This research examines the career of Robert Searle, an English privateer, that conducted state-sponsored attacks against the Spanish and Dutch in the Caribbean from 1655 to 1671. Set within the Buccaneering Period of the Golden Age of Piracy (1650-1680), Robert Searle’s personal actions contributed to the rise of the English in the Caribbean to a position of dominance over Spain, which dominated the region from 1492 until the 1670s. Searle serves as a window into the contributions of thousands of nameless men who journeyed to the Caribbean as a member of Oliver Cromwell’s Western Design Fleet. These men failed in their endeavor to take Hispaniola from the Spanish, successfully invaded Jamaica, and spent the next fifteen years securing England’s largest possession in the region, transitioning Jamaica from a military outpost to a successful plantation colony. These men, including Searle himself, have been overshadowed in the history of English Jamaica by more well-known figures such as Sir Henry Morgan, the famed “Admiral of the Buccaneers.” Searle and his compatriots pursued the objectives of the core in London throughout the contested periphery of the Caribbean region. These goals were first framed as the complete destruction of the Spanish Empire in the Americas and later as achieving trade between Jamaica and Spain’s American colonies. The examination of Robert Searle through the core-periphery relationship between the metropole and the Caribbean illustrates how the totality of his actions contributed to the rising English position in the Caribbean. Ultimately, Searle and his fellow privateers proved vital to Spain conceding to England the rights of trade and formal recognition of their colonies in the region with a series of succeeding Treaties of Madrid.