The history of American modern art has largely excluded the US empire in its narrative and overlooked the massive direct investments in art education by the US government and private institutions during the 20th century. This essay revisits archival sources on two generations of Filipino pensionados, who were educated during the American colonization of the Philippines (1898-1945) and the immediate postwar period (1946-1964), to reconstruct an artistic genealogy of the impact of US art schools on Philippine art. It traces how Filipino artists formulated a decentralized and non-hierarchical notion of cultural exchange to reconfigure the aesthetic of the Modernist movements they encountered in the United States into an emancipatory and critical strategy. Focusing on the lives and works of Victorio Edades (1895-1985), Purita Kalaw Ledesma (1914-2005), Constancio Bernardo (1910-2003), and to a lesser extent, of Fernando Zóbel (1924-1984) Juan Nakpil (1899-1986), and Angel Nakpil (1914-1980), I trace the importation of various Western styles of modernism in art and architecture as a confrontation between comparable values of form—Distortion, Cubism, and Bauhaus styles in visual art—and the struggle for independence in the socio-political life of the colony. Emphasis is given on the pensionados’ polemical writings on race and ethnicity and their observations on American culture. I argue that the pensionados’ turn to modernism is an assertion of the evolving idea of national identity as much as it was an effect of Americanization. In so doing, the essay models a visual analysis and historicist reading that grasps the relationship between artistic and political struggles.