Based on today’s argument in New York Rifle & Pistol Association, the unconstitutionality of New York City’s obscure transportation restriction on licensed handguns seems to be a foregone conclusion, with the only real question being how the Supreme Court will respond to the City’s strategic attempt to moot the case by repealing the law before a ruling could be handed down.
On that question, the justices appear divided along predictable ideological lines, with Justices Ginsburg and Sotomayor taking a hard line in their questioning that the case is moot, and Justices Alito and Gorsuch pushing back with equal force for the proposition that the controversy remains live and the city should not be rewarded for its blatant efforts to frustrate Supreme Court review of its now abandoned policy.
The mootness issue is particularly significant in this case because it involves such a clear attempt by a government litigant to obtain favorable rulings in the lower courts (which have been generally—but not uniformly—supportive of gun regulations in Second Amendment challenges) while denying the Supreme Court the opportunity to reverse those rulings and order the lower courts to stop rubber-stamping gun regulations and apply a more searching level of judicial scrutiny.
Notably, the sort of bad-faith case mooting on display in New York Rifle & Pistol is not remotely limited to Second Amendment cases and has been successfully deployed in a number of areas, including particularly civil forfeiture cases, where the government has been quite effective at thwarting Supreme Court review of highly dubious practices.
Another point that cuts against New York City's strategic efforts to moot the New York Rifle & Pistol case is how far mootness and standing doctrine often drifts from its constitutional rationale, which is to avoid putting judges in the position of offering what amount to "advisory opinions" in situations where there is really no genuine dispute between the parties and nothing for the judiciary to remedy.
Nevertheless, courts have have held that even something as materially insignificant as a nominal damages claim for, say, $10 may be sufficient to keep an otherwise defunct case alive. And indeed, much of this morning's argument focused on the question about whether the plaintiffs did, or should have, or might one day be able to assert a potentially case-saving low-dollar damages claim.
Well. If the question for Article III case-or-controversy purposes is really, "Hey buddy, can you spot me a Hamilton?" then Neil Gorsuch's answer—and perhaps that of four more justices as well—appears to be, "For this case? Delighted to."