Examining dialogue about the Jamaican maroon treaties of 1739, this article locates the Haitian Revolution within a wider constellation of events that contributed to a reconceptualization of slave resistance in the United States. During the early republic, Americans drew on combined images of the Haitian Revolution, the Second Maroon War, and the Second Seminole War as they reconceived of the Jamaican maroons and their association with the violent assertion of liberty. Between 1739 and the 1780s, Anglo-Atlantic whites viewed the maroons as having rightfully won their liberty through violent resistance and as helpful allies of the Jamaican slave society. During the 1790s, confronted with the violence in Saint-Domingue and the Second Maroon War in Jamaica, some white observers began to question the mid-eighteenth-century wisdom of compromising with rebellious blacks. Others referenced the maroon treaties in recommending pragmatic negotiations with Saint-Domingue to reestablish stability in the Caribbean. Such references signified the surprising persistence of the notion that legitimizing slave resistance by treaty could diffuse an otherwise disastrous race war. Finally, between the 1810s and the Civil War, Americans dichotomized discourse about the maroons into pro- and antislavery narratives, both of which strayed from predominant eighteenth-century descriptions of the maroons. Advocates of slavery challenged the perception of the maroons as a legitimately free body of people contributing to the stability of society. In contrast, slavery’s detractors cast them as racial warriors fighting against bondage rather than as a community of free blacks allied with the slavocracy.