In December 2014, U.S. president Barack Obama presented his ideas for a “Cuba policy détente.” His underlying goal was “to cut loose the shackles of the past so as to reach for a better future” (Obama, 2014a). The president used the remainder of this second term to implement this policy. True, Obama's Cuba policy did share certain assumptions with the policies pursued by his predecessors, including emphasizing the necessity of both domestic reform in Cuba and reciprocity in terms of actions aimed at reducing tensions (LeoGrande and Kornbluh, 2014: 400). Having said that, Obama's “adventurous” (The Economist, 2016b) Cuba policy turned out to be fundamentally different from those of his predecessors. Indeed, terminating “one of the most misguided chapters in American foreign policy,” Obama's “historic move” ushered in “sweeping changes to normalize relations with Cuba” and possibly even a “transformational era for millions of Cubans who have suffered as a result of more than 50 years of hostility between the two nations” (NYT, 2014a). LeoGrande (2020: 449) similarly refers to a “historic reversal” on par with Nixon's policy toward China.

This chapter opens with a discussion of whether U.S.–Cuba policy during the Obama administration actually qualifies as an instance of major policy change. It suggests that this is indeed the case as per Charles Hermann's typology. The chapter then explores whether President Obama had a systematic and predictable effect on the redirection of U.S. policy toward Cuba. To that end, following the “leader- centered theory of foreign policy change” with its three- step analytical framework introduced in Chapter Two of this volume, the chapter first examines whether Obama considered the Cuba policy of his predecessors as a major policy failure, which is considered as main trigger for the initiation of policy change (“triggering change”).