This book focuses on the peoples of Hispaniola and their deep, intimate, and persistent embrace of smuggling, and situates their story at the crossroads of the fields of colonial Latin American, Caribbean, and Atlantic history. Hispaniola residents traded extralegally in order to circumvent the increasingly marginal space the island occupied within the Spanish colonial system, one which left them on the fringes of lawful commercial connections. During the long seventeenth century (which I define as the years between the 1580s and 1690s), the Atlantic world was a growing network of interconnected port towns and cities and their hinterlands that developed simultaneously to the integration of those port cities into their own imperial systems. With this twin dynamic in mind, I argue that the inhabitants of the Spanish colony of Hispaniola overcame their peripheral status within the Spanish empire by embracing the possibilities that the people, networks, and goods of the nascent new Atlantic world provided. Elites wove themselves into the fabric of the trade and dominated it as they could; other residents also made their lives through the trade.