Due to laws and restrictions in place in Cuba, baseball athletes born there--including many who are considered to be some of the most talented in the world--are not legally permitted leave the country to play for Major League Baseball (MLB) teams. Consequently, a phenomenon of baseball athletes defecting from Cuba to play in MLB emerged in 1991 and has since resulted in more than 250 Cuban ballplayers illegally emigrating from Cuba to play professionally in the United States. Even still, our understanding of their migration experiences, as well as those of their families remains incomplete. By using a lens of transnationalism, this study attempts to provide a more complete portrayal of these experiences. A baseball defection case study based on an original semi-structured interview is also presented to demonstrate the kinds of questions that have not been sufficiently asked regarding these experiences. Lastly, as a means of eliminating the circumstances that create and maintain the demand for baseball defections, an historical examination of "baseball diplomacy" is presented to scrutinize its potential for helping to renew US-Cuban relations in the current socio-political environment.