Machiavelli isn’t known for his moral qualms but he did have a good head on his shoulders nevertheless. The Florentine historian and statesman made an outstanding and perhaps under-appreciated contribution to the theory of emergency powers in a republic.
All modern republics take their cue from the Roman republic (res publica is Latin, of course). However, around the time Machiavelli was writing, the scholarship on Roman politics was quite underdeveloped; much Roman scholarship was devoted to the arts and literature although Cicero’s On Duties was second only to the Bible in popularity. Machiavelli set about understanding Roman political history and he was the first truly modern theorist of republicanism.
Machiavelli did fantasize in many respects about the virtues of the ancients and did so to critique his own age, rather like Nietzsche would do over three hundred and fifty years later. Yet with dictatorship, he did produce an original but accurate analysis, one that has stood the test of time.
Much of what Machiavelli states directly about dictatorship can be found in books 30 and 34 of Discourses on Livy, his masterpiece and second most famous book after The Prince. He clearly understood that dictatorship was a device that was actuated by a republic in times of crisis and also that dictatorship is a world away from how we interpret the term nowadays. The brilliance of his analysis can be gleaned from the fact that little has been contributed in the five centuries since to Machiavelli’s general theory of dictatorship.
Machiavelli’s analysis, as well as that of other thinkers of the Renaissance and Enlightenment vis-a-vis dictatorship, will be given in chapter 3 of my forthcoming book The Terrible Beauty of Dictatorship.