Batista was a bastard and his Cuba was a den of vicious criminals. However, I am willing to bet that the Castro brothers were willing to let the island become a radioactive pile of slag and kill millions in '62 solely because they just wanted to poke the United States in the eye.
As for Chavez, he was just a clown whose over-the-top and bellicose anti-Americanism provided us with so many laughs, especially when the King of Spain verbally smacked him.
Castro was a case of the USA pushing the pendulum too far. If the USA had been more receptive to his initial revolution I think Castro could have been guided into a more moderate view. Instead the first thing that happened was the Eisenhower Administration demanded that the Batista regime be returned to power which was kind of laughable after they were defeated. Then when Kennedy had a chance to establish good relations with Castro he instead gave tepid support to the Bay of Pigs invasion and pushed Castro squarely into the Soviet camp as a result.
The problem with Cuba was, in a nutshell, American racism.
After the US took Cuba in the Spanish-American War it really should have been encouraged to become a state but the bigots in power (racism being non-partisan back then) didn't want to see two brown guys in the US Senate. The end result was Cuba got spun off while we kept Puerto Rico as a territory because of strategic reasons.
With Castro about to join Chavez sometime soon there's another opportunity to reset US-Cuba relations and I hope Obama has the presence of mind to sit down all the players - including the Cuban expatriates in Florida - and to hammer out a fair and viable working relationship that benefits everyone involved.