In 2012, reggaeton artist Tego Calderón released a music video for his song “Robin Hood.” The video tells the story of a man who aids a group of undocumented Dominican immigrants to Puerto Rico. Through a close reading of “Robin Hood,” this essay argues that Calderón establishes connections between Puerto Ricans and Dominicans through an understanding of their shared marginalization as black subjects. This has important implications for African diaspora theory, which has typically neglected Puerto Rican and Dominican engagements with blackness. Calderón disrupts two common assumptions about Puerto Rican and Dominican racial politics: first, that Puerto Ricans and Dominicans are always in conflict and, second, that Puerto Ricans and Dominicans shy away from identifying as black. An analysis of the music video provides one example of how diasporic blackness operates in the Spanish Caribbean and calls for a better integration of the Spanish Caribbean into theories of the African diaspora.