For decades, New York City enforced uniquely onerous regulations that effectively prohibited licensed pistol and revolver owners from taking their weapons outside their homes, even when they were unloaded and stored in a locked container, unless they were traveling to or from one of seven gun ranges in the five boroughs. When several gun owners challenged those regulations, the city successfully defended their constitutionality for five years, obtaining favorable rulings from a federal judge and the U.S. Court of Appeals for the 2nd Circuit. But after the U.S. Supreme Court agreed to hear an appeal of that decision, the city rewrote its rules, backed a state law that eased restrictions on transporting guns, and urged the Court to drop the case, arguing that the regulatory and statutory changes made it moot. During oral arguments today in New York State Rifle & Pistol Association v. City of New York, several justices seemed skeptical of that claim, which is transparently aimed at avoiding a Supreme Court decision that could clarify the contours of the Second Amendment.

Chief Justice John Roberts asked Richard Dearing, the attorney representing New York City, whether a prior violation of the old transportation regulations might be held against a gun owner when he tries to renew his license. “It absolutely will not,” Dearing said, although the discretion to deny licenses for “good cause” seems to make that a real risk.

Justice Neil Gorsuch suggested that the possibility of obtaining compensation for economic damages related to the old regulations, although it was not specifically sought by the plaintiffs, might be enough to keep the case alive, as Principal Deputy Solicitor General Jeffrey Wall argued. “This litigation, I think, has taken five-plus years, and that [issue] has become relevant only at this late stage, after the city and the state have enacted a new law,” Gorsuch observed. “Why isn’t the prospect of allowing damages to be added to the complaint enough?”

Gorsuch also noted that it’s unclear whether the new rules allow gun owners to make stops while en route to ranges, competitions, or second homes outside the city. The city says such trips have to be “continuous and uninterrupted,” while the state law says gun owners have to be traveling “directly” to their destinations. If those restrictions might be read to preclude stops for coffee, gas, or bathroom breaks, Gorsuch wondered, “why isn’t there a live controversy remaining?” He suggested that “despite herculean, late-breaking efforts to moot the case,” there is still relief the plaintiffs could obtain only through a decision on the merits.

Dearing assured the justices that the NYPD would not look askance at “reasonably necessary” stops for coffee, gas, or bladder relief, prompting Gorsuch to wonder, “Is coffee reasonably necessary?” While that remark prompted laughter, Gorsuch emphasized his point: “What’s going to qualify? I’m just a little unclear about that.”

So was Dearing. Justice Samuel Alito, who like Gorsuch remarked upon “the quite extraordinary step of trying to moot the case after we granted review,” wondered about a gun owner who drives to a range in New Jersey and stops to “visit his mother for a couple of hours to take care of a few things for her.” Dearing was unsure whether that would be allowed. “I think that would have to be a question now to be litigated under the state law,” he said. “I hadn’t considered the mother or mother-in-law example before.”

Speaking for the plaintiffs, Paul Clement said Dearing’s assurances are not good enough to make the case moot. “The city took it on itself in Section 7 of the new regs to tell you what they, at least at that point, thought was sufficiently direct, which is ‘continuous and uninterrupted,'” he said. “They’re now making representations that the reg doesn’t mean what it seems to mean….My client[s] shouldn’t have to rely on those representations. They should get that in writing in an injunction that would be enforceable. That would be effectual relief.”

Perhaps the most telling exchange involved not the mootness issue but the constitutionality of the original rules:

Alito: Mr. Dearing, are the people in New York less safe now as a result of the enactment of the new city and state laws than they were before?

Dearing: No, I don’t think so. We made a judgment, expressed by our police commissioner, that it was consistent with public safety to repeal the prior rule and to move forward without it.

Alito: Well, if they’re not less safe, then what possible justification could there have been for the old rule, which you have abandoned?

Dearing did not have a very good answer, except to say that the city’s arbitrary restrictions on transporting firearms may have made its other rules a bit easier to enforce. As the petitioners note, “The only ‘evidence’ the City has ever mustered to support the tailoring of its policy is an affidavit from a former commander of the state licensing division hypothesizing, with no evidentiary support whatsoever, that the mere presence of a handgun—even unloaded, secured in a pistol case, separated from its ammunition, and stowed in the trunk of the car—might pose a public-safety risk in ‘road rage’ or other ‘stressful’ situations.” The city will have to do better than that if it wants to demonstrate that its rules were consistent with the constitutional right to keep and bear arms, which is why it is so desperate to stop the Supreme Court from considering that question.