This chapter explores the diversity, political significance, and legacies of Eastern European countries’ experiences with sports mega-events in the twenty-first century. It also discusses Russia’s “mega-event decade” and draws connections between hosting and Russia’s recent hostile geopolitical actions, examining its legacies in the stark geopolitical reality of the Russo-Ukrainian war. While Russia’s mega-events may have impressed domestic and international publics through spectacle and prestige, it also used these events to reduce resistance to the gradual introduction of authoritarian practices domestically and hostile geopolitical actions internationally. This case warns about the uneasy connection between mega-events and authoritarian practices more broadly. Still, the increasing volume of experiences with the whole spectrum of mega-events across Eastern Europe makes this region fascinating, as these nations continue to negotiate their international images and national identities in volatile geopolitical and economic environments.