The Annotated Prince - The Prince by Niccolò Machiavelli with notes by Gene Gessert
The Romagna region of the Papal States
The Papal States, the Campagna, the Rogmana, and the towns of the Papal Vicars, overlayed on a map of the Roman Roads.

Preliminary Note: Cesare Borgia, a Lion and a Fox

Here is another case where, to know what Niccolò’s audience would have known, the modern reader need some essential background.

Papal power slipped dramatically during the period of the Avignon Papacy (1309 – 1378), a time when the papacy moved out of Rome (to Avignon in modern France) and during a following period of the Great Schism (1378 - 1417) when there were rival Popes on both Avignon and in Rome.  During this period, the papacy lost control of city states in its north-east territories (called the Romagna and the Marches) and in the territory south of Rome (called the Campagna), which controlled the roads to Naples.  The Romagna was controlled by warlord princes, which were supposed to be Papal Vicars, but were in fact petty princes that hired themselves out as mercenary soldiers. The Campagna was controlled by families (such as the Colonna, the Orsini and the Gaetani).  These old, noble, land-owing families, which historians often refer to as the Roman Barons, had considerable power not only because they too could supply mercenary troops, but also because they were well represented in high offices of the Church.  

Pope Alexander VI and his son, Cesare Borgia formed a plan to reassert control in these areas.  Alexander would supply diplomatic and financial help, and Cesare would conquer the Romagna and become a sort of super papal vicar. 

Alexander took advantage of an opportunity created by the death of Charles VIII of France to procure for Cesare a title and lucrative marriage.  When Charles died without an heir in 1498, Louis Duke of Orleans became king.  Charles had extended the French state by marrying Ann of Brittany.  Now to keep Brittany firmly annexed to France, Louis needed to divorce his wife and marry Ann. For this he needed help from the Pope.  Alexander and Louis struck a bargain in which Louis got a divorce and a dispensation to marry his cousin and Alexander got for Cesare: (A) a rich and pretty wife Charlotte d’Albert (B) the Duchy of Valentinois and Diois, and (C) Louis pledged that during his planned invasion of Italy, he would lend Cesare troops to help conquer the petty city states of the Romagna.

Cesare first turned his borrowed army against Forlì, and Imola, which was then ruled by Caterina Sforza.  Imola surrendered but Caterina held out in her castle at Forlì.  Cesare besieged the town, and forced Caterina to surrender and eventually to retire to a nunnery.  However, shortly after his victory Cesare’s French auxiliary troops went on strike for back wages which he was unable to pay.  Louis then reabsorbed them into his army fighting against Lodovico Sforza in Milan. 

Alexander provided cash for another Army, which Cesare hired in part from Spain and in part from the Romagna and the Roman Barons such as the Orsini.  Cesare was no longer dependent on auxiliary troops from Louis, but he still had a, less than optimally reliable, mercenary army.  However, he was marginally better positioned because the mercenaries were local and in the pay of his father, the Pope.

With his new army Cesare menaced Rimini and Pesaro, both of which surrendered.  He then turned on Faenza, which held out for a time under Astorre Manfredi.  Cesare offered honorable terms, which Astorre accepted.  Astorre then voluntarily joined Cesare in his other battles.  When they returned to Rome Cesare had Astorre and his son murdered. 

Cesare now set out on the final leg of his mission, the conquest of Camerino and Urbino.  Urbino lies between Rome and the other Papal States that were now in Cesare’s hands and it was here the he struck first.  Alexander helped to weaken Urbino by convincing its invalid ruler Guidobaldo da Montefeltro to lend him Urbino’s artillery.  In June 1502 Cesare attacked; Guidobaldo fled and Cesare took Urbino.  Camerino surrendered without a fight.  Cesare looted Guidobaldo’s palace and sold off the Montefeltro family art collection to pay his soldiers. 

