Theodore Roosevelt is well known as an imperialist. The common understanding is both too weak and too strong. Too weak, because Roosevelt idealized an imperialism that could last forever in civilizing savages. Too strong, because Roosevelt prepared the American-occupied Philippines for independence within a generation. This article analyzes Roosevelt's philosophy of self-government and reinterprets his Philippines policy in light of the philosophy. Roosevelt emerges as a reluctant anti-imperialist—an imperialist by desire but an anti-imperialist in governance. His imperialist ambitions were thwarted by America's ideals of self-government and its democratic political system, channeled through the powers of Congress and the process of regular elections. At a crest of imperial opportunity, America eschewed empire. Imperial occupation remained a great aberration in American foreign relations.