Challenge: Have Fidel Castro install a democracy rather than dictatorship?

Is there any way Fidel could had brought Democracy to Cuba rather than become a dictator after the Revolution?
Well he wanted to bring socialism, and that could have been done democratically in principle. Problem is that change of regime is quite a Big thing if right to private property is allowed or withdrawn every 4-8 years.
 
In 1959, Fidel could easily have won a free election--but he could do so only because most Cubans assumed he was not a Communist. ("Maybe Raul and Che are Communists, but not Fidel" was a common belief.) As the leader of a democratic Cuba, he would have to deal with a Congress that would undoubtedly be insufficiently radical for his taste, dominated by the old parties that Batista had repressed. Even if he turned the 26th of July Movement into a party, and it won control of the Congress in the elections, that would not be enough, because as of 1959 the M-26-7 still contained many moderates.

And even if he purged the M-26-7 of moderates and it won control of congress and Fidel was elected on a frankly socialist platform, there is the awkward possibility that he might be voted out of power later--his near-universal popularity of 1959 would not necessarily last forever.
 
Would it be possible to have a lower level representative democracy while keeping power concentrated on the national level?
 
Would it be possible to have a lower level representative democracy while keeping power concentrated on the national level?

I guess a system similar to the Emperor of Japan or Supreme Leader in Iran but with more democracy. The actual governing, day to day running of the country and desicions done by the elected government, but with the supreme leader having the authority to stop and initiate policies unilateraly, with the understanding he is to use that power as little as possible.

OTL Cuba justifies a one party rule by constitutionally recognizing the Communist Party as the "Vanguard of the Revolution", so I guess its possible VoR to become an actual government position held by Fidel, while giving everything else to the elected governments in a multi party system.
 
He needed somehow to be approved by US first which is unlikely. Cuba may not turn Communist, but even moderately socialist government would be seen with great distrust. And moderation would not suit more radical comrades. Installing a democracy in that conditions would mean a loss of power very soon, and, I suspect, that perspective did not thrill Fidel the most. He wanted to be in charge.
 
If he nationalizes US property without compensation, US support goes away. Some partial nationalization, some compensation and things may be OK but full on nationalization,like OTL nope. There is no evidence Fidel was interested in "democracy", the local "self-governance" that exists in very constrained. More along the lines of "do we paint the town hall beige or blue?". In general, revolutions that overthrow dictatorships (like Batista) rarely lead to democracy and if they do it is usually after a significant evolutionary period.
 
Is there any way Fidel could had brought Democracy to Cuba rather than become a dictator after the Revolution?
His revolution is backed not by the Soviets but by the British Commonwealth and when he starts going dictatorial he and his brother have an S.O.E. type accident. Justification for this action is the large British possessions in the Caribbean and the threat that a communist Cuba would be, as well as eliminating the Mafia controlled existing regime running Cuba in the 50's.
 
Authoritarianism is a feature, not a bug, of revolutionary socialism. How else are you going to radically transform society if not by force?
 
Castro wanted open talks to remain an American friend but the sugar industry pressures after plantations nationalization convinced Eisenhower Administration to cut ties with him and to prepare plans for his ousting, leaving no choice that ask help to Soviet Union, with the consequent political alignment. If Washington is more tolerant (maybe with a Stevenson Presidency?) Castro will remain a progressive, socialist-like and "humanist" President and Cuba could have multi-partitism.
 
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