The Annotated Prince - The Prince by Niccolò Machiavelli with notes by Gene Gessert
Cesare Borgia

Cesare Borgia Attribution: Altobello Melone [Public domain], via Wikimedia Commons

Cesare Borgia
(1475 - 1507)

Cesar Borgia is Niccolò’s case study of a prince who comes to power through the help of a patron.

Cesare Borgia had both luck and skill.  Unlike Francesco Sforza, who was the son of a small-time mercenary soldier, Cesare was the son of the Spanish Cardinal Rodrigo Borgia who, in 1492, became Pope Alexander VI. 

Like Francesco, Cesare had skill; he was if anything a more accomplished leader than Francesco.  He knew how to use not just brute force but also cunning.  He was, as Niccolò put it both a lion and a fox.

However, Cesare lacked two things that Francesco had: time, and control of his own resources.  Francesco’s career spanned 42 years (from his father’s death in 1424 to his own death in 1466). Cesare’s political career spanned only 5 years.  It began in 1498 (when he renounced his position as a Cardinal) and ended shortly after his father’s death in 1503.

Throughout his political career, Cesare could not command his own resources, but had to rely on the resources that his father controlled as Pope, that is, the wealth and influence of the papacy. In the end, in spite of his personal abilities, Cesare lacked the time to build his own self-sustaining productive organization and when his father died Cesare’s power, cut off from its source, quickly withered and died, as did Cesare himself 4 years later.

Alexander did not push Cesare forward in the world simply because of the tender emotions of nepotism.  He was not just chief priest, but also the ruler of a large territory in Italy, the Papal States.  As a temporal ruler, the Pope had his own political ambitions, which were to:

  • Recover effective control of the Church land, especially in the Romagna.
  • Make Rome itself secure from coercion by powerful families in the region just south of Rome (the Campagna).

Alexander’s ambitions had historical roots. The Pope was (in legal theory) the feudal lord of the Papal States, a band of land, which Charlemagne and his predecessor had deeded to the Church and which stretched across central Italy from Rome in the west to Ravenna in the east.  After the decline of the Holy Roman Empire feudal power had again devolved onto local power centers throughout Europe, but this problem became particularly acute in the Papal States.  Papal power slipped dramatically during the period of the Avignon Papacy (1309 – 1378) 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.

Within the Papal States there were two areas of internal weakness.

First, the towns of the Romagna and the Marches (poor areas on the Adriatic side of the Papal States, where the main industry was supplying mercenary troops) were dominated by families of hereditary despots.  While in principle, each family ruled its territory as a vicar of the Church, in practice they did as they pleased.  Historians often refer to these families as the Papal Vicars.

Second, the Campania (a rural area to the south of Rome) was dominated by families of feudal aristocrats. These families (the Gaetani, Colonna, and the Orsini), which historians often refer to as the Roman Barons, possessed private armies and from their estates and fortresses, controlled the countryside and the roads that communicated with Rome. They were also able to get family members appointed to high church offices and were thus able to pressure the Pope from inside as well as outside the Church.

Alexander wanted to be the man to reclaim control of the Papal States and he saw a bargain with Cesare as a means to that end.  The quid pro quo was that Cesare would gain control of Church lands, becoming a prince among Papal Vicars, and Alexander would gain a competent general who was more likely than any other candidate to be loyal.

Alexander probably had two particular objectives for Cesare.

  1. To create for him a permanent hereditary state within the Papal States centered in the Romagna. This put father and son at odds with the Vicars.
  2. To enable Cesare to control papal elections by giving him in addition to his power base in the Romagna, military power in Rome, and influence over Spanish cardinals who would elect future popes. To become the dominant military power in Rome, Alexander and Cesare would have to destroy the power of the Roman Barons.

Cesare realized that he needed to establish himself firmly before his father’s death.  To build a principality in such a short time Cesare needed resources.  His bargain with his father gave him what he could get in no other way, access to the Papacy’s money, influence, and diplomatic organization.

Alexander used papal diplomacy to exploit circumstances arising out of the death of Charles VIII of France to launch Cesare’s career.  When in 1498 Charles died without an heir, Louis Duke of Orleans became king and reigned as Louis XII. 

Upon his ascension, Louis at once asserted his claim to the Duchy of Milan.  However, before he could launch a foreign war, Louis had to secure his power base. 

