This study compares democratization in the postcommunist region (or the twenty-seven countries that emerged from the Soviet Union and Eastern Europe) in order to evaluate some of the assumptions and arguments in the literature on recent democratization in southern Europe and Latin America. Five conclusions are drawn, all of which challenge the received wisdom about democratization in southern Europe and Latin America. First, the uncertainty surrounding the postcommunist transitions to democracy varied significantly. This influenced, in turn, the strategies of transition and their payoffs. This also meant that the most successful transitions in the postcommunist context involved a sharp break with the old order. Second, popular mobilization often functioned to support the democratic project. Third, nationalist mobilization was also helpful, though this depended upon whether it began with the breakdown of authoritarian rule or had a longer history—with the latter compromising the democratic project. Fourth, if the timing of nationalist mobilization was critical for the success of democratization in those cases where such mobilization occurred, then the strength of the opposition was the key factor in the remaining cases. Finally, while democratic consolidation necessarily enhances the prospects for democratic sustainability, the failure to consolidate democracy does not necessarily threaten the continuation of democratic rule. Indeed, as in the Russian case, such a failure may prolong democratic rule. This suggests, in turn, that a key distinction must be made between the optimal conditions for democratization and optimal strategies.