This dissertation explores the making of racial understandings in early twentieth century Cuba, a period in which the nation's ideology of a raceless nationality coexisted with ongoing practices of racial discrimination. It does so by highlighting the tensions between social understandings articulated in racial terms and the changing social, political, and economic conditions that unfolded in Cuba between 1912 and 1944. Based upon research in more than a dozen archives in Cuba, the United States, and Great Britain, the dissertation explores the dynamic interaction between local and transnational processes in the making of racial interpretative frameworks in Cuba. These connections were shaped by the island's integration into the United States' empire in the Caribbean during the opening decades of the century. An important product of the Cuban/U.S. imperial encounter was a transnational information network constructed by Cubans and North Americans of various racial groups. These circuits served as vehicles for the circulation of racial ideas and practices between the two countries, making the production of racial knowledge in Cuba fundamentally a transnational phenomenon.