Alexander made Cesare papal vicar and Cesare styled himself Duke of Romagna.  Having completed his re-conquest of the Romagna, Cesare reformed the administration and much improved the government of his new realm.  In particular, he hired Messer (knight) Ramiro d'Orco (or. Ramiro de Lorqua) to restore law and order.

Unfortunately, some of Cesare’s mercenaries came from towns that Cesare’s conquests now threatened.  These men (led by Vitellozzo Vitelli) formed a coalition, attacked Urbino, expelled the Papal troops, and restored Guidobaldo. 

Cesare’s resources were once again insufficient to meet the pressing demands.  Once again Alexander stepped in.  Fortunately, Cardinal Ferrari died and his considerable wealth, which reverted to the Pope, gave Alexander enough cash to rent for his son another army.  Alexander also pitched in by using papal wealth and patronage to buy off many of the conspirators.  Guidobaldo hobbled off leaving Urbino nominally in Cesare’s control but actually occupied by troops of the Orsini family, conspirators who were reconciled by Alexander’s “dollar diplomacy”. 

Cesare set about consolidating his conquests.  By a ruse, he trapped four of the conspirators, including two members of the Orsini family, after his siege of the Adriatic coastal town of Senigallia.  In March 1503 he .moved against the Orsini stronghold at Ceri and captured the “godfather” Giulio Orsini.  He forced a peace settlement in which the Orsini fortresses in Papal territory were surrender to the Church. 

Since Cesare had only two assets, his father’s resources and his own skill, it was a critical blow when in August 1503, father and son were both incapacitated with Malaria.  Alexander died after a brief illness. Riots broke out in Rome.  Cesare was able to seize the Papal treasury, but the Colonna and Orsini were able to re-occupy their fortresses. 

In the papal election that followed, Cesare, having planned ahead, was able to control the votes of the Spanish Cardinals, and secure the election of Pope Pius III.  Pius, however, lived less than a month.  In the next election, Cesare was in a weaker position, not having a source of money to buy votes.  However, Machiavelli believed that Cesare might have been able to prevent the election of a hostile candidate, but this he did not do.  Instead he attempted to reconcile with an old enemy of the Borgia family, Cardinal Giuliano Della Rovere, who became Pope Julius II. 

Venice fomented revolutions throughout the Romagna even before the new pope’s coronation.  Julius at first feigned reconciliation and asked Cesare to help him raise an antirevolutionary army.  However, as Cesare was gathering his forces Julius appointed old Guidobaldo commander of the papal armies and ordered Cesare to turn over to Guidobaldo all the papal fortresses in the Romagna. Cesare refused but returned to Rome, were Julius arrested him and held him until he turned over the fortresses.  On his release Cesare took refuge in Naples with his sister Lucrezia (who was, by the way, a nice lady who never poisoned anyone). Cut off from his resources, Cesare was not able to stage a comeback, but died in a petty battle in 1507.

Chapter 7: Concerning New Principalities Which Are Acquired Either by the Arms of Others or by Good Fortune

Those who solely by good fortune become princes from being private citizens have little trouble in rising, but much in keeping atop; they have not any difficulties on the way up, because they fly, but they have many when they reach the summit. Such are those to whom some state is given either for money or by the favor of him who bestows it; as happened to many in Greece, in the cities of Ionia and of the Hellespont, where princes were made by , in order that they might hold the cities both for his security and his glory; as also were those who, by the corruption of the soldiers, from being citizens came to empire.  [1] Such stand simply elevated upon the goodwill and the fortune of him who has elevated them - two most inconstant and unstable things. {2] Neither have they the knowledge requisite for the position; because, unless they are men of great worth and ability, it is not reasonable to expect that they should know how to command, having always lived in a private condition; besides, [3] they cannot hold it because they have not forces which they can keep friendly and faithful.

