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The son of a gardener in a village near Florence, Zoroastro claimed to be the illegitimate son of
Bernardo Rucellai
, brother-in-law of Lorenzo the Magnificent. Rucellai, also a patron of Leonardo, took an interest in Zoroastro and may have helped place him in the studio. Zoroastro became a metalworker and a magician, an expert in casting bronze, and something of a court jester, but was also trusted with the household money and purchases. A vegetarian like Leonardo, he “would not kill a flea for any reason,” wrote one biographer, and “preferred to dress in linen so as not to wear something dead.” Later in life, Zoroastro took up alchemy. He seems to have been universally liked and respected – in the words of his epitaph, “a man outstanding for his probity, his innocence, and his liberality.”

During this period, Leonardo produced three notable works. The first, the “Benois Madonna,” is a small gem: Flawed in detail, seemingly unfinished, and showing signs of later repainting, it is nonetheless an unforgettable depiction of Mary as an unsophisticated young mother, delighting in the baby on her lap as he takes in the beauty of a small flower. It is the essence of the Renaissance painters’ newfound ability to show spontaneous, informal human moments. As he would do in later paintings, most notably the “Madonna of the Yarnwinder,” Leonardo introduced a note of foreboding: The flower that fascinates the child is the bitter cress, a four-petaled member of the Crucifera family and a portent of his death.

The second, more powerful, striking work of Leonardo’s first Florentine period is “
St. Jerome in the Wilderness
.
” Produced for an unknown patron and never finished, it shows the saint as a hermit in the Syrian Desert, anguished and emaciated, striking himself with a stone as he gazes at a crucifix. In the foreground is a huge lion, the saint’s symbol, posed in a sweeping curve with its tail in a counter-curve. The lion is lightly and powerfully sketched, but every muscle and tendon in the saint’s arm and neck stands out as if in an anatomical drawing.

In 1481, Leonardo received his first important postwar commission, an altarpiece for the monks of the monastery of San Donato a Scopeto, just outside Florence. Leonardo’s father had been handling the monastery’s business affairs and may have had a hand in obtaining the commission, but since the monks knew about the unfinished altarpiece in the Chapel of San Bernardo, the contract required Leonardo to finish the job in two and a half years at most.

Leonardo was paying a heavy price for his independence and lack of dependability. The monks gave him no cash in advance, and his payment was to be only about 150 florins in the form of a property in the Val d’Elsa, south of Florence. In debt to the monastery for sums advanced to buy pigments for the painting, he was buying food and wine on credit and decorating the monastery clock in return for firewood.

Leonardo chose the Adoration of the Magi as his subject, and he planned an ambitious tableau of the Nativity. In a series of detailed drawings, he worked out the painting’s perspective, changing it repeatedly and switching the sixty-seven figures around in intricately composed groups. Yet once again, after working on it for seven months, he gave up on his painting.

Leaving his altarpiece unfinished, he closed his studio and packed his goods and went to Milan. Along with hundreds of drawings and many notebooks, he made an inventory of his recent work, including: “. . . certain figures of St. Jerome . . . drawings of knots . . . some machines for ships [and] for water . . . many heads of old men . . . a Madonna, finished . . . another almost, which is in profile.” Zoroastro went with him, and so did
Atalante Migliorotti
, a model who would become a singer and maker of musical instruments. Leonardo also took a letter of introduction to
Ludovico Sforza
, his prospective new patron, describing the marvels of engineering that he could perform – and mentioning almost in passing that he could paint, too.

It was a major gamble. Leonardo wasn’t a boy with the world before him; he was a man of thirty, competing on unfamiliar turf with new and talented rivals for the favor of a patron he had never met. He knew how capricious any patron’s favor could be and how even a major talent could be spurned or ignored. But he had the certainty of a genius: He would prevail.

