This report has been professionally converted for accurate flowing-text e-book format reproduction. The United States and Cuba have long had a contentious relationship. Following Fidel Castro's revolution, the antagonism was bolstered by the Soviet Union's support for Cuba. After the collapse of the Soviet Union and the end of the Cold War, it was predicted by some that the end of Castro's regime was near and the United States would be there to help with democratization of Cuba. Instead, Castro has managed to stay in power and the U.S. and Cuba have failed to achieve rapprochement. This thesis analyzes the Balsero rafter crisis of 1994, the use of Guantanamo Bay (and subsequent controversy) as a detention center for enemy combatants from the Afghanistan conflict, Obama's normalization of diplomatic relations with Cuba, and finally the enactment of the Cuban Liberty and Democratic Solidarity Act (LIBERTAD), otherwise known as Helms-Burton. In doing so, the aim is to determine whether culture, structure, or the actions of individual leaders factored more predominately into the outcome of the four events.

This compilation includes a reproduction of the 2019 Worldwide Threat Assessment of the U.S. Intelligence Community.

Chapter II details the historical events of the Balsero rafter crisis during the Clinton Administration, the decision to use Guantanamo Bay for the holding of detainees and subsequent controversy during the Bush administration, and lastly, the normalization of relations and re-opening of U.S. and Cuban embassies during the Obama administration. Chapter III analyzes how the Helms-Burton Act came to be codified into law. Clinton, who had been opposed to the Helms-Burton Act, switched his opinion on February 24, 1996, when two planes flown by Brothers to the Rescue, a Cuban-American humanitarian organization were shot down by Cuban Mig-29 fighters. A detailed look into what the impetus for the original writing of the bill will be addressed as well as what amendments that had been taken out of the bill before February 24, made their way back in after the shooting down of the planes. Chapter IV is the full analysis and assimilation of chapters two and three. Each event is broken down behind the backdrop of the several political science theories explored in the literature review. Were public opinion, interest groups, and other cultural influences strong enough to have an effect on individuals? Did individuals or organizations succumb to parochial interests or were the individuals in the driver's seat and shaping events to their desired outcome? Additionally, was there a gradual breaking of the ice as Armstrong argued as effective or was there a sudden shift in policy? Asking these questions will allow a testing of the two hypotheses and add to the literature as to why the U.S. and Cuba have not had a full rapprochement since the end of the Cold War.