U.S. public and private imperial interests confronted the problem of labor and labor power in the late nineteenth and early twentieth century as the U.S. empire expanded into Latin America and the Caribbean. The question of how to make an empire work spurred the creation of new labor regimes reliant on black West Indians who traveled to work in the Panama Canal Zone and on United Fruit Company (UFCO) banana plantations. Just as importantly, new labor regimes engendered new categories for troublesome laborers. One of these classifications, “tramp,” surfaced in the United States after the U.S. Civil War as a shorthand for vagrant, vagabond, and hobo. This thesis examines the so-called “tramp crisis” of the late nineteenth century to show how questions of labor invariably shaped problems of empire. As a category, the tramp moved outside of the United States where various U.S. foreign policymakers, writers, and business officials created the idea of the “tropical tramp” in U.S. imperial spaces. This label, tropical tramp, offers scholars a different starting point to analyze larger issues of whiteness, masculinity, sexuality, class, and the U.S. empire. By following discursive formations of the tramp and tropical tramp into Central and South America, this thesis argues that the figure of the tramp represented someone unbefitting the U.S. empire’s desired sociopolitical order.