The man who lowered himself from the tower window had no way of knowing how the night would end. He had somehow obtained a rope, and now, in the darkness of a Spanish fortress, Cesare Borgia was making his escape. He clambered over the sill and began to descend, the stone wall rough against his hands. Then a guard spotted him.

From above, a blade sliced through the rope. Cesare fell, crashing to the ground, badly injured. Yet he rose. He fled, and for the first time in nearly two years, he was free.

He had been one of the most feared men in Italy, the son of a pope, a general who had carved out his own duchy through conquest and blood. Now he was a fugitive, broken but not finished, seeking refuge with the brother of the wife he had abandoned years ago. He was still a man with enemies everywhere, and the story of how he had arrived at this desperate moment was a long one, stretching back to a scandalous birth and a family that had schemed its way to the very throne of Christendom. Cesare Borgia was born in 1475 in the town of Subiaco, then part of the Papal States.

He was the illegitimate son of Rodrigo Borgia, a Spanish-born Catholic cardinal, and his mistress, a married woman named Vannozza dei Cattanei. Together, Rodrigo and Vannozza would have four children: Giovanni, Gioffre, Cesare, and Lucrezia. Rodrigo Borgia, ambitious and keen to climb the ranks of the Church, kept up appearances by presenting his children as his nieces and nephews. For a man with so many secrets, it was no surprise that he resorted to bribery to secure the highest office of all.

In 1492, he became Pope Alexander VI. The power at his fingertips was immense. From his new position, he legitimized the children he had had with Vannozza dei Cattanei. This was only the first step in what would become sheer nepotism.

At fifteen years old, Cesare Borgia was already a bishop. As soon as his father became pope, he made the eighteen-year-old Cesare a cardinal in 1496. Then came the murder. Cesare’s brother Giovanni was found dead, and the thirty golden ducats he had been carrying had not been taken, suggesting a personal motive.

This development changed Cesare’s destiny. He was now the eldest surviving sibling, and the family’s plans shifted. Before, Cesare had been groomed for advancement within the clergy. Now things were different.

In 1498, he made history as the first person ever to resign his position as a cardinal. Few knew it at the time, but it was done to make room for bigger things. Cesare had a powerful friend: King Louis XII of France. Not long after he quit his cardinalate, King Louis made him a duke.

He would now be known as the Duke of Valentinois. Cesare’s father, the pope, wanted him to marry someone with royal blood. He called in a favor with King Louis, who arranged a match with Charlotte d’Albret, the sister of the King of Navarre. In 1499, Cesare and Charlotte were wed.

Since the marriage was purely political, it was no surprise that things did not go well. Nor did it help that Cesare had a voracious appetite for infidelity. Marriage would not stop his habit of having affairs. During this period, it was common practice for a newly wed couple to publicly consummate their marriage.

Their first time together ended up being truly humiliating for Cesare. To help him complete the deed, he had asked an apothecary to provide him with something to ensure his flagpole was at full mast. Instead, whether intentionally or not, the apothecary gave him a laxative. The night went as well as one might imagine.

Nonetheless, Charlotte soon became pregnant. Things seemed to be going better when they went on their honeymoon, and he lavished her with gifts. But oddly enough, soon after, Cesare simply left his wife in France and never saw her again. It is possible that in his mind, his duty was done: they were married, and he had gotten her pregnant.

Charlotte would later give birth to a daughter named Louise in the year 1500, but Cesare was long gone and never cared to see them again. He had too many political ambitions and other motivations on his mind. Meanwhile, the French king desired land in Italy. Up until now, the Italian nobility and the papacy had resisted French advances.

But now he had a Borgia on his side, which was a great asset. When a French army invaded Milan, Cesare was there by its side. Additionally, Cesare began capturing small cities all over Italy. The people in these towns did not think much of the local vicars who had been ruling over them.

They were often ambivalent about being conquered by Borgia, and in some cases even welcomed Cesare with open arms. This fed Cesare’s ambitions, with the backing of his father the pope, and a French king running rampant all over Italy. Despite his cruelty and cunning, Cesare was nonetheless an incredibly intelligent and calculating leader. Not able to rely on Louis XII’s men all the time, Cesare and his father the pope devised a devious way to gain more land.

They would create positions of power for noblemen to occupy, and it was often the case that the positions had to be bought with gold. With the income generated, the pope would funnel the money to Cesare, who would hire condottieri, mercenaries, to do his bidding and conquer lands. The more power the Borgias created, the more enemies they made. They faced massive opposition from the Papal States, the territories of Italy where the pope had power.

There were entire campaigns against them, and some of the claims were very far out. Many even claimed that Cesare was the real puppet master behind his father the pope. They also claimed that lust and cruelty were the forces behind everything he did. We now think of Cesare Borgia as a ruthless, calculating, cold-blooded man, but in the first years of the sixteenth century, he was basically their version of a rock star: dashing, powerful, and brilliant.

He definitely had an effect on people. After he established himself as a general, he even wore mostly black, adding to the mystique. After he captured Romagna and returned to Rome, he received a hero’s greeting, basking in the fame. He even participated in a bullfight and took out seven bulls in a row.

In 1502, Cesare Borgia won an unexpected fan. We now know him as a writer, but at the time, Niccolò Machiavelli was acting as a diplomat. After observing how Cesare worked, Machiavelli recounted the violent methods that Cesare used to depose the ruling classes, particularly in Romagna, where he became duke. Machiavelli wrote about him with both reverence and fear.

