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This article shows that post-communist regime trajectories have been largely circumscribed by historical legacy differences, but the question about which particular legacy matters most is much harder to answer, since statistical results are sensitive to model specification and to the choice of democracy indicator. While some of these discrepancies reflect the inherent limitations of traditional statistical methods, others reflect the different dimensions of democracy captured by different indicators. Therefore, the article contributes to a more nuanced explanation of post-communist democratization by showing that different legacies drive different aspects of democratization. Finally, the results demonstrate that several prominent alternative explanations—initial election outcomes, institutional choices, geographic diffusion, and external conditionality—played a relatively modest role in explaining democratization patterns beyond the constraints imposed by historical legacies.