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1898
Cuba and Puerto Rico were at this date Spanish colonies, and on Cuba a war of independence had been under way for years. The Insular Cases in the Supreme Court held from 1901 that the constitution did not fully follow the flag: the new territories were "appurtenant to but not a part of" the United States. The doctrine still stands, and is why 3.2 million American citizens in Puerto Rico cannot vote in presidential elections. Cuba became formally independent, but the Platt Amendment gave the United States a right to intervene — a clause that shaped the relationship until 1959.
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