At the start of the seventeenth century the eastern Cuban town of Bayamo became a regional entrepôt. Merchants from France, England, Genoa, and the fledgling Dutch Republic arrived at the shores of the port of Manzanillo to trade linens, silks, and enslaved Africans for hides from the Cuban interior. The governor of Cuba, Pedro de Valdés, sought to stop this unlicensed trade and sent his lieutenant governor to Bayamo to investigate. His investigation found that Bayamo was a microcosm of the Caribbean itself, with people from all nations congregating on the shores of the Cauto River, where they formed both mercantile and social bonds in defiance of Spain’s trade monopoly. The lieutenant governor’s efforts to end contraband trade provoked a rebellion in Bayamo and a raid in the nearby city of Santiago de Cuba, where English raiders attempted to capture the investigator. The townsfolk appealed to the Real Audiencia of Santo Domingo and reaffirmed their loyalty to the Spanish empire, while simultaneously playing overlapping jurisdictions against each other. This article demonstrates the complex relationships between local Spanish colonists, foreign merchants, and the regional colonial institutions that impacted the way local actors navigated commercial and legal channels.