Weaving together thousands of archival fragments, this study explores a shared Black Atlantic world where the meanings of slavery and freedom were fiercely contested and claimed. It recreates the worlds of extraordinary individuals and communities in the long sixteenth century, whilst mapping the development of early modern Black thought about slavery and freedom. From a free Black mother's embarkation license to cross the Atlantic Ocean, to an enslaved Sevillian woman's epistles to her freed husband in New Spain, to an enslaved man's negotiations with prospective buyers on the auction block in Mexico City, to a Black man's petition to reclaim his liberty after his illegitimate enslavement, Chloe L. Ireton explores how Africans and their descendants reckoned with laws and theological discourses that legitimized the enslavement of Black people and the varied meanings of freedom across legal jurisdictions. Their intellectual labor reimagined the epistemic worlds of slavery and freedom in the early modern Atlantic.