Today, the anniversary of the death of Franklin Roosevelt, is especially appropriate for a discussion of the political evolution of two territories whose development, before and after his death, was shaped by Roosevelt’s enlightened vision of world public order. The Trust Territory of the Pacific Islands (TTPI) was an inheritance of a war waged by the United States in affirmation of “the right of all peoples to choose the form of government under which they live.” Puerto Rico’s progressive dismantlement of colonial government had its origins in the New Deal. It was furthered by Roosevelt’s support of Puerto Rico’s Popular Democratic Party and a policy favoring self-determination and decolonization entrusted by Roosevelt to a succession of sympathetic and imaginative administrators. Both territories emerged in the postwar period as natural objects of the concern of the world community which Roosevelt helped to organize.