Although Hispaniola was the point of initial contact between Europe and the Americas and is a microcosm of the social, political, and economic tensions in the Caribbean, it remains peripheral to the modern world system (except when tragedy strikes). On the island, political and economic elites have exploited these tensions for centuries, belying fundamental commonalities between Haitians and Dominicans. My project examines how (mainly) diasporic writers negotiate Hispaniola's long-disputed internal border in recent fiction addressing the 1937 massacre of 15,000 Haitian laborers in the borderlands–an area that historically has resisted national control. I argue that cultural divisions between Haiti and the Dominican Republic are shifting as transnational cultural production exposes the strategic and problematic construction of competing discourses of cultural and racial legitimacy.