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Why do some regional entrepreneurs engage in conflicts with the heads of the subnational units of the Russian Federation within a system that puts economic elites in a deliberately unequal position in relation to the authorities? Based on the analysis of conflicts between governors and businessmen in Karelia, the author hypothesizes that contradictions around redistribution, combined with the availability of the independent resources e.g., branchy patronal networks, drive such confrontation. According to the author’s conclusion, the federal center also plays a significant role. When deciding whether to start confrontation with governors, regional actors could count on the support from Moscow and resignation of an undesirable regional leader. However, due to the peculiarity of the external environment, primarily institutional and informational, the rationality of such behavior often turns out to be low. The opaque informal rules, which electoral authoritarianism relies upon, affect the ability of actors to create adequate cognitive schemata. The informational environment, in which the regional elites operate, sends them unclear and contradictory signals about the limits of acceptable actions and their possible consequences. In turn, the formal preservation of an institution of elections and parties leads to the formation of identities that narrow the set of available behavioral strategies. The mechanism of mutual learning does not work either: under conditions when the resources available to counter-actors cannot be verified, and the rules of the game change with a governor’s turnover, reliance on the previous experience is fraught with strategic miscalculations.