This article examines the medical career of an enslaved physician in Virginia named Nassaw from the mid eighteenth-century until the period of the American Revolution. I develop a taxonomy of Nassaw’s labours as a nurse caring for the sick, a healer administering medicines at the behest of his enslaver and as a doctor in his own right making medical judgements as he treated his patients. Nassaw is in some ways comparable to other enslaved healers of African descent in the Atlantic world, including well-known Mohanes and ritual specialists in Brazil and Latin America. However, due to his role as a physician employed by his slaveholder to principally heal other enslaved people, Nassaw struggled to find satisfaction in his labours as a healer as other enslaved people rightly perceived him as an agent of their enslaver whose medical work healed their bodies while extending their oppression. I argue that Nassaw became frustrated and depressed, and turned to drinking because of his inability to pursue or experience what Sharla M. Fett terms a ‘relational vision of health’ in the Chesapeake. Moreover, I interpret his drinking as a rebuke to the racist pretensions of his enslaver – who instructed him in pharmacy and surgery – who aimed to transform Nassaw into an Enlightened ‘black exhibit’ by training him to be a doctor. I conclude by returning to how precisely different Nassaw was from other enslaved healers in the Chesapeake like Tom of Nomini Hall or Romeo, and make the case that Nassaw deserves a place in histories of slavery and medicine precisely because he was an enslaved plantation doctor rather than a popular healer or conjuror.