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Machiavelli, Leonardo & Borgia: A Fateful Collusion

What happened when a philosopher, an artist and a ruthless warrior – all giants of the Renaissance – met on campaign in northern Italy? Paul Strathern explains. – From History Today March 2009 | Volume: 59 Issue: 3 | Page 15-19


During the latter half of 1502, when the Italian Renaissance was at its height, three of its most distinguished yet disparate figures travelled together through the remote hilly region of the Romagna in north-eastern Italy. Cesare Borgia (1475-1507), backed by his father Pope Alexander VI (1431-1503), was leading a military campaign whose aim was to carve out his own personal princedom. He had hired Leonardo da Vinci (1452-1519) as his chief military engineer whose brief was to reinforce the castles and defences in the region as well as to construct a number of revolutionary new military machines, which he had designed in his notebooks. Accompanying this unlikely duo was the enigmatic figure of Niccolò Machiavelli (1469-1527), who had been despatched by the Florentine authorities as an emissary to the travelling ‘court’ with instructions to ingratiate himself with Borgia and, as far as possible, discover his intentions towards Florence whose position to the west, just across the Apennine mountains, left it particularly vulnerable to Borgia’s territorial ambitions.

In a characteristically Machiavellian situation Borgia knew perfectly well what Machiavelli was up to and Machiavelli knew that he knew this. Machiavelli had been instructed to send regular diplomatic despatches back to Florence, reporting on all he had discovered. Machiavelli well understood that Borgia was intercepting these despatches and reading them himself, discarding those he felt should not be sent. As a result, Machiavelli would often resort to alluding in the most oblique form to what was actually taking place. Borgia, a man whose considerable intellect matched his reputation for treachery and violence, was not fooled by this. He knew that the Florentine authorities would certainly have established a simple code with Machiavelli before he had set out. Remarks about the mountains, the local people, the weather and even the state of Machiavelli’s accommodation might all refer to vital intelligence.

Machiavelli’s information came from a number of unlikely sources. Sometimes it even came directly from Borgia himself, but could he believe what Borgia told him? Machiavelli had to be guarded about any other sources of information, which usually came from careless remarks let drop by secretaries or high-ranking officers among Borgia’s entourage whom Machiavelli had befriended. Though everyone knew Machiavelli was a spy, there was something wittily subversive in his character which seemed to appeal to them. This also appealed to Borgia himself: here was a man of some learning, whose intellect matched his own, who genuinely appeared more interested in discussing philosophical ideas than in performing the task of a mere envoy.

Such a man was rare company among the rough and ready mercenary commanders with whom Borgia was surrounded. And, unlike his commanders, in a curious way he knew that he could trust Machiavelli, man to man: up to a point, that is. Many of Borgia’s most daring and sensational plans relied upon the notion of secrecy and betrayal, elements which he was not even willing to pass on to his military commanders until the last moment, when there was no chance of such secrecy being compromised.

For obvious reasons, Machiavelli frequently made misleading remarks about the sources of his information in order to protect their identity. However, one particular source – referred to only as a ‘friend’ – was a combination of various informants, who observed intelligence and bits of gossip picked up here and there. Or so Machiavelli would have had us believe. It has now become clear that most of the information from this ‘friend’ did in fact come directly from one source and that this vital informant was none other than Machiavelli’s friend and fellow Florentine Leonardo da Vinci.

Borgia’s reasons for hiring Leonardo da Vinci were obvious. Besides being known as a great artist, he had already established himself as the most ingenious and talented military engineer in Italy. Yet why on earth should an artist of such refined sensibilities as Leonardo simply abandon painting to face the rigours as well as the dangers of campaign life with a man as notorious as Borgia. The evidence suggests that Leonardo was going through something of a crisis at this time. He had grown tired of painting – so much so that he had already become notorious for leaving canvases and frescoes unfinished because he had ‘solved’ their difficulties and they thus no longer interested him. He wished to have time to pursue his inventive and ingenious scientific pursuits, which he secretly jotted down in his coded notebooks, and perhaps felt that the freedom given to him by Borgia would let him do this.

Borgia’s instructions allowed Leonardo to roam the Romagna almost at will, coming up with ideas for new defences and infrastructure as he saw fit. Another quirk of Leonardo’s character was that he seemed to be attracted to, and do his best work for, men of powerful and unpredictable temperament who nonetheless allowed him freedom to develop his own ideas in between his undemanding public duties. Many of Leonardo’s most accomplished and ingenious creations literally disappeared into the air – intricate ice sculptures, technically sophisticated machines which would explode into fireworks, sensational dramatic stage devices which would be discarded after the night’s performance.

In his time, Leonardo da Vinci would be employed by some of the most powerful and flamboyant figures of his age – ranging from Lorenzo the Magnificent of Florence to Galleazzo ‘il Moro’ Sforza, who murdered his way to becoming Duke of Milan; from the young Francis I of France, king of the most powerful nation in Europe, and to Cesare Borgia, a man whose misdeeds were of such enormity that he has become a byword for evil.

Borgia was the illegitimate son of Pope Alexander VI, a pontiff whose notoriety placed him in a class of his own, even among the popes of the period. (Cardinal Rodrigo Borgia, as he was at the time of the papal elections, was the first man to ensure himself the papal throne by unashamedly buying – with mule trains of jewels and gold – the requisite amount of cardinals required to ensure his election.) His second son Cesare carried on the Borgia traditions to the best of his considerable abilities: he may well have murdered his older brother to ensure his place as his father’s son and heir, and had a psychologically intense relationship with his notorious sister Lucrezia, which was at the very least subconsciously incestuous. (A suspicious number of her husbands and lovers met a gruesome end while he was around.) And, where treachery was concerned, he was second to none – in an age and culture where treachery was very much the norm.

