Since the United States began its embargo of Cuba, Cuban-born men have defected from their homeland to pursue their dreams of freedom and playing Major League Baseball. Attempts at defection from Cuba pose significant risks to these players, ranging from death during the treacherous 90-mile journey from Cuba to the Florida coast, to their capture in route and repatriation back to Cuba to face harsh punishment from the Cuban Communist government. This paper examines the history of Major League Baseball’s impact on the United States-Cuba relations pre-embargo compared to the restrictions the embargo placed on Cuba after enactment and the effect the embargo had on Cuban men competing in the Major Leagues. It will examine how the Major League draft differs from the free agency system and the incentive free agency provides to Cuban men to defect. This paper discusses how the game of baseball has affected the relationship between the United States and Cuba. It concludes by discussing future implications of the embargo unless there is an end to Castro regime and an end to the embargo.