This article analyzes how the Russian annexation of Crimea in March 2014 has been represented and discussed on social networks. It argues that the key metaphors and discursive strategies, which have been developed in the digital environment, have been prefigured in Russian geopolitical culture and popular imagination since Crimea’s first accession to Russia in 1783. The central geopolitical trope of Crimea as either a “metonymy” of the empire or its “alter ego” reverberates in today’s online discussions. Engaging with the debates on the political potential of the Russian “blogosphere,” the article comes to conclusions that Russian “digital geopolitics” tries to foster grass-roots activism but at the same time paradoxically disempowers them. The government’s project to mobilize people’s support of its policy in Ukraine lies at the core of this failure. Using geopolitical rhetoric and the tongue-in-cheek criticism of the Western liberal model, the state inhibits the development of people’s political subjectivity, undermines the belief in their ability to comprehend and influence the “great geopolitical game,” and nurtures the culture of corrosive irony toward any master-narrative, the Kremlin’s one included.