Leonardo’s opinion on the Medici vases, delivered to Francesco Malatesta in May 1502, is the last we hear of him in Florence this year. In early summer he is on the move again. He has a new employer: Cesare Borgia, illegitimate son of Pope Alexander VI, a byword for ruthlessness and cunning, the model for Machiavelli’s ‘prince’. Tales of murder, debauchery and incest cluster round his family: his younger sister Lucrezia Borgia has a particularly lethal reputation. Some of it is mythology; some of it is not. Like the Moor, but even more so, Borgia was not a patron for the squeamish. Freud believed that these strong men to whom Leonardo gravitated were substitutes for the absent father of his childhood.
The Borgia family, originally Borja, was of Spanish origin (and bullfighting was one of Cesare’s macho accomplishments). In 1492 Cardinal Rodrigo Borja ascended the papal throne as Alexander VI. Sixty years old, he was a notorious libertine and was fanatically devoted to the advancement of his illegitimate children. A portrait of him by Pinturicchio shows a bald, jowly man in a sumptuous robe kneeling unconvincingly before a holy image. Guicciardini said of him, ‘He was perhaps more evil, and more lucky, than any other pope before him… He had in the fullest measure all the vices of the flesh and of the spirit.’28 The Florentine Guicciardini was hardly neutral, but his judgement is echoed by others.
Cesare was Rodrigo’s son by his Roman mistress, Giovanna or Vanozza Cattanei. He was born in 1476; Lucrezia was born to the same mother four years later. He was made a cardinal at the age of seventeen, though a visitor to his palazzo at Trastevere found his style anything but churchy: ‘He was ready to go hunting, dressed in very secular silk and heavily armed… He is intelligent and charming, and bears himself like a great prince. He is lively and merry and loves society. This cardinal has never had any inclination for priesthood, but his benefices bring him in more than 16,000 ducats a year.’29 In 1497 his younger brother Giovanni was found floating in the Tiber with his throat cut: the first of many murders attributed to Cesare. It was said that Cesare envied his brother’s secular powers (he was Duke of Gandia), whereas he had been given only church benefices. In 1498 he ‘doffed the purple’ in order to become captain-general of the Church, essentially commander of the papal troops. In France he negotiated an alliance between the Pope and the new king, Louis XII. In 1499 he married Louis’s cousin, Charlotte d’Albret, and was created Duke of Valentinois; from this comes his Italian sobriquet Il Valentino, by which he was generally known to his contemporaries. In this year he was part of the French invasion force into Italy, and entered Milan alongside Louis XII. It was probably then that Leonardo first met him: twenty-three years old, tall and powerful, with blazing blue eyes; a brilliant soldier, a ruthless aspirer. His motto, recalling his imperial namesake, was ‘Aut Caesar aut nullus’ – ‘Caesar or nothing’.
Borgia’s plan, for which Louis promised military support, was the conquest of the Romagna, a sprawling and lawless region north of Rome which was nominally under the suzerainty of the Pope but was in effect controlled by independent princelings and prelates. Over the next few months, with a large detachment of French troops, Borgia established a power-base in central Italy, brilliantly creating, as Machiavelli later saw it, a de facto ‘principality’ out of a hitherto formless region. By the end of 1500 he was master of Imola, Forlì, Pesaro, Rimini and Cesena. Faenza fell to him in spring 1501, giving him control of Florence’s chief trade-route to the Adriatic. Swaggering under the new title of Duke of Romagna, Borgia now advanced threateningly on Florence itself. The republic parleyed nervously, with the upshot that Borgia was ‘engaged’ as a condottiere at the enormous salary of 30,000 ducats per annum – a Florentine spin on what was essentially the payment of protection-money. Borgia moved off, down to the Tyrrhenian coast, where he added the port-town of Piombino to his possessions.
For a while things were quiet, but in the early summer of 1502 came disquieting news. On 4 June the city of Arezzo rose unexpectedly against Florentine dominion, and declared for Borgia. A couple of weeks later, in one of his characteristic lightning-strikes, Borgia took Urbino, expelling his former ally Guidobaldo da Montefeltro. A Florentine envoy, Francesco Soderini, Bishop of Volterra, was swiftly sent to Borgia at Urbino, and with him went a high-flying civil servant in his early thirties, Niccolò Machiavelli.
In a dispatch of 26 June Machiavelli recounted their audience with Borgia.30 Darkness had fallen; the doors of the palace were locked and guarded; the Duke was in peremptory mood, demanding ‘clear sureties’ of Florence’s intentions. ‘I know your city is not well-minded towards me but would abandon me like an assassin,’ he said. ‘If you refuse me for a friend you shall know me for an enemy.’ The envoys murmured assurances and requested the withdrawal of the Duke’s troops from Arezzo. The atmosphere was electric with tension, and Machiavelli’s dispatch concludes in a tone of awestruck fascination:
This Duke is so enterprising that nothing is too great to be discounted by him. For the sake of glory and the enlarging of his dominions, he deprives himself of rest, yielding to no fatigue, no danger. He arrives in one place before anyone knows he has left the other, he gains the good will of his soldiers, he attracts to him the best men in Italy, and he has constant good luck. For all these reasons he is victorious and formidable.