One issue was Brittany.  Charles had extended the French state by marrying Ann of Brittany.  To keep Brittany firmly annexed to France, Louis needed to divorce his wife and marry Ann, who was his second cousin.  Another issue was strategic. To secure his flank, Louis needed and soon signed a peace agreement with Venice. 

Alexander realizing that a French invasion in the north was inevitable turned his attention to finding ways to profit from it, and from Louis’ need for marriage counseling.

Alexander dispatched papal diplomats to Louis’ court, and after many twists and turns, Cesare, and Louis struck a bargain.  According to its terms, Cesare would gain (A) the Duchy of Valence, (B) Marriage with Charlotte d’Albert, the sister of the King of Navarre, and (C) French troops for his conquest of the Romagna. With Valance, Cesare acquired the title by which Niccolò often referred to him, Duke Valentino. From the bargain, Louis would gain (A) his divorce (B) a Cardinal’s hat for a favorite counselor, George d’Amboise, (C) Cesare’s assistance in Louis’s planned invasion of Milan.

Alexander made room for Cesare’s new state in the Romagna by asserting in a Papal Bull that the Papal States of Camerino, Faenza, Forlì, Imola, Rimini, Pesaro, and Urbino were all ruled by tyrants and demanding that they resign or be forcibly deposed.

Papal Vickers
In the Papal States, Cesare Borgia attacked these towns, which were then ruled by autonomous warlord princes. All these rulers should have held their towns as vassals of the papacy, but in fact did as they pleased. For example, when Louis XII invaded Italy they all declared themselves his allies. In chapter 3, Machiavelli notes that Louis would have been wise to accept their alliance. Instead, he helped Cesare attack and ruin them. Thus weakening these already weak princes and in the process strengthening the, already strong, Papacy. Niccolò advises the prudent prince to strengthen the weak, weaken the strong, and never to strengthen the strong.
Person Title Place
Francesco Gonzaga Marquis Mantua
Ercole I d’Este Duke Ferrara
Giovanni Bentivoglio Lord Bologna
Caterina Riario Sforza Lady Forlì
Astorre Manfredi Lord Faenza
Giovanni Sforza Lord Pesaro
Pandolfo Malatesta Lord Rimini
Cesare da Varano Lord Camerino
Jacopo IV d’Appiano Lord Piombino

In September 1499 Louis marched on Milan and the newly made Duke Valentino was among his honor guard. Milan’s ruler, Ludovico Sforza, quickly fled to Austria.  The French lent Cesare 1,800 cavalry and 4,000 Swiss and Gascon infantry, under Yves d’Alègre, with which to “cleanse the Papal States from tyranny” and Cesare set out at once on his conquest of the Vicars of the Romagna. 

Machiavelli says that to succeed, a prince must be both a lion and a fox.  Cesare showed that he could be both.


Cesare first turned his borrowed army against Forlì, and Imola, which were then ruled by Caterina Sforza as regent for her son Ottaviano. Imola and its fortress surrendered quickly, but Caterina as she had after her husband was assassinated held out in her castle at Forlì.  Cesare after a siege that ended only in February 1500 forced Caterina to surrender (she would eventually retire to a nunnery). 

While Cesare was occupied on his first campaign, Alexander began his own effort to pacify the Roman Barons. He confiscated the Gaetani estates and sold them to his daughter Lucrezia. Alexander also captured Subiaco and the fortresses of the Colonna family at Genazzano, Marino, and Rocca di Papa.

Cesare’s first campaign came to a close when the French recall their troops (under Yves d’Alègre) from his service to reinforce the French forces in Milan where Ludovico Sforza was attempting to recapture the city with a force of Swiss mercenaries.  Cesare resolved to return to Rome and to build up a more reliable mercenary force, for which purpose Alexander put the resources of the Papacy at Cesare’s disposal.

The Pope’s resources were considerable, and included.

  • Alum mines at Tolfa, which allegedly generated income for the crusades.
  • A Tax of One Tenth, which applied to all Christendom.  The Tenth tax on cardinals generated huge revenues, which were also supposed to be for the Crusades.
  • First Fruits, a system where new cardinals paid to the Papacy an amount equal to the first year’s income from their benefice.
  • The return of cardinals’ possessions to the Papacy at the time of their death.
  • The sale of other church offices.

