Does Puerto Rico’s prison system harbor any of the same kinds of structural racism as the United States mainland? In this paper, I argue that the question is misplaced. The predicament of Puerto Rican carcerality arises from the island’s place in a world order dominated by new sorts of empire; an imperial order that invisibilizes race, impoverishes Blackness, and penalizes poverty. But there is another side to all this. Despite race’s invisibility in Puerto Rico, the only ever national study to measure racial disparities in Puerto Rican prisons found that Puerto Ricans who identify as Black are over-represented in correctional facilities. In probing the paradox of persistent racial disparities despite race’s invisibility, I argue that Puerto Rican carcerality foreshadows a racialized prison boom in the Latin American post-colonies that is now well in the making.