The article analyzes historical monuments as instruments of Russia’s attempts to impose its aesthetic hegemony in the post-Communist world. Drawing on case studies from the Czech Republic and Estonia, it argues that this hegemony is precarious and vulnerable due to inability to deal with the inherent ambiguity and complexity of historical events and figures. The Russian approach regards historical truth in absolute terms and is underpinned by a zero-sum game understanding of historical narratives. It does not tolerate a multiplicity of perspectives on history and has no appreciation for postmodernist deconstruction of historical symbols. This conflicts with a more diverse, reflexive and inclusive politics of memory as an intrinsic element of cityscapes of Prague and Tallinn where some of the controversial monuments connected with the Soviet occupation have been removed. Russia’s reaction to these changes reveals an inherently vulnerable nature of its aesthetic hegemony which is deeply dependent on recognition of the absolute nature of its historical truth that the monuments are supposed to embody.