This article critically examines Machiavelli’s and Schmitt’s views on emergencies. Both philosophers are known for their emphasis on the unpredictable nature of politics, which cannot be fully captured by legal norms. Thus, they both state that every political order requires an extraordinary figure who could act beyond laws during emergencies. For Machiavelli, this figure is called a dictator; for Schmitt, it is the sovereign. The author aims to show that, despite this apparent similarity, Machiavelli and Schmitt conceptualize the extraordinary figure in a significantly different manner. Machiavelli regards dictatorship merely as a legal instrument bound by the constitution. A dictator only acts to protect the existing order, which he cannot alter. On the contrary, Schmitt’s conceptualization of exception suggests that the sovereign is not bound by any legal norm. Sovereignty implies that this extraordinary figure can suspend and even alter the existing legal order. The author concludes that the difference between Machiavelli’s and Schmitt’s diverse attitudes towards law stems from their different views on the nature of political unity. While Machiavelli perceives polity as composed of two distinct groups with incompatible interests, Schmitt defines polity as a homogenous one. For Machiavelli the survival of political unity depends on a mixed constitution and respect for laws that hold society together. On the other hand, for Schmitt, it depends on the preservation of its homogeneity.