The article discusses the contemporary transformations of the culture of Soviet cynicism in Russia. Emerging as a tactics of survival and adaptation in the ambivalent social reality of the regime, previously truth-oriented cynical satire became a debased play with political forms that indirectly supported the regime’s legitimacy. The regime, following the collapse of the Soviet Union, incorporated this culture of political cynicism, utilising it as a transgressive tool of power, best demonstrated internationally after Ukraine’s Maidan in 2014. This change from passive towards active use of cynicism in political culture marks the end of the post-Soviet or post-Cold War era and the beginning of a new one. Cynicism emerges as a systemic element within the contemporary domestic and international politics as consciously utilised political tool of confusion and horror. However, the article argues, this approach is perilous to the cynic itself as it is detrimental to its own political integrity.