The Caribbean archipelago—the site of convergence for imperial powers, enslaved Africans, Asian indentured laborers or “coolies,” and indigenous peoples—bears markers of cultural, linguistic, and racial hybridity. Using literature from the Anglo- and Francophone Caribbean, I seek to illuminate how Afro-, Indo-, and mixed-race Caribbean peoples negotiate their subjectivity in relation to imagined homelands and, often, reinscribe old, colonial forms of power to create hierarchies in the postcolonial moment. Afro- and Indo-Caribbeans, specifically, maintain a tenuous relation to representations of ‘old’ Africa and India, and mixed-race Caribbeans are bifurcated by disparate origins. Likewise, the descendants of enslaved Africans and indentured South Asians alternately inherit and resist colonial legacies. I seek to define how hybridity informs the articulation of a Caribbean imagi(nation) for diasporic subjects.