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This paper assesses the effects of Italian colonialism on long-run political development in East and North Africa. Using comparative-historical methods and shadow case analysis, it shows that Italian colonialism had adverse consequences for postcolonial state development and democracy (i.e., Somalia and Libya) unless critical junctures (national revolution in post-1961 Eritrea) caused a rupture with the colonial legacy of weak state institutions, authoritarianism, and deep social cleavages. The paper explains divergent trajectories of political development in former Italian Africa, while adding to renewed scholarly efforts to understand colonialism and state capacity, ethnic conflict, and democracy in Africa and beyond.