The Bay of Pigs invasion was maybe the biggest fail of Kennedy. It began with a plan to overthrow the Fidel Castro regime in Cuba coming from Eisenhower administration. The plan for the invasion had been led by the CIA with the help of the US Army. The invasion had been made with 1500 Cuban people exiled in USA and trained by the Army. It began on April 17, 1961 in the famous « Bay of Pigs ». The problem was that there had been no US air support and the invasion failed. 1189 men had been captured by the Cuban government and Kennedy had been forced to negociate their release in exchange for 53 million dollars of food and medecine.
This fail contributed to reinforce the power of Cuba and reduce the faith in the US president Kennedy. The critics said that he focused on the political repercussion of the invasion instead of the military considerations. He personnaly took the responsibility of the failure with another famous speech : « ...We got a big kick in the leg and we deserved it. But maybe we'll learn something from it. »
See more about the Bay of Pigs invasion : http://bbd3mawilsmegane2013.blogspot.be/