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| 1958 |
| | Dictator Fulgencio Batista flees from Cuba, leaving Havana open to Fidel Castro and his victorious guerrillas | |
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| 1959 |
| | Fidel Castro begins more than four decades of authoritarian rule in Cuba | |
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| 1959 |
| | West Indian poet and playwright Derek Walcott founds the Trinidad Theatre Workshop | |
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| 1961 |
| | An invasion force of about 1500 Cuban exiles comes ashore in Cuba's Bay of Pigs in an attempt to topple the Castro regime | |
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| 1961 |
| | Two days after landing in the Bay of Pigs, 114 Cuban exiles are dead and about 1300 have been captured | |
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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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