The history of U.S.-Americanization in Puerto Rico's public schools is complex and often misunderstood. The literature suggests that de jure U.S.-Americanization culminated in 1949 when an administrative order was signed making Spanish the official language of instruction in public schools. However, the same literature seems to indicate that Puerto Rican students continue to experience the impacts of U.S.-Americanization because Puerto Rico remains a colony and there has been limited systematic political intentionality to decolonize the educational system from the U.S.-Americanization process. In this article, I argue that, although there were changes once the de jure U.S.-Americanization of Puerto Rican schools ceased, the U.S.-Americanization of Puerto Ricans will continue as long as the colonial legal system imposed by the United States on the Puerto Rican archipelago remains in force. Against this backdrop, it is inevitable that Puerto Rican educational policies and curricula will begin a process of intentional decolonization, revealing how U.S.-Americanization reflects coloniality. In the meantime, the Philosophy with Children program can provide pedagogical and curricular tools for public schools in the archipelago to carry out self-organizing educational processes of decolonization.