Justice Brett Kavanaugh said he was troubled that New York’s system allows officials “blanket discretion” to accept or reject a request for a permit. “That’s just not how we do constitutional rights,” Kavanaugh said.

Chief Justice John Roberts expressed similar reservations.

“You don’t have to say when you’re looking for a permit to speak on a street corner that your speech is particularly important,” Roberts said. “The idea you need a license to exercise the right, I think, is unusual in the context of the Bill of Rights.”

Much of the nearly two-hour court session Wednesday sounded more like a history lesson than a typical legal argument. Those challenging New York’s law contended that it is out of step with how other states view the Second Amendment, while defenders of New York’s approach pointed to a long tradition of many states putting a variety of limits on gun possession in public.

The liberal justices said gun control opponents were asking to invalidate a slew of laws dating back through American history, even to the colonial era and to England.

“What it appears to me is that the history and tradition of carrying weapons is that states get a lot of deference on this,” Justice Sonia Sotomayor said. “I don’t know how I get past all that history.”

Justice Stephen Breyer said the competing historical claims demonstrated the shortcomings of turning to history to interpret constitutional protections.

“This is a wonderful case of showing both sides. I’m not sure how to deal with the history,” said Breyer.

And Justice Elana Kagan conceded that many states allowed possession of weapons without any permit, but she noted that those states often banned concealed carrying and favored open display.

“If you look to the history, you end up with a completely different set of rules form the ones that you are suggesting. … It’s an example, I think, of the difficultly of looking to history,” Kagan said to Paul Clement, a lawyer for two New York state gun owners suing over that state’s law.

Clement acknowledged that some mores around guns have “flipped,” but said that doesn’t mean the justices should ignore the fact that carrying guns in public was legal in most states for most of U.S. history. “You cannot sort of throw it all out,” he said.

The case argued Wednesday explores an issue left unresolved by the Supreme Court in its 2008 ruling, District of Columbia v. Heller, a 5-4 decision which found a constitutional right for individuals to keep a gun at home.

The challenge to New York’s law prompted the justices also to debate whether recognizing a right to carry a gun in public would trigger a flurry of suits over efforts to restrict the possession of weapons in particular places ranging from government buildings to universities to bars.

Clement said the right should cover places “typically open to the general public,” but Roberts asked whether that meant one could or could not bring a gun to a football game. Clement offered a noncommittal answer, saying, “You’d probably take it on its own and look to the historical analogues.”

That prompted Kagan to swoop in. “How does it cash out? What does it mean?” she said, asking if a university campus was generally public or not.

Justice Amy Coney Barrett asked Clement whether his test would require the state to allow guns in Times Square on New Year’s Eve, since it is generally open to the public, although access tends to be more controlled on that night.

Clement said he’d view that as the kind of time, place and manner restriction that courts already allow for First Amendment activity such as protests or rallies.

Justice Samuel Alito offered some unique arguments against New York’s law, suggesting that it was rooted in racism against Irish and Italian immigrants who streamed into the state about a century ago. He also contended that the statute is effectively elitist because it is more difficult for typical citizens to get a concealed carry permit.

“There is the right to self-defense for celebrities and state judges and retired police officers, but pretty much not for the ordinary kind of people who have a real, felt need to carry a gun to protect themselves,” Alito said.

New York Solicitor General Barbara Underwood acknowledged that permits to carry a gun for hunting or target shooting are widely available in New York, while those for self-defense are harder to come by, particularly in the more urban parts of the state. She warned that allowing anyone who worked in Manhattan late at night to carry a gun would mean flooding the city’s subways with weapons, raising what she called “the particular specter of a lot of armed people in an enclosed space.”

While some justices acknowledged that most constitutional rights aren’t seen as applying differently in one part of the country than another, others seemed to see valid reasons for distinguishing in the gun rights context between urban areas and rural ones.

“It seems completely intuitive there should be different gun regimes in New York than in Wyoming … but it’s a hard thing to match with our notion of constitutional rights generally,” Kagan said. “We would never really dream of doing that for the First Amendment.”

A lawyer representing the Biden administration, Deputy Solicitor General Brian Fletcher, encouraged the justices to embrace such an approach when it comes to guns, given the country’s long tolerance of widely varying gun regulations. “The Second Amendment has a distinct history and tradition,” Fletcher said.

Perhaps the most colorful line at Wednesday’s arguments came from Clement who seemed to paraphrase a famous bit of dialogue from the diner scene in “When Harry Met Sally” as he said his clients want the permitting regime many other states have where applicants are presumed eligible to carry a gun for self-defense unless there is a basis to deny a permit.

“The thrust of this case is: We’d like what they’re having,” Clement said.

A decision in the case is expected by the end of June or early July.