Following a demonstration that the Dependency Theory still has much to offer as a vehicle for explaining underdevelopment and development in the periphery (Third World), this study uses the dependency approach as the theoretical framework in an examination of Cuba's pre-revolutionary condition of underdevelopment and dependency, and the socialist path undertaken in the first decade of revolution. The study concludes with a summation of how the interrelation of external and internal forces in pre-revolutionary Cuba resulted in a classic form of dependency, followed by revolutionary victory, and eventually socialism. Finally, the study offers four observations based on socialist Cuba's development effort of the 1960s and the nation's failure to limit external dependence during this period.