A tale of adventure and intrigue, The Caribbean Legion studies the political struggles of the peoples of Costa Rica, Cuba, the Dominican Republic, Guatemala, Honduras, and Nicaragua in the years following World War II. Taking their inspiration from the D-day–style invasions of occupied Europe, groups of political exiles organized a series of armed expeditions that kept the Caribbean in turmoil for five years. Although their actions were independent, the groups became known collectively as the ''Caribbean Legion.''

Charles D. Ameringer examines the myth and reality of the Caribbean Legion, as well as the evolving foreign policy of the United States. Faced with the contradiction between the promotion of representative democracy and the principle of nonintervention, the United States tolerated dictatorship in the postwar Caribbean, which eventually led to serious consequences such as the Cuban Revolution.

Ameringer utilizes never-before-consulted documents from 1949 and 1950 on ''the situation in the Caribbean'' from the Inter-American Peace Committee of the Organization of American States. Accordingly, The Caribbean Legion presents new information and documentation on the difficulties, complexities, and costs of organizing armed uprisings from exile, the purposes and actions of pro-democratic Caribbean exiles and their allies and sponsors, and US policy toward Latin America in the early Cold War period.