We contribute to research on the democratic role of middle classes. Our paper distinguishes between middle classes emerging autonomously during gradual capitalist development and those fabricated rapidly as part of state-led modernization. To make the case for a conceptual distinction between these groups within one national setting, we employ author-assembled historical district data, survey, and archival materials for pre-Revolutionary Russia and its feudal estates. Our analysis reveals that the bourgeois estate of meshchane covaries with post-communist democratic competitiveness and media freedoms, our proxies of regional democratic variations. We propose two causal pathways explaining the puzzling persistence of social structure despite the Bolsheviks’ leveling ideology and post-communist autocratic consolidation: (a) processes at the juncture of familial channels of human capital transmission and the revolutionaries’ modernization drive and (b) entrepreneurial value transmission outside of state policy. Our findings help refine recent work on political regime orientations of public-sector-dependent societies subjected to authoritarian modernization.