Cesare Borgia’s Spanish Imprisonment

The castle of Chinchilla, Spain

Towards the end of 1503, after the death of his father and a particularly virulent illness, Cesare Borgia found himself faced with the election of one of his family’s worst enemies as Pope. Giuliano della Roverre was elected to the chair of St Peter’s in the October of 1503 and took the name of Pope Julius II. And Cesare had a decision to make – was he to support the new Pope, or would he continue with the enmity? Indeed, Borgia made a last minute decision during the conclave of 1503 to support della Roverre’s election as Pope which he has received criticism for by many both at the time but there really wasn’t much he could have done; the majority of the cardinal’s in the conclave supported della Roverre and even had Borgia tried to block his election, it would have had little to no effect at all. Cesare tried to make a sensible move, extract promises out of the man who would be Pope before his election to ensure his safety and to keep hold of his lands and titles, knowing that della Roverre was a man who kept to his word.

It was probably the biggest mistake that Cesare Borgia ever made.

In the early months of his reign as Pope, Julius made an outward show of cordiality towards Cesare which the young Duke Valentino took at face value, needing to believe that every word Julius spoke was sincere. And to start with it seemed as if Cesare had made the right decision as two days after his election, Julius wrote to the people of Faenza asking them to obey Cesare as their leader. Cesare believed that the Pope was desperate to recover the states of the Romagna, to bring them back into the Papal fold after all hell had broken lose during Cesare’s illness – and more importantly Cesare still held several key fortresses in the Romagna, which he knew would be incredibly important to the Pope. Borgia believed that this would keep him safe, and in the Pope’s good books. Moreover, the people who lived in the towns where Cesare still held onto his fortress were still loyal to him. He began to make plans to leave for the Romagna as soon as Julius has reinvested him as Gonfalonier of the Papal armies. Julius, however, held back – he knew Cesare could easily cause a lot of trouble for him despite the fact he was considered as one of the greatest soldiers of the time. And by the second week of November 1503, Cesare began to notice that Julius’ attitude towards him was hardening.

On the 11th November, in an interview with Giustinian, it became all too clear exactly how Julius felt towards Cesare Borgia and the Romagna:

“We do not wish that he [Cesare] should persuade himself that we will favour him, nor that he shall have even one rampart in the Romagna, and although we have promised him something, we intend that our promise should extend only to the security of his life and of the money, and goods which he has stolen”.

As the political sands began to shift and fall away beneath his feet, the situation began to take its toll on his mental state – something which had never been all that stable to begin with. During a meeting with Cesare in the first week of November, Niccolo Machiavelli found a completely different man to the man he had known in the Romagna. Cesare Borgia was now uncertain of himself, no longer self controlled or masterful and would burst into fits of bitter, hysterical anger. According to Machiavelli, he burst out on a tirade against Florence, blaming the Florentines for not supporting him and said that Florence would be ruined and he would laugh at the city when it fell – Machiavelli recorded that, “He went on at length with words full of poison and anger”.

On 9th November, Julius confirmed to Cesare that he would be re-investing him as Gonfalonier yet despite promising Cesare that he would bring it up in the consistory, he didn’t say a word. Hiding his disappointment, Cesare began getting his troops together to leave for the Romagna. He had his troops and began trying to sort out safe conduct for him and his army. He needed safe conduct through Florence, but Florence were seriously terrified of the famous Valentino and had vowed never to let him into Tuscan territory ever again following his previous behaviour. They refused him safe conduct, and he received the news on the 14th and finally began to realise that Florence and Julius were working against him. The bubble of hope he had built up around himself was now completely shattered, and he fell into one of his famous depressions and it is likely that he had a serious breakdown – men who saw him during that period noticed the change in him. His own friend, the Cardinal of Elna told an envoy, “he believed the Duke to be out of his mind: not knowing what he wanted to do, he was confused and irresolute”. It is said to that at this point, when Machiavelli heard about it, he wondered whether he had been wrong about Cesare Borgia all along, and asked whether the image of the strong Duke Valentino had been nothing more than a mirage and that he could not decide, “whether he was so by nature or whether these blows from Fortune have stunned him, and since he in unaccustomed to receive them, his mind is confused”. Indeed his behaviour in another interview with Machiavelli only proved his fragile state of mind. Cesare raged against Machiavelli, threatening Florence with employing all the friends he had left to do the city harm.

