The United States’ relations with Cuba are rooted in the US intervention in the process of Cuba’s independence from Spain in the 1890s. The US preserved its interest-based approach towards Cuba during the first half of the 20th century, which culminated in the Cuba’s counter-hegemonic revolution in 1959. This revolution led to more than fifty years of hostility between two countries, which took a new form under President Obama’s administration. Indeed, Barack Obama and Raul Castro surprised the world in 2014, announcing that they would reinstate full diplomatic relations and pacify bilateral tensions. Since World War II, United States has been the hegemon of the world relying on three pillars of its liberal bloc, i.e. liberal values and culture, economic and military capabilities, and international organizations. However, during Obama’s administration, the occurrence of events such as the rise of new economic powers, Global Financial Crisis and the rise of left-turn in Latin America caused some speculations about the declining US hegemony and its transition to leadership. However, qualitative content analysis of the US Inter-American policies indicates that US hegemony in Latin America including Cuba is deeply rooted in the early decades of US formation. Moreover, the continuation of US economic embargo on Cuba and its long-lasting military presence in the island indicate that Obama’s policy did not provide a leveled playing field to resolve Cuba’s problems. Hence, US leadership in Cuba and true and equal partnership between both countries still seem unattainable.