Ambition's Regret
Niccolo Machiavelli
The Prince

A reflective confession where the author admits that a less ambitious path might have resulted in a smaller but more secure and peaceful state.

...saddle and the last out of it. Here Castruccio stood exposed to a wind which often rises at midday on the banks of the Arno, and which is often very unhealthy; from this he took a chill, of which he thought nothing, as he was accustomed to such troubles; but it was the cause of his death. On the following night he was attacked with high fever, which increased so rapidly that the doctors saw it must prove fatal. Castruccio, therefore, called Pagolo Guinigi to him, and addressed him as follows:
“If I could have believed that Fortune would have cut me off in the midst of the career which was leading to that glory which all my successes promised, I should have laboured less, and I should have left thee, if a smaller state, at least with fewer enemies and perils, because I should have been content with the governorships of Lucca and Pisa. I should neither have subjugated the Pistoians, nor outraged the Florentines with so many injuries. But I would have made both these peoples my friends, and I should have lived, if no longer, at least more peacefully, and have left you a state without a doubt smaller, but one more secure and…
But Fortune, who insists upon having the arbitrament of human affairs, did not endow me with sufficient judgment to recognize this from the first, nor the time to surmount it. Thou hast heard, for many have told thee, and I have never concealed it, how I entered the house of thy father whilst yet a boy—a stranger to all those ambitions which every generous soul should feel—and how I was brought up by him, and loved as though I had been born of his blood; how under his governance I learned to be...
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The Imitation Paradox
Niccolo Machiavelli
The Prince

The author explains that a new prince must carefully choose which historical figures to imitate based on his specific circumstances, rather than following any one model blindly. He suggests that the qualities needed to found a state are different from those required to maintain one that is already stable.

...hereditary or a newly formed principality; because the sons of the old prince are not the heirs, but he who is elected to that position by those who have authority, and the sons remain only noblemen. And this being an ancient custom, it cannot be called a new principality, because there are none of those difficulties in it that are met with in new ones; for although the prince is new, the constitution of the state is old, and it is framed so as to receive him as if he were its hereditary lord.
But returning to the subject of our discourse, I say that whoever will consider it will acknowledge that either hatred or contempt has been fatal to the above-named emperors, and it will be recognized also how it happened that, a number of them acting in one way and a number in another, only one in each way came to a happy end and the rest to unhappy ones. Because it would have been useless and dangerous for Pertinax and Alexander, being new princes, to imitate Marcus, who was heir to the principality; and likewise it would have been utterly destructive to Caracalla, Commodus, and Maximinus to have imitated Severus, they not having sufficient…
CHAPTER XX. ARE FORTRESSES, AND MANY OTHER THINGS TO WHICH PRINCES OFTEN RESORT, ADVANTAGEOUS OR HURTFUL? 1. Some princes, so as to hold securely the state, have disarmed their subjects; others have kept their subject towns distracted by factions; others have fostered enmities against themselves; others have laid themselves out to gain over those whom they distrusted in the beginning of their governments; some have built fortresses; some have overthrown and destroyed them. And although on...
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The Scapegoat's Execution
Niccolo Machiavelli
The Prince

Through the example of Duke Valentino and Ramiro d’Orco, the author illustrates how a ruler can use a cruel agent to establish order and then publicly execute that agent to deflect popular hatred. This strategy allows the prince to satisfy the people's desire for justice while simultaneously leaving them awed and intimidated.

...nciled, so that their simplicity brought them into his power at Sinigalia.[3] Having exterminated the leaders, and turned their partisans into his friends, the duke laid sufficiently good foundations to his power, having all the Romagna and the Duchy of Urbino; and the people now beginning to appreciate their prosperity, he gained them all over to himself. And as this point is worthy of notice, and to be imitated by others, I am not willing to leave it out. [3] Sinigalia, 31st December 1502.
When the duke occupied the Romagna he found it under the rule of weak masters, who rather plundered their subjects than ruled them, and gave them more cause for disunion than for union, so that the country was full of robbery, quarrels, and every kind of violence; and so, wishing to bring back peace and obedience to authority, he considered it necessary to give it a good governor. Thereupon he promoted Messer Ramiro d’Orco, a swift and cruel man, to whom he gave the fullest power. This man in a short time restored peace and unity with the greatest success. Afterwards the duke considered that it was not advisable to confer such excessive…
[4] Ramiro d’Orco. Ramiro de Lorqua. But let us return whence we started. I say that the duke, finding himself now sufficiently powerful and partly secured from immediate dangers by having armed himself in his own way, and having in a great measure crushed those forces in his vicinity that could injure him if he wished to proceed with his conquest, had next to consider France, for he knew that the king, who too late was aware of his mistake, would not support him. And from this time he began...
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Popular vs Noble Support
Niccolo Machiavelli
The Prince

Machiavelli contends that it is safer to rule with the support of the people than the nobles, as the people's desire—to not be oppressed—is more easily satisfied.

..., or anarchy. A principality is created either by the people or by the nobles, accordingly as one or other of them has the opportunity; for the nobles, seeing they cannot withstand the people, begin to cry up the reputation of one of themselves, and they make him a prince, so that under his shadow they can give vent to their ambitions. The people, finding they cannot resist the nobles, also cry up the reputation of one of themselves, and make him a prince so as to be defended by his authority.
He who obtains sovereignty by the assistance of the nobles maintains himself with more difficulty than he who comes to it by the aid of the people, because the former finds himself with many around him who consider themselves his equals, and because of this he can neither rule nor manage them to his liking. But he who reaches sovereignty by popular favour finds himself alone, and has none around him, or few, who are not prepared to obey him. Besides this, one cannot by fair dealing, and without injury to others, satisfy the nobles, but you can satisfy the people, for their object is more righteous than that of the nobles, the latter wishing…
It is to be added also that a prince can never secure himself against a hostile people, because of there being too many, whilst from the nobles he can secure himself, as they are few in number. The worst that a prince may expect from a hostile people is to be abandoned by them; but from hostile nobles he has not only to fear abandonment, but also that they will rise against him; for they, being in these affairs more far-seeing and astute, always come forward in time to save themselves, and to o...
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Preventative Action
Niccolo Machiavelli
The Prince

A recommendation for proactive leadership, comparing political foresight to medical diagnosis where early intervention is easy but late treatment is impossible.

...wers to gain authority. Greece appears to me sufficient for an example. The Achaeans and Ætolians were kept friendly by them, the kingdom of Macedonia was humbled, Antiochus was driven out; yet the merits of the Achaeans and Ætolians never secured for them permission to increase their power, nor did the persuasions of Philip ever induce the Romans to be his friends without first humbling him, nor did the influence of Antiochus make them agree that he should retain any lordship over the country.
Because the Romans did in these instances what all prudent princes ought to do, who have to regard not only present troubles, but also future ones, for which they must prepare with every energy, because, when foreseen, it is easy to remedy them; but if you wait until they approach, the medicine is no longer in time because the malady has become incurable; for it happens in this, as the physicians say it happens in hectic fever, that in the beginning of the malady it is easy to cure but difficult to detect, but in the course of time, not having been either detected or treated in the beginning, it becomes easy to detect but difficult to cure.
Thus it happens in affairs of state, for when the evils that arise have been foreseen (which it is only given to a wise man to see), they can be quickly redressed, but when, through not having been foreseen, they have been permitted to grow in a way that every one can see them, there is no longer a remedy. Therefore, the Romans, foreseeing troubles, dealt with them at once, and, even to avoid a war, would not let them come to a head, for they knew that war is not to be avoided, but is only to b...
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