 

Ludovico wasn’t yet the actual Duke of Milan; he was acting as regent for his ten-year-old nephew, who was too young to take over when his father, Ludovico’s brother, was assassinated in 1476. But Ludovico kept the heir isolated and powerless. Burly, ruthless, and unscrupulous, he was called “Il Moro,” the Moor, because of his dark complexion and as a pun on one of his names, Mauro. (Quattrocento Italians were obsessed by puns, and Leonardo was no exception; several times he paired his name with
leone
, lion.) Ludovico liked his nickname and used a moor’s head as part of his coat of arms.

Ludovico wanted to reinforce the fortress of Casalmaggiore on the Po River, and Leonardo’s offer of military expertise probably caught his attention. Leonardo’s drawings in Milan include both an armored car and a portable cannon that “fires out small stones, almost as if it were a hailstorm” – an early version of the grapeshot widely used in naval and land battles of the eighteenth century.

Because he was a Florentine, Leonardo had a certain edge in Milan. The two cities had a relationship rather like New York and Chicago or London and Paris; Milan both recognized and resented the cultural superiority of Florence. There was a prominent Florentine faction at the court of Ludovico, including the Medici banker Benedetto Portinari, the diplomat Benedetto Dei, and the Hellenist scholar Bartolomeo Calco, Ludovico’s secretary, who had been hired to help “purify the coarse speech of the Milanese.” All were in the inner circle and could be of help to Leonardo.

The painter and architect
Donato Bramante
, regarded as the foremost artist in Milan at the time, soon became a good friend. But it was Leonardo’s friendship with two local painters - Ambrogio and Evangelista de Predis - that resulted in his first Milanese commission. The three were hired by a religious group, the Confraternity of the Immaculate Conception, to paint an altarpiece that became the dark, elusive, haunting “
Virgin of the Rocks
.” It was to hang in the Confraternity’s chapel in the church of San Francesco Grande, then the biggest church in Milan except for the Duomo.

Ambrogio de Predis was already established as a “painter to Ludovico,” but Leonardo’s reputation preceded him: The contract called Leonardo magister and assigned him to paint the central panel of the altarpiece, with Ambrogio de Predis responsible for the two smaller side panels and his brother Evangelista to decorate the frame. They were promised 800 florins and given a deadline of eight months. The content of the painting was stipulated in almost comic detail: The Madonna and Child would be grouped with a band of angels and two prophets, and each side panel would feature four angels singing or playing instruments. Perhaps needless to say, hardly any of this materialized.

The painting shows the meeting of the infant Christ with the infant John the Baptist during the Holy Family’s flight from Egypt. They are in a grotto in the wilderness. With Mary’s hand on his shoulder, John is worshiping the Christ child, who blesses the Baptist in return, while an angel, seated beside Jesus, points to John. The Virgin’s left hand hovers over her son with its own sign of blessing.

There are two versions of the “Virgin of the Rocks” - one at the
Louvre
in Paris and the other in London’s
National Gallery
. The painting in the Louvre is thought to be the original and entirely the work of Leonardo; the London painting was probably painted later and by both Leonardo and Ambrogio de Predis. The Louvre version better reflects Leonardo’s early Florentine style, with the Virgin’s lovely face, graceful pose, and long ringlets. The London version is darker and more austere, and the figures are equipped with haloes, which Leonardo usually shunned.

One theory that explains the two paintings holds that after the artists finished the first version, Ludovico himself bought it and sent it to Holy Roman Emperor
Maximilian
in 1493 when Maximilian married Ludovico’s niece. Antonio Billi, a sixteenth-century merchant who wrote extensively about Quattrocento artists, has a note supporting this account, and it is a matter of record that Ambrogio de Predis was at the imperial court in Innsbruck for the wedding. If it happened this way, the Confraternity could have used part of the payment from Ludovico to hire Leonardo and Ambrogio to paint the second version for their altarpiece.

