The Mona Lisa Foundation

The ‘Earlier Version’ of the Mona Lisa as the Portrait of Lisa del Giocondo described by Vasari

By Prof. Jean-Pierre Isbouts

Graduate Professor, Fielding Graduate University, Santa Barbara; National Geographic author, and co-author of “The Mona Lisa Myth” (2013).


To understand Leonardo’s frame of mind in the Spring of 1503, it is instrumental to review the chronology of events that preceded his return to Florence in the beginning of that year. Young Leonardo had been apprenticed to the workshop of Andrea del Verrocchio in 1466, at the age of 14, and by all accounts the apprenticeship was a successful one. In 1472, Leonardo was permitted to paint an angel in Verrocchio’s Baptism of Christ, a painting commissioned by the monks of the San Salvi monastery just outside the Porta alla Croce. Recent X-ray tests of the Baptism show that, whereas Verrocchio still painted his figures as contours in tempera on a white lead base, Leonardo used thin, superimposed glazes of colored oils in the sections assigned to him.i Six years later, Leonardo scribbled in his notebook, “I have begun the two Virgin Marys,” which may refer to the Madonna of the Carnation, now in the Munich Alte Pinakothek, and the Benois Madonna, currently in St. Petersburg.

In 1481, Leonardo received the first “big” commission of his career: a panel of the Adoration of the Magi for the Augustinian monks of San Donato a Scopeto. Adoration paintings were popular in Florence, because they gave artists the opportunity to dress the three kings from the East in the rich cloth and silk that had made the city famous. But Leonardo’s design rejected the typical Quattrocento stereotype of the subject, with Mary and the newborn Jesus in center foreground, while worshippers dutifully line up to pay their respects. Instead, he placed Mary in the center of an intense psychological drama: a beautiful young woman with her newborn child, surrounded by a vortex of human emotions. Some of the supplicants express surprise and wonder, while others convey confusion or even despair. The characteristic joy of traditional Annunciation iconography is nowhere in evidence. As such, the Adoration is the first of Leonardo’s “literary” works: a painting focused on allegorical clues and symbolic meaning, rather than explicit representation.

Adoration of the Magi, ca. 1481.

Unfortunately, this quality was entirely lost on the good friars. The panel was left unfinished—and not, as is so often assumed by historians, because Leonardo walked away from it. On the contrary: it is more likely that the monks, shocked by such an iconoclastic work, terminated the commission and went looking for another, more conventional artist.

There followed the long interlude in Milan, at the court of Duke Ludovico “Il Moro” Sforza, where Leonardo was fêted as a celebrity impresario, charged with a steady stream of entertainment including sets, costumes and vainglorious monuments to Sforza rule. In between, Leonardo was also called upon to produce portraits of various Milanese beauties, specifically two of the Duke’s mistresses, Cecilia Gallerani and Lucrezia Crivelli. It is because of this fortunate happenstance that Leonardo directed his prodigious talent to the problem of secular portraiture.

A Revolution in Portraiture

We should remember that secular portraiture—that is, the depiction of everyday citizens, rather than prominent kings, aristocrats, or clerics—was still a recent development in Italy at that time. Unlike in Northern Europe, and particularly among the rich burghers of Flanders, the idea of having one’s portrait painted simply because one could afford it, was a relative novelty. The Quattrocento Renaissance accelerated the spread of the genre, but demanded that portrait artists—like their brethren in architecture and sculpture—follow the example of classical models. The only form of ancient portraiture still extant, however, was Roman coins. Thus, the portrait en profil became the preferred style among the upper classes because of its obvious classicizing tenor; it signaled that the sitter was a connoisseur fully au courant with ancient art.

A typical example is Leonardo’s portrait of Isabelle d’Este, executed around 1500 in either Venice or Mantua. Though at this point Leonardo’s portrait style was already fully developed, with a posture and placement of the hands that clearly anticipate the Mona Lisa, the Marquess’s face is rigorously turned away so that she can present herself in the same manner as the Roman worthies portrayed in her extensive coin collection.

