In this talk, Prof. Moulton presents a draft chapter that is part of his book project The Black Grounds: Marronage, Black Placemaking, and the Exercise of Freedom. The chapter focuses on Captain Cudjoe considering what else we might be able to apprehend about marronage, the social life of fugitivity, and the relations of disability in early colonial Jamaica. Captain Cudjoe of the Leeward Maroons is perhaps the most frequently invoked figure in discourses about marronage that following the hero-traitor narrational trajectories. The dichotomized reading of marronage gives us an iconography of Cudjoe as either an exemplifying Black liberatory impulse and placemaking vision, or Black sycophantism and selfishness. The hero-traitor framework demands that we choose which Cudjoe is authentic, a false dilemma fallacy based on a reductive narrative of Black sociality. Against the dilemma, I read Cudjoe as evincing the contingent nature of social coalitions. Rather than one or the other kind of Black leader figure, Cudjoe is a migrator figure. His shifts through character roles on relation to Black community and freedom show the varying relationship between resistance, integration, and recognition to racial formation and racial projects. I read a depiction of Cudjoe as having a sever spinal curvature as a metaphor for the disabling and deforming outcomes of efforts at Black placemaking and freedom in an antiblack world. I consider how the fact of Cudjoe’s ascent to the leadership of his community invites celebration of Black communal practices of care that refuse hierarchies of worthiness.