We know that Borgia and Machiavelli formed a close, if somewhat wary, friendship. Leonardo’s reactions to his companions are less clear: Borgia is mentioned just once, in an aside, in his notebooks. What we do know is that during the course of Leonardo’s travels of inspection for Borgia he came across the mountainous landscape in the upper Arno valley that would form the mysterious background to the Mona Lisa, one of the few paintings he would keep in his possession to the end of his days, constantly returning to it, pondering its composition, emphasising or toning down details and so forth. The present somewhat podgy-faced beauty which hangs in the Louvre is now known to be a travesty of the original. Over centuries the surface of the lighter pigments of her face have developed many tiny fissures, thus broadening and rounding her cheeks, while the darker pigments which depict her more definite features have lesser fissures and have thus retained a much closer approximation to their original form. This continuous retouching of the Mona Lisa was a symptom of a psychological trait in Leonardo, which became much more accentuated after his service with Borgia.

Leonardo’s tendency to leave works unfinished and to flit from one subject to another in his notebooks, his inability to order this work into separate topics, or execute any overall extensive plan, all these minor traits became exaggerated to almost pathological proportions after his work with Borgia. Despite Leonardo’s later attempts to order his voluminous notebooks, nothing whatsoever came of this project except a comparatively brief treatise on painting (which was probably put together by his faithful assistant Melzi). As a result, Leonardo’s scientific legacy – to say nothing of the groundbreaking anatomical investigations that took him so much effort and caused him so much trouble – would play no part whatsoever in the advancement of science.

All those ingenious devices, the working machines (from helicopters to submarines), the screws, the gears, the ‘hodometer’ (for the precise measuring of distances, invented for Borgia), all this came to nothing. In the event, the notebooks would be sold off after Leonardo’s death, sometimes a few separated sheets at a time, to rich collectors. These souvenir hunters had no conception of what Leonardo’s notebooks were about and regarded them merely as curiosities of genius. They could not even read the mirror-written Latin instructions beside the drawings, a simple code whose secretive crabbed script was not fully deciphered until well over a century later. The waste is inestimable. If Galileo (born less than half a century after Leonardo’s death) had been able to peruse Leonardo’s notebooks, entire new branches of science might have come into being, while others would have made significant advances, in some cases centuries before they in fact did so.

How did Borgia contribute to this psychological flaw in Leonardo? And why did Machiavelli make Borgia the exemplary hero of his notorious political treatise The Prince? Ironically, the reason for these two disparate effects is the same: Borgia’s duplicitous ruthlessness. A supreme example of this was witnessed by both Machiavelli and Leonardo on the occasion when Borgia charmed his treacherous commanders into meeting him for a reconciliation at the town of Sinigallia, assuring them that he could not fulfil his ambitions without them – then had them all murdered. Some were garrotted in his presence, others transported in cages and slaughtered later.

Machiavelli’s initial despatch to Florence describing these events indicates that he was almost out of his wits with terror. News of the betrayals spread fast and Sinigallia was in mayhem as Borgia’s troops went on the rampage, beyond the control of even their redoubtable commander. We can only imagine how this must have affected the sensitive mind of Leonardo, who was with Machiavelli on this occasion. The oblique, ever-secretive Leonardo makes no mention of this event in his notebooks. Such an omission is not unusual; he often simply shut out from his mind any upsetting reality he could not face. But this horrific event would have its effect nonetheless – almost at once it would accentuate what might be termed his ‘intellectual stutter’. The meticulous details of his observations would lose any semblance of overall fluency as the intensity of his mind darted from one idea to another. It was at this time that he attempted to explain this curious mental tic (to himself?) by writing beside a diagram in his notebook that he would not complete this project because of ‘the evil nature of man’.

The more resilient and realistic Machiavelli would eventually take a diametrically different attitude. Indeed, he even went so far as to embrace the ‘evil nature of man’. If a prince was to conquer a territory, rule it and continue to govern it amid the treacherous politics of Renaissance Italy, then Borgia’s ruthless lack of moral concern was the only way he could succeed. All this Machiavelli would later set down in The Prince, whose amorality would inspire indignant outrage across Europe and beyond.

As for Borgia himself, the truly astonishing extent of his ambitions only gradually emerged after his death. His plan had been to establish his own princedom in the Romagna. Backed by the diplomatic machinations of his powerful father he would then take Florence and eventually unite the whole of Italy under his power. To give Machiavelli his due he probably realised this earlier than most; he too wished to see a united Italy that would achieve a power it had not seen since the collapse of the Roman Empire over a millennium before. Yet even Machiavelli did not suspect the full enormity of what Borgia had planned with his father. Upon the death of Alexander VI a new pope would be elected by the college of cardinals. There is some evidence that Borgia planned to dispense with this centuries-old tradition for voting in St Peter’s successor to the rule of Christendom. Instead, he intended to seize the papacy, declare himself pope and turn this office into a secular hereditary institution ruled by the House of Borgia. As Machiavelli had seen, the key to Borgia’s success lay in his astonishing ability to outwit his enemies by means of treachery beyond wildest imagination.

Ironically, when Borgia’s luck finally ran out, it was he who would fall victim to others, betrayed by Pius III, the Pope who succeeded his father, and then by his ally and protector the Viceroy of Naples. Shipped in irons to Spain, here too he would be dogged by bad luck. Despite escaping from his castle prison, the once mighty Cesare Borgia would suffer an ignominious end in a minor military skirmish far removed from Rome in obscure rural Spain, all his grand ambitions unachieved.