This article treats the links between the 1890s literature of urban reform in the United States, which focused on the downtown "other half" of New York, and the war literature of 1898, when American troops intervened in Cuba's war of independence. The article focuses on the work of Stephen Crane, who worked as a New York police reporter, slum novelist, and Cuba war correspondent in this turbulent decade. Leary shows how, in the martial culture of the American 1890s, the rhetoric of militarism informed the practice of urban reform, while the rhetoric of urban reform informed the military campaign in Cuba. This article argues that the United States' urban underdevelopment, represented famously by the Lower East Side of Manhattan, was imaginatively displaced onto Cuba. The War of 1898 was therefore an important landmark in the creation of a Third World imaginary in the United States, when "underdevelopment" would become a distinctly Latin American condition. In the twentieth century, the gap between modernity and underdevelopment would not be found in the sprawling tenement cities, but in "other Americas" to the south, below the Mason-Dixon line and in Cuba. After 1898, Cuba, once so close to the United States as to be nearly a state in the union, now belonged to another time—indeed, almost another world.