 Why Machiavelli? That question might naturally and legitimately occur to anyone encountering an entry about him in an encyclopedia of philosophy. Certainly, Machiavelli contributed to a large number of important discourses in Western thought—political theory most notably, but also history and historiography, Italian literature, the principles of warfare, and diplomacy. But Machiavelli never seems to have considered himself a philosopher—indeed, he often overtly rejected philosophical inquiry as beside the point—nor do his credentials suggest that he fits comfortably into standard models of academic philosophy. His writings are maddeningly and notoriously unsystematic, inconsistent and sometimes self-contradictory. He tends to appeal to experience and example in the place of rigorous logical analysis. Yet there are good reasons to include Machiavelli among the greatest of political philosophers, some of which are internal to his writings. In spite of the temptation to emphasize his political pragmatism, a lively scholarly debate rages about the presence of a coherent and original philosophy, addressed to topics of concern to philosophers, at the core of his thought (Benner 2009; Zuckert 2017, 2018; Baluch 2018).