This presentation invites us to imagine afrodescended Latin@s—who live, think, and feel colonial modernity between different nations, regions, and subaltern positionalities—as subjects with inherently fragmented and “entangled” ontologies. Drawing from the writings of the Martinican poet-philosopher Edouard Glissant about the protean condition of the Caribbean (post)colonial subject, we will analyze various Cuban and Puerto Rican activist intellectuals from the early 20th century that self-identified as Black political subjects, but also as Latin Caribbean national subjects. Specifically, we will analyze traces left behind by those that sought to reconcile anti-racist and anti-imperialist/nationalist discourses and practices that were inherently contradictory due to the notion that in Latin America, the nation and Latin@ pan-ethnicity made racial alterity insignificant. A close reading of the identitarian aporias apparent in the letters, essays, and the journalism of those who sought to unravel these contradictions affords us a window for reconceptualizing the instabilities but also the possibilities of afro-latinidades as a spectrum of heterodox onto-political strategies that are inherently transnational and relational.