The once confident Duke was now on a road that he saw no other way of getting out of, blundering his way down it because he could see no other way out. He needed to get to the Romagna, and had already sent his cavalry ahead through Tuscan territory despite not having safe conduct. Without self conduct, the way through Tuscany was blocked to him and that route was the only feasible way to get there across land and he certainly couldn’t go through Urbino. The best idea would have been to stop planning altogether, but he didn’t. He hadn’t given up his will to fight and couldn’t bear to think of letting go of his lands in the Romagna. And so, he made the decision to make the trip by sea, and thus headed to Ostia.

Yet as he was there waiting to take his boat, news reached Rome that made Julius realise the Romagnol lands needed to be placed into the hands of the church. Faenza had fallen to the Venetians, and the Pope needed those lands in his control. On 21st, a message was sent to Cesare ordering him not to leave and on 22nd Cardinal’s Soderini and Remolines arrived in Ostia, demanding that Cesare give up his fortresses. Cesare, of course, refused – it threw Julius into one of his famous rages and he sent a message demanding Cesare’s arrest.

By 29th November, Cesare was back in Rome under heavy guard. He was lodged in the apartments that had once been his own (now the famous Raphael rooms) and it was to be the start of a long game of cat and mouse in which Julius would demand Cesare’s fortresses and Cesare would refuse. On 1st December, Cesare received news that his executioner Micheletto had been arrested and the news broke Cesare, destroying his hopes and his will to resist anything else – he even turned to Guidobaldo de Montefeltro, one of his long term enemies in his desperation to find a friend. In a meeting between the two, Cesare fell to his knees before Montefeltro, cursing his father for making him take the duchy of Urbino and Montefeltro raised Cesare to his feet embracing him kindly. Cesare promised to return the goods stolen from Urbino and also handed over the passwords to some of his castles in the Romagna. In return, Cesare got promises from the Pope of his liberty. This never happened. Instead he was kept to his apartments, and his enemies swarmed around him, demanding reparations for all the damages he had done to them.

On 20th December, after Julius flew into another of his rages, Borgia was locked in the famous Torre Borgia. This must have been a bit of a blow to Cesare as the very rooms he was locked in were the ones in which he had ordered Alfonso D’Aragona to be strangled. Cesare was thrown into the Torre due to Diego Ramires refusing to hand over the castle of Cesena. Ramires sent a message to the Pope, saying that as long as Cesare was imprisoned, they would never hand the castle over to his enemies. Despite being thrown into the Torre, Cesare had regained his mental composure and he kept his courage in the face of his imprisonment. His courage impressed those who guarded him, and they reported that he remained cheerful as he watched his friends and servants spending their days gambling. His composure was impressive and it showed his determination not to give up in the face of adversity; a strength of character he would show in the years of his imprisonment. This strength of character inspired devotion and loyalty in the men who were close to him, not only in his imprisonment but also when he was a free man. Despite how dangerous he was, despite how much he was hated and feared; those close to him never deserted him. He even had loyalty that stayed from his friends the Spanish cardinals, who stood by him during the papal election. Two days after he was imprisoned in the Torre Borgia, the cardinals went to the Pope to petition for Cesare’s release, pointing out that if Cesare were free the keepers of the castles in the Romagna may be more inclined to hand them over. The pope of course refused.

By 18th January the Spanish cardinals came to an agreement with the Pope. In exchange for Cesare’s freedom, his castles in the Romagna would be given over to the Pope within 40 days. Within the next few weeks, due to Julius not wanting Cesare free but wanting the castles and Cesare’s desperation to be free, the arrangements changed somewhat. On 10th March 1504 Cesare agreed to surrender the castles of Cesena and Bertinoro as well as paying the castellan of Forli 15000 ducats to give up the Rocca di Ravaldino. Yet Cesare did not intend to give up Forli quite yet as it contained incredibly valuable goods that he didn’t trust the Pope would give back to him. And as news reached Ostia of the surrender of Cesena and Bertinoro (before Rome, as it was intended it would), Cesare’s custodian Carvajal had arranged ships and safe conduct from Gonsalvo de Cordova to carry Cesare to Naples; and Carvajal released Cesare from the Torre Borgia before permission from the Pope had been formally given.

