where prosecutors and regulators plan, research, and, indeed, concoct probable cause over months, if not years. As the Supreme Court held in Lozman v. City of Riviera Beach, “official retaliatory policy is a particularly troubling and potent form of retaliation, for a policy can be long term and pervasive, unlike an ad hoc, on-the-spot decision by an individual office.” 585 U.S. 87, 100 (2018).  In the NRA’s case, the years long and self-reinforcing statements from both the Attorney General and Governor fit this definition. 

While Court’s are rightly reluctant to prosecute crime. Dissenting from Fifth Circuit’s denial to hear Trevino en banc, Judge James Ho cautioned that government officials rarely “admit that they abuse the coercive powers of government to punish and silence their critics,” and can “often able to invent some reason to justify their actions.” Gonzalez v. Trevino, 60 F.4th 906, 907 (5th Cir. 2023) (Ho, J., diss.). He understated the problem. Under the harshest reading of Nieves even if a regulator or prosecutor admits they are seeking to silence their critics—as Attorney General James and Superintendent Vullo did to the NRA—they will argue courts cannot consider this evidence. 

Whatever one thinks of the NRA or Second Amendment, New York’s ability thus far to openly target a political enemy without consequence demonstrates why the Supreme Court’s should keep the expansive Nieves defense to arrest decisions but not apply it to First Amendment retaliation claims for regulatory enforcement. 

Adam Candeub is a professor of law and the Director of the Intellectual Property, Information & Communications Law Program at Michigan State University College of Law.