Abstract
The objective of this research is to provide a better understanding as to why Cuba, more than any other Latin American nation maintained its enormous place in the American imaginary throughout the tensest decades of the Cold War. Immediately following the success of the Cuban Revolution, misinterpretations of Cuban objectives, fears of Soviet style Communist expansion, and the resulting failures in American policy turned Cuba from ally to enemy. By examining recently declassified government documents, recorded conversations, and interviews with the most influential figures involved in producing this Cold War foreign policy quagmire, this paper will illuminate one of the most misunderstood aspects of American Cold War history. This research will bring better understanding as to why the US Government’s frequent mishandling of Cuban affairs only intensified America’s obsession with Cuba and its seemingly invincible dictator.