The concept of the political in Carl Schmitt’s works is not only defined by the distinction between friend and enemy, but also by the criterion of breaching the rules in a normatively unbound act of decision. According to Schmitt, this decision is, however, not arbitrary, but provoked by the necessity of a historical situation. This aspect of necessity calls the freedom of the decision into question and leads to tensions within Schmitt’s theory of the political. More explicitly than in Schmitt’s political and legal writings, this conflict between freedom and necessity is exposed in his theory of tragedy. In a reading of his book Hamlet or Hecuba , published in 1956, I will show, in a first step, how the act of breaching the rules is not external to normativity, but occurs from within normativity itself. It is the act of self-breaching – of breaking the rules of its own genre – by which, according to Schmitt, modern tragedy is defined. This breach, however, is compelled by the necessity of a real, i. e. extraliterary, event. In a second step, I will expound on how this idea of self-breaching, which also characterises Schmitt’s understanding of the political, leads to a loss of decision which not only questions his idea of sovereignty, but also topples his concept of the political.