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The erosion of democracy in the face of waxing authoritarianism is the central problem of our time. Central Europe, where citizens joined together in 1989 to reject authoritarianism and establish democracy, yet where “illiberal democracy” gained its first foothold in the European Union, provides important evidence for understanding this development. In this paper, I examine the past 35 years of commemorations of key dates in 1989—dates on which citizens and politicians have annually debated the meaning of democracy and how well the regimes established in 1989–90 have lived up to citizens’ visions in that year. The paper is based on a unique dataset: my own field notes, recordings, photographs, and collections of ephemera from significant anniversaries in five countries from 1992 to 2024. Supplemented by research in relevant periodicals and online, this corpus enables me to track shifts in civic mentalities and practice and to identify key turning points. The rise of new generations with no personal memory of the revolutions or the preceding era has necessarily changed patterns of commemoration, with telling variety among the six countries under study and bearing significant consequences for future development. This paper will summarize findings, present explanatory hypotheses, and suggest implications for the approaching fortieth anniversary, which promises to be momentous.