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[W]hoever becomes the master of a city accustomed to living in freedom and does not destroy it may expect to be destroyed by it, for during a rebellion it always takes refuge in the name of liberty and its ancient institutions, which are not forgotten either with the passage of time or because of benefits received. And no matter what one does or foresees, if the inhabitants are not separated or scattered, they will not forget that name and those institutions, and they will have recourse to them instantly[.]

[I]n completely new principalities where there is a new prince, one encounters more or less difficulty in holding onto them depending on whether the one who acquires them is more or less skillful [virtuoso]. And because the transition from private individual to prince presupposes either skill [virtù] or Fortune, it appears that either one or the other of these two would, in part, mitigate many difficulties; nevertheless, he who has depended less on Fortune has maintained his position better.

[T]hose who become princes through their prowess, obtain their principality with difficulty, but hold onto it with ease, and the difficulties they have in acquiring the principality arise in part from the new rules and measures that they are forced to introduce in order to found their state and make themselves secure . . . [T]here is nothing more difficult to manage, or more doubtful of success, or more dangerous to handle than to take the lead in introducing a new order of things.

Cesare Borgia, called Duke Valentino by the common people, acquired his state through the fortune of his father and lost it in the same manner, and that despite the fact that he did everything that a prudent and capable [virtuoso] man should do to put his roots down in those states that the arms and fortune of others had granted him . . . [I]f he did not profit from what he established, it was not his fault but resulted from the extraordinary and extreme malice of Fortune.

[B]ecause he knew that the rigorous measures of the past had generated a certain amount of hatred toward him, in order to purge the minds of the people of it and to win them over for himself completely, he wanted to show that if any cruelty had taken place, it did not come from him, but from the harsh nature of his minister . . . [O]ne morning he had him put in the piazza at Cesna in two pieces . . . The ferocity of such a spectacle left those people both satisfied and stunned.

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