The game of baseball, a shared cultural affinity linking Cuba and the United States, has played a significant part in the relationship between those nations. Having arrived in Cuba as a symbol of growing American influence during the late nineteenth century, baseball would come to reflect the political and economic connections that developed into the 1900s. By the middle of the twentieth century, a significant baseball exchange saw talented Cuban players channeled into Major League Baseball, and American professionals compete in Cuba's Winter League. The 1959 Cuban Revolution permanently changed this relationship. Baseball's politicization as a symbol of the Revolution, coupled with political antagonism, an economic embargo, and an end to diplomatic ties between the Washington and Havana governments largely destroyed the U.S.-Cuba baseball exchange. By the end of the 1960s, Cuban and American baseball interactions were limited to a few international amateur competitions, and political hardball nearly ended some of these. During the 1970s, Cold War détente and the success of Ping Pong Diplomacy with China sparked American efforts to use baseball's common ground as a basis for improving U.S.-Cuba relations. Baseball diplomacy, as the idea came to be called, was designed to be a means toward coexistence and normalization with the Castro government. Ultimately, despite a taking few swings during that decade, baseball diplomacy--unable to surmount the obstacles, either within politics or within professional baseball--failed to produce any actual games between Cuban and Major League Baseball teams. As Cold War détente evaporated into the 1980s, baseball's role in the U.S.-Cuba political relationship changed. Efforts to boost Cuban exposure to Major League Baseball developed as part of a general policy to use American culture and influence to erode Communism. This practice of deploying baseball as a political weapon continued into the 1990s. Unlike earlier efforts at baseball diplomacy, which were designed to improve U.S.-Cuba relations, baseball deployment aimed to provoke a democratic regime change in Cuba. This dissertation examines how politics have complicated U.S.-Cuba baseball exchanges, and traces the sport's contradictory use through baseball diplomacy and baseball deployment.