This chapter places Eastern Europe into a broader history of decolonization. It shows how the region’s own experience of the end of Empire after the World War I led its new states to consider their relationships with both European colonialism and those were struggling for their future liberation outside their continent. Following World War II, as Communist regimes took power in Eastern Europe, and overseas European Empires dissolved in Africa and Asia, newly powerful relationships developed. Analogies between the end of empire in Eastern Europe and the Global South, though sometimes tortured and riddled with their own blind spots, were nonetheless potent rhetorical idioms, enabling imagined solidarities and facilitating material connections in the era of the Cold War and non-alignment. After the demise of the so-called “evil empire” of the Soviet Union, analogies between the postcolonial and the postcommunist condition allowed for further novel equivalencies between these regions to develop.