Since the time of the Spanish conquest of Latin America in the late fifteenth century, Cuba as a small Caribbean nation has been of significance for several global powers—Spain, the United States, Soviet Union/Russia, etc. Using a variety of primary and secondary sources, this chapter tracks and traces (1) Cuba’s geopolitical history; (2) the interests of great powers such as China, Russia, and the United States in Cuba; (3) and Cuba’s agency within these relationships before (4) considering the constraints which Cuba faces within its international interactions. This chapter also offers thoughts on Cuba’s future relationships with China, Russia, and the United States and also on Cuba’s future in general. With regard to Cuba’s geographical location, this chapter concludes that despite constrained circumstances, particularly economic, Cuba continues to have global influence far greater than could be expected of a Caribbean nation.