Abstract This article explores the transnational politics of hunger, philanthropy, and rural reconstruction during the U.S. occupation of Cuba (1899–1902). In the wake of Cuba’s final War of Independence (1895–1898), tens of thousands of reconcentrados—rural civilians forcibly removed from their lands by Spanish forces during the war—continued to face starvation, disease, and homelessness in the island’s western towns and cities. The Cuban Industrial Relief Fund, a U.S.-based philanthropy, hoped to return the reconcentrados to their now-overgrown lands and help them rebuild their homes and farms. The organization connected rural Cubans and ordinary Americans through the complex bonds of transnational philanthropy just as Americans were working out the meanings of American power and responsibility in the new post-1898 world. Early during the U.S. occupation of Cuba, debates over rural reconstruction and relief became a central locus for Americans to articulate the meanings of U.S. power in Cuba. These meanings, however, were refracted through American understandings of childhood, race, and poverty, as paternalist understandings of poverty as cultural failure and colonial depictions of Latin Americans as childlike and untrustworthy shaped debates over the future of rural Cuba. Based on newly available organizational records as well as Cuban and U.S. archival and popular press sources, this article argues that while the goals of the CIRF were to return the Cuban peasantry to a state of self-sufficient independence, entrenched racialized U.S. perceptions of the Cuban poor as lazy, irresponsible, and essentially dependent doomed the prospects of any large-scale industrial relief for Cuban reconcentrados.