This article sheds new light on the end of the Cold War and the fate of anti-imperialism in the twentieth century by exploring how the Soviet Union and the Islamic Republic of Iran achieved a rapprochement in the late 1980s. Both the USSR and Iran had invested significant resources into presenting themselves as the leaders of the anti-imperialist movement and “the global movement of Islam,” and both the Soviet and Iranian governments sought to export their models of anti-imperialist postcolonial statehood to Afghanistan. However, by the mid-1980s both the Soviet Union and revolutionary Iran were forced to confront the limits to their anti-imperialist projects amid the increasing pull of globalization. Elites in both countries responded to these challenges by walking back their commitments from world revolution and agreeing to maintain the Najibullah regime in Afghanistan as a bulwark against Islamist forces hostile to Marxism-Leninism and Iran's brand of Islamic revolution. This joint pragmatic turn, however, contributed to a drought in anti-imperialist politics throughout the Middle East, leaving the more radical voices of transnational actors as one of the only consistent champions of anti-imperialism. Drawing on new sources from the former Soviet Union and Eastern Europe, as well as sources from Iran, Afghanistan, and the “Afghan Arabs,” the article sheds empirical and analytical light on discussions of the fate of anti-imperialism in the twilight of the Cold War.