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This paper examines the development of Americanization projects surrounding Puerto Ricans, briefly discussing from the early schooling policies under U.S. colonial rule on the island to their movement to Chicago in the 1940s, and the problems that manifested within the city and community because of these practices. City agencies in Chicago focused on creating Americanization projects, centered on English language acquisition and American customs, in order to facilitate the movement of the population to the city. However, these programs ignored the decades long relationship between the U.S. and the island, which had already shifted educational policies in Puerto Rico and thus essentially creating American schools in Puerto Rico since 1898.