You should definitely check out Lars Schoultz's That Infernal Little Cuban Republic: The United States and the Cuban Revolution (2009). (Lars was my dissertation advisor and remains a good friend, so you can take that bias as you will). At 745 pages it is a doorstop of a book, but well worth it.
For those who have read his Beneath the United States, you will recognize the method. He has sat down in a number of different archives, read virtually everything U.S. policy makers had to say about Cuba, and then let them speak for themselves. Cuban archives are not open, but he uses Fidel Castro's speeches and even interviews (such as Ricardo Alarcón) to highlight the Cuban responses. Meanwhile, he pays very close attention to detail (there are 158 pages of notes) so that all the specifics of each crisis and/or policy are made clear. All the while, it is an entertaining read.
The central theme is power, and its punitive uses. LBJ once said, "We ought to pinch their nuts more than we're doing."
Nut-pinching has been U.S. policy ever since (p. 5).
Along with that, though, come countless examples of insanity. We can talk about the Cold War, or the influence of Miami, etc. but in many ways it comes down to policies that are truly unhinged and divorced from reality.
During the JFK years, the State Department said why not "take advantage of Castro's vanity, accuse him of sporting a beard simply because he has no chin. His proprietor Khrushchev needs no beard, dare his vassal to be man enough to shave" (p. 199). Senator Jesse Helms claimed that Wall Street was part of a plot with the Soviets to create a socialist world order (p. 477). Otto Reich compared the Baltimore Orioles baseball game in 1999 to the 1936 Berlin Olympics (p. 502), which of course was followed by a Hitler reference--a comparison to Hitler (usually accompanied by a Chamberlain reference to emphasize appeasement) has been a stock response to anything about Castro.
He also notes that the Helms-Burton law was the very first law to begin with a list of "findings," 28 in all. He adds dryly that "The closest historical parallel is the Declaration of Independence list of grievances against King George III, and his indictment was limited to only eighteen transgressions" (p. 484). Cuba, it seems, is worse even than our former colonial rulers.
It is sprinkled throughout with humor. One of my favorites was how the Bush administration's funding of USAID was "Hogs at the Trough Day" (p. 546). But there is also the idea that Cubans might want "a type of democracy that would seem strange to U.S. citizens--perhaps one where the popular vote determines who becomes president" (p. 566).
Toward the end he gives a good, concise explanation of U.S. policy:
when it comes to Cuba, U.S. officials have always seemed to assume that they can do more or less what global opinion will tolerate, and sometimes a bit more, especially if they insist, as Teddy Roosevelt did in 1907, that he was only trying to make Cubans good, or, as President George W. Bush did in 2008, that the United States sought only to help Cubans enjoy "the blessings of liberty" (p. 554).
And, finally, not too much has changed since 1901, when Governor-General Leonard Wood said, "No one wants more than I a good and stable government, of and by the people here, but we must see that the right class are in office" (p. 556). After more than a century, we still pursue delusional policies while claiming the moral high ground.