A monster. A murderer. The Antichrist. People have called Cesare Borgia a lot of names over the years—but few know just how twisted his story really is. Cesare went from Renaissance heartthrob to public enemy #1 in just a few short years. His conniving and scandalous behavior paved the way for a legacy that would make anyone blush. And when his wild behavior finally caught up with him, he met a fate so disturbing, it’s impossible to forget.
1. His Father Wasn’t Supposed To Be One
Considering the circumstances of his birth, it’s no wonder that Cesare Borgia went on to life such a scandalous life—and we’re not just talking about his family name. Cesare was the son of the head of the Borgia family, Rodrigo…who was a man of the cloth. So, how does an unmarried Catholic cardinal become a great patriarch? Use your imagination…
2. He Was Illegitimate
Cesare’s mother was Rodrigo Borgia’s chief mistress, Vannozza dei Cattanei, who was very much married at the time. They had to keep things on the up and up, so people whispered that Rodrigo Borgia had been the one to arrange her marriage. He did so in order to divert attention from her pregnancy and their affair. It must have worked, because she and Rodrigo had four children in total: Giovanni, Cesare, Lucrezia, and Gioffre.
But despite being illegitimate, this quartet wasn’t exactly Daddy’s dirty little secret…
3. His Father Got A Big Boost
Rodrigo Borgia had been born in Spain, but now, he was climbing the ranks of the Catholic Church in Italy. As such, he pretended his four children were his nieces and nephews. At first. In 1492, he bribed his way into becoming pope. Forget kings and queens—in Italy, the pope called all the shots. As the new Pope Alexander VI, the man once known as Rodrigo Borgia had unimaginable power.
One of the first things he did was completely unheard of before that point. He acknowledged his four children from Vannozza dei Cattanei. It was incredibly controversial—but that wasn’t his only controversial move.
4. He Had No Choice In The Matter
While Alexander VI prepared his eldest child, Giovanni, to lead the papacy’s forces, he expected Cesare to work exclusively in the church. By 15, Cesare was a bishop. When Alexander VI became pope, he immediately used his power to make his 18-year-old son a cardinal. In fact, Alexander had barely been in office a year when he began to manipulate his position in order to grant high-paying appointments to his children.
He was transparently corrupt—and Cesare was profiting greatly from it. However, there was a dark surprise in store for the Borgias.
Wikipedia Portrait of a young Cesare Borgia, the Archbishop of Valencia
5. Their Family Faced A Tragedy
On the night of June 14, 1497, Cesare Borgia and his siblings were all gathered in their mother’s home for a lavish feast. The next morning, a disturbing omen arrived at the home of his brother Giovanni—and soon after, it became clear that something terrible had happened. Giovanni’s horse had returned home riderless that morning, with one of its stirrups cut.
Cesare and the family organized a search party, and soon after, they made a truly chilling discovery.
6. Someone Was After Them
The search party found Giovanni’s lifeless body in the Tiber river, along with that of one of his attendants. Immediately, the evidence pointed to something sinister. He’d been stabbed nine times, and his throat was slit. Giovanni, in his elegant clothing, would’ve been an easy target for a mugging—except that whoever had taken his life hadn’t touched the 30 golden ducats he’d been carrying at the time.
It all pointed to murder with very personal motives. It was a dangerous time to be a Borgia…
7. He Was First In Line
Giovanni’s murder left his family devastated, and Alexander VI called for an investigation into it. However, he called it off soon after. Rumors flew about the identity and motive of the killer, but Alexander had bigger things on his mind. Suddenly, Cesare was the eldest sibling—and his father’s most valuable pawn in the game of thrones that he’d been playing for years.
Cesare was about to step into his big brother’s shoes—but would they even fit?
Borgia, Atlantique Productions
8. He Turned His Back On Everything He’d Known
For his entire life, Alexander VI had raised Cesare Borgia to become a member of the clergy, first giving him an expensive education and then appointing him to cardinal at an extraordinarily young age. But Giovanni’s loss had changed everything—and behind the scenes, Cesare was plotting a move that would shock everyone.
In 1498, just before his 23rd birthday, Cesare became the first person in history to resign the cardinalate—and his motives would soon reveal themselves.
