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This book examines the history of United States foreign policy toward Cuba, focusing on critical junctures and recent strategic shifts. Restoring diplomatic relations with Cuba, which were severed officially in January 1961, was a huge shift in U.S. foreign policy. Relations between Cuba and the United States were tumultuous throughout the nineteenth and twentieth centuries, and almost escalated into full blown nuclear war in October1962 during the Cuban missile crisis. The restoration of diplomatic relations marks a fundamental departure as the two countries chart a new course into the twenty-first century. This book traces over seven hundred years of history, setting the context to base an argument in favor of rapprochement. It illustrates the importance of the Cuba deal to break with the past and delegitimize anti-Americanism in the world.