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.