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Still dodging his easel, Leonardo left Florence again in the summer of 1502 to serve an even craftier and more unscrupulous patron than Ludovico Sforza:
Cesare Borgia
, scion of Italy’s most notorious family and the model for
Niccolo Machiavelli
’s
The Prince
.

Originally known as the Borjas, the family hailed from the kingdom of Valencia in what is now Spain and came to power in 1455 when Alphonso Borgia, Bishop of Valencia, became Pope
Callixtus III
. He held the papacy for only three years, but that was time enough to name his nephew, Rodrigo, a cardinal. Rodrigo, in turn, became Pope Alexander VI, a brilliant but corrupt statesman who was arguably the greatest libertine in the long and colorful history of the papacy. As Florentine historian
Francesco Guicciardini
wrote of him, Alexander “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.”

Alexander had at least four children, three of them by his longtime mistress Vanozza de’ Cattanei, and he dedicated himself to their advancement. His oldest son, Giovanni, inherited Alexander’s former title and riches as
Duke of Gandia
and became commander of the papal troops, while Cesare was made
Bishop of Pamplona
at the age of fifteen and got his cardinal’s red hat just three years later. Daughter
Lucrezia
was married off three times at varying levels of nobility to enrich her and cement Alexander’s shifting alliances.

All three siblings became infamous throughout Italy. They were accused of a variety of murders, and no doubt committed at least some of them. Both Giovanni and Cesare are said to have slept with the wife of their half-brother,
Gioffre
, while Lucrezia was accused of incest with both Cesare and her father. When Giovanni was found floating in the
Tiber
with his throat cut in 1497, the investigation was abruptly terminated. Cesare was widely suspected of ordering the assassination. The accusations were never proved, but Cesare soon resigned as cardinal to assume his brother’s former title as captain-general of the church and head of the pope’s armies.

Cesare then negotiated an alliance between his father the pope and the King Louis XII of France; he married the French king’s cousin,
Charlotte of Albret
, and the king named him
Duke of Valentinois
, after which Italians called him
Il Valentino
. A strapping man with piercing blue eyes, Cesare was intelligent, charming, unscrupulous, and a canny military leader, whose speedy maneuvers and surprise attacks kept his enemies constantly off balance.

Leonardo had met Cesare Borgia when Cesare came to Milan with Louis XII in 1499 as Ludovico’s sometime ally. By 1502, however, the strategic situation was considerably different. Ludovico was in a French prison, and Cesare had embarked on a campaign to pacify the turbulent
Romagna
region north of Rome. Nominally under papal control, the Romagna was actually a patchwork of independent principalities. Beginning in 1500, with a large force of French troops and Swiss mercenaries supplied by Louis XII, Cesare rapidly subdued city after city culminating with Faenza, Florence’s trade route to the Adriatic. Then he marched on Florence, which, still trying to quell the revolt in Pisa, couldn’t resist Cesare’s troops. So the Florentines bought him off, hiring him as a
condottiere
– a mercenary champion – for the handsome fee of 30,000 ducats per year.

Throughout his campaign, Cesare Borgia showed no scruples. How Leonardo came to join him is not recorded. Whatever the particulars, Leonardo was with Cesare in July 1502, having made a quick reconnaissance through much of Borgia’s newly won territory, notes on terrain and fortifications.

Leonardo met the duke at Urbino, where Cesare had commandeered the luxurious palazzo of the former ally he had betrayed. When the duke left for Milan to court Louis XII, Leonardo, armed with Cesare’s passport giving him license to survey anything he wanted, toured more of his territory. According to
Rafael Sabatini
in his biography of Borgia, Leonardo supervised the building of a canal from
Cesena
to the Adriatic port of
Cesenatico
, drew maps of the valley of
Chiana
, and created a large-scale map of the rivers of central Italy featuring contour shading that conveyed a topographical sense of the terrain. When Cesare returned and resumed his campaign to subjugate the Romagna, a vivid picture of Leonardo at work was recorded by the historian Luca Pacioli: “One day Cesare Valentino, Duke of Romagna and present Lord of
Piombino
, found himself and his army at a river which was twenty-four 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 sixteen 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.”

Cesare set up his winter headquarters at the small fortress town of
Imola
. Leonardo drew a beautifully detailed and shaded map of the town, recording ground plans and measurements of the fortress, with a forty-foot moat and fifteen-foot-thick walls. Machiavelli joined the group there; as secretary of Florence’s Second Chancery, he had been assigned by the Signoria, against his wishes, to keep an eye on the duke and report on his doings.

There was plenty to report. On the day after Christmas, Machiavelli wrote: “This morning Messer Rimino was found lying in the piazza cut into two pieces; he still lies there, so that everyone has had an opportunity to see him.” Beside the body was a bloody knife and a wooden wedge used by butchers to split animal carcasses. Why Rimino was killed wasn’t clear, the envoy wrote, “except that such was the pleasure of the Prince, who shows us that he can make and unmake men according to their deserts.”

Leonardo’s notebooks during his service to Cesare Borgia are filled mainly with sketches – a bunch of grapes, a window, a drawing of the duke – and innocuous notes on the local design of carts. It is as if the usually keen observer weren’t there at all; biographer Nicholl sensed “a deep ambivalence about the nature of his employer and of the destruction and violence he was helping to spread.” If Leonardo had once been an enthusiastic designer of war machines, Cesare Borgia had taught him the reality of war – as he would later write, “the most brutal kind of madness there is.”

