The paper analyzes the key concepts in the US President’s speech announcing the reestablishment of relations with Cuba in December 2014 from a critical discourse point of view. His arguments make a clear distinction between what America represents (Us) and what Cuba lacks (Them), glorify the half-a-century-old blockade and acknowledge its failure. Obama’s words also reflect the policy change is a one-sided dialogue, a one-lane road, ignoring the needs and hopes in the island when he neglects or only vaguely mentions important areas that are undoubtedly within the Cuban national interests. When read in different geopolitical contexts, the speech, built around the same arguments the US has been using for more than fifty years, envisions a change in Cuba through empowering given population sectors to achieve the same historical objectives.