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Historian Michael Beschloss on the Cuban Issue

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Kennedy was very concerned about getting rid of the Cuban issue. He knew that as long as Castro remained in Havana, as long as a communist regime was allowed to flower, he would have a very bad domestic political problem. In 1961 the CIA came to him and said that Eisenhower had ordered them to plan for an invasion of Cuba. In retrospect the plans for the invasion look a little bit silly. You would think that Kennedy with his great shrewdness and skepticism would have seen that a thousand Cuban exiles in leaky boats were not likely to overthrow the government of Castro who even by then was very well armed. One diamond in the chandelier may be this: it has been said that before the Bay of Pigs, John Kennedy was aware that there were assassination plots against Castro. One explanation of Kennedy approving the Bay of Pigs may be this: Kennedy may have felt that Castro was likely to be killed before the Cuban exiles reached the beaches of Cuba. If that happened, there would be chaos and pandemonium and in that kind of a situation the Cuban government would be much more easily overthrown and those thousand Cuban exiles could have served as a rallying point.
This was really John Kennedy's first enormous defeat. He had against all expectations won the Presidency. He was newly in office, very popular and then he felt that he had just kicked it all away. He had, without greater forethought, approved this doomed invasion of Cuba. He had looked very soft and not like someone who was a very intelligent President and he felt that in a way he had blotted his copy book forever. There were scenes of the President walking on the south grounds of the White House at 2 a.m., his hands in his pockets, looking very much dismayed. His wife later said that he wept in her arms on hearing of the imprisonment of these Cuban exiles by Castro, exiles for whom he felt very responsible.
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