This chapter engages with theories of democratic origin and persistence, late developing states (following Gerschenkron), and workforce dependencies in post-communist settings to suggest how understanding the genesis of the middle class/bourgeoisie in imperial Russia, and distinguishing it from a middle class that is state-fabricated rapidly as part of communist late development catch-up, could help refine theories of the links between the bourgeoisie/middle class and democracy. Based on analysis of author-gathered regional and district data on estate structure and voting for the imperial First, Second, Third, and Fourth Dumas and post-communist parliament, and ascertaining that the “old” middle class exhibits greater democratic proclivities than the “new,” I corroborate the theory of a two-pronged middle class. I first explain how unpacking the genesis, resilience, and political orientations of the multilayered stratum of the educated estates nuances ongoing debates about the interaction between distinct sets of legacies associated with pre-communist and communist regimes. Next, I present analysis that systematically extrapolates the insights from the dissection of the reproduction of the social structure to explain variations in subnational democratic quality in Russia. I also perform a placebo test demonstrating how the deportation of entire communities, the Volga Germans, wipes out the effect of a social legacy.