In the essay “What is Freedom?”, Hannah Arendt argues that freedom is the meaning, the “raison d’être” of politics and that political life from which it is absent is meaningless (Arendt 1977, 161). Hardly anyone denies the importance of freedom for any human or political society. It is no novelty either that freedom is a highly contested conception, the meaning of which is bound up with numerous controversies and disagreements. Yet, it is customary to distinguish between the “negative” and “positive” concepts of liberty in accordance with the dualistic framework presented by Isaiah Berlin in 1969. Notwithstanding its popularity, this categorization is at very least problematic. This paper elaborates on the Machiavellian understanding of freedom, which arguably cannot fit in Berlin’s categorization. Besides, it draws parallels with Hanna Arendt’s understanding of political freedom and argues that the complexity of her conception challenges the validity of Berlin’s framework.