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Cruelty can be considered well-used if carried out in one stab, the wicked deeds executed all at once, and if it can be interpreted as necessary for self-preservation.
That this chapter follows a chapter exclusively devoted to criminal princes is telling. Machiavelli seems unsure whether to condone what he labels as “cruelty” or to condemn it. He seems to take a certain pleasure in recounting the wicked deeds of an Agathocles or an Oliverotto da Fermo; what these men did is indefensible, and yet it worked. Machiavelli, ever the theoretician, proceeds to meditate on why it worked. He nearly traps himself in a philosophical cul-de-sac when, about to explain what he means by well-used cruelty, he writes: “if it’s permissible to say good words about something which is evil in itself.”
Why are the actions of Agathocles and Oliverotto evil, while those of Cesare Borgia are not? We are reminded of Borgia, since it was he who lured Oliverotto to his death. Never would Machiavelli refer to Borgia as a criminal prince, yet he murdered the leaders of rival factions to clear the way for his own ascent, much as did Agathocles and Oliverotto, and he made an example of his lieutenant general after using him to pacify his kingdom, just to save face. To Machiavelli, this is cleverness at its best: actions justified by their very brilliance. It’s not hard to see why everyone from Macbeth to the Corleone family to Stalin have been labeled Machiavellian at various junctures. But would Machiavelli approve? It seems that because the deeds of Agathocles and Oliverotto reflected not so much urgent necessity as a kind of deep-seated bloodlust, they are distinguishable from Borgia’s moves. Whatever the reasoning, Machiavelli’s distinction is notable.