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Is Puerto Rico Unconstitutional?
Michael Ramsey

Today the Supreme Court hears oral argument in Financial Oversight and Management Board for Puerto Rico v. Aurelius Investment, LLC, a case of potential originalist interest.  It presents the seemingly uninspiring question "[W]hether the appointments clause governs the appointment of members of the Financial Oversight and Management Board for Puerto Rico."  But it might suggest that the entire government of Puerto Rico is unconstitutional (I doubt it) or that the odious (from an originalist perspective) Insular Cases should be overruled (one can hope).  For competing views: 

At Slate, Adriel I. Cepeda Derieux: The Supreme Court Has a Chance to Bring Constitutional Equality to Puerto Rico.  An excerpt:

More than geography or distance, Supreme Court case law has framed Puerto Rico’s relationship with the United States—and the second-class constitutional status of Puerto Ricans—for more than a century. As long as U.S. territories were populated principally by white citizens, the court commonly treated the Constitution as “following the flag.” It governed in the territories just as it did in the states.

At the turn of the 20th century, however—around the same time that it upheld “separate but equal” in Plessy v. Ferguson—the court created an unprecedented rule in decisions known as the Insular Cases. Going forward, the Constitution would not fully follow the flag to newly acquired overseas territories. Some of its protections—including the fundamental right to jury trial—did not apply.

But in the New York Times, Nikolas Bowie: Will Puerto Rico Still Be Allowed to Govern Itself? (arguing that a ruling against Aurelius -- that the appointments clause does apply in Puerto Rico -- would make the island's entire governmental structure unconstitutional).

... Article IV grants Congress “power to dispose of and make all needful Rules and Regulations” for territories. Congress can structure territorial governments as it chooses.

For instance, the Northwest Ordinance of 1789 provided for a territorial legislature with one house that was popularly elected and another comprised of appointees chosen by the President from lists proposed by the elected house and confirmed by the U.S. Senate.

The Court has long held that the Constitution’s structural safeguards including the Appointments Clause do not apply to territories. As Antonin Scalia noted in Freytag (1991), “Congress may endow territorial governments with a plural executive; it may allow the executive to legislate; it may dispense with the legislature or judiciary altogether.”

UPDATE:  Sounds like there's little interest on the Court to make it a big case.