The painters delivered an altarpiece in 1485, but a legal dispute over the payment followed. In 1492, still squabbling, Leonardo and the brothers asked the court again for a fair payment or for permission to take back the painting, saying they had another offer. Litigation with the Confraternity erupted again in 1503 and lasted for five years, again over payment for “Virgin of the Rocks.” It seems likely that this dispute involved the second painting.

Leonardo’s obsession with flying machines - a dream that would stay with him all his life – showed up again in Milan. He had drawn his first such machine in Florence in a doodle probably done between 1478 and 1480; it showed a bat-like wing over a pod for the pilot, with a control mechanism that allowed only limited movement of the wings, suggesting a glider rather than a machine designed for self-propelled flight. In his early Milan notes, he conveys the idea of air having substance: “See how the beating of its wings supports a heavy eagle in the highly rarefied air . . . Observe also how the air in motion over the sea fills the swelling sails and drives heavily laden ships . . . So a man with wings large enough, and duly attached, might learn to overcome the resistance of the air, and conquer and subjugate it, and raise himself upon it.” He even envisioned a helicopter, with a giant linen screw for a propeller, noting that if it were turned rapidly, “the screw will find its female in the air and will climb upward.”

It took Leonardo several more years to design the more complex ornithopter, a flying machine with wings that mimicked an eagle’s. Ever the pragmatist, he was already imagining what could go wrong in the air and what to do about it, and around 1485, he sketched a working parachute. In the shape of a pyramid, twenty-four feet square with pine poles bracing the open bottom, the design was eminently practical – as proved in the year 2000 when an English sky-diver built one and jumped from a hot-air balloon 10,000 feet above the Kruger National Park in South Africa. He floated down gently, taking five minutes to descend 7,000 feet. Then, because Leonardo’s parachute weighed nearly 200 pounds and might crush him on landing, the skydiver cut himself loose and made the final drop with a modern parachute. He reported “a feeling of gentle elation and celebration,” adding: “It took one of the greatest minds who ever lived to design it, but it took 500 years to find a man with a brain small enough to actually go and fly it.”

Leonardo’s notes show his mind ranging incessantly, with allegorical drawings of pain entwined with pleasure and virtue with envy. Perhaps because Milan was enduring a three-year bout of the bubonic plague, he was also musing about designs for the “ideal city.” Leonardo’s city would be built on two levels. The upper one was designed for pedestrian traffic, with shops, public buildings, palazzos, piazzas, gardens, sculpture, and loggias. The lower level, with tunnels and canals as well as streets, would be for warehouses, animals, carts transporting goods, and the dwellings of “ordinary” people. Leonardo recommended spiral staircases between the levels, noting that people tended to urinate in the dark corners of square staircases.

To this point, Leonardo’s notes were a jumble of loose sheets, which he would rearrange from time to time; over the centuries, they floated from hand to hand and can be roughly dated only by changes in his mirror-script handwriting and drawing style. But in the mid-1480s, he began keeping proper notebooks. The earliest of these, which scholars now call Paris MS B, is in the
Institut de France
in Paris; besides the ideal city and the ornithopter, it contains designs that include churches, submarines, a steam-powered cannon, and a helicopter.

Another early notebook, now in London’s
Victoria & Albert Museum
, features a series of drawings of Archimedean screws for lifting water, with a long spiral turning inside a snugly fitted tube to force the water upward. There are also notes on grammar and vocabulary, lists of books he owns, drafts of letters, abstruse riddles, architectural notes and drawings, satiric stories written to entertain his friends, and jokes. The jokes were dense with puns, which was sometimes their only point – for example, his tongue-in-cheek substitution of
lauro
, the bay-tree, for Laura, to whom the poet
Petrarch
addressed his love poems: “If Petrarch was so madly in love with bay-leaves, it’s because they taste so good with sausage and thrush.”

