During the 1930s and 1940s, W. E. B. Du Bois was not only interested in European colonialism in Africa, but he also approached the racial situation in the Americas, particularly Haiti, Brazil, and Cuba. In this article, I examine how Du Bois engaged strategically in a critique of racism in Cuba and the United States. I analyze how Du Bois discussed the Cuban color line as linked to colonial dispossession and explore the formation of the anti-colonial critique within global sociology. Du Bois’s letters, manuscripts, and field notes during his first visit to Cuba in 1941 reveal how, to a large extent, Du Bois shared the prevailing vision of Cuba as a society free from racism. Although Du Bois only partially captured how racism worked in Cuba, he constantly affirmed how the analysis of the Cuban color line implies dealing with the analysis of American imperialism. Thus, Du Bois’s approach to Cuba was fundamental in two senses. First, it led him to consider the contradictions between cultural integration and social and economic equality in a setting other than the United States. Second, Du Bois developed the fundamental place assigned to the critique of U.S. imperialism within global sociology. At the same time, Du Bois’s connection with Cuba elaborates the understanding of Du Bois’s global sociology.