This paper presents a case study of the relationship and lives of Henry Bromfield, a Massachusetts merchant, and Othello, an African man he enslaved in Massachusetts until his death in 1817, from the colonial, revolutionary, and early republic periods to interrogate how, why, and under what conditions de facto slavery persisted, unchallenged by local communities, into the 19th century in the interior of Massachusetts despite widespread recognized legal emancipation in the state and the largely actualized lived freedom of many formerly enslaved Black New Englanders. The paper is broken up into three sections; the first interrogates the beginnings of Othello’s and Henry Bromfield’s relationship and outlines the commercial and domestic worlds of Colonial Massachusetts they found themselves operating within and how slavery functioned in the colony; the second section focuses on their lives from 1770-1790 during the Revolutionary war years, and defines the motivations for Massachusetts colonists resort to armed revolt and declarations of independence, while also contextualizing how slavery and a tradition of Black resistance informed white colonists ideals of liberty and freedom, which offered ways for Black New Englanders to employ a myriad of tactics during the 1770s and 80s to morally and legally challenge slavery; the third section outlines how Black New Englanders were ablet to actualize legal emancipation while also shedding light on de facto slavery’s persistence in communities throughout the interior of Massachusetts by focusing on Henry and Othello’s lives post 1790 together in Harvard, MA and analyzing the intricacies and circumstances of their homo-platonic, intimate, long-term dependency and power dynamic riddled relationship that allowed a de facto slavery relationship between the two to persist unchallenged by the local community.