This article seeks to analyze Frederick Douglass’ responses to U.S. empire formation in Santo Domingo, between 1870-1872, and in Haiti, between 1889-1891. As U.S. Minister to Haiti and as Assistant Secretary of U.S. President Ulysses S. Grant’s commission to annex the Dominican Republic, Douglass fully supported the virtues of U.S. expansion and U.S. Pan-Americanism as long as it promoted effective and egalitarian development in Caribbean and Latin American nations. However, Douglass opposed U.S. empire if it perpetuated U.S. notions of racial domination. His ideas on these subjects shifted over time, and, as I argue, proved to be linked to the progress and hardships of African American life in the U.S. South. Inevitably, this research highlights the political challenges and contradictions of Frederick Douglass, a commited abolitionist, intellectual and diplomat, who fought to remain loyal to race and nation.