Portrait of Isabella d’Este, ca. 1500.
It is in this milieu that Leonardo forged his first major breakthrough in secular portraiture with his portrait of the Lady with an Ermine. The revolutionary features of this picture—its soft chiaroscuro; the sharp contrast between living flesh and the dark limbo of the background; and the attentive gaze of the sitter, as if caught by something outside our view—have been imitated in portraiture and modern photography so many times that it is difficult for us to grasp the painting’s originality. Liberated from the contours of the numismatic profile, the portrait is a textbook example of contrapposto, the classical ideal of moving the head, torso, and limbs of a human body in different positions from its center axis. “When seen from varied viewpoints,” Leonardo wrote in his Treatise on Painting, preserved by his pupil Francesco Melzi, “each human action is displayed as infinite in itself.”ii

Lady with an Ermine, ca. 1490.

Then came the fall of Ludovico and Leonardo’s reluctant return to Florence in 1500. It is likely that Leonardo’s father, Ser Piero, came to his aid and brokered a contract with the monastery of Servite friars, or “Servants of Mary” as they were officially known, who were looking for an artist to paint an altarpiece for their church of the Santissima Annunziata. The subject is uncertain, but in the end Leonardo produced a large drawing for a Virgin and Child with St. Anne, which may have been a further development of an earlier drawing featuring a similar group, known as the Burlington Cartoon. The drawing was publicly displayed in the monastery for two days and drew a huge crowd—a foreshadowing of the massive publicity that attends public exhibitions of Leonardo’s art in our modern day.

But the work was left unfinished once again. Leonardo accepted an offer to serve as military engineer in the entourage of Cesare Borgia, who at that moment was hard at work subjugating the Romagna for the Papal States. If Leonardo had hoped for a long-term engagement as a courtier-artist at the Borgia papal court, those ambitions were dashed. For whatever reason, he left Borgia’s campaign and returned to Florence in March of 1503—without a job, without commissions and, apparently, without money. That month, he took the unusual step of withdrawing fifty gold florins from his savings account at the Ospedale di S. Maria Nuova, and would continue to do so every three months until the summer.iii

This is when a character named Niccolò Machiavelli enters the story. A secretary of the Second Chancery in Florence, which at the time was governed by Gonfaloniere Piero Soderini, Machiavelli would later garner fame for his controversial book The Prince, largely based on his close observations of the ruthless doings of Cesare Borgia. In fact, it was during Machiavelli’s brief sojourn in Cesare’s entourage that he had first been introduced to Leonardo da Vinci. Florence was mired in a war of attrition against its erstwhile vassal, the city of Pisa. Machiavelli believed he had come up with a brilliant plan to bring the war to a close: by diverting Pisa’s lifeline, the Arno River, thus depriving the city from its trade and supplies. Leonardo obliged his friend with a series of designs, some of which have survived. Despite Machiavelli’s efforts on Leonardo’s behalf, the Signoria would ultimately accepted Leonardo’s designs but not the man: the execution of the scheme, which by far exceeded the manpower and resources of Florence, was entrusted to a Maestro Colombino, a waterworks official. Perhaps Leonardo’s reputation as a man who had abandoned not one, but two major commissions from prominent monasteries in the city played a role in the decision.

The Anghiari Commission

Machiavelli may have felt a sense of obligation towards his friend. Indeed, it’s attractive to think that it was Machiavelli who introduced Leonardo to another civic commission, namely a large fresco of the Battle of Anghiari—one of Florence’s few victories in its rather checkered military history—which Soderini wished to have painted in the newly built Grand Council hall of the Palazzo della Signoria (now known as the Palazzo Vecchio). Machiavelli’s role is evident from the fact that it was his secretary, Agostino Vespucci, who provided Leonardo with a detailed description of the battle, translated from a Latin elegy entitled Trophaeum Anglaricum (‘Victory at Anghiari’), originally written by the humanist Leonardo di Piero Dati.