Greek cononies ruled by Darius
Ionian cities ruled by Darius, but founded by Greeks. Attribution: By Alexikoua [CC BY-SA 3.0 (], via Wikimedia Commons


Darius I was king of the vast Achaemenid Persian Empire.  He ruled the cities of Anatolia (across the Aegean Sea from Greece) through puppet princes. These cities had originally been settled by Greeks and because the citizens were Greek, when the cities rebelled from Persian rule Athens supported them.  The ensuing clash between Athens and Persia touched off the famous wars with Persia (499 BCE -449 BCE).  

Roman Emperors

In the later years of the Western Roman Empire, emperors ceased to be made by constitutional means.  Rather, upon the death of an emperor, a particularly powerful army simply declared that one of its generals was the emperor.  This practice meant that the emperor was not autonomous, but was instead dependent on the good will of his military commanders. An emperor could easily be deposed by his army or by a rival army.  If fact, after 235, “right down to the end of the Western Empire [in 476], there were only a handful of decades when there was not a major civil war. – Adrian Goldsworthy How Rome Fell.

States that rise unexpectedly, then, like all other things in nature which are born and grow rapidly, cannot leave their foundations and correspondences fixed in such a way that the first storm will not overthrow them; unless, as is said, those who unexpectedly become princes are men of so much ability that they know they have to be prepared at once to hold that which fortune has thrown into their laps, and that those foundations, which others have laid before they became princes, they must lay afterwards.

Concerning these two methods of rising to be a prince by ability or fortune, I wish to adduce two examples within our own recollection, and these are Francesco Sforza and Cesare Borgia. Francesco, by proper means and with great ability, from being a private person rose to be Duke of Milan, and that which he had acquired with a thousand anxieties he kept with little trouble. On the other hand, Cesare Borgia, called by the people Duke Valentino, acquired his state during the ascendancy of his father, and on its decline he lost it, notwithstanding that he had taken every measure and done all that ought to be done by a wise and able man to fix firmly his roots in the states which the arms and fortunes of others had bestowed on him.

Because, as is stated above, he who has not first laid his foundations may be able with great ability to lay them afterwards, but they will be laid with trouble to the architect and danger to the building. If, therefore, all the steps taken by the duke be considered, it will be seen that he laid solid foundations for his future power, and I do not consider it superfluous to discuss them, because I do not know what better precepts to give a new prince than the example of his actions; and if his dispositions were of no avail, that was not his fault, but the extraordinary and extreme malignity of fortune.

Alexander the Sixth, in wishing to aggrandize the duke, his son, had many immediate and prospective difficulties. Firstly, he did not see his way to make him master of any state that was not a state of the Church; and if he was willing to rob the Church he knew that the Duke of Milan and the Venetians would not consent, because Faenza and Rimini were already under the protection of the Venetians. Besides this, he saw the arms of Italy, especially those by which he might have been assisted, in hands that would fear the aggrandizement of the Pope, namely, the Orsini and the Colonnesi and their following. It behooved him, therefore, to upset this state of affairs and embroil the powers, so as to make himself securely master of part of their states. This was easy for him to do, because he found the Venetians, moved by other reasons, inclined to bring back the French into Italy; he would not only not oppose this, but he would render it more easy by dissolving the former marriage of King Louis. Therefore the king came into Italy with the assistance of the Venetians and the consent of Alexander. He was no sooner in Milan than the Pope had soldiers from him for the attempt on the Romagna, which yielded to him on the reputation of the king. The duke, therefore, having acquired the Romagna and beaten the Colonnesi, while wishing to hold that and to advance further, was hindered by two things: the one, his forces did not appear loyal to him, the other, the goodwill of France: that is to say, he feared that the forces of the Orsini, which he was using, would not stand to him, that not only might they hinder him from winning more, but might themselves seize what he had won, and that the king might also do the same. Of the Orsini he had a warning when, after taking Faenza and attacking Bologna, he saw them go very unwillingly to that attack. And as to the king, he learned his mind when he himself, after taking the Duchy of Urbino, attacked Tuscany, and the king made him desist from that undertaking; hence the duke decided to depend no more upon the arms and the luck of others.

