Separating the Man from the Myth
Few surnames in European history have acquired quite the reputation of Borgia.
Poison.
Incest.
Murder.
Corruption.
Sex.
Nepotism.
Assassination.
A pope with mistresses and children.
A beautiful daughter supposedly sharing her father’s and brother’s beds.
And towering above much of the legend stands Cesare Borgia: cardinal turned warlord, ruthless conqueror, suspected fratricide and one of the men who helped inspire Niccolò Machiavelli’s The Prince.
It is an irresistible story.
There is only one problem.
Some of it probably isn’t true.
The Borgias were certainly corrupt by modern standards. Pope Alexander VI openly promoted his children. Cesare employed violence and political treachery. Enemies sometimes had an unfortunate tendency to die. Vast sums of church money and influence served family ambitions.
Yet Renaissance Italy was already violent, nepotistic and politically ruthless before the Borgias arrived.
What made the Borgias exceptional was partly what they did.
But their enduring reputation was also shaped by something equally powerful:
their enemies told the story afterwards.
Separating Cesare Borgia the historical man from Cesare Borgia the Renaissance monster therefore becomes an intriguing detective story.
And the historical Cesare hardly needs fictional embellishment.
The Pope’s Son
Cesare was born around 1475, the son of Cardinal Rodrigo Borgia and his mistress Vannozza dei Cattanei.
That sentence alone requires us to abandon modern assumptions about the Renaissance papacy.
Rodrigo was a senior churchman.
He also fathered several children.
Cesare’s siblings included Giovanni — usually called Juan — Lucrezia and Gioffre.
Rodrigo acknowledged them.
Then, in 1492, Rodrigo Borgia was elected pope.
He became Pope Alexander VI.
The children of a cardinal had suddenly become the children of the pope.
And Alexander intended to use them.
Nepotism Was Not Invented by the Borgias
Alexander VI is notorious for promoting relatives.
He did.
But nepotism was deeply embedded within Renaissance papal politics.
Popes had no legitimate dynastic heirs.
Yet they needed trustworthy political allies.
Who could be trusted more than family?
The Italian word nipote, meaning nephew, became intimately associated with papal favour because popes routinely elevated “nephews” and other relatives.
Sometimes those nephews were actually sons.
The Borgias therefore did not invent papal nepotism.
They practised it spectacularly.
Cesare was directed towards the church.
His brother Juan was groomed for secular dynastic leadership.
Cesare became a bishop while still extremely young.
Then an archbishop.
Then, in 1493, a cardinal.
He was approximately eighteen.
Calling this a meteoric ecclesiastical career would be an understatement.
Dad was pope.
Cesare Didn’t Want to Be a Cardinal
Cesare appears to have been much better suited to politics and warfare than church administration.
His father’s original arrangement created a division:
Juan would become the soldier.
Cesare would become the churchman.
Then something happened that changed everything.
Juan Borgia died.
Violently.
A Body in the Tiber
On the night of 14 June 1497, Juan Borgia disappeared.
The following day he was missing.
Eventually witnesses were questioned.
A man reported seeing several figures throwing a body into the River Tiber.
The river was searched.
Juan’s corpse was recovered.
He had been stabbed repeatedly.
His purse still contained money.
Robbery therefore seemed unlikely.
Rome erupted in rumours.
Who murdered the pope’s son?
Political enemies?
The Orsini family?
A jealous husband?
Someone involved in a sexual dispute?
Or Juan’s own brother?
Cesare.
Did Cesare Murder His Brother?
This is perhaps the most famous accusation against Cesare Borgia.
And we simply do not know.
Cesare certainly benefited from Juan’s death.
With Juan gone, Cesare eventually assumed the secular military role previously intended for his brother.
That makes an excellent motive.
It does not make evidence.
Importantly, suspicion of Cesare does not appear to have dominated the earliest accounts of the murder. Other suspects and political explanations circulated.
The image of Cesare murdering Juan became much stronger later.
Could he have done it?
Certainly.
Can historians demonstrate that he did?
No.
This distinction matters enormously when dealing with the Borgias.
Possible is not proven.
Unfortunately for Cesare’s reputation, later writers frequently converted the first into the second.
