The History of U.S.-Cuban Relations

How did the United States and Cuba—two nations separated by a mere 90 miles of water—drift so far apart? Why has a country as small as Cuba played such an outsized role in U.S. foreign and domestic politics? Why do the heroes of the Cuban Revolution, by now either long dead or spending their retirement in tracksuits, still hold such power over the American imagination?

The relationship between the United States and Cuba, with all its paradoxes, passion, and personalities, has been the subject of hundreds of books—so many that casual readers can feel as overwhelmed as a balsero floating across the Florida Straits. To compile this short list, I made the tough choice to eliminate entire categories of books that also merit reading. I left aside the excellent biographies of Fidel Castro, Che Guevara, John F. Kennedy, and José Martí, as well as the gripping analyses of single events like the Bay of Pigs invasion and the Cuban Missile Crisis, in favor of books that cover wider swaths of time or people.

The books that did make it on to the list share a number of traits. With the exception of Che Guevara’s guide to guerrilla warfare, all the books are by top scholars who have devoted years, if not lifetimes, to understanding Cuba and the United States. In addition, the books all combine in-depth research with engaging prose. Many of the authors on this list are not historians, but they all write with a deep appreciation for the importance of history.

Despite these common characteristics, the books on this list approach the subject of U.S.-Cuban relations in vastly different ways. Some focus more on Cuba, others focus more on the United States. Some concern themselves more with international relations, others with the domestic implications of U.S.-Cuban ties. Some look at national leaders, others look at everyday individuals. Some emphasize the ties that connect the two countries, others emphasize the conflicts that divide them.

But if there’s a common motif that emerges, especially in light of the two countries’ rapprochement in 2015, it is that Cuba and the United States can’t quit each other. For better and worse, geography and history have brought the two nations together in numerous ways over the centuries. Taken together, these books reveal that no matter how widely their politics may diverge, the destinies of the United States and Cuba remain intimately linked.

Places to Start

Julia Sweig, Cuba: What Everyone Needs to Know, 2nd ed. (2012)

This engaging book is a great place to begin. It gives an in-depth overview of the history and recent state of Cuba, including its relations with the United States, in an informal, question-and-answer format.

Louis A. Pérez Jr., On Becoming Cuban: Identity, Nationality, and Culture (1999)

This vast cultural history of the U.S.-Cuban relationship explores the unique ties that developed between the two countries in the hundred years preceding the Cuban Revolution. The book shows how everyday encounters with the United States and its people, sports, entertainment industry, markets, and values shaped Cubans’ varied understandings of their own national identity.

Lars Schoultz, That Infernal Little Cuban Republic: The United States and the Cuban Revolution (2009)

Though less than a decade old, this book became an instant “classic” thanks to its clear and comprehensive overview of fifty years of U.S. policy toward the Cuban Revolution. It provides a nuanced analysis of the ideological roots of U.S. leaders’ multiple misguided attempts to determine Cuba’s fate.

Digging In

Ada Ferrer, Insurgent Cuba: Race, Nation, and Revolution, 1868-1898 (1999)

While this book focuses mostly on domestic Cuban struggles for independence from Spain in the late nineteenth century, its insights into racial politics help readers appreciate the significant cultural distance between the United States and Cuba. Ferrer convincingly demonstrates that Cuban nationalism and the effects of U.S. imperialism are impossible to understand without looking at the multiracial fighting force that led and then lost Cuba’s war for true independence and racial equality.

Van Gosse, Where the Boys Are: Cuba, Cold War America, and the Making of a New Left (1993)

This book explores the Cuban Revolution’s impact in the United States and the ways that fidelismo helped inspire the political and social struggles of the sixties. U.S. culture was transformed by that captivating yet controversial revolution next door.

Susan Eckstein, The Immigrant Divide: How Cuban Americans Changed the US and Their Homeland (2009)

This fascinating book analyzes generational shifts in the Cuban exile community, as well as how and why this uniquely influential group’s impact on U.S.-Cuban relations, the United States, and Cuba has changed over time.

New Moves

Piero Gleijeses, Conflicting Missions: Havana, Washington, and Africa, 1959-1976 (2002)

Together with its sequel, Visions of Freedom, this book tells the epic tale of Cuban, U.S., and (to a lesser extent) Soviet struggles over the fate of Africa. Gleijeses was the first historian allowed access to classified Cuban archives, and he uses them to great effect to uncover the surprising roles that the tiny Caribbean island played in Africa’s decolonization and postcolonial struggles.

William M. LeoGrande and Peter Kornbluh, Back Channel to Cuba: The Hidden History of Negotiations Between Washington and Havana (2014)

While most books on U.S.-Cuban relations focus on the hostile aspects, this one uncover the long history of secret bilateral attempts to repair the damaged relationship following the Cuban Revolution. Published mere weeks before Obama and Castro made their announcement of rapprochement, this book provides insight into the various obstacles that stymied previous efforts.

Voices and Lives

Che Guevara, Guerrilla Warfare (1961)

In this short book, Che Guevara presents a theory of guerrilla warfare based on his experience in the Cuban Revolution. His ideas, which inspired a generation of revolutionaries, give insight into the Cold War context that helped poison U.S.-Cuban relations.

Carlos M.N. Eire, Waiting for Snow in Havana: Confessions of a Cuban Boy (2003)

Eire’s memoir of his childhood in Cuba and his lonely escape to the United States in 1962 at the age of eleven is haunting and beautiful. His evocative description of the world he and his family lost helps readers better understand the human costs of the Cuban Revolution.

Renata Keller is an Assistant Professor of International Relations and Latin American Studies in the Pardee School of Global Studies at Boston University, and author of Mexico’s Cold War: Cuba, the United States, and the Legacy of the Mexican Revolution.