The English conquest of Jamaica in 1655 was a turning point in the history of Atlantic World colonialism. Conquest displaced the Spanish colony and its subjects, some of who fled into the mountainous interior of Jamaica and assumed lives in isolation. This project reconstructs the historical experiences of the “negro” populations of Spanish and English Jamaica, which included its “free black”, “mulattoes”, indigenous peoples, and others, and examines how English cosmopolitanism and distinct interactions laid the groundwork for and informed the syncretic identities and communities that emerged decades later. Upon the framework of English conquest within the West Indies, I explore the experiences of one such settlement alongside the early English colony of Jamaica to understand how a formal relationship materialized between the entities and how its course inflected the distinct socio-political identity and emergent political agency embodied by the Jamaican Maroons. To this end, this study reconceptualizes the social and political foundations of the “negroes” who became the Jamaican Maroons removed from the teleology of the Maroon Wars and its resultant Treaty of 1738-1739.