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In a better world, we would be remembering Fidel Castro the way we remember Nelson Mandela, Jawaharlal Nehru or, for that matter, George Washington – as one of a handful of figures who have led their people from subjugation into freedom, from dictatorship into self-determination, and then stood back to let the new country take its shape.

But that better world did not unfold – not in Cuba, at least. You can pinpoint the moment when Mr. Castro's role in world history changed: July 17, 1959, seven months after his rebel army defeated dictator Fulgencio Batisita after a three-year struggle and seized control of Cuba in the name of its people.

Up to that date, Fidel Alejandro Castro Ruz, a middle-class, Jesuit-educated child of Spanish immigrants, had promised the Cuban people that the revolution he led was intended to bring liberal-democratic multi-party government, and an open economy with less foreign ownership and more economic equality, to the island.

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Cubans had every reason to expect this: Their country had long been a success, with a strong economy, a progressive constitution that guaranteed rights and democracy, and one of the best medical systems in the world. Its living standards were better than any country in what was then known as the Third World; its levels of literacy, infant mortality and life expectancy in the 1950s were closer to those of Canada than those of Latin America, according to historian Richard Gott, and its health system was better than those of Britain, France, the Netherlands and Japan.

But Cuba's democracy had come unhinged in 1952, when Mr. Batista, previously an elected president, albeit one with unsavoury ties to organized crime and sugar-plantation owners, had staged a military coup, suspended the constitution, imposed martial law and launched a cruelly repressive and punitive regime.

Mr. Castro had won the trust of many Cubans by promising, in his 1956 "five laws" statement, to restore the democratic rights that had existed before 1952, make the already-great medical system free and universal, end legal race discrimination, restore land-ownership rights to Cubans and invite foreign investment. Despite a past that included flirtations with Marxism, he reassured everyone, including U.S. diplomats, that he believed in democracy and market economies. This was sold as a liberal revolution, not a socialist revolution.

And, after defeating the Batista regime, that is what he delivered, at first.

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"I have said in a clear and definitive fashion that we are not Communists," Castro declared in a speech in April of 1959. "The doors are open to private investments that contribute to the industrial development of Cuba." That January, days after his victory, he had told journalists from the Cuban magazine Bohemia that "the new government will decline any relations with dictatorial states… first of all the Soviet Union." He had repeatedly made it clear that the reforms he wanted to see in Cuban were those of Franklin D. Roosevelt, not those of Joseph Stalin. He appointed, as president, Manuel Urrutia Lleó, a liberal who pledged to restore open elections and a more fair market economy.

Then, on July 17, it all came crashing down: Mr. Urratia was pushed out of office, elections were not to be held, and the leadership of Cuba, including the presidency, was filled with figures from the authoritarian Marxist side of Mr. Castro's movement. There had been ominous signals before, such as Mr. Castro's decision to take the Prime Ministership in February without elections, but things changed dramatically after July: Relations with the United States broke down, thousands were executed without trial, and Cuba embraced the Soviet Union as its partner, model and chief benefactor.

The results, in an era of stark Cold War polarities, would be calamitous for Cubans. Mr. Castro collectivized agriculture and launched a series of mandatory-labour campaigns, which failed to create a functioning economy, leaving the country reliant on Soviet aid and donations. The embargo imposed by the United States and its allies (though not Canada) hurt badly.

It is certainly true that Washington helped maintain this Soviet dependency by isolating Cuba economically (in the process probably keeping Mr. Castro's regime in power decades longer than it would have otherwise; without Washington's enmity as a catalyst, Cubans would certainly have overthrown him early). And Dwight Eisenhower's administration did little to bring Mr. Castro into the Western mainstream while they had a chance.

What caused Fidel Castro to abandon his democratic and humanitarian principles on that July day in 1959 for the temptations of lifelong dictatorial power and a closed state? One theory holds that he was a "Trojan Horse" revolutionary, like the Ayatollah Khomenei in Iran 20 years later, who never believed in democracy or liberalism and held an authoritarian Marxist agenda all along.

Others believe that Mr. Castro was caught between his movement's liberal and authoritarian factions – the latter dominated by his friend Ernesto "Che" Guevara, who was a devout Stalinist years after Stalin's mass atrocities had been revealed. At some point in 1959, the democrats lost favour and the authoritarians won sway, taking over the commanding heights of the state and Mr. Castro's imagination.

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It is equally possible that Mr. Castro's transformation was driven by nothing more than ego: The temptations of Soviet assistance and revolutionary bravado over the compromises and negotiations of a functioning democratic state and market economy; the grandiosity of a lifetime of absolute power, of the nation glued to six-hour speeches and the thill of unchallenged rule over the bathos of eventual election defeat and a modest retirement as a beloved liberator.

Mr. Castro's choice that July day changed his fate, and his role in history, from just such a beloved liberator into a different sort of figure, one we've seen in Iran in 1979 and Egypt in 2011 and, for that matter, in Russia in 1917: The bait-and-switch revolutionary, who promises history-altering change and then delivers, after emerging victorious, a rather different, darker sort of change.

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