[terio]

First of all, Fidel Castro had the support of most of the Cuban population. Everybody opposed the old brutal dictatorship. Second, Batista regime did not have the support of the US. Quite the opposite, there was an arms embargo against it.

[ced]

That's not what Wikipedia says:

For several years until 1959, the Batista government received financial, military, and logistical support from the United States.

The Kennedy speech they link to is amazing:

The real question is: What should we have done? What did we do wrong? How did we permit the Communists to establish this foothold 90 miles away?

The answer is fourfold.

First, we refused to help Cuba meet its desperate need for economic progress. In 1953 the average Cuban family had an income of $6 a week. Fifteen to twenty percent of the labor force was chronically unemployed.

Only a third of the homes in the island even had running water, and in the years which preceded the Castro revolution this abysmal standard of living was driven still lower as population expansion out-distanced economic growth.

Only 90 miles away stood the United States - their good neighbor - the richest Nation on earth - its radios and newspapers and movies spreading the story of America's material wealth and surplus crops.

But instead of holding out a helping hand of friendship to the desperate people of Cuba, nearly all our aid was in the form of weapons assistance - assistance which merely strengthened the Batista dictatorship - assistance which completely failed to advance the economic welfare of the Cuban people - assistance which enabled Castro and the Communists to encourage the growing belief that America was indifferent to Cuban aspirations for a decent life.

This year Mr. Nixon admitted that if we had formulated a program of Latin American economic development 5 years ago: "It might have produced economic progress in Cuba which might have averted the Castro takeover." But what Mr. Nixon neglects to mention is the fact that he was in Cuba 5 years ago himself - gaining experience. He saw the conditions. He talked with the leaders. He knew what our aid program consisted of. But his only conclusion as stated in a Havana press conference, was his statement that he was "very much impressed with the competence and stability" of the Batista dictatorship.

Mr. Nixon could not see then what should have been obvious - and which should have been even more obvious when he made his ill-fated Latin American trip in 1958 - that unless the Cuban people, with our help, made substantial economic progress, trouble was on its way. If this is the kind of experience Mr. Nixon claims entitles him to be President, then I would say that the American people cannot afford many more such experiences.

Secondly, in a manner certain to antagonize the Cuban people, we used the influence of our Government to advance the interests of and increase the profits of the private American companies, which dominated the island's economy. At the beginning of 1959 U.S. companies owned about 40 percent of the Cuban sugar lands - almost all the cattle ranches - 90 percent of the mines and mineral concessions - 80 percent of the utilities - and practically all the oil industry - and supplied two-thirds of Cuba's imports.

Of course, our private investment did much to help Cuba. But our action too often gave the impression that this country was more interested in taking money from the Cuban people than in helping them build a strong and diversified economy of their own.

The symbol of this shortsighted attitude is now on display in a Havana museum. It is a solid gold telephone presented to Batista by the American-owned Cuban telephone company. It is an expression of gratitude for the excessive telephone rate increase which the Cuban dictator had granted at the urging of our Government. But visitors to the museum are reminded that America made no expression at all over the other events which occurred on the same day this burdensome rate increase was granted, when 40 Cubans lost their lives in an assault on Batista's palace.

The third, and perhaps most disastrous of our failures, was the decision to give stature and support to one of the most bloody and repressive dictatorships in the long history of Latin American repression. Fulgencio Batista murdered 20,000 Cubans in 7 years - a greater proportion of the Cuban population than the proportion of Americans who died in both World Wars, and he turned democratic Cuba into a complete police state - destroying every individual liberty.

Yet, our aid to his regime, and the ineptness of our policies, enabled Batista to invoke the name of the United States in support of his reign of terror.

http://www.presidency.ucsb.edu/ws/index.php?pid=25660