The Grand Council Hall in the Palazzo della Signoria, which was substantially remodeled and enlarged by Vasari in 1537, and renamed the Salone dei Cinquecento (“Hall of the Five Hundred”), for the purpose of extolling the benefits of Medici rule.

Whether Machiavelli was also in a position to swing the support of the Signoria, the Florentine government, behind the selection of its wayward son Leonardo da Vinci, is debatable. Gonfaloniere Soderini favored a prodigy of Lorenzo de Medici, a brash young artist named Michelangelo Buonarroti. No doubt there were others among the Signoria who bridled at the idea of conferring this important commission on an artist who had yet to complete a major painting in his native town—in glaring contrast to the works he’d seen fit to finish in the capital of Florence’s sworn enemy, the Duchy of Milan.

Enter Francesco del Giocondo, a silk merchant who by 1503 had held four prominent positions in Florence’s republican government, most recently in 1499 as a member of the advisory council of the Dodici Bonuomini. Giocondo and his extended family had connections throughout town; between 1480 and 1520, Giocondos held no less than forty positions at various levels of the Florentine government.iv Here was a man who could very well bring his influence to bear to grant Leonardo the Anghiari commission. But Giocondo was a shrewd businessman with a reputation for hardknuckle negotiating skills; a police document of 1510 describes him as confrontational, unscrupulous, and quite ruthless.v True to form, the merchant wanted something in return for his advocacy of Leonardo’s talents. He wanted a small portrait of his young wife, Lisa del Giocondo, who had just presented him with their third child.

It is very likely that at any other time in his life, Leonardo would have dismissed such a commission out of hand. He was a painter to the greatest courts of Italy, not a fawning petitioner to the mercantile parvenus of Florence. Most recently, he had fended off insistent demands from Isabelle d’Este, the most formidable woman of her time, to paint her portrait—and Isabella was Marquess of Mantua, not a Florentine housewife.

But these were unusual times. Leonardo was subsisting from his savings at the Santa Maria Nuova, and the account was dwindling at an alarming rate. He needed to come up with a new source of revenue to support himself and his entourage, while demonstrating his bona fides to the city fathers. Giocondo was a man who could help him to accomplish both.

The Via della Stufa in Florence, principal residence of the Giocondo family.

Seen in this context, the claim by our leading witness, the 16th-century artist and author Giorgio Vasari, that “Leonardo undertook to execute, for Francesco del Giocondo, the portrait of Monna Lisa, his wife,” is eminently Giocondo was Leonardo’s key to restoring his reputation in Florence and to receiving the biggest and most challenging art project in Italy since his Last Supper fresco in Milan of 1498.

Nevertheless, Vasari’s paragraph on the Mona Lisa commission has been under vigorous attack for some time, and for two reasons. One, it offers a detailed description of the painting, even though it is universally accepted that Vasari could have never seen the Louvre Mona Lisa, for the excellent reason that in the 1530’s the Louvre portrait was already in France, a country Vasari never visited. And two, Vasari claims that the Mona Lisa portrait was left unfinished, though the Louvre panel is perhaps the most polished and complete of all of Leonardo’s paintings.

Consequently, Vasari’s text was chalked up by many modern scholars as another example of the author’s penchant for hyperbole and vivid imagination. But any serious student of Vasari’s Lives of the Artists will recognize that, while the author might sometimes embellish his narrative, he would never go as far as to fabricate a two hundred-word description of a painting out of whole cloth. In fact, in all of Vasari’s Vite, this detailed descriptive passage of the Mona Lisa is unprecedented.

