Few names are as synonymous with depravation, lust for power and skilful poisoning, as the Borgias. Despite being under the spotlight for a 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. Apart from school bullies, bastards had quite a troublesome time when applying for jobs. But thanks God (or rather the corrupted Church) the Pope himself had bastardi, and in 1480, dispensed Cesare of having to prove his non-existent legitimacy.

Portrait of Cesare Borgia with his title of Duke of Valentinois
Portrait of Cesare Borgia. Duke of Valentino

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 daddy being the Pope. And because in politics one is seldom satisfied in politics, Rodrigo, now known as Alexander VI, also made him a Cardinal.

Pope Alexander VI praying
Pope Alexander VI. Notice the Papal triple crown at his feet

Link to Rodrigo Borgia’s article here: 


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. Hilariously ironic, considering he would eventually cause his own demise.

Cesare Borgia's plain Coat of Arms
Cesare upgraded his coat with flames to boost the speed

#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, out of jealousy of his brother’s titles. Hearsay. Giovanni’s son inherited the Duchy of Gandía. It’s more likely he was turned into a sieve by some vengeful husband, brother, or father. After all, even the Pope himself admitted Giovanni’s promiscuity.

Giovanni Borgia. 1474/76-1497
Giovanni Borgia, 1474/76-1497. 2nd Duke of Gandía

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 shag without feeling guilty at all.

Louis XII of France, who casually needed a marriage annulment from Alexander, 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. The road to kingdom making

Now commanding French troops, and with the titles Gonfalioner and Captain General of the Church listed on his LinkedIn profile, Cesare began looking for a cosy home in the beautiful Romagna. You probably think him a jerk, for relocating 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.

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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 oddly enough, were a rarity then.

#4 A book about Cesare. The Prince

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.

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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. Meanwhile, his thugs had sacked the Vatican’s treasury, 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 Julius II, spoke honeyed words in Cesare’s ears, but still relentlessly worked to annex the Romagna fiefs to the Papal States. The Romagna protested and rioted at this change of management, demanding Cesare’s restoration.

A convalescent Cesare borgia leaving the Vatican
A convalescent Cesare being carried away from the Vatican

#6 The exile of Cesare Borgia

The despised Borgia was expelled from his native Rome, never to return. He was packed up to Castile, and given a suite in the comfortable prison of Chinchilla. But, tired of the awful meals there, Cesare broke out. Flawlessly. Well, almost. The rope was too short, as Cesare discovered when a few of his bones broke.

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 his ally, the Count of Lerín, was trenched in Viana at the time, in open defiance of John III.

The Catholic Monarchs. Ferdinand and Isabella
Ferdinand II of Aragon and Isabella of Castile. The Catholic Monarchs

#7 Cesare Borgia’s death

Cesare, leading the Navarrese army, 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 bastardi. Sorry 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.

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. Neither TV actor, neither videogame character

Cesare was left to pay the bills of his family, from Rome, which they had treated as a 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 should remember, Machiavelli represented Florence, a sworn enemy of Cesare. The praise didn’t come from his grandma, but from his 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: