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.