The Cardinal Takes Off His Red Hat
In 1498 Cesare did something extraordinary.
He resigned from the College of Cardinals.
He became the first cardinal in history to formally surrender the cardinalate.
The churchman became a secular prince.
And Cesare finally entered the world for which he seems to have been considerably better suited.
Politics.
Diplomacy.
War.
France Enters the Story
Cesare’s ambitions required powerful allies.
France provided them.
King Louis XII wanted papal cooperation concerning his marriage and his claims in Italy.
Alexander VI wanted advancement for Cesare.
A deal emerged.
Cesare travelled to France.
Louis XII made him Duke of Valentinois.
Hence one of Cesare’s famous nicknames:
Il Valentino.
Cesare also married Charlotte d’Albret, sister of the King of Navarre.
The pope’s son was becoming a European dynastic figure.
Cesare the Conqueror
Now Cesare began building something extraordinary.
With French support and papal authority, he launched military campaigns through the Romagna and surrounding territories.
One ruler after another fell.
Imola.
Forlì.
Pesaro.
Rimini.
Faenza.
Other territories followed.
Cesare combined military force with political calculation.
He could negotiate.
Threaten.
Bribe.
Besiege.
Reorganise.
And betray.
This was not simply random violence.
Cesare was attempting to construct a territorial state in central Italy.
And for several years he was remarkably successful.
Enter Caterina Sforza
One of Cesare’s most formidable opponents was Caterina Sforza.
She ruled Imola and Forlì.
She was no helpless Renaissance damsel.
Caterina had survived assassinations, political upheaval and military threats and had developed a reputation for extraordinary determination.
Cesare eventually defeated her.
She was captured.
And here we encounter another Borgia scandal.
Cesare was accused of sexually abusing or raping Caterina during her captivity.
The evidence is contested and the surviving accounts are politically charged.
Once again, the responsible historical position is uncomfortable:
The allegation existed.
Cesare was capable of brutality.
But certainty exceeds the evidence.
That distinction does not exonerate him.
It simply prevents allegation from becoming automatic fact.
The Man Who Terrified the Romagna
Conquest creates another problem.
Someone has to govern what has been conquered.
The Romagna had suffered from factional conflict, violence and weak government.
Cesare appointed Ramiro de Lorqua — usually known as Remirro de Orco — to impose order.
Remirro did so brutally.
Then, in December 1502, the inhabitants of Cesena awoke to an extraordinary sight.
Remirro’s body had been cut in two and displayed publicly in the town square.
Beside it lay a bloody knife and block.
Who ordered it?
Almost certainly Cesare.
Why?
That is where Machiavelli becomes fascinated.
Machiavelli Watches Cesare
Niccolò Machiavelli was in Cesare’s territory as a Florentine diplomatic representative.
He watched.
He listened.
He reported.
And years later, when writing The Prince, he remembered.
Machiavelli described Cesare’s strategy in the Romagna.
A brutal subordinate had imposed order.
The population hated the brutality.
Cesare then eliminated the subordinate.
The cruelty became associated with Remirro.
The restoration of order became associated with Cesare.
It was political theatre.
Terrifying political theatre.
And Machiavelli recognised its effectiveness.
This is important because Machiavelli did not simply invent an abstract ruthless prince.
He had watched actual Renaissance politicians operating.
Cesare was one of them.
The Trap at Senigallia
If one incident demonstrates Cesare’s political ruthlessness, it is what happened at Senigallia at the end of 1502.
Several of Cesare’s commanders and political associates had rebelled against him.
Among them were Vitellozzo Vitelli and Oliverotto da Fermo.
Eventually reconciliation appeared possible.
Cesare behaved as though peace had returned.
The conspirators came to Senigallia.
Cesare received them.
Then the trap closed.
Vitelli and Oliverotto were seized.
They were strangled.
Others were subsequently killed.
Machiavelli witnessed the political aftermath and wrote an account of Cesare’s methods.
Here we do not require later Borgia propaganda.
Cesare really was capable of calculated political killing.
Did Cesare Poison His Enemies?
Now we reach one of the most persistent Borgia legends.
Cantarella.
