It has traditionally been assumed that the relationship between Moscow and Havana commenced with the victory of the Cuban Revolution. Although it subsequently developed to unprecedented levels, this paper will examine the relationship in the period between the Russian and Cuban Revolutions. This analysis will be conducted within the framework of Soviet policy towards the Developing World, and the realist paradigm of International Relations theory. It will conclude that prior to January 1959 the Kremlin took a considerable interest in Cuba and did not suffer from “geographical fatalism” as has previously been presumed. This is important in itself, but also for the relationship that rapidly developed in the aftermath of the Cuban Revolution as a number of factors that were important in the pre-1959 relationship would also be significant after 1959. Furthermore, this analysis is also important for the contemporary bilateral relationship as both governments have made increasing reference to the multifaceted relationship that existed prior to 1959.