In addition, Cesare and Alexander had the good fortune that 1500 was a jubilee year.  This meant that in addition to his normal sources of revenue Alexander could sell indulgences.  Indulgences were like spiritual pollution credits.  The many good deeds of the Christian saints (being unused for the remission of their too few sins) accumulated as a legacy of the Church.  This reservoir constituted an asset which the Church could sell to those who were producing too much sin.  This windfall from indulgences gave Alexander the cash to stake Cesare to another Army.

During the summer of 1500, Cesare engaged Spanish and Italian mercenary captains and troops. His new force included 10,000 mercenaries with only a small additional force of 300 French lances. Unfortunately, several of the Italian captains (such as Gianpaolo Gaglione Paolo Orsini, and Vitellozzo Vitelli) came from the Romagna or the Campagna, and hence had conflicting interests with respect to Cesare’s domination of the region.

In Oct 1500, Cesare marched his new army from Rome for his second campaign, with the goal of capturing the Romagna cities of Pesaro, Rimini, and Faenza.  These cities had been subordinate allies of Venice, but it was too weakened by Turkish pressure to help its allies resist Cesare’s advance.  Pesaro and Rimini succumbed quickly, but Faenza held out until April of 1501.

While Cesare was campaigning against Faenza, Louis was planning to make good France’s claim on Naples.  He planned to do this in the way that Hitler planned to conquer Eastern Europe, by first making a pact to divide the territory and later push out his partner.  Louis version of the (Molotov-Ribbentrop Pact of 1939) was the Treaty of Granada in which France and Spain agree to partition the Kingdom of Naples.  When we speak here of Spain we are referring to the lands of Ferdinand (the Catholic) of Aragon and Isabella of Castile. France was to get the city of Naples, the Campania, Abuzzi, and Basilicata.  Spain was to get Puglia and Calabria.  The Spanish king’s relative, then on the Neapolitan throne was (like Finland, Estonia, Latvia, Lithuania, Poland, and Romania) to get nothing.

Cesare capped his successful campaign by extorting the Castel Bolognese from Bologna and then returning to Rome while his captain Vitellozzo Vitelli conquered Piombino. By August 1501 Cesare (in return for French support in the Romagna) was spearheading a successful French attack on Capua in the Kingdom of Naples.  In the face of overwhelming French military force and lacking support from his kinsmen in Spain, King Federigo of Naples surrendered and went into exile in France.  Having fulfilled his obligation to King Louis, Cesare returned to Rome to embark on a tour with his dad inspecting Papal fortresses and plotting his third campaign.

Cesare’s third campaign aimed at extending his conquests beyond the Romagna.  Most people thought that he would begin by attacking Camerino (located just south of the Romagna and a logical extension of Papal control.  In June 1502 Alexander set the stage by republishing his excommunication of Giulio Cesare Varano, who ruled Camerino as a vicar of the pope.  Cesare asked the Duke of Urbino (Guidobaldo da Montefeltro) for special permission to move his artillery into Urbino.  The stage was set for the attack on Camerino, but Cesare was about to show that he could be a fox as well as a lion. 


When his artillery moved into Urbino, Cesare moved 2,000 infantry by forced march up the Via Flaminia and attacked, not Camerino, but Urbino itself.  The combined force quickly overwhelmed the city and Montefeltro, Italy’s leading mercenary soldier fled his city with little time to spare. Cesare soon followed his success by Camerino, but this was now an anticlimax. .  The stealthy and audacious move on Urbino catapulted Cesare into the first ranks of Italian warlords. 

Cesar’s success in Urbino, triggered a conspiracy among his mercenary captains, many of whom had estates in the Romagna and feared that they might be the next to be assimilated into Cesare’s new state.  In October 1502, Cesare’s captains met at Magione with Giovanni Bentivoglio (lord of Bologna), Guidobaldo da Montefeltro, and Pandolfo Petrucci (lord of Siena) to plot a revolt against Cesare. Several members of the Orsini family also joined the Magione conspiracy.  These included Cardinal Orsini, mad Paolo Orsini, and Francesco Orsini, Duke of Garvina.

The mercenary captains commanded most of Cesare’s troops, so their prospects were good if they made a swift strike. Two of the conspirators, Baglione and Vitelli, began at once to assist revolts in Urbino and Camerino. However, the other captains (ignoring Niccolò’s principle of decisive action) delayed, and Cardinal Orsini began negotiating on his family’s behalf with Alexander in Rome.

