This article reconstructs and analyzes the philosophical hermeneutics of the political events of perestroika and regime change in Russia in 1991 as well as the political and economic atmosphere of the “wild 90s” proposed in the works of Russian philosopher Vladimir Bibikhin. Bibikhin’s attention to this theme owes as much to the traditional themes of Russian philosophy as to Heidegger’s thesis on historical factuality of thought. An examination of Bibikhin’s philosophy is impossible if these two sources are separated: it is only by mutually enriching each other that they contributed to the specificity of Bibikhin’s philosophical work linked with contemporary events. Characteristically, while recognizing the significance of historical context for Bibikhin’s thought different researchers often propose opposite interpretations of the philosopher’s reaction to current events. While Artemy Magun believes that Bibikhin fully shared the political enthusiasm of the pioneers of perestroika, Mikhail Bogatov discerns Bibikhin’s critical attitude to such enthusiasm. Looking at the whole body of Bibikhin’s texts it becomes clear that the reason for such a wide spread of possible interpretations was the complexity of Bibikhin’s attitude to the events referred to. On the one hand, the philosopher, while being highly critical of the scale of privatization, was also very sensitive to the change of ideology; on the other hand, Bibikhin recognized the significance of the events that happened and urged intellectuals to think about them deeply. Bibikhin believed that the only adequate response to the newly available freedom was philosophical work that links the interpretation of historical context to eternal themes of the original philosophy. At the same time, he stressed the significance of the Russian philosophical tradition for such interpretation and therefore perceived perestroika and the 1990s as a new chance for the evolution of Russian philosophy. His main intent was the search for non-ideological thinking.