But the early success in Milan seemed hollow. After five years as one of Ludovico’s courtiers, Leonardo had little to show for it. There’s no record of any ducal commissions, stipends, or even handouts. One of Leonardo’s drawings involves remodeling a pavilion in the Sforza castle garden, but it’s unknown if the plan was carried out or whether Leonardo was paid for it. But then, in 1489 or 1490, Leonardo was chosen to paint Ludovico’s young mistress,
Cecilia Gallerani
.

Cecilia was in her mid-teens, the daughter of a good but not wealthy Milanese family, and her affair with Ludovico has been underway for some two years. By all accounts, he was so besotted with Cecilia that he was delaying his arranged marriage to
Beatrice d’Este
, daughter of the Duke of Ferrara.

The wedding did occur, in January 1491, if only because it was part of a triple alliance that would cement a new political order in northern Italy. As Ludovico married Beatrice, her sister Isabella married
Francesco Gonzaga II
, Marquis of Mantua, and her brother
Alfonso d’Este
, who would become the Duke of Ferrara, was being wed to Ludovico’s niece,
Anna Sforza
. The Gonzaga had feuded with the Visconti while they ran Milan, but the three marriages linked to the d’Este clan, one of the oldest in Italy, now gave Mantua Milan as an ally. And the parvenu Sforza now had both Ferrara and Mantua on his side.

Even after Ludovico’s wedding, however, the Ferraran ambassador to Milan reported that the duke had confided to him that he wanted to be with Cecilia and that Beatrice was refusing to consummate the marriage until he gave up his mistress. Soon, nature took a hand: Cecilia was heavily pregnant and was sent from Ludovico’s private rooms to an apartment in the city. Her son was born in May.

It was probably early in the pregnancy when Leonardo painted Cecilia’s portrait, “
Lady with an Ermine
.” Slim and graceful, fashionably but not richly coiffed and dressed, she is cradling an ermine – a kind of weasel whose coat turns white in winter. (In the portrait, the ermine’s pelt has been yellowed by layers of varnish.) Since the animal’s name in Greek is
galè,
it is a visual pun on her name, Gallerani. Perhaps more significant, Ludovico himself had recently been invested in the Order of the Ermine by the King of Naples and was using the title,
L’Erminello
. In Leonardo’s painting, the ermine is vigilant and muscular, with its claws clutching Cecilia’s sleeve, an obvious invocation of the duke guarding his treasure.

Like many of Leonardo’s works, the portrait has a twisting, pyramidal composition. Cecilia sits facing diagonally to her right, but her head turns back to her left; her expression is expectant, and her eyes focus on something or someone outside the frame, where the ermine seems to look as well. Cecilia’s skin is luminous, almost translucent, and her hand caressing the animal is so finely modeled that a close viewer can see each wrinkle around the knuckles and the flexing of the tendon in her bent forefinger.

The painting was an immediate success. Ludovico’s court poet,
Bernardo Bellincioni
, wrote in a sonnet: “O Nature how envious you are / of Vinci who has painted one of your stars, / The beautiful Cecilia, whose lovely eyes / Make the sunlight seem dark shadow.” Cecilia kept the portrait after her liaison with Ludovico ended.

The modeling of Cecilia Gallerani’s hand was no accident. By the late 1480s, Leonardo had begun the systematic anatomical studies that he would pursue for the rest of his life, underpinning his painting with scientific knowledge that gave his works lifelike energy and realism. He had studied anatomy under Verrocchio, which was reflected in the arm and neck of “St. Jerome.”

But Leonardo’s intellectual interest in anatomy led him far deeper into the subject than other painters considered necessary. Some of his contemporaries and early biographers deplored his scientific work as a waste of time. In the course of his life, Leonardo would dissect some thirty human cadavers, working without the benefit of refrigeration and in spite of the taboos and doctrinal bans of church and state alike. From the beginning, he probed well beyond the joints, tendons, and muscles visible in a painting; in 1489, he drew eight studies of a human skull in finely shaded detail from multiple angles, showing hidden features that no painting could ever reflect.

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