For the first thing he weakened the Orsini and Colonnesi parties in Rome, by gaining to himself all their adherents who were gentlemen, making them his gentlemen, giving them good pay, and, according to their rank, honoring them with office and command in such a way that in a few months all attachment to the factions was destroyed and turned entirely to the duke. After this he awaited an opportunity to crush the Orsini, having scattered the adherents of the Colonna house. This came to him soon and he used it well; for the Orsini, perceiving at length that the aggrandizement of the duke and the Church was ruin to them, called a meeting of the Magione in Perugia. From this sprung the rebellion at Urbino and the tumults in the Romagna, with endless dangers to the duke, all of which he overcame with the help of the French. Having restored his authority, not to leave it at risk by trusting either to the French or other outside forces, he had recourse to his wiles, and he knew so well how to conceal his mind that, by the mediation of Signor Pagolo—whom the duke did not fail to secure with all kinds of attention, giving him money, apparel, and horses—the Orsini were reconciled, so that their simplicity brought them into his power at Sinigalia. 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.

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 authority, for he had no doubt but that he would become odious, so he set up a court of judgment in the country, under a most excellent president, wherein all cities had their advocates. And because he knew that the past severity had caused some hatred against himself, so, to clear himself in the minds of the people, and gain them entirely to himself, he desired to show that, if any cruelty had been practiced, it had not originated with him, but in the natural sternness of the minister. Under this pretense he took Ramiro, and one morning caused him to be executed and left on the piazza at Cesena with the block and a bloody knife at his side. The barbarity of this spectacle caused the people to be at once satisfied and dismayed.

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 to seek new alliances and to temporize with France in the expedition which she was making towards the kingdom of Naples against the Spaniards who were besieging Gaeta. It was his intention to secure himself against them, and this he would have quickly accomplished had Alexander lived.

Such was his line of action as to present affairs. But as to the future he had to fear, in the first place, that a new successor to the Church might not be friendly to him and might seek to take from him that which Alexander had given him, so he decided to act in four ways. Firstly, by exterminating the families of those lords whom he had despoiled, so as to take away that pretext from the Pope. Secondly, by winning to himself all the gentlemen of Rome, so as to be able to curb the Pope with their aid, as has been observed. Thirdly, by converting the college more to himself. Fourthly, by acquiring so much power before the Pope should die that he could by his own measures resist the first shock. Of these four things, at the death of Alexander, he had accomplished three. For he had killed as many of the dispossessed lords as he could lay hands on, and few had escaped; he had won over the Roman gentlemen, and he had the most numerous party in the college. And as to any fresh acquisition, he intended to become master of Tuscany, for he already possessed Perugia and Piombino, and Pisa was under his protection. And as he had no longer to study France (for the French were already driven out of the kingdom of Naples by the Spaniards, and in this way both were compelled to buy his goodwill), he pounced down upon Pisa. After this, Lucca and Siena yielded at once, partly through hatred and partly through fear of the Florentines; and the Florentines would have had no remedy had he continued to prosper, as he was prospering the year that Alexander died, for he had acquired so much power and reputation that he would have stood by himself, and no longer have depended on the luck and the forces of others, but solely on his own power and ability.

But Alexander died five years after he had first drawn the sword. He left the duke with the state of Romagna alone consolidated, with the rest in the air, between two most powerful hostile armies, and sick unto death. Yet there were in the duke such boldness and ability, and he knew so well how men are to be won or lost, and so firm were the foundations which in so short a time he had laid, that if he had not had those armies on his back, or if he had been in good health, he would have overcome all difficulties. And it is seen that his foundations were good, for the Romagna awaited him for more than a month. In Rome, although but half alive, he remained secure; and whilst the Baglioni, the Vitelli, and the Orsini might come to Rome, they could not effect anything against him. If he could not have made Pope him whom he wished, at least the one whom he did not wish would not have been elected. But if he had been in sound health at the death of Alexander, everything would have been different to him. On the day that Julius the Second was elected, he told me that he had thought of everything that might occur at the death of his father, and had provided a remedy for all, except that he had never anticipated that, when the death did happen, he himself would be on the point to die.

