Abstract: The subject of this research is the evolution of sociopolitical orientations of small and medium business in the post-Soviet period. The activity of representatives of the aforementioned socioeconomic group is an essential factor of development of the market relation and establishment of the middle class, which is the foundation of civil society, as well as the guarantor of sustainability of liberal democracy in the developed democratic states. Therefore, the problem of formation of the sociopolitical orientations of the Russian small and medium entrepreneurship in post-Soviet time is relevant. The main conclusion consists in the fact that the representatives of small and medium business of 1990’s, although fragmentary, but positively overall, perceived the implemented liberal values, practically without demonstrating the paternalistic moods. At the same time, the absence of effective protection of their interests by the state encouraged the distrust in government. Throughout the 2000’s the statist trends in politics, the course towards “restoring the order” led to the shift in orientations of the small and medium business, the more positive (or neutral) apprehension of government and revival of the paternalistic moods. In addition, the entrepreneurs have demonstrated the high level of alienation from any socio-corporate forms. The evolution of sociopolitical orientation of the substantial segment of entrepreneurs is a factor that suppresses the establishment of civil society and challenges the likelihood of democratization of the Russian political system on the Western model.