The study examines the connection between the democratizing aspirations of perestroika and conservative populism, the latter embodied in Belarus by Aliaksandr Lukashenka. Following the Soviet collapse, Belarus experienced a significant shift in public opinion. Initially open to the liberal ideas of perestroika, focused on individualism and market, by 1993, Belarusian society had become dominated by various populist sentiments, expressed through critiques of the elites’ corruption, moral decline, and the rise of crime and poverty. Although often considered polar opposites, these two ideologies—the democratic aspirations of perestroika and the populist backlash against reforms—shared a nuanced relationship with the legacies of European Romantic thought. The book outlines the content, contexts, and trajectories of these ideologies, mapping their mutual entanglements and influences and tracing the key ideas and arguments underpinning them. By situating the ideological struggles of the perestroika era within a broader context, my study reveals their deep roots, which extend into the wider European cultural and intellectual heritage. This approach offers a more nuanced understanding of post-socialist political transformations in the early 1990s while providing a novel interpretation of perestroika—how it emerged, the ideas it propagated, and how its appeal collapsed.