Reconsidering nineteenth-century Cuban history from the perspective of African-identified people requires that we read Cuban history as tragedy. While there were several important socio-political transitions during Cuba’s long nineteenth century, including slave emancipation in 1886, de-Africanization, or the processes by which colonialists and their successors endeavored to corral, contain, control, co-opt, and eliminate African influences in Cuba persisted well into the twentieth century. Even though these repressive efforts were never fully successful, centering traditional forms of resistance alone leads us to ignore alternative paths/ideas/options that surfaced in response to White supremacy. Simply put, these alternatives garner less attention because they do not fit our narrative constructs and are hard for us to “think.” Centering de-Africanization as process offers a helpful corrective to progressivist and romantic narratives. This essay situates one historical case study in a differently conceived nineteenth-century Cuba to explore forms of resistance that were effectively silenced at the time of their enunciation. In exploring the methodological approaches to understanding this specific case, the essay contributes to a rising trend in Latin American and Latinx studies that centers the importance of Afro-diasporic peoples’ roles in shaping the histories of Latin America and of Latinx experiences in the United States.