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| 1900 |
| | | Puerto Ricans are granted limited democracy in a bill of rigfhts introduced after two years of US military occupation | |
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| 1902 |
| | | Cuba becomes independent after three years of US military rule, with certain restrictions imposed by the Platt Amendment of 1901 | |
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| 1903 |
| | | Cuba is forced to accept a permanent US military presence in Guantanamo Bay | |
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| 1912 |
| | | President Taft sends US marines to Cuba because of political unrest in the island | |
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| 1915 |
| | | Woodrow Wilson sends US marines to take control in Haiti after a spate of political assassinations | |
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| 1916 |
| | | Haiti becomes a US protectorate, under the terms of a treaty signed in the previous year | |
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| 1916 |
| | | Woodrow Wilson sends the marines to maintain order when the Dominican Republic slips towards civil war | |
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| 1917 |
| | | The Jones Act gives Puerto Ricans US citizenship and a popularly elected Senate and House of Representatives | |
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| 1928 |
| | | Caribbean-born author Jean Rhys publishes her first novel, Postures, based on her affair with the writer Ford Madox Ford | |
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| 1930 |
| | | Rafael Trujillo establishes a dictatorship in the Dominican Republic that will last for 30 years | |
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