Cesare moved quickly to pull his forces north from the southern cities into the Romagna and to provision his fortresses.  The conspiracy failed to attract allies for the same reason that Cesare’s camp remained in high morale.  As Machiavelli said in his dispatch, everyone was convinced Cesare would succeed because “the King of France would help him with men and the Pope with money.” - Quoted in Michael Mallett 1969 <strong>The Borgias</strong> Barnes and Noble, Inc., p 199.

Without allies, the conspirators tripped over one another to be the first to make peace.  Cesare offered generous terms. Cesare was to get back Urbino and Camerino. The captains would get back there mercenary contracts but would serve only one at a time and would tender to Cesare one son to serve as a hostage guaranteeing good conduct.

However, Cesare no longer relied on the conspirators. With financial help from Alexander, he engaged new mercenaries and prepared to continue his campaign with an assault on Senigallia.   On 30 December 1502, Cesare called the conspirators and his other captains to Senigallia. However, he moved his new troops to the area in small groups to conceal their true strength.  Faced with Cesare’s troops the city of Senigallia immediately surrendered but the citadel commander refused to surrender to anyone but Cesare himself, who had not yet arrived on the scene. 

Except for Gianpaolo Baglione who refused the summons and remained in Perugia, the other conspiring captains arrived at Senigallia.  Under the pretext of a planning conference Cesare invited the captains to join him in the city, while leaving their own troops outside.  Once inside Cesare arrested the captains.  He executed Oliverotto Euffreducci and Vitellozzo Vitelli during the night, but sent word to the Pope (as any dutiful son would) before executing Paolo Orsini, a relative of a prominent cardinal.

On hearing the news from his son, Pope Alexander arrested Cardinal Orsini and other prominent members of the Orsini family in Rome.  Cesare then executed Paolo Orsini and Francesco Orsini, Duke of Garvina. Cardinal Orsini later died in prison.  With the deaths of many prominent Orsini, Alexander and Cesare had crippled the last of the great families of Roman Barons. Cesare then confiscated Vitellozzo Vitelli’s lands at Città di Castello and those of Gianpaolo Baglione’s Perugia.

Cesare and Alexander had won striking victories against both the Vicars of the Romagna and the Roman Barons.  Only mopping up operations remained. But on 12 August 1503, both Alexander and Cesare fell critically ill with malarial fever.  The Pope died on 18 August 1503, while Cesare remained seriously ill.  Revolts broke out in the Romagna, and Urbino.  French troops who were already in Rome waited to press the best advantage of the King in the new power vacuum.  Spanish troops hurried up from Naples to do the same.  The presence of two large foreign armies neutralized Cesare’s small force in Rome.  The rump of the Orsini clan, seeing an opportunity began to gather forces.  Cesare was attacked on all fronts and was cut off from both the benefits of the French/Papal alliance and from his ongoing access to the Papal treasury.

Cesare managed to confiscate the Pope’s private cash hoard and set about using what influence he still had to manipulate the College of Cardinals and the conclave that was about to select a new Pope.  With lobbying from Cesare and his allies among the Spanish Cardinals, the conclave elected Cardinal Piccolomini, Pope Pius II.  Pius may have proved a safe choice from Cesare’s perspective, but the new pope died the following month.

In the new Conclave Cardinal Giuliano della Rovere (a lifelong enemy of the Borgias) gained overwhelming support.  Cesare (still holding Castel Sant’ Angelo and still with some influence with the Spanish Cardinals) offered his support to Rovere in return for Rovere (later as Pope) confirming Cesare’s offices and possessions in the Romagna.  On 1 Nov 1503 the conclave elected Giuliano, who chose the unbiblical name of Julius II.

However, Julius II soon found reasons to arrest Cesare in order to force him to turn over his fortresses in the Romagna, which he still held because they were in the hands of his loyal Spanish mercenaries.  After protracted negotiations Cesare’s fortresses at Cesena and Bertinoro surrendered in April 1504, his papal warden Cardinal Carvajal released him at the port of Ostia, from whence Cesare promptly fled to Naples.  However, Naples proved no safe haven. King Ferdinand of Spain, to curry favor with the new Pope, had his general in Naples (Gonsalvo de Cordoba) arrest Cesare.  After Cesare’s last fortress (at Forlì) surrendered, Cordoba packed Cesare off to prison in Spain.  Cesare escaped but never regained anything like his former position and in 1507 he died in Spain, fighting for his brother-in-law.