In a period of less than a year, two decisions of the newly established Constitutional Court of the Republic of Kosovo resulted in the resignation of two Presidents of the new State. Ruling on the unconstitutionality of the act of simultaneously holding the position of the head of State and that of his political party, in one case; and ruling on the unconstitutionality of his election due to procedural irregularities in the other, the Court prompted fundamental changes to the political landscape of Kosovo that in the first case led to new and extraordinary elections, whereas in the second to a political arrangement that would ultimately lead to constitutional reforms. Following the Court’s decisions, both Presidents (Sejdiu and Pacolli) resigned from their posts. This article offers a textual analysis of the merits and controversies surrounding both decisions, which will be situated in the broader context of the seemingly powerful role of Constitutional Courts in certain societies in transition. The overall analysis demonstrates the weaknesses inherent to the initial stages of State formation, and to the foundational constitutional instrument, indicating the importance of the Constitution’s clarity for political stability. In an environment characterized by a dominant perception of a politicized judiciary, the Court’s decisions testify to the judicial activism of the Constitutional Court and, in terms of the substance and consequences of its key decisions, also to judicial supremacy. The Court’s decisions have also had some significance for testing the country’s political culture, a test that has been met in both cases eventually with compliance by those most affected.