The Borgias, Showtime Networks
9. He Had A Powerful Friend
With his older brother Giovanni gone, the weight of the world had fallen on Cesare Borgia’s shoulders. The loss forced him to go where his father needed him most, which, at that point, was the armed guard. It didn’t hurt that Cesare had made an extremely powerful friend—no less a figure than the newly-crowned King of France, Louis XII.
The day after he quit his position as cardinal, Louis XII made him Duke of Valentinois. This little gift made Cesare deeply obliged to the ruler—and the king was about to call his debt in.
Wikimedia Commons Cesare Borgia, Duke of Valentinois
10. She Rejected Him
Forget love. All of the Borgia children married for political gain, and Cesare was no exception. By the time Cesare reached adulthood, every person in a position of power was jockeying for control of Naples—including the Borgias. Cesare made overtures to marry Charlotte, eldest daughter of the King of Naples, but she rejected him outright.
If she thought she was saving her kingdom, she was wrong. Within a few years, Cesare’s ally Louis XII would help oust her father. The rejection didn’t bother Cesare, either—he’d already set his sights on a new target.
Borgia, Atlantique Productions
11. They Forced Them Into It
Nobody in 15th century Europe did anything for free. There was always a "you scratch my back and I’ll scratch yours" mentality—and Pope Alexander VI had a lot of back to scratch. When Louis XII came to him for a favor, he asked for one right back. He wanted a princess with royal blood to marry Cesare. Well, Louis XII had many nobles in need to pick and choose from.
One of them was the King of Navarre—who had a very-single sister named Charlotte of Albret. The deal was made—Cesare would wed Charlotte, and everyone would be happy. Well, maybe not everyone…
Borgia, Atlantique Productions
12. He Didn’t Care For Her
In 1499, Cesare wed Charlotte, the sister of the King of Navarre—but few knew the dark secret he was hiding behind closed doors. Cesare was a prolific ladies’ man, and his appetites were voracious and unstoppable. He’d had affairs before Charlotte, and continued to have them after they’d tied the knot. Sure, the union was purely political, but he could’ve given her a shot, right? Well, maybe it was their rocky start that made him lose interest…
The Borgias, Showtime Networks
13. They Had A Rough Start
According to rumors, Cesare and Charlotte’s first time together was extremely humiliating. At the time, public consummation was a common practice. That’s right, they were supposed to ahem, perform for witnesses. This prospect was obviously intimidating, so Cesare asked the apothecary for some medication to help him ensure he’d be able to complete the act. His request led to a truly brutal mix-up…
Borgia, Atlantique Productions
14. They Humiliated Him
Maybe it was an honest mistake. Or maybe someone was mad about the way that an illegitimate son of the Spanish pope had marched into France and taken one of their princesses. Either way, the apothecary did not provide Cesare with the Renaissance-era version of that infamous little blue pill. No, the apothecary "accidentally" gave him a laxative. So, he had to consummate the marriage for witnesses in between trips to the bathroom. Yikes.
Regardless, Cesare wrote home to Pope Alexander VI that he’d been able to do the deed a total of eight times that day. Immigrants, they get the job done…or something like that.
The Borgias, Showtime Networks
15. He Ran Away
Unsurprisingly after that performance, Cesare got Charlotte pregnant. At first, it seemed like it might actually work. He lavished his new wife with gifts on their honeymoon. But in reality, their marriage was less of a fairy tale, and more of a horror story. After a short time with his new wife, Cesare fled the French territories where they’d been staying, never to return. That’s right, they never saw each other again.
He’d fulfilled his marital duties in this political union and was more than ready to continue his climb for power in other areas.
16. He Started Conquering
Louis XII wanted land in Italy, and for the most part, the nobility and papacy had resisted French advances. But now, he had a Borgia on his side. Cesare had become captain-general of the papal army, and he even accompanied the French king into Milan. With the French backing him up, Cesare began to capture small cities where local vicars had ruled without challenge for decades.
Considering his family’s reputation, their reactions were surprising.
17. He Had A Surprising Reception
People generally did not think much of the Borgias—but the people in these small Italian territories also didn’t think much of the local vicars who’d been ruling over them. They actually welcomed Cesare with open arms. This led to Cesare, with the backing of his father and of Louis XII, running rampant over Italy. But he wasn’t just blessed by circumstance—he was, by all accounts, an incredibly intelligent and calculating leader.