Indeed, the re-emergence of the Isleworth Mona Lisa from its long exile in a Swiss bank vault, and the subsequent authentication of the work as a genuine Leonardo by John Asmus and others, enables us to see Vasari’s text in a dramatically new light. Every observer will be hard-pressed to recognize Vasari’s description of the lady’s “rosy and pearly tints” in the gloomy hues of the Louvre Mona Lisa, even allowing for centuries of varnish, soot and dirt. But looking at the Isleworth Mona Lisa, Vasari’s rapturous description of “that luster and watery sheen” in the lady’s eyes is spot on, just as her mouth does indeed “unite the red of the lips to the flesh-tints of the face” and her nose, “with its beautiful nostrils, rosy and tender,” truly appears to be alive. In sum, Vasari’s description fits the Isleworth Mona Lisa to a remarkable degree, which strongly argues for the Isleworth portrait being an earlier version of the Mona Lisa.

A Mona Lisa Chronology

If we assume that Leonardo began to work on the portrait of La Gioconda in the spring of 1503, then it stands to reason that by the end of that year, when preparations for the Battle of Anghiari project began in earnest, the face and hands—always the most important passages in a portrait—would have been completed. But not much more was done to the portrait once Leonardo threw himself wholeheartedly in the challenging task of painting the huge fresco. That the Mona Lisa portrait was still unfinished in October of 1503 is borne out by the now-famous note written in a collection of Cicero’s letters, entitled Epistulae ad Familiares (‘Letters to His Friends’) published in Bologna in 1477. While reading the book, Machiavelli’s secretary, Agostino Vespucci, came across a passage in which Cicero described how the Greek artist Apelles had begun to paint the portrait of the goddess Venus, but left it unfinished. Vespucci grabbed a pen and wrote in the margin, “That’s the way Leonardo da Vinci works in all of his paintings, like, for example, the portrait of Lisa del Giocondo and Anne, the mother of the Virgin,” referring to both the Mona Lisa and the ill-fated commission from the Servite monks of the Santissima Annunziata. The note clearly shows that at the time of Vespucci’s writing, both of these works had been left unfinished as well.

Vespucci was well aware of Leonardo’s reputation for leaving things undone, for he added, “We will see what he’s going to do with the chamber of the great council, the thing for which he’s just come to terms with the gonfaloniere.”vii

This crucial piece of evidence has now solved two important issues in Mona Lisa scholarship: one, that the sitter of the Mona Lisa portrait is beyond question Lisa del Giocondo, as Vasari maintained all along, and two, that Leonardo left the Mona Lisa incomplete as he began his work on the Battle of Anghiari.

For the next two and a half years, Leonardo was subsumed by the task of creating the vast Anghiari cartoon, and transferring the design to a fresco painting. The difficult project was made even more challenging by Leonardo’s insistence of using the same type of oil-based glazes with which he had previously revolutionized the art of portraiture, rather than the usual, quick-drying tempera-based pigments on wet plaster. According to the anonymous Gaddiano, Leonardo created a concoction based on Pliny the Elder’s book Natural History, using Greek pitch to seal the plaster wall. The experiment didn’t work. The wall refused to absorb the oil-based pigments, and the paint began to drip and run. Paolo Giovio, historian and personal physician to Giulio di Giuliano de Medici, later wrote that the undercoat turned out to be “resistant to paints mixed with walnut oil.” As with the Last Supper, the fresco began to deteriorate almost as soon as Leonardo’s brush left it.viii By early 1506, Leonardo recognized that the fresco that was to be the crowning achievement of his career was ruined.

Battle of Anghiari, cartoon, ca. 1505. Copy by Peter Paul Rubens, ca. 1603.

Deeply disappointed by the outcome of his labors, Leonardo once again set his sights on the city of his erstwhile glory: the Duchy of Milan. A perfect pretext presented itself: he and his Milanese collaborator, Ambrogio de Predis, were still owed payments for their work on the second version of the Virgin of the Rocks, which de Predis had delivered to the Confraternity of the Immaculate Conception in 1502. The Confraternity claimed, however, that the painting was still “unfinished.” Ergo, Leonardo had to return to Milan and do whatever it took to see the client satisfied, and he and his partner paid.

Leonardo, however, was not free to pull up the stakes and leave Florence on a whim. He was still under contract to the Signoria, the Florentine government, and they were not likely to let him go when the Anghiari fresco was still unfinished and in urgent need of repair. What followed in 1506, therefore, was a period of tense negotiations between Leonardo and representatives of the Signoria, which stretched over several months.

