In history, few names are as synonymous with depravation, lust for power and skilful poisoning, as the Borgias. Despite being under the spotlight for a relatively short time, many Borgias got a handsome slice of the cake, and lived to enjoy it. But none had his buttocks smacked harder for it than Cesare Borgia.

#1 Cesare, son of Christ

Born around 1475-76 in Rome, Cesare was the illegitimate son of Vanozza dei Cattanei and Cardinal Rodrigo Borgia, the future Pope Alexander VI. Apart from school bullies, back then bastards could have quite a troublesome time when applying for jobs, but this the immorality of all seemed not to trouble the Church or the Pope Sixtus IV, who in 1480 dispensed Cesare of having to prove his non-existent legitimacy.

Portrait of Cesare Borgia. Duke of Valentino. Author unknown. Photography: Scan from Uwe Neumahr: Cesare Borgia. Der Fürst und die italienische Renaissance, Piper, München 2007, ISBN 978-3-492-04854-5. Source

From tender age, Cesare was groomed for an ecclesiastical career, while his brother, Giovanni, inherited the paternal lands and became Duke of Gandía. Cesare studied in Perugia and Pisa, and in 1492, aged just 18, he was elected Archbishop of Valencia. Perks of his dad being the all-powerful Pope. Furthermore, he was also ordained as a Cardinal.

Pope Alexander VI praying
Pope Alexander VI. Notice the Papal triple crown at his feet. Artist: Pinturicchio. Source

Cesare, the Church’s poster-boy, was athletic, handsome and vigorous, like the bull that represented the Borgias. An animal that he enjoyed killing for the amusement of Rome. Ironic, considering he would eventually cause his own demise.

The coat of arms of the Borgia. Artist: Henry Salomé. Source

#2 Cesare an assassin?

In 1497, Giovanni Borgia’s stabbed corpse was found, dropped in the river. Cesare, who shortly after renounced his cardinalate, was accused of killing him, out of jealousy of his brother’s titles. Hearsay if you ask me, since Giovanni’s son inherited his father’s title of Duke of Gandía. It’s more likely he was made short work by some vengeful husband, brother, or father. After all, even the Pope himself admitted Giovanni had a slight problem with promiscuity.

Giovanni Borgia. 1474/76-1497
Giovanni Borgia, 1474/76-1497. 2nd Duke of Gandía. Artist: Girolamo Marchesi. Source

Minus one heir, the Pope, defended Cesare’s abdication: “It was clearly necessary for the salvation of his soul”. I agree. Out of priesthood, one can sleep with other men’s wives without fearing divine retribution. Louis XII of France, who at the time needed a marriage annulment from Alexander VI, bestowed Cesare with the Duchy of Valentinois (Valentino) and sealed the alliance by offering him the hand of Charlotte d’Albret, sister of John III, King of Navarre. With the Pope’s blessing, the French had an open road to conquering their troublesome neighbour, Milan.

#3 Cesare Borgia and Leonardo da Vinci. 

Now commanding French troops, and with the titles Gonfalioner and Captain General of the Church under the arm, Cesare marched his armies to the beautiful Romagna. You probably think him a jerk (or a hero) for prodding his new neighbours with the sword, but the Romagna lords were perceived as tyrannical and the ‘bad boys’ of Italy. Worth mentioning too, is that they were late in paying their rent to the Church.

Despite his lack of experience on the battlefield, the ex-priest fell upon Imola, Forli, Pesaro, Rimini, and Faenza like a thunderbolt. With the utmost discipline, he forbade his army from pillaging, under pain of death, and gallantly allowed the natives to retain their administrative structure and laws. A cool dude, realized the Romagna folk, tired of the depravations of their former lords, the Sforza and company, and very often they gladly surrendered to Cesare without a fight.

Worthy to mention in 1502 Leonardo da Vinci entered the service of Cesare as a military engineer and architect, providing Cesare with maps, which were quite an oddity back then.

#4 The Prince. A book about Cesare. 

On the other hand, the tyrant lords and their fortresses, weary of Cesare’s methods against their kind, resisted. Can’t blame them, since Astore and Gianevangelista, the Faenza rulers, had ended up strangled. In Sinigalia, the bloody episode was repeated. Vitellozzo Vitelli and Paolo Orsini, Cesare’s former condottieri (mercenaries and military leaders), who had plotted against his life, pleaded for pardon and allegiance. Cesare welcomed them to dinner, and served them strangulation as the main dish. Buon appetito.

Clever and smooth, wrote Niccolò Machiavelli, the Florentine ambassador, who met Cesare while in Urbino. Machiavelli, known nowadays as the author of The Prince, defended Cesare like a zealous mother. He validated the murderous strangulations, since a dead ruler can’t reclaim lost lands. A bit cold in our 21st century eyes, but pragmatic back then.

