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Retired Cuban dictator Fidel Castro has died at the age of 90, Cuban state television reported Friday night.

Castro was a pivotal figure of the Cold War and the second half of the 20th century. His insurgency overthrew Cuba’s pro-U.S. dictator, Fulgencio Batista, and established a new communist regime aligned with the Soviet Union. After his victory, Castro remained Cuba’s dominant political figure for nearly 50 years, holding total power from 1959 until 2008, when he turned over authority to his younger brother, Raul Castro.

During his five decades of rule, Castro was repeatedly a thorn in the side of the United States. He easily crushed an abortive U.S. effort to overthrow him at the Bay of Pigs, took the world to the brink of nuclear war in 1962 when he accepted Soviet nuclear missiles, and attempted to export communism around the world by supporting communist regimes and insurgencies in Angola, Chile, Nicaragua, and elsewhere.

Castro’s defiant attitude towards the American superpower made him a hero to many in the Third World (and to many on the American left), but he was also branded a tyrant due to his suppression of political dissent. Throughout his rule, hundreds of thousands of Cubans fled the country for the United States, establishing a thriving exile community in South Florida that strongly shapes the region to this day.

Castro’s pro-Soviet leanings caused the U.S. to impose a trade embargo in 1960, followed shortly by a total break in diplomatic relations. Diplomatic relations were finally normalized in 2015 after a rapprochement initiated by President Barack Obama, but the embargo remains in effect to this day, albeit in a substantially weakened form.

Initially, thanks to Soviet subsidies and trade, Cuba performed relatively well despite the economic embargo, but following the USSR’s collapse its economy collapsed, and the country has never fully recovered. But despite the collapse of communist governments around the world, Castro managed to hang on.

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