According to later stories, the Borgias possessed a secret poison used to eliminate inconvenient enemies.
Sometimes it supposedly appeared as a mysterious white powder.
Sometimes it was slipped into wine.
Sometimes Alexander and Cesare supposedly invited wealthy cardinals to dinner, poisoned them and confiscated their property.
It is wonderful Gothic material.
Evidence for a special Borgia poison called cantarella is extremely weak.
Poisoning certainly occurred in Renaissance Italy.
Fear of poisoning was widespread.
But the image of Cesare wandering around Rome with a proprietary Borgia poison kit belongs substantially to legend.
The Poisoned Banquet
The most spectacular poisoning story concerns Alexander VI’s own death.
According to one version, Alexander and Cesare planned to poison Cardinal Adriano Castellesi.
Unfortunately, the poisoned wine was accidentally served to themselves.
Alexander died.
Cesare survived because he received treatment.
It is almost too perfect.
The poisoner poisoned by his own poison.
Unfortunately for lovers of poetic justice, malaria or another infectious fever provides a considerably more plausible explanation.
Rome in August was notoriously unhealthy.
Both Alexander and Cesare became seriously ill.
Alexander died on 18 August 1503.
Cesare survived.
And Cesare’s political world collapsed almost immediately.
The Corpse of Alexander VI
Even without poison, Alexander’s death generated lurid descriptions.
His body decomposed rapidly in the summer heat.
Contemporary accounts describe swelling and discoloration.
Later writers transformed the decomposing corpse into almost supernatural evidence of evil.
The devil had apparently come for the Borgia pope.
There is a more mundane explanation.
Dead bodies decompose.
Rome was extremely hot.
Alexander had been seriously ill.
But when someone already possesses a reputation for wickedness, even decomposition becomes propaganda.
And What About Lucrezia?
No discussion of Cesare can avoid his sister.
Lucrezia Borgia became perhaps the greatest victim of the Borgia legend.
She has been portrayed as poisoner, seductress, incestuous lover and accomplice to murder.
The historical Lucrezia appears considerably more conventional — although conventional for a daughter of Alexander VI was hardly ordinary.
Her marriages were political arrangements.
Her father annulled her first marriage.
Her second husband, Alfonso of Aragon, was attacked in 1500.
He survived.
Then he was murdered.
Suspicion fell heavily upon Cesare.
Did Cesare Murder Lucrezia’s Husband?
This accusation is considerably more plausible than many Borgia legends.
Alfonso’s political usefulness had diminished as papal foreign policy shifted towards France.
After surviving the first attack, he was recovering under Lucrezia’s care.
Then Cesare’s associate Micheletto Corella became involved.
Alfonso was killed, apparently strangled.
Cesare seems to have been responsible or at minimum closely connected with the killing.
The precise circumstances remain disputed.
But here we are on considerably firmer historical ground than with tales of secret poison.
Cesare did not need cantarella.
He had Micheletto.
Cesare and Lucrezia: Incest?
And now we reach the scandal everyone remembers.
Did Cesare have a sexual relationship with his sister?
There is no convincing evidence that he did.
Incest accusations circulated around the Borgia family, particularly during the bitter disputes surrounding the annulment of Lucrezia’s first marriage to Giovanni Sforza.
Sforza had been humiliated.
He retaliated.
Accusations of incest were politically devastating.
They were also extremely difficult to disprove.
Was Lucrezia sexually involved with her father?
No credible evidence demonstrates it.
With Cesare?
Again, no convincing evidence.
With Juan?
Likewise uncertain.
But scandal has greater longevity than documentation.
Five centuries later, the accusation still follows her name.
The Banquet of Chestnuts
Then there is the infamous Banquet of Chestnuts.
According to the account associated with Johann Burchard, master of ceremonies at the papal court, an extraordinary sexual entertainment occurred in the Vatican in October 1501 involving courtesans, naked participants, chestnuts scattered across the floor and prizes supposedly awarded for sexual performance.
Alexander and Cesare were allegedly present.
Historians have long debated the reliability and interpretation of the account.
Some accept that an event of this general character occurred.
Others question details or later embellishment.
