The island of Puerto Rico has a rich culture and a storied history. This history is also plagued by legal and political ambiguity, which is still visible in recent Federal and Supreme Court jurisprudence. The purpose of this Article is to conceptualize the complicated legal and political relationship between Puerto Rico and the United States—from Puerto Rico’s colonial inception to the Insular Cases, which defined Puerto Rico’s status as a territory to its current political stalemate. Further, these decisions created a familiar Plessy v. Ferguson-type legal doctrine in the form of second-class citizenship for the inhabitants of Puerto Rico.

First, this Article briefly discusses the history of Puerto Rico, from its colonial incarnation of Spanish rule to the signing of the Jones-Shafroth Act, which established United States citizenship for the people of Puerto Rico. Next, this Article details the inconsistency that the federal courts have shown to Puerto Rico. In Puerto Rico v. Sánchez-Valle, Justice Breyer’s dissenting opinion demonstrates how the majority oversimplified Puerto Rico’s judicial autonomy. To exemplify further this inconsistency, Puerto Rico went from having the ability to construct its own Constitution in 1952 to the 2016 Supreme Court decision in Puerto Rico v. Franklin California Tax-Free Trust, which denied Puerto Rico the ability to control its own debt management during its fiscal crisis.