When the Borgia siblings were young, amid his father’s political machinations, Cesare became very close with his sister Lucrezia and somewhat of a protector figure. This dynamic would have effects later on. In one case, when their father was trying to marry off Lucrezia to a man for political reasons, Cesare intervened by warning the man about it; he then fled. In another instance, a rumor abounded that Lucrezia had become involved with a man named Pedro, who had accidentally gotten her pregnant.

This was problematic, as for Lucrezia to be married, she had to be a virgin. Cesare came up with a plan to solve the situation. When the baby was born, the Borgias introduced it as Cesare’s own child from a liaison before his marriage. Darkly enough, Pedro’s body was soon discovered floating in the Tiber.

Many believed that Cesare had been behind this, and it would not be the first time he was accused of such transgressions. Another occasion involved Cesare, Lucrezia, and Lucrezia’s second husband. Her new husband, Alfonso of Aragon, had been married to her for two years. Things had been fine until he eventually came on the wrong side of Cesare’s political advances.

An assassination attempt occurred and failed. While Alfonso was recovering, a mercenary entered his chambers and finished the job. The mercenary just so happened to be an old friend and confidant of Cesare. These incidents and rumors greatly darkened Cesare’s reputation.

Before, he had been known for his bravery and intelligence. People now considered him cruel and ruthless. However, it is unlikely that he cared much. With his father advancing in age, he continued on the path of acquiring as much power and land as possible, for once his papal connection was gone, he would be on his own.

As Cesare continued on his trail of conquests, he left a trail of enemies in his wake. A number of his own men grew to fear him and began a plot against him. Cesare, ever cunning and smart, found out about the plan. He reached out to them and, lying, assured them he harbored no ill will.

Pacified, the men continued conquering. Once inside a newly captured town, Cesare’s own trusted forces encircled the plotters and had them all garroted. Few people trusted Cesare before this incident, but afterward, no one would. In 1503, during a sumptuous feast with the pope, Cesare, and one of their cardinals, all three of them fell ill shortly after.

Rumors of poisoning abounded. His father the pope would perish. When Cesare heard this, instead of responding in grief or shock, he immediately had his men sack the papal residence and take anything of value. With the pope gone, Cesare’s position was uncertain.

The new pope, however, supported him. This was good, until the new pope swiftly died. The pope following him ended up being one of Cesare’s worst enemies: Giuliano della Rovere, who would be named Pope Julius II. Pope Julius offered Cesare an olive branch and said he supported Cesare’s continuing rule in Romagna.

However, it was only a ruse. Within days, he betrayed Cesare, and Cesare was forced to flee Rome in a rage. Soon enough, he was captured and placed under arrest. The pope demanded that he give up many of his castles and possessions.

Cesare relented. As a result, he was allowed to travel to Ostia under supervision. Once again, Cesare attempted to flee and was promptly captured once more. This time, they decided that as punishment, he would be sent to his family’s homeland, Spain.

Once he arrived in Spain, instead of being welcomed as a returning hero, he would face an even harsher imprisonment. From his cell in a Spanish fortress, Cesare made his daring escape attempt. He fell, was badly injured, yet somehow managed to escape. He was free for the first time in nearly two years.

He now fled to one of the few allies he had left: his estranged wife’s brother, King John III of Navarre. King John desperately needed help defending Navarre. Cesare quickly dusted off his armor and recaptured some of the regions that John had lost back in battle. It was here that he would finally meet his end.

While laying siege to the town of Viana, he suddenly found himself alone and surrounded by enemy soldiers. Outnumbered, he could not fend them all off. They circled and stabbed him, killing him after many blows. Ironically, the men did not realize who they had just killed.

It was only later, when the armor they had stolen from his body was identified, that they found out just who it was: the famous Cesare Borgia. After a life of plotting, fighting, vicious power grabs, and betrayals, he was finally dead. King John would have a small mausoleum in Viana built for him. The inscription read: “Here lies in little earth he whom everyone feared.

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Even though Cesare was now dead, many of the enemies he had made while living were alive and angry. The Aragonese desecrated his grave and destroyed the church in Viana where he was buried. A local bishop demanded that his body be removed and buried on unconsecrated ground. His remains were removed and buried elsewhere.

In 1953, nearly 500 years later, the remains were finally interred in the Church of Santa Maria. At the height of his power, when his father was pope, Cesare Borgia was known to have very debauched parties at the Vatican, where guests were encouraged to participate in very depraved rituals. The Banquet of the Chestnuts was a regular event where chestnuts would be scattered on the ground and courtesans would gather them with their mouths. Strangely, Cesare would watch the festivities with his father and his sister Lucrezia.

From the time they were little and into adulthood, Cesare and his sister Lucrezia were very close. Many rumors surrounded their relationship. Many thought that it was Cesare who had had two of her former partners murdered. They also whispered that Cesare and Lucrezia were sleeping together.

Although there is no proven evidence of this, the rumors have persisted for centuries. Another dark allegation, one even worse than the idea that he was sleeping with his own sister, concerned his older brother Giovanni. Gioffre Borgia, their younger brother, was married to Sancha of Aragon. It was rumored that she was having an affair with not only Giovanni but Cesare as well.

Allegedly, Cesare had killed Giovanni in a jealous rage. Whether or not this is true, it is possible we will never know. To this day, Cesare Borgia remains a complex and polarizing figure. His ambition, ruthlessness, and cunning make him one of the most notable people of the Italian Renaissance.

His rise to power under the shadow of his father, the powerful Pope Alexander VI, and his relentless quest to consolidate authority in Italy illustrate his political shrewdness and moral ambiguity. Machiavelli’s depiction of him in *The Prince* immortalizes Cesare’s legacy as a ruler willing to do whatever it takes to achieve power.