Despite the fact that the China case fell exclusively within the Cold War and broken US diplomatic relations with Cuba bridged the Cold War and post–Cold War eras, the five decades of estrangement between the US and Cuba conform to a similar pattern as the China case, and Tsou’s pattern will be used to analyze it. From the late nineteenth century until the revolution of 1959, the US pursued contradictory policies towards Cuba which invited a revolutionary response that initially was misunderstood and underappreciated by Washington. As Cuba had been acquiescent to American prerogatives for six decades, American foreign policy makers failed to realize Cuba’s potential impact as an enemy of the United States in a Cold War dynamic influenced by virulent anti-Americanism and the capabilities of ballistic missile technology during the early 1960s. As with the PRC during the Korean War, the United States reacted to the new threat with an ill-conceived and insufficient military response that contributed to the legitimacy of the Castro regime rather than undermining it, setting the stage for an unprecedented military threat to the United States.