Cesare Borgia was at the peak of his power. The next year, his father, Pope Alexander VI, died. Cesare managed to install his own candidate as Pope
Pius III
, but the new pope died after only twenty-six days in office. Cesare’s enemy, Cardinal Giuliano della Rovere, promised him money and continued support in exchange for Borgia’s backing in the next conclave. The ailing Cesare accepted the offer, but after della Rovere was elected Pope
Julius II
, he broke his promises – a betrayal that a healthier Cesare Borgia would probably have foreseen. Another ally turned on Cesare and imprisoned him in Naples in 1504, and Julius II confiscated his lands. He escaped from a Spanish prison, but died ignominiously in 1507 in an ambush in
Navarre
.

Leonardo was back in Florence at the beginning of March.

 

Leonardo’s time in the Borgia camp hadn’t restored his taste for the paintbrush or sated his appetite for large-scale works of engineering, even if they might end in failure. For years, he had been pondering a grand scheme to make the Arno River navigable by turning it into a canal all the way from Florence to Pisa on Italy’s west coast. The Signoria recognized the benefits of this idea, especially in light of the opening of trade with the Americas, but had no appetite for its staggering cost. Now, however, there was a reason to tackle one segment of the plan: to cut off Pisa’s access to the sea.

Florence’s dispute with its former tributary had been underway for years. Pisa was well fortified and could hold out indefinitely as long as it could get supplies by way of its port at the mouth of the Arno, ten miles downstream. If the river could be diverted, Florence could retake the city by siege.

Piero Soderini
was now Florence’s
gonfalonier
, or prime minister, with Machiavelli as his chief assistant, and both were impressed when Leonardo proposed to divert the river. In June 1503, they sent a detachment of troops to occupy a fort above Pisa; from there, Leonardo made two preliminary surveys and reported that the project was feasible.

The plan was to dig a huge ditch, a mile long and thirty-two feet deep, which would then fork into two smaller trenches to carry the river another ten miles south of its normal course to a marshland near Livorno on its way to the sea. By Leonardo’s calculations, about a million tons of earth would have to be excavated. At the bottom of the main ditch, he figured, every bucket of dirt would have to be handled by fourteen workers before it reached the top. He concluded that it would take 54,000 man-days to complete the project – unless “machines” were used to help. He had a design in his notebook for just such a mechanical digger.

Inexplicably, when the excavation began a year later, another engineer, Colombino, was in charge, and, after 80,000 man-days, the job was only in its earliest phases. Then, in October, a storm flooded the ditches, which led to the collapse of their walls. Eighty men were killed. The surrounding farms and plain were inundated, and the project was abandoned. When the Florentine troops left the scene, the citizens of Pisa filled in the ditches.

A somewhat less ambitious, but no less risky proposal by Leonardo involved building a bridge across the
Golden Horn
, linking the peninsular city then called
Constantinople
with
Galata
to the north. On a brief trip to Rome with Cesare Borgia in 1502, Leonardo heard the Sultan was looking for an engineer; Michelangelo, then squabbling with Pope Julius II, had expressed interest, too. Leonardo’s letter was flowery and obsequious: “I, your servant, have heard about your intention to build a bridge from Stamboul to Galata, and that you have not done it because no man can be found capable of it. I, your servant, know how . . . I will make it so that a ship can pass under it even with its sails hoisted . . . May God make you believe these words, and consider this servant of yours always at your service.”

There is no record of any reply, but Leonardo’s notebook from that time shows a working drawing of a 1,200-foot-long bridge spanning the water – exactly the width of the Golden Horn. Strikingly modern in design, the bridge would have risen to 140 feet above water level; at the time, it would have been the longest bridge in the world.

During this period in Florence, Leonardo also started work on arguably the most famous painting in the world, the “Mona Lisa,” propelled into notoriety in 1911 when it was stolen from the Louvre. The painting was recovered two years later when the thief, Italian painter Vincenzo Perugia, took it out of hiding, beneath his stove, and was arrested trying to sell it.

For centuries, a great deal of needless mystery has been generated regarding the identity of the woman who posed for “Mona Lisa.” In the simplest version, as Giorgio Vasari reported some fifty years after the fact, “For Francesco del Giocondo, Leonardo undertook to paint a portrait of his wife, Mona Lisa; he worked on it for four years and left it unfinished.” Vasari was referring Francesco del Giocondo, a prosperous silk and cloth merchant in Florence; his third wife,
Lisa Gherardini
, would have been about twenty-four years old in 1503, when Leonardo started work on the painting.

Speculation over the sitter’s identity was fueled by a visitor to Leonardo’s studio in 1517, who wrote that Leonardo told him it was the portrait of “a certain Florentine lady, done from life at the instigation of the late Magnifico Giuliano de’ Medici.” Giuliano was, in fact, Leonardo’s patron, but that was in Rome from 1513 to 1515. Lovers of intrigue have focused on women who might have been Giuliano’s mistresses. But Lisa Gherardini fits the bill neatly.

Like many of Leonardo’s patrons, Francesco del Giocondo never got his painting; it was still in Leonardo’s studio as late as 1517. In all likelihood, as he did with his “Virgin and Child with St. Anne,” he kept rethinking and reworking “Mona Lisa” until he was satisfied with it. A painting called
La Gioconda
was listed in Salai’s estate when he died in 1524; Leonardo may have left it to him – or it may have been one of Salai’s many copies of Leonardo’s works.

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