In 1804, Haiti, the former French colony of Saint-Domingue, became the second independent republic in the Western Hemisphere and the first governed by men of African descent. African Americans immediately recognized the importance of this stunning conclusion to the Haitian Revolution even as their white counterparts denounced the "Horrors of St. Domingo." While some enslaved African Americans drew inspiration from the nation born out of anti-slavery rebellion, others, particularly blacks in the urban North, recognized Haiti as an "experiment in self-government" that might vindicate black self-determination and equal rights as well as freedom for men of all races. This preoccupation with Haitian independence assumed heightened urgency for aspiring class and elite African Americans in the post-Emancipation era. Journalists, politicians, diplomats, missionaries, educators, artists, and other black professionals came to understand a link between black sovereignty in Haiti and the prospect of full political and civil rights during the period of Reconstruction and the tumultuous decades that followed. In their estimation, Haiti's ability to demonstrate progress according to American standards and refute charges of backwardness leveled against it by white foreigners would determine African Americans' ability to exercise the rights, responsibilities, and privileges that ostensibly accompanied citizenship. This dual anxiety about Haitian progress and the status of black citizens of the United States eventually coalesced during the U.S. occupation of Haiti, which lasted from 1915-1934. But, before black leaders articulated staunch Pan-Africanist opposition to the erosion of Haitian autonomy, previous generations of outspoken African Americans demonstrated great ambivalence about Haiti, a symbol of black pride that, nonetheless, often failed to meet their outsized expectations or their understandings of civilization and progress. By examining how African Americans freighted Haiti with importance and regarded it with ambivalence for much of the period between its founding and the date of its "Second Independence," this dissertation thus reshapes our understanding of a transnational black political and intellectual culture that evolved throughout the nineteenth and early twentieth centuries.