The article compares the reckless socio-political dynamics in Russia in the 1990s, manifested in a series of crises and turning events, with the concept of mechanisms of the Russian historical cycles. The paper lists the main stages of dynamics — complexes of interrelated events that change the balance of power, structural conditions and the direction of subsequent processes. The author also lists the main actors and social groups involved in the political dynamics of that time period: supreme power, reformers, insiders, oligarchs, representatives of special services, “pro-soviet” and democratic opposition, urban educated class, workers and miners’ movements, “ordinary people”. The author concludes that the rapid sweeping changes in the politics of the 1990s took place, as they did before, in the parametric space with the axes of “state success” and “freedom”. Transitions occurred between the phases that were typical for much longer cycles of the Russian historical past — “crisis”, “liberalization”, “authoritarian rollback”, “state collapse”, “military-political triumph”. At the same time, the mechanism of the general democratic backsliding trend and the growth of authoritarian tendencies calls for clarification. The authors propose a phase model that explains this change through the patterns of response strategies of the supreme power to challenges and threats under different conditions. Weakness and failures of the state policy coupled with a shortage of resources led to mass disillusionment, delegitimization of the supreme power and reform policy, which manifested itself in elections and inspired the adherents of the restoration. The increase in the corresponding threats placed a premium on administrative and violent measures. Once sufficient resources were accumulated, those measures were becoming successful and received positive reinforcement. With each crisis, the supreme power took an upper hand, while the collegial separation of powers was reduced, and the reforms lost their original focus on economic freedom, the rise of small and medium-sized businesses, and the growth of democracy. As a result, the opportunities for the political modernization were missed, giving way to the authoritarian trends.