Over the last few decades social movements and race scholars have begun to uncover and critically examine the social, economic, and political linkages shared between Puerto Ricans and African Americans. Much of this literature has focused exclusively on the period of the Civil Rights Movement with particular emphasis on the Young Lords and Black Panthers. Despite this rich and informative literature, we know very little of the connective social histories and relationships between African Americans and Puerto Ricans that preceded these later social movements. This article traces the historically contingent and multifaceted ways in which African American journalists, between 1942 and 1951, found new political meanings in Puerto Rico as the island underwent a massive economic and social transformation, and how they used that knowledge to reconceptualize challenges to Black personhood in the United States. Examining the Black popular press in Puerto Rico during this period reveals that Black journalists took an active interest in the island because it represented a useful point of comparison for understanding the internal colonial model of social inequality hampering the U.S. African American community during the first half of the twentieth century. The racialized nature of U.S. colonialism experienced by the island, the sociopolitical and economic effects of its monocultural sugar economy, and the second-class citizenship of Puerto Ricans were among the most salient factors that led African American journalists to a broader anti-imperialist understanding of racism, illuminating the lack of civil and economic rights Blacks experienced within the United States.