One key factor may be the crucial element, in the future of the relationship of the United States with the Caribbean is the future of its political relationship with Puerto Rico. What the island and its metropolis do, together, will have a decisive impact on the future shape of the Caribbean. This article examines the geopolitical and economic context of that relationship, departing from a paradigmatic distinction between the territory and its people, which has determined the history under the hegemony of the United States. A brief economic history is followed by the political-economic foundations and a description of the traditional political views on the relationship. A new paradigm is proposed, based on a new understanding of the people, the society, and the culture. The aspects of migration, exile, and return as well as the role of state and clandestine violence are examined. Finally, the article reviews the metropolitan view of the relationship and the political dimensions of the present situation, and it makes a policy proposal for a new option for Puerto Rico and the United States.