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This series contains correspondence, between Matthews and numerous political, intellectual, and artistic figures of the twentieth-century world, that documents Matthews' journalism and the relationships he forged with many of these individuals through his work. The bulk of the correspondence, which also includes interview transcripts and notes, is related to Matthews' reporting and editorials on Latin America, and particularly Cuba, for the New York Times in the 1950s and 1960s. This includes most notably Matthews' notes from his famous interview with Fidel Castro in the Sierra Maestra in 1957, an interview with Fulgencio Batista, and correspondence with Ernest Hemingway. Other correspondence related to Matthews' coverage of Latin America includes communications with various Latin American presidents, such as Romulo Betancourt of Venezuela, Francois Duvalier of Haiti, and Juscelino Kubitschek of Brazil.

This series contains Herbert L. Matthews' correspondence with his family and the personal papers of several relatives. Matthews' correspondence to his brother John L. Matthews constitutes the bulk of the correspondence and conveys Herbert Matthews' perspectives and opinions on many American and world events from the mid-1940s to his retirement after 1967 and into the 1970s. John L. Matthews' papers on World War I, his writings, and family photographs provide information about the life of Herbert Matthews' brother.

This large series consists of material related to the Cuban Revolution and its aftermath, both in Cuba and the United States. These documents chart Matthews' life after his reports on the Revolution, particularly his celebrated 1957 New York Times article announcing the survival and progress of Fidel Castro and his guerrillas whom the dictatorship claimed had been defeated. This part of the Matthews Papers represents a considerable collection of material from Cuban revolutionaries and the revolutionary government, including statements and publications. The American reaction to the Cuban Revolution is present here in responses to Matthews' writing for the New York Times. This series also contains manuscripts and notes for Matthews' several books on the Cuban revolution.