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This paper discusses the role of philanthropic organizations in the American imperial project in Cuba during the 1898-1902 military occupation through an exploration of the work of the New Yorkbased Cuban Educational Association. I argue that the Association’s efforts to recast Cuban and Puerto Rican students in the American image represented a nexus of thought between the architects of the American imperial project and the adherents of a particular Americanized strain of Cuban nationalism. Significantly, some of the Association’s strongest supporters were members of the Cuban political elite, such as Tomás Estrada Palma (who would go on to become the first president of the Cuban republic) Benjamin Guerra, and Fidel Pierra. These men clearly understood the Association’s mission to Americanize Cuban and Puerto Rican students and actively assisted Harroun in his work, most notably through their authorship of Spanishlanguage essays to be distributed to the Association’s students that extolled the virtues of physical labor. The paper will also discuss the close regulation of students’ weight, fitness, and progression towards “manliness” by the organization’s founder Gilbert K. Harroun, which was in support of the overarching mission to instill Cuban students with an “American” appreciation for hard work and personal sacrifice.