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Whoever conquers a free town and does not demolish it commits a great error and may expect to be ruined himself.
Niccolo Machiavelli
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Interpretation

What this quote means

This quote suggests that failing to fully dominate a conquered territory can lead to one's own downfall.

Machiavelli emphasizes the importance of complete control in conquest, implying that leaving a free town intact can lead to resistance and ultimately threaten the conqueror's power. It reflects his broader views on political strategy, suggesting that success requires not only victory but also the assurance of loyalty and suppression of dissent among those subdued.

Themes

ConquestControlDominanceStrategyPolitics

In practice

Example use cases

A discussion on military strategy at a defense conference.

More from Niccolo Machiavelli

Every one sees what you appear to be, few really know what you are, and those few dare not oppose themselves to the opinion of the many, who have the majesty of the state to defend them.
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For that reason, let a prince have the credit of conquering and holding his state, the means will always be considered honest, and he will be praised by everybody because the vulgar are always taken by what a thing seems to be and by what comes of it; and in the world there are only the vulgar, for the few find a place there only when the many have no ground to rest on.
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Many have imagined republics and principalities which have never been seen or known to exist in reality; for how we live is so far removed from how we ought to live, that he who abandons what is done for what ought to be done, will rather bring about his own ruin than his preservation.
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And here one must not that hatred is acquired just as much by means of good actions as by bad ones; and so, as I said above, if a prince wishes to maintain the state, he is often obliged not to be good; because whenever that group which you believe you need to support you is corrupted, whether it be the common people, the soldiers, or the nobles, it is to your advantage to follow their inclinations in order to satisfy them; and then good actions are your enemy.
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The chief foundations of all states, new as well as old or composite, are good laws and good arms.
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In war, discipline can do more than fury.
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Quote by Niccolo Machiavelli | QuoteProject