Articulations of heritage are, among other things, rhetorical tools that explain the shape of the past and also plot out particular visions for the future. During “the American Century,” overlapping, intersecting, and conflicting interpretations of the Puerto Rican past have served, at turns, as a justification for US colonialism, as a call to revolutionary arms to overthrow the US government, and as expressions of numerous positions between.1 But always, narratives of the past reflect the positionality of the individuals and the political vision of the groups and agencies shaping it. This article provides a brief overview of the ways in which heritage has operated as a body of ideas and practices on the island in the twentieth century. Beginning with the US military occupation of 1898 and throughout the twentieth century, heritage has acted as a contest in which the hearts and minds of the Puerto Rican people have been the prize. A case study of Puerto Rican public history and collective memory provides an example of the ways in which narratives about the past operate within and on colonial power, grassroots movements and resistance, and in the arena of statecraft. This study of Puerto Rico adds to the growing body of scholarship on the role of heritage in the political arena, either in service of policymaking or cultural activism.2 This study also, and perhaps most centrally, reveals the ways in which discourse about the past is inherently political, and illuminates the ways that power flows through our interpretation of history.