And eventually, he caught the eye of someone important.
Borgia, Atlantique Productions
18. He Had An Important Admirer
In 1502, Cesare Borgia won an unexpected fan. We know him as a writer, but at the time, Niccolo Machiavelli was acting as a diplomat. After observing how he 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.
Cesare had this effect on people, and used it to his advantage—but he was in constant danger of having it backfire on him. Eventually, it would.
19. They Took Bribes
So, how did Cesare Borgia capture so many areas in Italy, despite the fact that he couldn’t always rely on Louis XII’s men? Well, he and his father came up with a characteristically devious plot. Pope Alexander VI would create positions of power for noblemen to occupy and then, ahem, coincidentally, end up with all this money. Weird how that happens, right?
He would then funnel the money to Cesare, who would hire condottieri—AKA, mercenaries. You can pay a man to fight for you, but can you ever really trust him? It was a question that Cesare would have to answer the hard way.
The Borgias, Showtime Networks
20. He Made Many Enemies
Certainly, Pope Alexander VI and his son Cesare Borgia were not the first to use violent or calculating tactics in order to expand their base of power. Perhaps it was their undeniable aggression that rubbed people the wrong way. Either way, they faced massive opposition from the Papal States, the territories of Italy where the pope had power. There were entire campaigns against them—with some seriously wild propaganda
The Borgias, Showtime Networks
21. They Said He Was A Master Manipulator
The cardinals and vicars who orchestrated the propaganda against Pope Alexander VI and Cesare Borgia pulled no punches—and their allegations were absolutely scandalous. They said that Cesare was the real puppet master of the operation and that he was in complete control of his father. They also claimed that lust and cruelty were the two guiding forces behind everything he did.
In a sense, they were right on that count…
22. He Never Saw His Daughter
As you’ll remember, Cesare’s wife Charlotte had become pregnant before he returned to Italy. She gave birth to a healthy daughter named Louise in 1500. But to say Cesare Borgia was something of a deadbeat dad would be an understatement. Not only did he basically flee from his home with Charlotte almost immediately, he never came back to meet his daughter.
Sure, it was a political union, but he could’ve at least tried. Well, he was pretty preoccupied elsewhere at the time…
Borgia, Atlantique Productions Things don't always happen as depicted on TV...
23. He Was Prolific…Literally
In between corralling his band of mercenaries and conquering Italian towns for his father, Cesare was a busy guy. As mentioned earlier, he was an absolutely prolific ladies' man. And as we all know, the end of the Middle Ages in a Catholic state wasn’t exactly the place to find the latest advancements in birth control.
As a result of his many affairs, Cesare had at least (!) eleven illegitimate children. Like father, like son! And that wasn’t the only thing he got from his many affairs.
24. There Were Grim Consequences
Sure, Cesare had spent his teenage years as a cardinal in the Catholic Church—but much like his father, that didn’t stop him from having fun of the carnal variety. But before he even wed Charlotte of Albret, he’d paid a gruesome price for his indiscretions. Cesare contracted a raging case of syphilis. It left him with gruesome facial scars, which made him reticent to enter France and meet the French court ahead of his marriage.
While it eventually subsided, the reprieve was only temporary, and the infection would come back to haunt him later in life. But in the meantime, the incredibly vain Cesare suffered. Why was he so preoccupied with his looks? Well, I can’t exactly blame him for that one.
The Borgias, Showtime Networks
25. He Was A Celebrity
When people talk about Cesare Borgia now, they paint him as a calculating, cold-blooded killer. But in the first years of the 16th century, he was basically their version of a rock star. He was good-looking, powerful, and brilliant—and he acted the part. After he’d established himself as a general, he wore mostly black, adding to the mystique. Then, there was the summer he returned to Rome after capturing Romagna for himself.
Borgia, Atlantique Productions
26. He Amazed Everyone
When Cesare, the new Duke of Romagna, visited Rome, he received a hero’s greeting. He knew how to work a crowd, and he gave them what they wanted with a series of impressive feats. In one instance, he participated in a bullfight and took out seven of them in a row. People went wild for him. It was definitely a golden era for Cesare—but good things rarely last forever.
