The article tries to explore the factors that allow Cuba’s political system to be still striking stability, a decade after the fall of the Berlin Wall. At the beginning, the exogenous and endogenous structural elements of Cuban socialism are introduced and the history of the crisis is presented. The reform process and the measures taken on the island are then extensively documented. The following analysis shows that Cuban society is in a dynamic process of social heterogeneisation that is destroying political stability on the island. Taking into account theoretical aspects of the political sociology of social inequality, the special stabilising factor of Cuban socialism is identified as close. Finally, the attempt is to uncover a possible reform scenario that could give island society a last historical opportunity for civil and social transformation.