Enslaved New World illuminates sixteenth-century Santo Domingo as the site of the Americas' earliest plantation and slave society and the first place where slavery became limited to people of African descent. Yet Santo Domingo was also home, Turits shows, to widespread continual flight from bondage and an ecology providing escapees with relatively easy refuge. This transformed the colony into a land in which predominantly self-emancipated Black people became the largest population group by the late seventeenth century, 150 years before slavery's abolition. Afterwards, slavery and legal racial hierarchy persisted, but the White elite often remained too poor and weak to overcome resistance and competing constructs of status and color emerged. By focusing on Santo Domingo's understudied African-descended majority population within novel frameworks, Turits opens up new understandings of Dominican history, slavery's racialization, race and racism's historical contingency, and an extraordinarily successful Afro-American trajectory of resistance.