Cover page of a 1500 edition of Machiavelli’s ‘The Prince’. You can see Cesare’s title, Duke of Valentino, written on it. Source

Cesare was making a name for himself, and, despite still relying on French military aid, his productive levies on the Romagna, and the ongoing French-Aragonese conflict for the domination of Naples, granted him considerable influence over his French allies.

Machiavelli believed Cesare had made preparations enough to withstand even his father’s eventual death. He had gained considerable influence over enough cardinals to ensure they would support a Papal candidate favourable to his own interests. But even Cesare was unprepared for one thing. One that none of us can be prepared for at all.

#5 The last supper of Alexander

In 1503 Alexander VI and Cesare fell victim of the vicious fever that raged through Italy. In just a few days, Alexander died, and Cesare had experienced a close shave. Afraid of their master’s downfall (and their luck down with him) his thugs had the Vatican’s treasury ransacked, like hotel guests taking soap and towels before the check out.

Alexander’s successor, Pius III, didn’t live long, and then Cesare committed the one mistake that cost him everything. He chose to support his father’s former enemy, Giuliano della Rovere. Elected as the new Pope, Julius II, he spoke honeyed words in Cesare’s ears while secretely plotting to annex the Romagna fiefs to the Papal States. When the people of Romagna found out about this, they protested and rioted at this change of management, and demanded Cesare’s restoration.

A convalescent Cesare borgia leaving the Vatican
A convalescent Cesare is carried away from the Vatican by his supporters. Author: Giuseppe Lorenzo Gatteri. Source

#6 The exile of Cesare Borgia

The despised Borgia was evicted from the Vatican and expelled from his native Rome, never to lay eyes on her again. He was packed up to Castile, where he was given a suite in the comfortable prison of Chinchilla. But not wholly happy with the prison meals, Cesare broke out. Flawlessly. Well, almost. The rope was too short, as Cesare discovered when a few of his bones broke on landing.

Pestered by his former ally, Louis XII of France, Cesare fled to Navarre, with his brother-in-law, King John III. Usually a visit of the in-laws can only mean trouble but John probably thought it was a happy coincidence. Ferdinand II of Aragon coveted Navarre, and the Count of Lerín (erstwhile ally of John turned traitor) was trenched in Viana at the time, in open defiance of John. Given the military expertise of Cesare, John saw a potential ally on his fugitive brother-in-law.

Ferdinand II, King of Aragon. He was also King of Castille by his marriage with Isabella of Castile. Together they had passed down to history as the Catholic Monarchs. Painter: Michael Sittow. Photographer. Source

#7 Cesare Borgia’s death

Leading the Navarrese army, Cesare relieved Viana and, catching sight of the Count of Lerín himself, began a chase on horseback. Have you ever been walking with your buddies behind you, and suddenly turned around to discovered they’re not following anymore? The same happened to our favourite bastard. Though luck, John Snow.

When Lerín realised this, the prey became the hunter. Sword in hand, Cesare fought until his last breath. Having lived like a conqueror, Cesare Borgia died like a mercenary, on 11th March 1507.

He was buried in the Church of Santa Maria, in Viana. Decades later, a bishop with fussy aesthetic tastes, or who simply disliked the Borgias; deemed it the grave of a degenerate, and threw Cesare’s bones in a common pit. His remains were rediscovered in the mid-20th century, and reburied in front of the Church. In 2007, 500 hundred years after his death, the Church gave in to Viana’s popular demands, and agreed to return him inside.

Church Santa Maria in Viana. Cesare’s final resting place. Author: Pitert. Source

The original tombstone was supposed to say:

He lies in scarce earth
He who everyone feared
He who war and peace 
In his hand held
Oh, you who searches
Of worthy deeds to praise
If you praise the worthiest
Here halt your way
You don’t need to go any further

#8 Cesare Borgia. Nor TV actor, neither videogame character

Cesare was left to pay the bills of his family, who had treated Rome as their private hotel. Unjustly branded as a power-hungry murderer and of laying with his sister, Cesare was only guilty of appropiating the Vatican’s resources for his own ends. And, of mercilessly strangling rivals and potential threats. However, his exemplary administration of the Romagna makes him somebody very different of the son of a b**** depicted in the media.

In The Prince, Machiavelli wrote about him like a kid would of Messi. One would do well in remembering however, that Machiavelli represented Florence, a sworn enemy of Cesare. The praise didn’t come from his grandma but from an adversary. I believe that, at least in death, the infamous bastard who fought to prove his legitimacy for a place in the world, deserves the benefit of doubt.

Would you like to be a succesful leader in the XVI century Romagna? Bet you do! The celebrated treatise ‘The Prince’ is still in vogue nowadays, because of the flexibility and immutability of the basic principles on politics. Check a free preview or buy the book here: