The Supreme Court heard oral arguments in NRA v. Vullo on Monday. In this case, the NRA accuses a New York State official of improperly using regulatory authority to pressure banks and insurers to cut ties with the group in the aftermath of the Parkland High School shooting.

The case arose out of a series of guidance letters that Maria Vullo sent to banks and insurers in New York State. These letters suggested that banks review their ties to the NRA and that insurers could limit liability by cutting ties with the NRA.

This case is notable both for its wide-ranging regulatory and free speech law implications as well as an unlikely alliance. The generally left-leaning American Civil Liberties Union represents the conservative-leaning NRA, a group that supports the right of Americans to purchase and carry firearms. This alliance has brought outsized media attention to the case.

The NRA argues that the official targeted the group based on their political speech and that this violates the First Amendment of the Constitution. It argues that if this is held to be permissible, the government could use its regulatory authority as a weapon against any speech that goes against the government’s interests.

The official, Vullo, argues that she was acting properly within her regulatory authority. She also argues that US courts have long held that government officials have the free speech rights necessary for the functioning of government. Vullo also argues that ruling in the NRA’s favor could have the effect of chilling government speech. Some regulatory law experts have said that issuing the type of guidance that Vullo did is a necessary and everyday aspect of the job.

The court did not clearly indicate how it would rule during oral arguments, though it appeared receptive to the NRA’s arguments.