Borgia, Atlantique Productions
27. He Tried To Help Her
When the Borgia siblings were young, there was no doubt that their father used them as pawns, perhaps none more severely than Lucrezia. Cesare played a vital role in his sister’s life. When her father decided to discard her first husband and marry her to someone more advantageous, Cesare was the one to tell her about the plan.
As a result, Lucrezia warned the man, who fled. But as the years went on and Cesare became the enforcer of the family, he gained a dark reputation that forever tarnished the name he’d built.
The Borgias, Showtime Networks Holliday Grainger as Lucrezia Borgia in the TV series The Borgias
28. He Was The Family’s Problem Solver
The Borgias had Lucrezia’s first marriage annulled, and planned a more politically motivated union—but in the meantime, she got into some trouble. Rumors abounded that a dalliance with a man named Perotto had resulted in an unplanned pregnancy. A guarantee of Lucrezia’s virginity was necessary for any future attempt at marriage, so this was a problem. Enter Cesare.
29. He Pretended For Her
Cesare was instrumental in the plan to cover up his sister’s indiscretion—and his methods went from scandalous to utterly chilling. When the baby was born, the Borgias introduced it as Cesare’s child from a liaison before his marriage. Then, curiously, he was passed off as Pope Alexander VI’s son. But this scandal was nothing compared to what happened to Lucrezia’s lover. Around the time she gave birth, his body was found floating in the Tiber.
Many believe that Cesare had been the one behind it all—and it wouldn’t be the last time that people accused him of such devious transgressions.
The Borgias, Showtime Networks
30. No One Escaped His Grasp
Fool me once, shame on you. Fool me twice, shame on me. Any man who crossed Lucrezia’s path should’ve known to tiptoe around her older brother Cesare. Unfortunately, her second husband wasn’t that smart. He made it through two years of marriage, but when he wound up on the wrong side of Cesare’s political advances, an assassination attempt occurred.
It failed, but as he was recovering, a mercenary entered his quarters and finished the job. That mercenary happened to be Michelotto Corella—Cesare’s oldest friend and closest confidante. Weird coincidence, huh?
31. He Made A Plan
After these incidents, Cesare’s good name was in the tank. Where he’d once been known for bravery and intelligence, people now considered him a cruel, ruthless monster. It didn’t matter to him anymore, as he had one goal: essentially, "Caesar or bust," referring to the Roman title for emperors. With his father advancing in age, Cesare Borgia had to acquire as many of the Italian states for himself as possible.
He knew that once he no longer had that sweet papal connection, he’d be on his own. And with his reputation already in the trash, he had zero qualms about getting what he wanted by any means possible.
Borgia, Atlantique Productions
32. He Went Too Far
As Cesare burned through Europe, taking what he wanted and leaving a trail of enemies in his wake, his cruel streak got out of control—and it wound up coming back to bite him. A number of his men grew to fear him, and some of them began to plot against him. However, you can’t get much past Cesare Borgia. He reached out to them and assured he had no ill will toward them.
Pacified, they accepted his orders to take the town of Senigallia. They should’ve known better.
The Borgias, Showtime Networks
33. He Got His Vengeance
Cesare had the mercenaries who’d briefly turned against him right where he wanted them. His revenge was swift and brutal. He came to Senigallia to take the citadel they’d conquered for him and greeted them with a smile. His forces slowly filled in, cutting the traitors off from their own men. At that moment, he moved. He imprisoned them for a few hours before fashioning a device to take out two of the ringleaders by strangulation.
The others had to wait—but within a month, he had them garroted as well. Surprisingly, people lauded him for the plot. But that praise didn’t last for long…
34. He Suffered A Hit
Very few people trusted Cesare Borgia before this incident—but afterward, no one did. And soon after, everything in the Borgias’ lives began to fall apart. One of their cardinals, Adriano Castellesi, was hosting Pope Alexander VI and Cesare in the summer of 1503 when tragedy struck. After a sumptuous feast, all three fell ill, but it didn’t appear to be a typical case of food poisoning.
The illness came on quickly and viciously—and it would portend the ruin of the House of Borgia.
