Santo Domingo, the first European colony in the Americas, was the original thread at the edge of an expansively woven Spanish imperial tapestry. From 1784-1822 this hem frayed, threatening to unbind the most basic stitches that tied Caribbean colonies to Spanish imperial power. My dissertation analyzes colonial Santo Domingo's cultural, racial, political trajectories amidst influences of the Haitian and French revolutions, Spanish reaction, African Diaspora, and Latin American independence movements. A uniquely Dominican cultural politics of race and nation were born at the intersections of these social and cultural forces, unraveled colonialism, and set terms of engagement with their Haitian neighbors for generations to come. Across the 1790s Spanish colonialism regressed from inclusive counterrevolution and popular piety to linking blackness with impiety and violence while Dominicans of color pursued their own often radical social ambitions. From 1802-1809 Spain surrendered Santo Domingo to French occupation, and despite Spanish recolonization from 1810-1821 Dominicans increasingly abandoned decrepit empires to explore national self-definitions. Popular Dominicans undertook frequent anti-colonial, pro-republican conspiracies in collaboration with Haitian conspirators. By 1822 demands for citizenship and sovereignty propelled Santo Domingo toward two competing independence movements – one more elite and moderate, the other popular and pro-Haitian. I argue that Dominicans navigated the signature contests of this era to ultimately achieve the most progressive Spanish American independence – immediate emancipation, unqualified citizenship, and stable sovereignty – as they were bound into a New World fabric of anti-colonial racial solidarity via annexation in 1822 to Haiti, the world’s first black republic.