This analysis re-examines Russo–Cuban relations in the period in which Boris Yeltsin was Russian President using previously unseen documents housed in the Ministerio de Relaciones Exteriores de Cuba [MINREX] archive in Havana. A number of conclusions offer themselves including that the relationship remained key for Havana throughout the 1990s, despite a Cuban ideological aversion to the Russian reforms of the early to mid-decade and the subsequent “new realities” of Russo–Cuban relations. Cuba desired a relationship that preserved a number of features of Soviet–Cuban relations, which MINREX officials strove to achieve by purposefully creating a political legacy from the Soviet era, whilst also specifically lobbying members of the Russian political elite who had sympathies with the Soviet period. This development has resonance for contemporary Russo–Cuban relations that are at their most robust politically since 1991. Consequently, the Soviet legacy remains both much greater than previously thought and deliberately created by Cuba.