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| 1961 |
| | Caribbean novelist V.S. Naipaul features his Trinidad family in A House for Mr Biswas | |
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| 1961 |
| | Rafael Trujillo, dictator of the Dominican Republic for the past 30 years, is killed by a machine-gun attack on his car | |
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| 1962 |
| | US intelligence reveals nuclear missile bases under construction in Cuba, causing an international crisis | |
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| 1962 |
| | President Kennedy sends the US navy to prevent delivery of Soviet missiles to Cuba | |
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| 1962 |
| | Fidel Castro releases, for $53 million in food and medicine, the Cuban exiles taken prisoner in the Bay of Pigs fiasco | |
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| 1963 |
| | Bob Marley and five others form a band, the Wailers, that will for the first time give Jamaican music a global following | |
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| 1964 |
| | Papa Doc Duvalier, ruling through the brutal Tontons Macoutes, makes himself president of Haiti for life | |
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| 1965 |
| | US marines intervene in civil war in the Dominican Republic to prevent a communist takeover | |
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| 1966 |
| | Joaquin Balaguer, a close associate of Trujillo, is elected president of the Dominican Republic | |
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| 1971 |
| | The 19-year-old Jean Claude Duvalier, succeeding his father as president of Haiti, becomes known as Baby Doc | |
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