Chapter 8 — Those Who Have Obtained a Principality by Wickedness

Agathocles the Sicilian is the chapter's central case — a man who cannot be counted among the truly excellent, since Machiavelli declines to place treachery and inhumanity among the qualities that earn glory, yet whose practical success cannot be denied. Born the son of a potter, he rose through military service to become king of Syracuse by calling an assembly of the Senate and most wealthy citizens, giving a predetermined signal to his soldiers, and having everyone present killed except himself. The act was total, deliberate, and effective. He then ruled Syracuse for twenty years, defended it against Carthage, and never faced a successful internal conspiracy.

The analysis Machiavelli offers to explain Agathocles's stability is the doctrine of cruelty well used — one of the book's most quoted formulations. Cruelties may be called well used — if it is permissible to speak well of evil — when they are done all at once out of necessity to secure oneself, not repeated afterwards, and converted as far as possible to the benefit of one's subjects. Cruelties are badly used when they are few at first but grow over time, rather than diminishing. The distinction turns on trajectory: a single overwhelming act of violence can establish a regime, if it removes all competitors at once and is not resumed. Violence that accumulates, that is applied piecemeal, that creates ongoing fear without resolution, is destabilising rather than consolidating.

Oliverotto da Fermo provides the Italian contemporary example: a man who murdered his uncle and all the leading men of his city at a banquet, seized the town, and ruled it until he was himself strangled by Cesare Borgia at Senigallia — one of the operations Machiavelli had observed directly as Florentine envoy. The chapter closes with the practical rule: those who take power by wickedness must do their injuries all at once, so that they may decrease and not continue, and so that the injured party, feeling less, is less offended. Benefits, on the other hand, should be distributed slowly, so they may be savoured.