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| 1975 |
| | | Cuban troops, sent by Castro to Angola, clash with South African forces attempting to combat communism | |
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| 1999 |
| | | Buena Vista Social Club, a nostalgic documentary by Wim Wenders, triggers a cult for Cuban music | |
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| 2002 |
| | | The US holds suspected al-Qaeda terrorists indefinitely, and without legal rights, in Guantanamo Bay, an American enclave in Cuba | |
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| 2008 |
| | | After 49 years as president of Cuba, Fidel Castro resigns for reasons of ill health | |
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| 2008 |
| | | The National Assembly elects Fidel Castro's brother Raúl to succeed him as president of Cuba | |
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| 2009 January 22 |
| | | One of President Obama's first acts in office is to sign an order that the Guantanamo Bay detention camp is to be closed within a year (a promise that fails to be fulfilled) | |
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