The Borgias, Showtime Networks
35. They Never Saw Each Other Again
Pope Alexander VI spent five excruciating days suffering from a horrible fever, but one person was notably absent from his bedside. Cesare never visited his father after they both fell ill, but it wasn’t out of any ill will. He was also incredibly sick—and the treatment that doctors gave him was truly gruesome. It was so bad that they dunked him in a giant bath of ice-cold water, which immediately caused his skin to peel from his body as a result of the shock.
Cesare was at death’s door—and only one Borgia was going to make it out of the dramatic illness alive.
The Borgias, Showtime Networks
36. He Was Scrambling
As Cesare began to recover, he saw the writing on the wall. He sent his commander and friend Michelotto Corella to watch over his father—but protection wasn’t his only motive. When Pope Alexander VI succumbed to his illness on August 18, 1503. Cesare, still incredibly ill, had Corella and his men quickly move in to sack the pope’s home and take whatever they could that appeared to be of value.
There were rumors that Cesare had been the one to poison his father, but he was still so ill that it was all somewhat hard to believe. Cesare also had much bigger things to worry about.
Borgia, Atlantique Productions
37. He Thought He Could Get His Way
Cesare had depended heavily on the pope’s backing, and now he had no idea who would replace his father. Luckily, the new pope allowed him to keep his position. Cesare had a brief reprieve after his horrible illness and the loss of his father—but it wouldn’t last for long. That pope passed suddenly, and the candidate for his replacement was one of Cesare’s worst enemies, Giuliano Della Rovere.
Well, Della Rovere had a surprise in store for Cesare.
38. They Betrayed Him
The prospective pope offered Cesare Borgia an olive branch, promising him that he’d support Cesare’s continued rule in Romagna. Immediately after becoming Pope Julius II, he broke that promise. Within days, Cesare realized he’d been betrayed—and his reaction was chilling. He could’ve stayed behind and negotiated with the new pope, but instead, he fled Rome in a rage.
It was a dire mistake.
39. It Was His Last Straw
Pope Julius II called for Cesare’s arrest. Soon enough, he was back in Rome, imprisoned in his former home. Next, Julius had Michelotto Corella detained as well. This devastated Cesare. Pope Julius demanded that Cesare give up his castles and goods. Even though Cesare had backing from the Spanish cardinals, he relented. As a result, he was allowed to travel to Ostia—little did Julius know, this was just part of the plan.
40. He Nearly Got Away
Cesare turned on the charm with his captor, who went against the pope’s orders and set his prisoner free. He even made the plans for a ship to take Cesare to Naples. However, Cesare’s luck was extremely short-lived. Pope Julius’s men caught him again, and this time, they sent him to his family’s homeland of Spain. Instead of being retreated as a returning hero, he faced an even harsher imprisonment.
Borgia, Atlantique Productions
41. He Was An Escape Artist
Multiple stories claim that Cesare tried to escape from his cell in the fortress in Spain—and at least one of them is true. In 1505, he and a servant tried to climb a rope down the side of the tower he was in—but then, disaster struck. While he was coming down, guards cut the rope from above. His men carried his badly injured and unconscious body from the scene.
Despite the hiccups, the escape worked, and Cesare was free for the first time in nearly two years.
42. He Got Back In The Action
Cesare had few allies left, but there was one man he could count on for sure: his estranged wife’s brother, King John III of Navarre. And King John desperately needed help defending Navarre. To say Cesare was up for the job would be an understatement. He quickly dusted off his armor and recaptured some of the areas that John had lost.
The enthusiasm is admirable, right? Well, unfortunately, it would spell his doom.
43. He Was Relentless
Cesare Borgia’s final stand was laying siege to the town of Viana—and he nearly decimated the place. Being in battle was the state in which he’d been at his peak in life, and his eagerness got away from him. Cesare Borgia was chasing away enemy forces as they fled with such frenzy that he barely noticed he’d completely outpaced his men.
Suddenly, he was alone—and completely surrounded by enemy forces.
Borgia, Atlantique Productions
44. He Made A Fatal Mistake
Cesare Borgia was under attack, and as he raised his arm to protect himself, one of the men he faced was able to stab him near his armpit, where the armor didn’t cover him. He kept fighting, but the men circled him and stabbed him. No one realized that it was the once-fearsome Cesare Borgia. It was only after the men who’d taken his life returned to Viana with his armor that one of his squires identified him.