What matters is that the story became perfect material for the developing Borgia legend.
Sex.
Vatican.
Pope.
Cesare.
Naked women.
Chestnuts.
Propaganda scarcely needed to improve it.
Though naturally it tried.
The Borgia Apartments
Alexander VI did little to conceal his family.
The magnificent Borgia Apartments in the Vatican proclaimed his dynasty visually.
Pinturicchio decorated them.
Classical mythology, Christian imagery and Borgia symbolism intertwined.
The famous Borgia bull appeared everywhere.
This was Renaissance dynastic self-promotion.
Alexander behaved not merely as pope but as patriarch of a family determined to establish itself permanently among Italy’s ruling dynasties.
That ambition terrified his enemies.
Why Everybody Hated the Borgias
Several factors contributed to their reputation.
First, they were outsiders.
The family originated in Valencia in Spain.
Italian rivals regarded them as foreigners.
Anti-Spanish prejudice helped shape attacks upon them.
Second, Alexander practised nepotism conspicuously.
Third, Cesare genuinely was ruthless.
Fourth, the Borgias accumulated powerful enemies.
The della Rovere family particularly despised them.
And this became crucial after Alexander died.
Pope Julius II
Cardinal Giuliano della Rovere eventually became Pope Julius II.
He had been one of Alexander’s great enemies.
Cesare initially believed he could work with the new pope.
That was a catastrophic miscalculation.
Julius had little intention of preserving Cesare’s territorial empire.
Without his father controlling the papacy, Cesare discovered how fragile his power actually was.
The Borgia state began collapsing.
The Great Weakness in Cesare’s Plan
Machiavelli recognised the problem.
Cesare had demonstrated enormous political skill.
But his power depended fundamentally upon something he could not control:
his father’s survival.
Alexander was pope.
Papal authority supported Cesare’s conquests.
Then Alexander suddenly died while Cesare himself was seriously ill.
Had Cesare been healthy at precisely that moment, history might have unfolded differently.
Machiavelli considered this terrible fortune.
Cesare had prepared for many possibilities.
He had not adequately prepared for being incapacitated when his father died.
Fortune — fortuna — had intervened.
Captivity
Cesare’s enemies closed in.
He was arrested.
Released.
Arrested again.
Eventually he was sent to Spain.
He was imprisoned in the castle of La Mota.
For the man who had terrorised central Italy, it was an extraordinary reversal.
But Cesare Borgia was not finished.
The Great Escape
In 1506 Cesare escaped.
He descended from the fortress using a rope.
The escape went wrong and he fell, suffering injuries.
Nevertheless, he got away.
He travelled to Navarre, where his brother-in-law King John III ruled.
Cesare once again became a soldier.
But the grand Borgia dream was gone.
The Final Battle
On 12 March 1507 Cesare participated in fighting near Viana in Navarre.
He pursued retreating enemies.
He became separated from his men.
He was surrounded.
Cesare Borgia was killed.
He was approximately thirty-one years old.
His body was reportedly found stripped of armour and clothing.
The man who had once dreamed of carving out a principality across Italy died violently beside a road in Spain.
It was an oddly appropriate ending.
Was Cesare a Monster?
By modern standards, Cesare committed appalling acts.
He used assassination.
He betrayed allies.
He conquered territories militarily.
He participated in brutal Renaissance politics.
He almost certainly ordered killings.
But calling him uniquely monstrous creates another problem.
Renaissance Italy was filled with political violence.
The Medici used violence.
The Sforza used violence.
The Orsini used violence.
The French used violence.
The Spanish used violence.
Popes employed armies.
City-states executed conspirators.
Rulers eliminated rivals.
Cesare was exceptionally effective at playing a game many others were already playing.
What distinguished him was partly his ambition.
He attempted to turn temporary papal family power into a permanent territorial dynasty.
For several years, it almost worked.
The Black Legend
After the Borgias fell, their enemies had little incentive to preserve their reputations.
Stories accumulated.
Every suspicious death became poisoning.
Every sexual rumour became incest.
Every political betrayal became evidence of pathological evil.
Cesare gradually transformed from Renaissance prince into something approaching a Gothic villain.
