Historians have enhanced our understanding of United States foreign policy in Asia, Latin, and Central America. My dissertation contributes to this literature by exploring U.S. foreign relations in the Caribbean by taking a close look at Haiti. While both nations achieved independence during the Age of Revolutions, by the turn of the 20 th century, the U.S. occupied Haiti from 1915-1934. In investigating the history of U.S. and Haitian diplomacy, one figure appeared repeatedly in my archival research and fieldwork in both nations, Charlemagne Peralte. During the U.S. intervention, Peralte rose as a leader of a Haitian guerrilla group known as the cacos who positioned themselves as nationalists fighting for Haiti's sovereignty. Under Peralte's direction, the cacosbattled the occupying forces and also promoted their cause as a global call for democracy. Though Peralte died in 1919, his significance to Haitians assumed epic proportions as Pancho Villa and Emiliano Zapata of Mexico, Augusto Sandino of Nicaragua, and Che Guevera in Cuba. Haitians on the island and across the Americas in the Diaspora revive Peralte's history and meaning throughout the 20 th and 21st centuries. Drawing on unexplored primary sources, marines' records, and oral histories, etc, my study seeks to move Charlemagne Peralte from the margins to the center in historiography surrounding `bandits,' rebels, and national leaders. The work first traces U.S. and Haitian relations from their revolutions to the various events leading to the occupation in 1915. It then captures the tenor of the early occupation years by analyzing the various modes of resistance that erupted because of the intervention. Embedded in this protest against imperialism were Peralte and the actions of the cacos. The dissertation also reflects on the post-occupation years from 1948 to 1986 to examine the nations' foreign relations. Finally, the work documents the apotheosis of the cacos leader to examine the meaning behind the ongoing historical preservations of Peralte in Haiti and amongst the Haitian Diaspora community in the U.S. and Canada. The study documents how Peralte's story, and the historical remembrances of him, shed light on U.S. and Haitian diplomacy from the 19 th through the 20th centuries.