[Cesare Borgia’s Ten Commandments]

When all the actions of the duke are recalled, I do not know how to blame him, but rather it appears to be, as I have said, that I ought to offer him for imitation to all those who, by the fortune or the arms of others, are raised to government. Because he, having a lofty spirit and far-reaching aims, could not have regulated his conduct otherwise, and only the shortness of the life of Alexander and his own sickness frustrated his designs. Therefore, he who considers it necessary to secure himself in his new principality, [1] to win friends, [2] to overcome either by force or fraud, [3] to make himself beloved and feared by the people, [4] to be followed and revered by the soldiers, [5] to exterminate those who have power or reason to hurt him, [6] to change the old order of things for new, [7] to be severe and gracious, [8] magnanimous and liberal, [9] to destroy a disloyal soldiery and to create new, [10] to maintain friendship with kings and princes in such a way that they must help him with zeal and offend with caution, cannot find a more lively example than the actions of this man.

Only can he be blamed for the election of Julius the Second, in whom he made a bad choice, because, as is said, not being able to elect a Pope to his own mind, he could have hindered any other from being elected Pope; and he ought never to have consented to the election of any cardinal whom he had injured or who had cause to fear him if they became pontiffs. For men injure either from fear or hatred. Those whom he had injured, amongst others, were San Pietro ad Vincula, Colonna, San Giorgio, and Ascanio. The rest, in becoming Pope, had to fear him, Rouen and the Spaniards excepted; the latter from their relationship and obligations, the former from his influence, the kingdom of France having relations with him. Therefore, above everything, the duke ought to have created a Spaniard Pope, and, failing him, he ought to have consented to Rouen and not San Pietro ad Vincula. He who believes that new benefits will cause great personages to forget old injuries is deceived. Therefore, the duke erred in his choice, and it was the cause of his ultimate ruin.

Francesco Sforza and Cesare Borgia
Francesco Sforza and Cesare Borgia. Attribution: Adapted from works by Altobello Melone [Public domain], via Wikimedia Commons and Bonifacio Bembo [Public domain], via Wikimedia Commons

Foundations and correspondences

In this chapter Machiavelli uses several architectural references.  Perhaps that is not surprising for someone living in Renaissance Florence.  However, to my mind it also serves as evidence of the central importance that Machiavelli attached to the notion of organization as an essential element of power. 

As additional evidence, I would point out that in the first 7 chapters, as we can now see, Machiavelli ranks the difficulty of retaining power according to the circumstances by which the prince came to his authority.  In each case, the difficulty is proportional to the amount of energy required to establish order and inversely proportional to the amount of time, and force at the prince’s disposal.  That is, more power is required to build an organization quickly (as Cesare Borgia had to do) than to build it incrementally as did Francesco Sforza.  Interestingly, to capture Machiavelli’s meaning, we can use the term “power” in something very like its physical sense, i.e., the rate at which you can do work.

Francesco’s power increased throughout his career, as he build his autonomous power base (military, political, and matrimonial).  Furthermore, when he took Milan it was already a well-organized state. Like Alexander in the conquest of Persia, he did not need to expend energy you create order. Cesare, however, had to expend considerable power organizing the conquered cities into a coherent state and fend off attacks from his turn-coat mercenaries.  Cesare needed more power, i.e. he had to do work more quickly.  He nearly succeeded, but in the end, his power was not autonomous, and when his father died, Cesare was cut off from his power supply.

At this point, we should remember that Lorenzo di Piero de’ Medici, to whom The Prince is dedicated, is in much the same elevation as Cesare Borgia.  He owes his position to the good fortune of his family relation to the Pope.  However, Lorenzo is not a bastard son of a foreign pope, he is a well-placed member of a powerful Italian family. Furthermore, he is not likely to suffer Cesare’s extreme bad fortune either in having his only patron die or in being himself incapacitated at the same time.