Machiavelli meets ‘The Prince’

By Samantha Morris

“It is better to be feared than loved, if you cannot be both” ~ Niccolo Machiavelli

On 24th June 1502, the Florentine politician and diplomat Niccolo Machiavelli came face to face with Cesare Borgia. Borgia’s name had long been known to Machiavelli and indeed the Florentine people – he was the son of Pope Alexander VI and an exceptional military tactician, whilst stories of his macabre and evil doings (many of them brought on by nothing more than rumours whispered by his enemies) had been heard throughout Italy for years. By the time Cesare and Machiavelli came to meet, Cesare had encountered military success in the Romagna – but Florence was worried. If Borgia had taken the Romagna, then what was to stop him from taking over Florence? Florence, in their terror, sent to Louis XII for help – Louis had previously been allied with Borgia, but after Borgia had completely gone against Louis’ orders not to have anything to do with Florence, the French King took away his support. 6000 troops were promised by the French in an effort to protect Florence.


But before the troops could arrive one of Borgia’s top commanders rode for Arezzo, a small town that had risen in revolt. The moment he, that is to say, Vitellozzo Vitelli, arrived he was welcomed by the people, their revolt was quashed. Vitelli then travelled throughout the surrounding area, taking the towns easily. When news arrived in Florence that Piero de’ Medici was in Arezzo, the Florentine people became horribly aware that their days as a Medici free republic could very well be numbered. And with Borgia involved, the Florentine people were convinced that the end would come sooner rather than later. He then sent word to Florence – he wanted to meet a delegation to discuss incredibly important matters.

Florence chose two men to go and meet the Captain General of the Papal armies – Francesco Soderini, Bishop of Volterra, and Niccolo Machiavelli, a young man who had proven himself time and time again as Florentine’s most gifted political diplomat. The two men set out to meet Borgia in the agreed location, but when they reached Pontasieve they were told that Cesare Borgia had decided to go to the now unguarded Urbino, as Guidobaldo De Montefeltro had fled for his life upon learning of Cesare’s treachery and the way in which he had been deceived into disarming his own city – it was a clever tactic by Cesare, as the city was in a prime location for him to take Florence.

Borgia and Machiavelli, by
Federico Faruffini (1833–1869). The work won the gold medal at the 1867 Paris International Exhibition

The moment that Soderini and Machiavelli arrived in the city of Urbino, they were immediately taken to the ducal palace where they were to meet the infamous Cesare Borgia. It must be remembered that it was Borgia who had requested this meeting, and Florence had readily agreed. The government of the republic were eager to know what Cesare’s plans were for the city – would he end up laying siege? And they wanted to delay Cesare long enough for Louis XII’s promised troops to arrive so that they would be protected if Borgia decided to turn on Florence.

Borgia immediately launched into what can only be described as a rant towards Florence’s attitude towards him. The previous summer the republic had promised him safe passage throughout their lands so that he could carry on with his campaign across the Romagna, but they had later changed their minds – something which Borgia was far from happy about. And when Louis sent a letter to Cesare demanding that he not invade any Florentine territory, it made Cesare even less happy. His main ally, the French, had seemingly turned against him and sided with Florence. Machiavelli sent a long letter back to the Signoria, the Ten of War, in which he states Borgia’s exact words, words that showed his distrust of the Florentine government and that he wanted their acquiescence.

“I don’t like this government, and I cannot trust it. You must change it and offer guarantees of the observance of what you promise me…If you don’t want me as a friend, you will find out what it is like to have me as an enemy”.

It was a threat, and not a very thinly veiled one, that gave the Florentine government just four days to make their decision. And it was a threat that the Florentine’s didn’t take seriously. During those meetings, Machiavelli and Soderini discussed other things with Borgia.


One of these discussions ended up with an agreement made that Leonardo Da Vinci would come and work for Borgia. Once the meetings were finished, and aware of the time limit that Cesare had given, Machiavelli himself rode as fast as he could back to Florence so he could discuss with the Signoria what had happened.

Official letter written by Machiavelli in November 1502 from Imola to Florence.

Machiavelli was already aware that part of what was discussed, that Vitellozzo had acted on his own, was a bluff. But what he wasn’t aware of was how much of a bluff it was. Borgia knew precisely what he was playing at, knew that he could very easily bully Florence into working with him before Louis’ promised troops arrived. It was a clever ploy to have everything work in his favour, and the guile and psychological games that he played to get his own way impressed Machiavelli from the moment he first met him.

It would end up with Borgia being used as a model for Machiavelli’s “Il Principe” in which he described the best types of leaders. He had watched as Cesare had ruled his states in the Romagna with a heavy, yet fair hand. He watched as Cesare punished those who went against him, including having one of his men executed and his body parts left outside to rot. And he watched as the man tamed the Romagna into peace. Borgia’s methods, his charm, his intellect and his ‘no nonsense’ attitude certainly struck a chord with Machiavelli, so that even after Borgia’s death in 1507 Machiavelli would still respect the man who had made demands of him on that fateful night in Urbino.


Samantha Morris is the author of Cesare Borgia In A Nutshell. You can find her at The Borgia Bull. You can also follow her on Facebook or on Twitter @TheBorgiaBuIl

Further Reading:

Paul Oppenheimer, Machiavelli: A Life beyond Ideology

Paul Strathern, The Artist, the Philosopher, and the Warrior: Da Vinci, Machiavelli, and Borgia and the World They Shaped

Sarah Bradford, Cesare Borgia: His Life & Times

Niccolo Machiavelli, The Prince

This article was first published in The Medieval Magazine – a monthly digital magazine that tells the story of the Middle Ages. Learn how to subscribe by visiting their website.