This paper explores the possibilities and pitfalls of Hispanism as a critique of Americanization in the U.S. insular empire (the Philippines, Cuba, and Puerto Rico) through a comparative intellectual history centered on the canonical literary figures of Jorge Mañach (1898-1961), Antonio Pedreira (1898-1939), and Nicomedes Joaquin (1917-2003). These cultural nationalist intellectuals have come under severe criticism for their unguarded comments that betray inclinations towards white supremacy, antifeminism, the negation of the violence of conquest, and the minimization of indigenous histories. Yet, even with these pitfalls, these intellectuals have remained a vital force in the intellectual histories and nationalist consciousness of their respective nations, and beyond. No doubt this has to do with the artistry of their works, their pioneering roles, and their provocative challenges to national identity. Alongside of these, this paper argues that their continuing power stems from their historic intervention in the colonial Americanization of their homelands, their challenge to the United States’ claims to Anglo-Saxon civilizational superiority, and their rearticulation of Hispanism from a language of colonization to a Hispanist national sensibility as against American industrial modernity. In this vein, as critics Rafael Bernabe, José Juan Rodríguez Vázquez, and Anke Bierkenmaier posit, these insular imperial intellectuals drew from a strain of conservative European and Latin American thought, from the Romantics to José Enrique Rodo and from Oswald Spengler to the Spanish philosophers, Miguel de Unamuno and José Ortega y Gasset.