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This article argues that Eastern Europe continues to be defined and redefined not just by the actual patterns of socio-economic and political reproduction of the distant and proximate regimes governing the region but also through the perceptions of such legacies as generating fundamental similarities. Such perceived similarities, whether or not closely mapped on the objective parallels among countries in Eastern Europe, facilitate intra-region diffusion that results in (further) spatio-temporal socio-economic and political similarities specific to the region. To illustrate this relationship between precommunist and communist legacies, intra-region diffusion, and the production of Eastern Europe, the article examines Slovakia’s diffusion entrepreneurship in the wave of electoral breakthroughs in Eastern Europe in the late 1990s and early 2000s. This article contributes to the literatures on Eastern Europe and comparative democratization in two main ways. First, it adds to the work on the impact of spatio-temporal dependence on transition outcomes, such as democratization, in Eastern Europe. Second, by doing so, the article also documents the impact of an understudied set of democracy promoters—the Eastern European countries. [ABSTRACT FROM AUTHOR]