This dissertation explains the perseverance of state socialism in Cuba in terms of elite composition and explores the efforts of this elite to preserve the state socialist system across generational change in its ranks. It is argued that four characteristics of the Cuban political elite have contributed to regime preservation in Cuba so far: That the first generation of Revolutionary leaders are still in command accounts for their reluctance to enact reforms toward systemic change; their siege mentality accounts for their readiness in confronting crises; low intra-elite institutionalization endows the regime with flexibility to adapt to stark changes in exogenous circumstances; and elite unity accounts for resistance to strong pressures for change. These characteristics combine in a model of "extraordinary elite" which represents a kind of agency likely, or at least able, to successfully withstand structural and institutional pressures for regime change. Explaining regime persistence in terms of elite composition raises questions as to the odds of regime continuation as the composition of the elite changes. Thus this dissertation also looks at the attempts at elite regeneration, or the attempts of the elite to maintain the regime across a generational shift in its ranks. This is accomplished by looking at the related processes of elite rejuvenation, as reflected by the turnover in the Central Committee of the Cuban Communist Party; the attempted transmission of values, beliefs, and skills across generations, as reflected in the speech of Cuban leaders and educational materials in the Cuban schooling system; and the formation of new leaders, as reflected by the policies on the recruitment, selection, training, and promotion of cadres in the party apparatus and the state administration. The findings suggest that the Cuban leadership has learned from the collapse experience of other state socialist regimes and that has applied this knowledge to try to perpetuate the Cuban state socialist system over time. Both the model developed and the processes described offer contributions to the interrelated literatures on political stability and change, elites, the Cuban Revolution, state socialism, and socialism.