Despite the Spanish ships being detained at Naples, Cesare wasn’t prepared to wait. He wanted out. On 19th April 1504 he rode from Ostia to Nettuno where he got on a small rowing boat and he rowed until he reached a point 30 miles from Naples. There, he got out of the boat and rode the rest of the way on horseback. On the 28th, he arrived in Naples and stayed at the house of Cardinal Ludovico Borgia. Despite another flare up of his syphilis, Cesare was finally free and began making plans. He sent letters asking for men, recruited men and cavalry and on 26th May Cesare went to the Castel Nuovo in Naples to take his leave from Gonsalvo de Cordova. That night, as he made ready to leave, one of Cordova’s men announced that he was under arrest.

In surprise and disbelief he cried out, “Santa Maria! I am betrayed! With me only has my Lord Gonsalvo dealt cruelly!”

Cesare, being arrested at the Castel Nuovo in Los Borgia

Cesare, imprisoned in Spain, in Los Borgia

Cesare had been deceived. And deceived by the man he had likely least expected to deceive him. He had trusted de Cordova, and been incredibly naive in doing so. Cordova was known as a man of honour and Cesare had set great store in that. De Cordova however was working for the Spanish Queen Isabella – the Spanish monarchs needed a dispensation from the Pope so their daughter could marry the future King Henry VIII of England and also wanted their investiture as monarchs of Naples. Cesare Borgia, a man whom the Pope feared above all others, would therefore be incredibly useful to them. If they had him in their grasp, a mere threat to put Borgia into play would bring the Pope to heel. It would also keep him out of French hands. And so, Cesare found himself once more behind bars and placed in a small cell known as “The Oven” – while at the same time in Rome, Micheletto underwent torture where he was questioned on the deaths of Alfonso D’Aragona and Juan Borgia. Yet Micheletto gave nothing away and implicated the now dead Pope Alexander, thus shielding his master. Yet all the while through June, as he was held in “The Oven”, he still refused to give up Forli until he finally relented on 11th August. He had been promised liberty in return for giving up Forli, but he did not get it. Within a few days he was placed on a ship bound for Spain, in the charge of Prospero Colonna and with only a pageboy for company.

By the end of September 1504, Cesare Borgia found himself imprisoned in the Castle of Chinchilla, 700 feet up in the mountains of Valencia. As can be seen from the picture at the start of this post, the castle is surrounded by a sheer drop. It was incredibly doubtful that Borgia would be able to escape from there. Here he was placed in incredibly strict confinement with just his page for company. It was whispered while he was there that Ferdinand and Isabella were planing to put him on trial for his life, to answer for the murders of his brother Juan and his brother in law Alfonso D’Aragona. But why would he be put on trial for the murder of his brother when his guilt had never been proven? The answer was simple – his sister in law, Maria Enriques de Luna was a favourite at the Spanish court and believed in Cesare’s guilt. In short, Cesare was completely alone – he couldn’t even get help from France. The King of France, angry at Cesare for his betrayal in his last  military campaign, stripped Cesare of his titles. No longer was he the Duke of Valentinois nor the Lord of Issoudon. And due to the fact the French had signed a peace treaty with Spain over Naples, he couldn’t hope to play them off against each other with that. Cesare Borgia was no longer useful. Yet his friends at home had not forgotten him – his sister Lucrezia and his brother in law Jean D’Albret bombarded the Spanish sovereigns to beg for his release. Whilst they were not successful in getting him his freedom, they did succeed in gaining him a little more comfort – he was allowed extra servants and a slightly better set of rooms. Reports reached Italy that Cesare was only being held for the things De Cordova had accused him of (the murders), and when these were proven to be untrue he would be released. But things would have to wait until Queen Isabella regained her health.

