Then you have not been paying attention...the Cuban dictatorship has been supporting the Venezuelan dictatorship which had been supporting the Cuban dictatorship with its oil which itself is increasingly under Putin's control via Rosneft which has been providing the hard currency required to keep the Venezuelan dictatorship afloat.

Cuban intelligence and military officers have been pouring into Venezuela since the days of Chavez, not to mention the inflow of Cuban doctors and nurses many of whom have been defecting to Colombia and then moving to the USA.