This paper explains political democratization in Post-Milosevic Serbia utilizing two different accounts of the democratization process: one rooted in the rational choice framework and the other in structuralism. While rational choice explains the decisive role of political leadership in overcoming path dependence, the structuralist explanations show the transnational linkages that encourage democratization in the face of domestic setbacks. This particular debate between the two types of explanations represents the larger debate concerning the role of internal factors and external linkages in propelling democratization in transitional societies. The paper concludes by integrating the two sets of explanations offered by each theoretical perspective, in order to develop a coherent understanding of Serbia's democratization.