As the only successful slave revolution in world history, the Haitian Revolution (1791-1804) represented a fundamental challenge to colonialism and slavery in the Americas. The slaves and free people of color who destroyed the slaveholding French Caribbean colony of Saint-Domingue and created the independent nation of Haiti played crucial roles in defining and advancing modern concepts of "freedom" and "citizenship." Nonetheless, scholars are only beginning to understand how these individuals interpreted and articulated the complex and conflicting political ideologies of the late eighteenth century. How did those who were most abjectly denied any semblance of "liberty" and "equality" themselves understand these concepts? How were these ideas transmitted among both the free and the unfree across colonial and imperial boundaries? In the Haitian Revolution, "emancipation" was not a singular event but rather a complex process that was fraught with ambiguities and contradictions. These conflicts are at the center of my comparative study of Saint-Domingue/Haiti and the neighboring colony of Santo Domingo (the modern Dominican Republic). Santo Domingo and Saint-Domingue were part of an interconnected history in which struggles against slavery in one colony were closely intertwined with similar battles in the other. I will conduct research in three major French and Spanish archives, focusing on two principal types of sources: correspondences composed by and to former slaves who attained positions of leadership in both colonies; and notarial records that document individual struggles to gain and defend freedom during this period. These documents contain invaluable traces of the voices and thought of slaves and former slaves, and I will use them to test my hypothesis that the political ideologies and discourses of slaves and free people of color profoundly shaped the complex and contradictory forms that emancipation took in both Santo Domingo and Saint-Domingue.