The Supreme Court heard oral arguments on Wednesday in the case of New York State Rifle & Pistol Association Inc. (NYSRPA) v. Bruen, which focuses on whether New York State violated plaintiffs Robert Nash and Brandon Koch’s Second Amendment rights by denying them unrestricted concealed carry permits. Lawyer Paul Clement is representing both men and the NYSRPA, which is an offshoot of the National Rifle Association.

A former solicitor general for the Bush Administration, Clement is known as the attorney who’s argued the most cases before SCOTUS since 2000—and has consistently represented parties on the wrong side of history. Clement famously left the law firm he was at in 2011 to continue trying to defend the Defense of Marriage Act and its sympathizers. He also fought against the Affordable Care Act in 2012 and defended tactics used by the Bush Administration during the war on terror.

It appears as if this time, however, Clement will score a win for his clients. Many Supreme Court Justices made no secret of the fact that they were skeptical of the New York law that only allows residents to concealed carry if they can provide “proper cause.” Justices Brett Kavanaugh and Samuel Alito pushed back against the requirement, with Kavanaugh at one point asking, “Why isn’t it good enough to say I live in a violent areas and I want to be able to defend myself?”

Nash and Koch are both NYSRPA members and sought concealed carry permits for the purpose of self-defense. They were issued restricted licenses allowing them to hunt and target shoot, but not to carry their weapons under any other circumstances. The two argued that their completion of firearms safety courses should allow them to carry weapons for self-defense, though a licensing officer still refused to grant them concealed carry permits.

Both men live outside of New York City in fairly rural areas, though the metropolitan city came up frequently throughout the nearly two hours of arguments. Chief Justice John Roberts insinuated that those in major cities have even more reason to be allowed to carry a weapon and mused about “how many muggings take place in a forest” as opposed to a big city. Nash, who lives upstate in Rensselaer County, previously stated that a spate of robberies was one of the reasons why he sought the permit in the first place.

While many of the justices looked to historic rulings to guide their eventual decisions, Justice Neil Gorsuch appeared willing to test just how far the Second Amendment should reach when it comes to carrying a gun outside the home. Participating via video due to a stomach bug, Gorsuch asked Clement about similar cases and how much history should weigh on a decision like this.

Gorsuch cited the last landmark SCOTUS case to do with gun control, 2008’s Columbia v. Heller, which allows for the “individual right to possess a firearm unconnected with service in a militia, and to use that arm for traditionally lawful purposes, such as self-defense within the home” under the Second Amendment. Clement argued earlier that the case shows how analysis of the Second Amendment has continued within a contemporary context as opposed to stopping in 1871 when the state of Texas passed a landmark law establishing guidelines for concealed carrying.

You can listen to the full oral arguments here. A decision on this case isn’t expected until next spring.