The question of this research project is how have U.S.-Cuba relations evolved since the mid-20th century? Understanding this is important for understanding the current political situation between the two countries and for determining how it will continue to change in the future. The Cold War, Cuban revolution, and Missile Crisis are all well-studied topics that most people learn about in school. But making the connection between those events and the current state of relations, which are less widely discussed outside of scholars on the subject, is important and can show how a strong continuity exists between historical events and modern ones. Relations between the United States and Cuba were inarguably as bad as relations can be between two countries short of outright violence, but they have improved considerably in a short time span over the last decade. The primary sources in this project demonstrate the conflict between the two countries at different points in the last seventy years and show a steady rise, peak, and fall in tension. These sources were found in historical and political journals as well as government documents from the U.S. National Archives. Analysis of these documents consisted of trying to interpret the reactions of Cuba and the U.S. when the other escalated the conflict as reflections of their deteriorating relations, as the history between the two countries is a constant escalation when either country does something the other does not like, while more modern sources are functionally the conclusion of the research that show how relations have steadied out. Hopefully, this research depicts a clear and digestible continuity of relations between the U.S. and Cuba that, by understanding the past and present, can be used to determine how the situation will evolve in the future.