They’d left his lifeless body in the field where they’d surrounded him.
45. He Was Larger Than Life
Cesare Borgia, after a life of scheming, fighting, and vicious power grabs, was dead. He was only 31—but his twisted story didn’t end there. Historians and scholars have grappled with Cesare’s legacy and the scandalous rumors that followed him beyond the grave for centuries. But first, there was the drama of his burial to deal with…
46. His Grave Told His Story
Cesare’s brother-in-law King John had a small mausoleum built in Viana for him—and the inscription is unforgettable. It began with the words "Here lies in a little earth, he whom everyone feared". Oh, how the mighty fall. But Cesare’s eternal rest wasn’t exactly, ahem, eternal. His reputation caught up with him in more ways than one.
47. They Desecrated His Grave
The enemies of the Borgia family hadn’t forgotten their transgressions—and even in death, they served Cesare one final indignity. Not only did the Aragonese destroy the church in Viana, but a local bishop demanded that his body be removed and buried on unconsecrated ground. Despite the fact that he’d been a cardinal as a teen and his father had been the pope, he wasn’t good enough for the church.
But hey, maybe the church had good reason to react so harshly.
48. He Was The Life Of The Party
At the height of his power, when his father was pope, Cesare Borgia was known to have debauched parties at the Vatican, where guests were encouraged to participate in utterly 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.
Add in a handful of male courtiers, offer them prizes for best performance, yadda yadda yadda, you’ve got the Banquet of the Chestnuts. Even more deranged? Cesare would watch the festivities with his father and his sister Lucrezia. Weird? You bet—but it gets even weirder.
49. They Were Maybe Too Close
Cesare was incredibly close with his sister Lucrezia. After all, many said that he’d taken out not one, but two of her paramours. But was there more to their relationship than that? After Lucrezia’s family forced an annulment out of her first husband, he accused her of having a relationship with his father—but that wasn’t the only disturbing allegation.
Many whispered that Cesare and Lucrezia were also sleeping together. There’s little historical evidence to prove this, but the rumors nevertheless have followed them for centuries. In the end, whether or not it’s true, Cesare paid a dire price for his debauched behavior later in life.
50. He Suffered The Consequences
Later in his life, Cesare Borgia took to occasionally wearing a mask to cover his face—and there was a gruesome reason for his unusual choice of accessories. As mentioned earlier, Cesare Borgia contracted syphilis before his marriage. It wrecked his body, and then went into remission—at least at first. It came back with a vengeance and damaged Cesare’s once-esteemed good looks.
Many also suspected that the infection had also ravaged his mind, and caused his reckless behavior toward the end.
51. One Story About Him Was Exceptionally Disturbing
You know you’re one of history’s most legendary bad boys when the most jaw-dropping rumor about you isn’t even the one about a relationship with your sister. There’s one story that followed Cesare Borgia through most of his life, and it’s absolutely twisted, so buckle up. Remember when Cesare’s older brother Giovanni was slain back in 1497?
Pope Alexander VI had ordered an investigation, only to call it off, right? Well, the reasons behind the abrupt stop were truly chilling.
Borgia, Atlantique Productions
52. He May Have Taken Out His Own Brother
Many people believed that their younger brother Gioffre had been the one to take Giovanni’s life. How come? Well, it was alleged that Giovanni had been having an affair with Gioffre’s wife, Sancha of Aragon—but that’s not all. Many claimed that Cesare was also sleeping with Sancha and had slain his eldest brother in a jealous rage.
There was never a conclusive answer to the mystery, but the majority of the blame seemed to get put on Cesare. It’s no wonder that the church wanted nothing to do with him…
53. He Found His Way Back
After a bishop had Cesare’s remains removed from the consecrated grounds of the church, they ended up underneath the ground in front of the church. However, that wasn’t the end of the saga. In 2007, the Bishop of Pamplona allowed his remains to be reburied in consecrated ground. They were interred in the church of Santa Maria—on the day before the 500th anniversary of his passing.
His reputation may never be rehabilitated, but at least he finally ended up in his rightful place.
Sources: 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17
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