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Simone Luzzatto’s political thought has been interpreted by several scholars as being linked to the tradition of the reason of state, which the Venetian rabbi constantly references in his work, particularly the Discourse. From an in-depth analysis of Luzzatto’s works, however, it is possible to recognise other fragments of a political reflection that cannot be traced back to the tradition of reason of state and that are in some cases contrary to it. Through a comparison of the different political positions that Luzzatto expressed in his works, a new political thought emerges, transformed by the use of the sceptical tradition. In fact, in both the Discourse and the Socrates, Luzzatto recognises the impossibility of formulating a “universal” political theory and identifies the sceptical concept of “the probable” as man’s only guide to living in a social community. This chapter aims to compare Luzzatto’s different positions and to acknowledge the sources of his most radical interpretations, the politics of the probable, which may be useful for reaching a more general understanding of the influence of scepticism on Jewish and Christian political thought in seventeenth-century Europe.