This essay addresses the limits of conventional Western political categories for apprehending post-colonial Caribbean political landscapes. Specifically, it suggests that in the case of the Dominican Republic standard political differentiations of periods of “dictatorship” and “democracy” obscure continuities and elide the crucial impact of US imperialism. The practice of the US military occupation (1916–24) in clothing itself in a discourse of democratization and modernization was perpetuated by the Rafael Trujillo dictatorship (1930–61) to long-lasting effect. Through close readings of key political discourses from the Trujillo era, the author highlights the dictatorship’s appropriation of key modern democratic vocabulary, terms including modern politics, democracy, progress, equality, and social justice. Ingrained for more than three decades, these meanings did not simply vanish with the arrival of “true” democracy in the country and remain partly alive today. The work of Argentine political theorist Ernesto Laclau on hegemony may help account for these continuities and be usefully brought to bear on other Caribbean postcolonial contexts.