The United States of America, as a name, is slightly misleading. It’s true that this country consists mostly of 50 states bound together in a federal union. It’s also true that, for various historical reasons, the United States also includes a constellation of territories that it acquired in the nineteenth and early twentieth centuries. Some of these lands, like Hawaii and Alaska, have since joined the Union as states. Others, like the Philippines, are now independent countries.

And then there are some, most famously Puerto Rico, that occupy a liminal space in the American empire. In a concurring opinion last week in United States v. Vaello-Madero, Justice Neil Gorsuch sought to close that gap by revisiting a group of the court’s most controversial rulings. “A century ago in the Insular Cases, this Court held that the federal government could rule Puerto Rico and other territories largely without regard to the Constitution,” Gorsuch wrote. “It is past time to acknowledge the gravity of this error and admit what we know to be true: The Insular Cases have no foundation in the Constitution and rest instead on racial stereotypes. They deserve no place in our law.”

Gorsuch’s call to overturn the Insular Cases is notable in and of itself. While the Supreme Court has signaled its unease with those precedents in recent years, he is one of only two sitting justices who has expressly said they should be scrapped. (In a footnote in her dissent in Vaello-Madero, Justice Sonia Sotomayor said she agreed with her colleague’s position on the cases.) What makes his concurring opinion even more interesting is what it says about how Gorsuch approaches the more uncomfortable chapters of American history, in this case and in others—and what it might mean for how he decides future cases.

Vaello-Madero, on its surface, is about a bureaucratic error in the Supplemental Security Income program, which generally provides benefits to people with disabilities. Jose Luis Vaello-Madero, the case’s namesake, moved back to Puerto Rico in 2013 after years of living in New York. He had collected SSI payments while in New York and continued to do so after his change in residence. Congress, however, had only authorized the program within the 50 states, the District of Columbia, and the Northern Mariana Islands. When the Social Security Administration discovered its mistake, it sued Vaello-Madero to recoup more than $28,000 it had sent him.

Vaello-Madero countered that it was unconstitutional for the federal government to deny him SSI benefits simply for moving somewhere else within the United States. Judge Gustavo Gelpí, who served on the federal district court in Puerto Rico at the time, ruled in Vaello-Madero’s favor and concluded that Congress could not “demean and brand” him with “a stigma of inferior citizenship” for living there. The First Circuit Court of Appeals agreed, ruling that the agency’s actions had violated his equal protection rights under the Fifth Amendment’s Due Process Clause.

Justice Brett Kavanaugh’s six-page majority opinion is a monument to brevity. He does not discuss Puerto Rico’s colonial history except to note that “for various historical and policy reasons,” Congress “has not required residents of Puerto Rico to pay most federal income, gift, estate, and excise taxes.” At the same time, Kavanaugh noted, Congress has also excluded Puerto Rico from various federal programs and benefits. Writing for an 8–1 majority, he argued that the Constitution’s Territory Clause gives Congress the discretion to make those decisions when administering the territories.

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Sotomayor, whose parents hailed from Puerto Rico, wrote the only dissenting opinion. {snip}

But it was Gorsuch who would lay out the most surprising take on the matter, in some ways going further than even Sotomayor did in the dissent. In a concurring opinion, he denounced a series of Supreme Court decisions that laid out the constitutional order in the former Spanish imperial possessions. Collectively, these rulings are known as the Insular Cases. In Downes v. Bidwell, which is often seen as the first of them, the Supreme Court upheld a customs law passed by Congress on imports from Puerto Rico, which appeared to violate the Constitution’s command that all customs duties be uniform “throughout the United States.” To uphold the law, the court defined Puerto Rico as an “unincorporated territory” where the Constitution’s full scope does not apply, as opposed to an “incorporated territory” where it remains in full force.

“The flaws in the Insular Cases are as fundamental as they are shameful,” Gorsuch wrote in his concurring opinion last week. “Nothing in the Constitution speaks of ‘incorporated’ and ‘unincorporated’ Territories. Nothing in it extends to the latter only certain supposedly ‘fundamental’ constitutional guarantees. Nothing in it authorizes judges to engage in the sordid business of segregating territories and the people who live in them on the basis of race, ethnicity, or religion.”

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This isn’t the first time that Gorsuch has reckoned with the more tragic chapters of American history. Shortly after his confirmation in 2017, the justices faced an unusual dispute over tribal sovereignty in Oklahoma. Two cases involving tribal members who committed crimes against other tribal members, Sharp v. Murphy and McGirt v. Oklahoma, compelled the justices to consider whether the reservations of the Five Civilized Tribes still legally existed. Under the court’s precedents, only Congress can disestablish a tribal reservation, and it must do so explicitly. Gorsuch, joined by the court’s four liberals, ruled that it hadn’t and that the reservations still lawfully existed.

If Gorsuch had simply written that in his majority opinion and nothing more, McGirt would have been one of the most important Indian law decisions in the last two decades. What really set his opinion apart was the sheer moral force that he brought to bear in it. “At the end of the Trail of Tears was a promise,” he said in his opening line. Gorsuch made a simple point—that the United States had promised those lands to the tribes in the nineteenth century and had not explicitly revoked that promise since then—and then hammered the dissenting justices and the state of Oklahoma for trying to set it aside.

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A few months before McGirt, Gorsuch also wrote the majority opinion in Ramos v. Louisiana, where the court struck down laws that allowed state juries to convict people without unanimous verdicts on their guilt. Writing for the court, he did not shy away from raising the sordid history of nonunanimous jury verdicts. Louisiana and Oregon, the only two states that recently had such laws on the books, both adopted them to preserve white supremacy: the former at a state constitutional convention that entrenched a wave of Jim Crow in the state Constitution, and the latter while state politics were under the sway of the Ku Klux Klan. “No one before us contests any of this; courts in both Louisiana and Oregon have frankly acknowledged that race was a motivating factor in the adoption of their States’ respective non-unanimity rules,” he wrote.

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