Justices Seem Likely to Side With N.R.A. in First Amendment Dispute

A majority of the Supreme Court appeared on Monday to embrace arguments by the National Rifle Association that a New York State official violated the First Amendment by trying to dissuade companies from doing business with it after a deadly school shooting.

The dispute, which began after a gunman opened fire in 2018 at Marjory Stoneman Douglas High School in Parkland, Fla., was one of two cases on Monday that centered on when government advocacy crosses a line to violate the Constitution’s protection of free speech.

After the shooting, which killed 17 students and staff members, Maria Vullo, then a superintendent of the New York State Department of Financial Services, said banks and other insurance companies regulated by her agency should assess whether they wanted to continue providing services to the N.R.A.

The gun rights group sued, accusing Ms. Vullo of unlawfully leveraging her authority as a government official.

“It was a campaign by the state’s highest political officials to use their power to coerce a boycott of a political advocacy organization because they disagreed with its advocacy,” said David D. Cole, the national legal director for the American Civil Liberties Union, who argued on behalf of the N.R.A., adding that the officials’ actions had cost the group “millions of dollars.”

The lawyer for the New York officials, Neal K. Katyal, pushed back, arguing that state officials were performing their ordinary duties. “We think that it was an exercise of legitimate law enforcement,” he said.

Solicitor General Elizabeth B. Prelogar, in a friend-of-the-court brief, described some of the N.R.A.’s claims as plausible, namely that Ms. Vullo may have crossed a constitutional line “by coercing regulated entities to terminate their business relationships” with the N.R.A. in a bid to stifle the group’s advocacy.

But the solicitor general urged the court to reject some of the N.R.A.’s broader arguments, claiming that they “would threaten to condemn legitimate government activity if applied in other, more typical circumstances.”

During oral argument, Ephraim McDowell, assistant to the solicitor general, drew a distinction between the N.R.A. case and another heard earlier in the day, on a push by Republican-led states to curb the Biden administration’s efforts to crack down on what it viewed as misinformation on social media. That case, Murthy v. Missouri, met with a rocky reception by the justices.

Like the Murthy case, the N.R.A. argument centered on the line between coercion and persuasion by government officials. Where to draw that line appeared to be front and center for the justices.

“There’s considerable overlap obviously with the first case,” Chief Justice John G. Roberts Jr. said. “Could you articulate what the significant differences are between your position in this case and the office’s position in the prior case?”

Mr. McDowell replied: “There are no differences as to the legal principles. The difference here is that there is a specific coercive threat.”

He was referring to an allegation by the N.R.A. that Ms. Vullo met privately with the organization’s insurance partners and demanded that one of them, Lloyd’s of London, stop “providing insurance to gun groups, especially the N.R.A.”

Mr. McDowell urged the justices “to hinge the First Amendment analysis on the Lloyd’s meeting.”

“It’s just a straightforward way of resolving this case,” he said.

After Justice Brett M. Kavanaugh repeated to Mr. Katyal that he understood the government to be arguing that “the meeting itself is enough” for a First Amendment violation, he pushed back, contending that the New York officials were engaged in normal plea bargaining.

“If that meeting is enough, Justice Kavanaugh, every meeting, every plea negotiation’s enough,” Mr. Katyal said. “That’s literally what they are. They’re done in secret, behind a closed door, to use their insidious language. That’s the natural give-and-take.”

He added that both Ms. Vullo and the governor of New York at the time, Andrew M. Cuomo, “have said things about the N.R.A.,” but “there’s nothing that ties that give and take” from the Lloyd’s meeting to “the feelings about the N.R.A.”

The case, N.R.A. v. Vullo, No. 22-842, arrived at the Supreme Court after a three-judge panel of the U.S. Court of Appeals for the Second Circuit, in New York, ruled against the N.R.A., prompting it to petition the justices for review.

In asking the court to hear the case, the N.R.A. cited what it described as Ms. Vullo’s enormous regulatory power. It added that she applied “pressure tactics — including back-channel threats, ominous guidance letters and selective enforcement of regulatory infractions.” The organization warned of the wide-ranging consequences of a ruling against it, saying that siding with Ms. Vullo would open the door to other government officials making similar pleas about other hot-button issues like abortion and the environment.

Ms. Vullo has pushed back against the claim that she undermined the First Amendment.

In 2017, the Department of Financial Services opened an investigation into an insurance product known as “Carry Guard,” which provided coverage for various issues arising from the use of a firearm, such as personal injury and criminal defense.

The program was brokered, serviced and underwritten by insurance companies and included the N.R.A.’s name, logo and endorsement.

The Department of Financial Services, which regulates more than 1,400 companies and more than 1,900 financial institutions, concluded that Carry Guard violated state insurance law, in part, by providing liability coverage for injury from the wrongful use of a firearm. The department entered into consent decrees with the insurance groups and imposed civil penalties.

In February 2018, after the Parkland shooting, the department re-evaluated “the implications of regulated entities’ relationships with gun-promotion organizations,” according to legal filings for Ms. Vullo.

That spring, the department issued two memos, one to insurance companies and another to financial institutions, titled “Guidance on Risk Management Relating to the N.R.A. and Similar Gun Promotion Organizations.”

The memos encouraged regulated institutions “to review any relationships they have with the N.R.A. or similar gun promotion organizations,” suggesting that they act promptly in the interest of public health and safety.

The same day, Mr. Cuomo released a statement explaining that he had directed the department to press insurance companies and other financial institutions in the state to “review any relationships they may have with the National Rifle Association and other similar organizations.”