News reached Italy in Early 1505 that Cesare had attempted to escape, and the stories are rather colourful! He was now under even stricter confinement due to his attempted escape, and the story goes that he invited the governor of the castle to join him on the ramparts outside his room. Whilst the governor was pointing out landmarks, Cesare attacked him and tried holding his arms and threatened to throw him off the tower. Due to his long imprisonment, Cesare’s strength failed and he was pinned to the ground. Other stories involve tales of Cesare knotting sheets together and climbing out of the window. Alas the sheets were too short, and he fell to the ground, fracturing his shoulder! Once he was found, he was carried back inside where he placed under even stricture surveillance.

La Mota, Medina Del Campo – Spain
La Mota, showing the Torre in which Cesare was imprisoned and escaped from.
In midsummer, 1505, Cesare was moved to the famous castle of La Mota in Medina del Campo and imprisoned in the main keep of Torre de Homenaje. This famous keep was basically a maximum security prison and it was thought that no one could ever escape its walls. They would eventually be proven wrong. While he was there, according to a Venetian report, he spent his time watching the falcons out of his window. Queen Isabella had died not long before – was he thinking of a way he could turn it all to his advantage? It is incredibly likely and indeed, it wasn’t long before he started playing the game of politics again. He became involved in the struggle between King Ferdinand and his son is law; and was far from a helpless pawn and he watched, biding his time and choosing his side. Indeed, knowing that he could easily be handed back over to the Pope, he stayed in close contact with Ferdinand’s party and played an active part in an intrigue between the Holy Roman Emperor, Maximilian, and his brother in law Jean D’Albret, King of Navarre. Cesare Borgia was playing the game of politics, choosing his side carefully and plotting how he would gain his freedom. His aim was simple: Get himself handed over to the King of Navarre, to his brother in law. And he knew if his plan was to succeed then he must put it into immediate action.
Cesare knew that a man by the name of Bernadino de Cardenas was desperate to integrate himself with Ferdinand, and had intimated to the envoy Ferrer that he was now willing to hand over Cesare. Ferrer had agreed in principle but said he must write to Ferdinand and find out what the King wishes to do with his prisoner. Cesare knew this was his best chance of freedom, and that his future with Maximilian and Jean were his last change for power and the destiny he so desperately believed was his. Yet if he waited until Ferdinand’s orders reached La Mota, his chance could be lost forever.
So he planned the impossible.
He would escape from La Mota.
The plan was to follow the same lines as his abortive escape attempt from Chinchilla but much more carefully prepared. Cesare had even managed to talk around one of the servants into getting hold of the ropes for him. And on the evening of the 25th October 1505, at the appointed hours, three men (including the chaplain who Cesare had befriended) waited for Cesare beneath the keep of La Mota. A rope was let down from the narrow window of the room where he was lodged at the top of the tower. One of his servants went first but the rope was too short and he fell, injuring himself badly. Cesare followed shortly after but the alarm had been sounded and the rope was cut from above. He fell, landing heavily from a great height and he was unable to stand. He had to be carried by the waiting men and lifted into the saddle of the waiting horse. There was no time to rescue the servant who had previously fallen and was badly injured, and so they left the poor man there – he was found shortly after by the guards who executed him there on the spot.
Cesare was unconscious from his fall and completely unable to support himself. Somehow his men kept him on the horse and carried him to the safety of Villanon. They stayed there for a month while Cesare recovered, and set out for Navarre at the end of November.
Cesare Borgia spent the majority of 1503-1505 as a prisoner, locked away while people decided his fate. But yet again he took fate into his own hands, playing the game of politics with the most powerful monarchs of his day, and winning; and achieving the impossible with his escape from La Mota. And as he headed into Navarre at the end of 1505, he was to begin the last stage of his life which he spent free, working as a soldier with his brother in law. He always said that he would prefer to die in the saddle than in bed, and he did so – dying alone on the 12th March, 1507 just three days before the Ides of March which had been so fatal to his namesake and idol, Caesar.
Aut Caesar, Aut Nihil – Either Caesar Or Nothing – a motto which spoke of everything that Cesare Borgia lived, worked and died for.
Further Reading

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