The history of Cuba is one of conquest and rebellion. Since the arrival of Columbus, it has had two colonial masters: Spain and the United States. Spain, after the collapse of its empire, ceased to be a threat to the peoples of America. Now, the Spanish are among the principal investors in Cuba, and make up a high percentage of tourists to the island. The United States, engaged in empire-building as sole superpower and continuing to pursue a half-century-old policy of regime change in Cuba, is still seen by the Cubans as the greatest threat to their independence and sovereignty. This article reviews the history of relations between the two countries, seeking to contextualize their social origins and political evolution, concluding that an improvement in relations is unlikely absent a profound change in the political economy of either country, or of both, a change that could occur internally or be caused by external factors.