Machiavelli was back in Florence by the end of the month. Not long after came the news that the ‘formidable’ Duke had taken Camerino and was setting his sights on Bologna.
It is in this context that Leonardo enters Cesare Borgia’s service in the summer of 1502. Borgia was not nominally Florence’s enemy, but he was a very dangerous and unpredictable new neighbour. Already stretched at Pisa, the Florentines could not expect to resist him if he chose to invade; the French, now alarmed by this voracious new baron they had in part created, were promising Florence money and soldiers, but could not be relied on. A game of rapprochement was Florence’s only immediate tactic: it was imperative to maintain contact with him, to ‘know him thoroughly’ as the Renaissance saying went. We do not know how or exactly when Leonardo entered Borgia’s employ, but it is plausible that his services were offered to Borgia by Soderini and Machiavelli – an offer of technical assistance which has also an overtone of intelligence-gathering. For Borgia, who attracts ‘the best men in Italy’, Leonardo is a skilled military engineer; for the Florentines he is a pair of eyes and ears – ‘our man’ at the court of Il Valentino.31
Leonardo’s movements can be tracked with the aid of the pocket-book he carried with him through this summer, Paris MS L, though the chronology is not always clear. On the notebook’s first page is a memorandum list which shows him putting together some of the necessary kit – compasses, a sword-belt, soles for boots, a light hat, a ‘swimming-belt’, and a leather jerkin. Also ‘a book of white paper for drawing’ and some charcoal. Another memo list, on a loose sheet now in the Codex Arundel, is probably contemporary. It begins, ‘Where is Valentino?’ (One recalls Machiavelli’s comment about Borgia’s lightning-fast progress: he is ‘in one place before anyone knows he has left the other’.) This list includes an item, ‘sostenacolo delli ochiali’, which might be either a frame for spectacles or a support for some optical device for mapping and surveying. (If the former, it is the first hint of the failing eyesight which becomes a problem in later years.) The list also mentions certain senior Florentines, including the diplomat Francesco Pandolfini, again suggesting a semi-official overtone to Leonardo’s Borgia adventure.32
Leonardo was in Urbino by late July 1502, but his route there was circuitous – a rapid swing through various parts of the scattered Borgia dominion: a research trip. The first leg of the journey takes him down to the Mediterranean coast, to Piombino, then a recent Borgia conquest, now a small town through which tourists hurry to board the car-ferry to the island of Elba. His notes concern the town’s fortifications and the capacity of the port. A note on the movement of waves is recorded as ‘fatta al mare di Piombino’. Some sketches show the coastline round Populonia, suggesting he travelled down the coast-road from Livorno.33 From Piombino he cuts inland, eastward to rebel-held Arezzo, where he perhaps meets for the first time Borgia’s confederate Vitellozzo Vitelli. Thence the road leads up into the highlands of the Apennines, where he gathers some of the topographical data that will later appear in his maps of the region. He perhaps saw at this time the graceful five-arched bridge spanning the Arno at Buriano, and the dramatic chimney-stack rocks, the Balze, which characterize the upper Arno valley from Laterina to Pian di Sco. It has been argued that this bridge and this landscape can be seen in the backgrounds of the Madonna of the Yarnwinder and the Mona Lisa.34The visual parallels are strong, and the dating is right, though the mountains of Leonardo’s landscapes (first seen as early as the Madonna of the Carnation of c. 1474) are a synthesis of many viewpoints, both real and imaginary.
In Urbino, at the great honey-coloured palazzo of the Montefeltro, he meets again the charismatic Duke: it is nearly three years since they had met in Milan, and the years are marked on their faces. In his pocket-book Leonardo sketches the staircase of the palace and notes an interesting dovecote.35 Maddening yet rather wonderful these tranquil, tangential observations: there is so much we want to know about his months at the court of the Borgia, and so little that he tells us. Apart from his query ‘Where is Valentino?’, Leonardo’s only mention of Borgia (or ‘Borges’, as he writes it) concerns a manuscript: ‘Borges will get me the Archimedes of the Bishop of Padua, and Vitellozzo the one at Borgo di San Sepolcro.’36 These manuscripts are the spoils of war: intellectual plunder. A red-chalk drawing of a bearded, heavy-lidded man, shown from three angles, is probably a portrait of Borgia.

Red-chalk portrait by Leonardo believed to show Cesare Borgia.

Niccolò Machiavelli in the portrait by Santi di Tito at the Palazzo Vecchio.
They were not together long, for at the end of July Borgia travelled north to Milan to reassert his former friendship with Louis XII. Perhaps Leonardo hoped to go with him, but he did not. Instead, no doubt with specific instructions, he embarked on a brisk tour of Borgia’s eastern territories. The itinerary can be reconstructed from a series of brief dated notes:
30 July – ‘the dove-cote at Urbino’.
1 August – ‘in the library at Pesaro’.
8 August – ‘make harmonies out of the different falls of water as you saw in the fountain at Rimini on the 8th day of August’.
