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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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| c. 1930 |
| | The steel-band tradition begins to develop in Trinidad, with adapted metal objects taking the place of traditional skin drums | |
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| c. 1930 |
| | The Rastafarian cult evolves in Jamaica, viewing Ras Tafari, the emperor of Ethiopia, as the black Messiah | |
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| 1933 |
| | Fulgencio Batista, as army chief of staff, begins a long career running the affairs of Cuba | |
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| 1934 |
| | The US military government is finally withdrawn from Haiti after nineteen years | |
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| 1948 |
| | The British government advertises in Jamaica for people to come and work in Britain | |
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