Although the end of the Cold War brought the transformation of the communist bloc, some states have resisted the ensuing wave of democratization. This study assumes that important mechanisms of continuity and change in communist states are situated in the belief systems of their leaders and that the years between 1985 and 1991 were a catalytic period. What did Fidel Castro of Cuba and Kim Il Sung of North Korea learn from the end of the Cold War? Their belief systems are examined prior to 1985 and after 1991, i.e., before and after the collapse of other communist regimes. If learning has occurred, it should be reflected in a comparison of their beliefs for these time periods. Our results from ANOVA analyses indicate that Fidel Castro engaged in some learning but Kim Il Sung did not. This finding is complemented by the results of a MANOVA analysis, which indicate that the end of the Cold War had only a modest impact on Fidel Castro and Kim Il Sung, independent of their specific personalities. We conclude by drawing attention to the ensuing debate between structural- and agent-level theorizing and by giving some suggestions for future research.