This dissertation explores the Guajira Peninsula during the eighteenth century to understand how Guajiro society evolved amid imperial growth and revolutionary turmoil. Covering approximately 8,000 km²—similar in size to Massachusetts—the peninsula was inhabited by Indigenous communities that governed access to ports and trade routes linking non-Spanish Caribbean regions to northern South America. Guajiro leaders established a lasting sphere of influence in the southern Caribbean by controlling trade and navigating relationships with colonial officials, merchants, and Afro-Caribbeans. They supplied livestock essential for Caribbean plantations and military forces, and they also traded pearls, wood, and human beings. Spanish officials often viewed Guajiro communities not only as prone to uprisings but also as possible allies of rival empires and conduits for illegal trade. During moments of conflict, officials considered the Guajiro’s ability to provide livestock, intelligence, and support as factors that could tip the scales in conflicts with Britain and other rivals. The dissertation makes two broad arguments. First, it shows that Guajiros relied on kinship networks, ritual authority, and customary law in their relationships with Spanish officials, missionaries, foreign traders, and Afro-Caribbeans. Accordingly, they often forced colonial actors to negotiate on Guajiro terms. Second, Guajiro participation in regional trade was central to how Caribbean economies and imperial strategies functioned at the edge of empires. The dissertation examines missionary encounters, the 1769 war, the sistema pacífico, and Guajiro responses to revolutionary upheaval in the French Caribbean. It draws on archival material from Spain, Colombia, Venezuela, France, the UK, and the United States that includes missionary reports, correspondence trade documentation and military logbooks (records kept by officers detailing troop movements and encounters), to reconstruct how Guajiros positioned themselves as political actors in a region long dismissed as marginal.