In March 1961, President John F. Kennedy announced the formation of the Alliance for Progress, a programme dedicated to creating prosperous, socially-just, democratic societies throughout Latin America. Despite spending $20 billion in pursuit of the Alliance’s goals, Latin American economies barely grew, Latin American societies remained inequitable, and 16 extra-constitutional changes of government rocked the region. In this analysis, the author aims to explain why Kennedy’s grand plan for Latin America proved to be such a policy failure. He investigates the nature of Kennedy’s intense anti-Communist crusade and explores the convictions that drove him to fight the Cold War throughout the Caribbean and Latin America, a region he repeatedly referred to as the most dangerous area in the world .