Milosevic’s regime in Serbia (1991-2000) is often depicted as a cruel autocracy that ordered the intervention of the Yugoslav-Serbian Army in Croatia (1991), Bosnia Hercegovina (1992-5) and Kosovo (1999), and who led the Yugoslav state to the disintegration. Thus, the academic literature tends to concentrate on the consequences of Milosevic’s regime but does not explain perfectly why Milosevic was able to stay in power for a decade. A part of the literature concentrates on the techniques that Misloevic put forward to prevent the opposition from disputing his power, but in these paper we propose a different approach and we propose to focus on why the opposition was not able to establish a common strategy to defeat Milosevic until October 2000, when Yugoslavia had already disintegrated, Serbia had been bombed by NATO and Kosovo put under the administration of the United Nations. Based on the literature on historical institutionalism and on authoritarian regimes, this article aims at emphasizing the role of the institutional legacies created under the communist period in Yugoslavia and the contingent events that occasionally redefined the strategies of the opposition parties and the civil society between 1991 and 2000. In so doing, the article will try to contribute to the debate about the persistency of the regime answering questions like: what were the necessary elements that explain its failure in 2000? Or conversely, what were the necessary elements that explain the support of all the opposition forces around Kostunica?