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The question of freedom together with its complex and dialectical manifestations seems to be at the same time unavoidable and impossible and has opened up different interpretative theories throughout the history of philosophical thought. One ideal-typical reading, which by now has become classic, schematically distinguishes two main concepts of the ambivalent experience of freedom, namely positive and negative liberty, which characterized respectively the ancient and the modern individual and collective way of life. While the former emphasizes the universal dimension of the community the individual belongs to, the latter understands freedom as the absence of impositions and as emancipation from the oppressive power of any internal or external despotism. This contribution aims to historically contextualize these two positions, showing their ambivalences and exceptions, in order to problematize the contemporary “immunitarian” comprehension of freedom invoking ancient practices, in order to rethink freedom as a necessary political construction in the public sphere.