10 August – ‘At the Feast of San Lorenzo at Cesena’.
15 August – ‘On St Mary’s day in the middle of August at Cesena’.37
At Cesena, the capital of the Romagna, his notebook is much in use. The place is picturesque, the customs particular. A drawing of a window is captioned, ‘Window at Cesena: a for the frame made of linen, b for the window made of wood, the rounding at the top is a quarter of a circle.’ Elsewhere he draws a hook with two bunches of grapes – ‘This is how they carry grapes in Cesena’ – and remarks, with his artist’s eye, that the workmen digging moats group themselves into a pyramid.38 He notes a rustic communication-system: ‘The shepherds in the Romagna, at the foot of the Apennines, make large cavities in the mountains in the form of a horn, and in part of this they place a real horn, and this little horn combines with the cavity they have made, and produces a huge sound.’39The land is flat: he considers the possibility of windmills, still unknown in Italy. And he criticizes the local design of carts, which have two small wheels in the front and two high ones behind: this is ‘very unfavourable to their momentum because there is too much weight on the front wheels’. This failing earns a sneer for this backward, broken-down region: the Romagna is ‘capo d’ogni grossezza d’ingegno’ – ‘the chief realm of all idiocy’.40 The tone is untypical; his mood is brittle.
On 18 August 1502 an impressively florid document was drawn up – Leonardo’s passport. This was inscribed at Pavia, where Borgia was with the French court.
Caesar Borgia of France, by the grace of God Duke of Romagna and Valence, Prince of the Adriatic, Lord of Piombino etc., also Gonfalonier and Captain General of the Holy Roman Church: to all our lieutenants, castellans, captains, condottieri, officials, soldiers and subjects to whom this notice is presented. We order and command that the bearer hereof, our most excellent and well-beloved architect and general engineer Leonardo Vinci, who by our commission is to survey the places and fortresses of our states, should be provided with all such assistance as the occasion demands and his judgement deems fit.41
The document gives Leonardo freedom to travel within Borgia’s dominions, with expenses paid ‘for him and for his’ – we perhaps discern Tommaso and Salai in this formula. He should be ‘received with friendship and permitted to view, measure and carefully survey whatever he wants’. Other engineers ‘are hereby constrained to confer with him and conform with his opinion’. It is a document to be flourished at roadblocks and checkpoints, at suspicious sentries and officious castellans – a reminder of the dangers out here on the frontiers of the new Borgia fiefdom.
Armed with these powers, Leonardo involves himself in various fortification works at Cesena and at Porto Cesenatico on the Adriatic. A sketch of the latter’s harbour and canal is dated 6 September 1502 at nine o’clock in the morning.42 Then Borgia returns from Milan and the campaigns begin again. A note in the Codex Atlanticus suggests that Leonardo was present at the taking of Fossombrone on 11 October. And a vivid anecdote in Luca Pacioli’s De viribus quantitatis gives us a glimpse of Leonardo on the march with Borgia’s troops:
One day Cesare Valentino, Duke of Romagna and present Lord of Piombino, found himself and his army at a river which was 24 paces wide, and could find no bridge, nor any material to make one except for a stack of wood all cut to a length of 16 paces. And from this wood, using neither iron nor rope nor any other construction, his noble engineer made a bridge sufficiently strong for the army to pass over.43
The measurements have been rounded out to make a mathematical point, but the story may well be authentic. Borgia’s ‘noble engineer’ can only be Leonardo, who is presumably the source of the story: he and Pacioli were together in Florence in 1503.
There emerges from this period a sense of strenuousness. Leonardo tracks between these occupied towns and cities, these fortresses and castles, and all the long miles in between, the commandeered inns, and the dawn departures, and the middays sheltering from the sun. He has thrown himself into a world of physical technical work: pacing out measurements, recording currents, examining fortresses – the disciple of experience on the road, with his quadrant and his spectacles and his notebook. One senses an impatient putting-aside of the comfortable urban life of the last twenty years, in which – as it seemed to him – so much had been begun and so little completed. One senses again the Leonardo who advises the painter to ‘quit your home in town’, to ‘leave your family and friends, and go over the mountains and valleys’ and ‘expose yourself to the fierce heat of the sun’. But we can also suspect that Leonardo’s service of the Borgia was accompanied by a deep ambivalence about the nature of his employer and of the destruction and violence he was helping to spread as the Borgia’s well-beloved military engineer. War is ‘the most brutal kind of madness there is’, Leonardo once wrote,44 and during these months of 1502 he saw something of it at first hand. Hence those momentary notations in his notebook, in one sense fragments yet also complete in themselves – a dovecote, a fountain, a bunch of grapes, or those notes which simply say, ‘I am here, on this day’, and perhaps, given that tinge of danger that seeps into everything that Borgia touches, ‘I am still alive.’