This article proposes a political economy approach to decolonization. Focusing on the industrial organization of agriculture, it argues that competition between colonial and metropolitan producers creates demands for decolonization from within the metropole when colonies have broad export profiles and when export industries are controlled by colonial, as opposed to metropolitan, interests. The author applies this framework to the United States in the early 1900s, showing that different structures of the colonial sugar industries in the Philippines, Hawaii, and Puerto Rico–diverse exports with dispersed local ownership versus monocrop economies dominated by large US firms–explain why protectionist continental-agriculture interests agitated so effectively for independence for the Philippines, but not for Hawaii or Puerto Rico. A comparative historical analysis of the three colonial economies and the Philippine independence debates complemented by a statistical analysis of roll call votes in the Hare-Hawes-Cutting Act supports the argument. In providing a new perspective on economic relations in the late-colonial era, the argument highlights issues of trade and empire in US history that span the subfields of American political development, comparative politics, and international political economy.