My dissertation explores the role of the largest and most powerful native community of the Lesser Antilles, the Caribs, transforming the circum-Caribbean into a fluid and contested space. Hundreds of small Carib bands achieved political influence by blending violence, diplomacy, trade, and kinship during the eighteenth century. They expanded their realm throughout the Lesser Antilles, transforming a world of sugar and slaves into a fluid space and a drain for colonial money. Far from being trapped between imperial powers, the Caribs consciously determined the course and outcomes of political events. They supported the French and American insurgents in overthrowing Great Britain's dominion over Saint Vincent and Dominica during the American Revolution (1775–1783). They also allied with the French Republic against British and French colonists who were loyal to the king during the French Revolutionary Wars in the Antilles. Frustrated by the Caribs' raids on sugar plantations and Carib disregard for imperial trade policies, the British took the drastic measure of forcefully relocating the entire Carib community to the Spanish Bay of Honduras in 1797. Once on Spanish soil, the natives established effective patronage relationships with the Spaniards, joined colonial militias, and functioned as intermediaries between Spanish, British, and North American smugglers. My research examines how the Caribs imposed their notions of space and sovereignty onto European hegemony and ultimately transformed the Lesser Antilles and the Gulf of Honduras into de facto borderlands. Ultimately, the Caribs derived their power from Old Regime practices and institutions such as smuggling, slave trading, and monarchical loyalism, while ideas of enlightened freedom and the consolidation of modern nation-states paradoxically undermined their autonomy and political influence.