Lucrezia became a seductive poisoner.
Alexander became Satan wearing the papal tiara.
The Borgias became shorthand for corruption.
Some of this reputation was deserved.
Much of it was exaggerated.
And separating the two remains difficult because the Borgias themselves operated in an environment where rumour was a political weapon.
And Then Came Machiavelli
This brings us to the man standing quietly nearby taking notes.
Niccolò Machiavelli.
He met Cesare.
Observed him.
Negotiated around him.
Reported on him.
And remembered him.
When Machiavelli later wrote The Prince, Cesare became one of his most important examples of political leadership.
Not because Machiavelli necessarily admired everything he did.
And certainly not because The Prince simply tells rulers to behave like psychopaths.
Machiavelli was interested in a far more disturbing question:
What actually works?
If cruelty produces stability, can cruelty be politically effective?
If generosity destroys a ruler’s finances, is generosity always virtuous government?
If keeping a promise destroys the state, should a ruler keep it?
If fear protects authority more reliably than love, which should a ruler choose?
These questions eventually produced an adjective:
Machiavellian.
Five centuries later we still use it.
And standing behind part of that word is the extraordinary young man Machiavelli watched conquering the Romagna:
Cesare Borgia.
Legend Versus Evidence
So let us put the great Borgia scandals on trial.
Cesare murdered his brother Juan:
Possible, but unproven.
Cesare arranged the killing of Lucrezia’s husband Alfonso:
Strongly plausible and supported by substantial contemporary evidence.
Cesare used political assassination:
Yes.
Cesare betrayed and killed former allies at Senigallia:
Yes.
Cesare possessed a secret poison called cantarella:
Probably legend or substantial embellishment.
Alexander and Cesare accidentally drank poison intended for someone else:
Highly doubtful; infectious disease is considerably more plausible.
Cesare had an incestuous relationship with Lucrezia:
No convincing evidence.
The Borgias participated in spectacularly sexual Vatican entertainments:
Some contemporary evidence exists, particularly surrounding the Banquet of Chestnuts, but individual details and later embellishments require caution.
Cesare was unusually ruthless:
Yes.
Cesare was uniquely evil by Renaissance standards:
Much harder to sustain.
And perhaps that is what makes him more interesting than the monster of legend.
The fictional Cesare Borgia is predictable.
He poisons everyone.
Sleeps with everyone.
Kills everyone.
Plots constantly.
The historical Cesare is considerably more complicated.
He was intelligent.
Ambitious.
Militarily capable.
Politically ruthless.
Occasionally brilliant.
Frequently brutal.
Spectacularly fortunate.
Then catastrophically unlucky.
He benefited enormously from nepotism.
He attempted something politically remarkable.
And he ultimately discovered that an empire constructed upon one man’s possession of the papacy could disappear almost as quickly as it had arisen.
Machiavelli watched.
Europe remembered.
And the Borgias became immortal.
Not because every terrible story told about them was true.
But because enough of the true ones were terrible already.
Tim Alderman ©️2026
Sources and Further Reading
Niccolò Machiavelli, The Prince, particularly Chapter VII and its discussion of Cesare Borgia.
Niccolò Machiavelli, diplomatic writings and Description of the Methods Adopted by Duke Valentino When Murdering Vitellozzo Vitelli, Oliverotto da Fermo, the Signor Pagolo and the Duke di Gravina Orsini.
Johann Burchard, Liber Notarum (At the Court of the Borgia), an indispensable contemporary source that nevertheless requires careful contextual reading.
Michael Mallett, The Borgias: The Rise and Fall of the Most Infamous Family in History.
Christopher Hibbert, The Borgias and Their Enemies.
Sarah Bradford, Cesare Borgia: His Life and Times.
Sarah Bradford, Lucrezia Borgia: Life, Love and Death in Renaissance Italy.
G. J. Meyer, The Borgias: The Hidden History.
The Encyclopaedia Britannica, biographical material on Cesare Borgia, Alexander VI and Lucrezia Borgia.
Machiavelli’s correspondence as Florentine envoy during Cesare’s campaigns provides particularly valuable contemporary evidence for Cesare’s political and military behaviour.
