Both Cuba and Venezuela sought to be a different nation, to be a better society. In Cuba, under Fidel Castro and Raúl Castro, they strove to be a communist, egalitarian society across social class and races. In Venezuela, under Hugo Chávez and Nicolás Maduro, they strove to achieve the socialism of the 21st century—a socialism without poverty. They also developed a formidable alliance—trading doctors for oil. But in the 21st century their societies have been riddled by deep seated crises—economic and political both. In this talk, Silvia Pedraza traces the nature of these recent crises in both countries.