Despite a series of local government reforms in the 1990s, Russia’s localities still lack serious autonomy. Only big cities maintain hopes for the emergence of local autonomy and local democracy. City politics has produced multiple conflicts between regional and local authorities; however, regional‐local relations merely reflect fundamental center‐periphery controversies on a smaller territorial scale. While big cities and their metropolitan areas serve as centers of political, economic and social modernization, other regional areas are lost in the peripheries. During Russia’s transition period, some large cities acquired more political and economic autonomy from regions than others did. This article concentrates on the crucial role of (1) political opportunities inherited from the late‐Soviet period; and (2) strategic choices of political actors in the post‐Soviet period. The constellation of initial conditions and outcomes of political conflicts have contributed greatly to the diversity of city politics and urban autonomy in Russia’s cities. Finally, the article considers the possible impact of local autonomy in Russia’s cities on national social, economic and political developments.