U.S. Supreme Court justices weighed tossing out a New York City firearms case, a move that would dash the hopes of gun-rights advocates seeking an expansion of Second Amendment protections.

The justices spent most of an hour-long argument in Washington Monday debating whether to issue a ruling at all, now that New York City has scrapped the handgun-transportation restrictions at the center of the fight. Gun-rights advocates, backed by President Donald Trump, are urging the justices to rule on the merits and bolster the Second Amendment.

The residents say the now-defunct rules forced them to stop attending shooting competitions and taking licensed handguns to a second home. After the court agreed to hear the case, the city and state changed the rules in an effort to have the dispute thrown out as moot.

A New York affiliate of the National Rifle Association is joining the three men in pressing the appeal. The city’s supporters include Everytown for Gun Safety, an advocacy group started by Michael Bloomberg, who is the founder and majority owner of Bloomberg LP, the parent company of Bloomberg News. Bloomberg, who is seeking the Democratic nomination for president, was mayor of New York from 2002 to 2013.

Chief Justice John Roberts, who could cast the pivotal vote, sought assurances from the city’s lawyer that the earlier restrictions wouldn’t have any lingering effects. Roberts asked whether a violation of the earlier law would be held against someone who applied for a license under the new rules.

“It absolutely will not,” New York’s lawyer, Richard Dearing, responded.