I read Brian Latell's Castro's Secrets: The CIA and Cuba's Intelligence Machine (2012). Based on interviews with high-level defectors, especially "Tiny" Aspillaga, it tells the story of the cloak-and-dagger struggle between the United States and Cuba in the 1960s.
The book's main attention has come from the claim that Fidel Castro had prior knowledge of the Kennedy assassination. I actually found this the least interesting part of the book, as there is no firsthand knowledge so dots are connected with speculation. And, admittedly, because I am uninterested in Kennedy conspiracy theories.
Of much greater interest is the clear professional--though obviously not ideological--admiration Latell (himself former CIA) has for how quickly Fidel and Raúl put together one of the most effective intelligence services in the entire world. It's quite remarkable. Time and time again, and even now, the U.S. government has underestimated Cuba and has guessed wrong. In the 1960s, moreover, Cuba's DGI routinely fooled the U.S. with double agents.
Today, what the U.S. knows about the inner workings of the Cuban government largely comes not from intelligence operations but from the Cubans who decide--for whatever reason--to leave on their own. Latell quotes multiple CIA sources as admitting they had lost the espionage war.
As with any account of U.S.-Cuban relations, there are a number of references to crazy ideas. My favorite quote from the book is about Desmond FitzGerald:
His most notorious idea, quickly discarded, seemed to his staff like a three-martini idea, except that it occurred to him one morning while shaving. He wanted the Agency's "dirty tricks department"--the technical services staff--to devise a waterproof explosive seashell (p. 159).
Maybe U.S. intelligence just needs some more martinis. In all, it's a fun glimpse at a particularly twisted relationship.