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The existing scholarship on irregular regime transitions is siloed. Scholars tend to examine the causes and consequences of coups d’état, domestic uprisings, and foreign interventions in isolation of each other. This paper advances a theory that brings these three types of irregular regime transitions together under a single, unified framework with a specific focus on democratization. We argue that the size of the coalition chiefly responsible for bringing a leader to power --- what we term the transitional coalition --- is one important factor influencing the prospect that an autocracy will democratize. A second relevant factor is the presence or absence of foreign intervention, whether on its own or in support of a coup or uprising. Irregular regime transitions involving large transitional coalitions (uprisings) are especially likely to result in democratic gains. The opposite is true for irregular regime transitions with small transitional coalitions (coups). External intervention is a mixed blessing for targets, advancing democracy in some contexts and authoritarianism in others. Analyzing the universe of successful irregular regime transitions since 1955, we find strong support for our theoretical claims. This paper advances understanding of regime transitions, democratization, and foreign meddling.