This article performs a relational historical reading of the colonial formations that have bound Puerto Ricans to other colonial subjects throughout the US empire. It begins with an overview of the connections between how the Supreme Court contrived a state of constitutional exception that sanctioned the conquest of Native American tribes and lands and how between 1901 and 1921 they derived a similar status for the United States' insular colonies. It then foregrounds another interrelationship between Puerto Rico and its homologues: connected geostrategic and economic logics from the early to mid-twentieth century that allowed US government and private interests to reap benefits and profits from the overseas territories while impeding their economic sustainability. Finally, this article illustrates how today an updated version of US colonialism through capital investment and debt is substituting the more direct modes of control that the US empire previously employed in its far-flung colonial archipelagos.

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