This book addresses the roots of the hostility that has characterized the United States'relationship with Cuba and has persisted for decades, even in the wake of the end of the Cold War. It answers the question of why America's Cold War era policy toward Cuba has not substantially changed, despite a radically changed international environment. Cuba is indeed a "curious case," as the title suggests, and the book uses it to shed light on the contours and paradoxes of US policy during the Cold War and beyond. Existing explanations for the unusual, even exceptional, place of Cuba in US policy are not sufficient. The book argues that US policy toward Cuba is not adequately explained by many of the standard rubrics. Neither the logic of US domestic politics (especially Florida politics), or of political realism, which suggests that US policy is and should be driven by threats or challenges to its material interests (e.g., security, economic prosperity, global power, etc.), are able to account for the anomalies in America's approach to Cuba. Economically-oriented arguments emphasizing American business interests or a larger US interest in the expansion of free markets are equally insufficient to explain American policy.In contrast, this book argues that American foreign policy is not an objective response to a set of self-evident challenges to US interests and principles. Rather, it is better understood as a policy that is rooted in and informed by historical understandings of American and Cuban identities, which are themselves historically contingent. Paying particular attention to the constructive qualities of language, I examine primarily official speeches and documents from the US (e.g., presidential speeches and announcements, Congressional testimony, State Department reports, but also some non-governmental publications that heavily influenced policymakers) to explore the origins and perpetuation of a policy perspective that emphasizes Cuban difference, illegitimacy, and inferiority juxtaposed against American virtue, legitimacy, and superiority. The two most significant areas of political contestation that contribute to these understandings of Cuba are 1) its place along with Latin America in the context of a regional hierarchy, and 2) its place in the context of the Cold War and anti-communism. In American representations of Cuba, the US is routinely characterized as superior by virtue of its democracy, freedom, exceptionalism, wealth, and peacefulness. Cuba is, by sharp contrast, portrayed in terms of its inferiority to the US through language that characterizes Cuba as underdeveloped, communist, dictatorial, subversive, and a routine violator of human rights.