Machiavelli is often characterized as a radical political thinker. This essay doesn’t challenge this view directly, but approaches Machiavelli’s originality through a new lens by considering the role of moderation in his political thought. Drawing upon The Prince, the Discourses and The History of Florence, it treats moderation as a binding principle with which to tie together Machiavelli’s views on prudence, the via di mezzo, and the model of well-regulated political order. Machiavellian moderation emerges as a dynamic means of managing forces of discord without insisting upon neutrality or passive compromise.