I believe that during this period, when Leonardo needed every ally in the Florentine government to support his petition to leave for Milan, the urgency of the Giocondo commission once again presented itself. Throughout the preceding years, the unfinished portrait had probably been languishing in Leonardo’s workshop once the master became absorbed in the problems of the Battle of Anghiari. I think we can also safely assume that Francesco del Giocondo, never a patient man, sent repeated missives to Leonardo’s bottega at the Santa Maria Novella, inquiring about the status of his wife’s portrait. But as long as Leonardo worked on the Battle of Anghiari, there was little Francesco could do: the interest of the state trumped everything else.

However, with the news that Leonardo intended to depart from Florence, that particular alibi went out the window. Francesco had considerable influence among the Signoria, which could work in favor of Leonardo, or against him. Therefore, if Leonardo wanted to be free to pursue a job in Milan, there was no way he could get past Francesco del Giocondo, unless this client was appeased in some way.

This is the moment when, I believe, Leonardo charged one of his assistants to complete the Mona Lisa portrait, and on an expedited basis. The meticulous care he usually applied to his work, even when it involved background elements painted by an assistant, had to make way for the urgency of this task. That is the only viable explanation for the rushed execution of the remainder of the Earlier Mona Lisa, particularly the background, which is notably inferior to the portrait figure itself. The artist charged with this task, I suspect, may have been Ferrando Spagnolo, ‘Ferrando the Spaniard,’ who had previously worked on the second version of the Madonna of the Yarnwinder (Buccleuch Collection). There is some similarity between the background in this painting and that of the Isleworth Mona Lisa, both in terms of the color palette and the execution of the rocky formations.ix

The Earlier Version of the Mona Lisa (the “Isleworth Mona Lisa”), ca 1503-1506; detail of the background.

And so it was that the Earlier version of the Mona Lisa was presented to Francesco del Giocondo in the first months of 1506, which would fully confirm the third and most controversial part of Vasari’s testimonial:

Leonardo undertook to execute, for Francesco del Giocondo, the portrait of Monna Lisa, his wife; and after toiling over it for four years, he left it unfinished.

Now we know that Vasari was right all along.

The Louvre Mona Lisa

But what about the Mona Lisa portrait in the Louvre? How did that come about? As almost all authors have noted, stylistically the Louvre portrait belongs to Leonardo’s late period, roughly between 1507 and 1515. An important marker, in my opinion, is Leonardo’s forced return to Florence in 1507, in order to fight a lawsuit by his half-brothers who attempted to deny him the inheritance of his uncle Francesco. Leonardo probably believed that the matter would be dealt with within the span of a few weeks; hence, he did not travel with his entourage of assistants. But the mood in Florence, and particularly the Signoria, was against him. The lawsuit dragged on for months, well into 1508, leaving Leonardo marooned in Florence with little to do, other than to appeal to various dignitaries—including Charles d’Amboise in Milan and Cardinal Ippolito d’Este, the brother of Isabella—for help in resolving the matter.

This forced interlude was fortunate, however, in that it led to two initiatives. One, with plenty of time on his hands, Leonardo began to organize his notebooks. And two, he turned to the Ospedale di Santa Maria Nuova, a functioning hospital, to begin anatomical dissections of cadavers. By law, only the bodies of paupers or “ignoble” corpses could be used for dissection, but Leonardo ignored this and, among others, dissected the bodies of various women.x In the months and years to come, he would produce some two hundred detailed anatomical studies, based on the autopsies of some thirty cadavers, most of which are now in the Royal Collection of Windsor Castle.xi In probing the mysteries of the female body, and that of unborn fetuses, Leonardo was inexorably drawn to the ultimate enigma: how a woman nurtures and sustains life within her. Or as he had written in Milan, he wanted to understand “the conception of man,” and study “the form of the womb, and how the child lives in it, and to what stage it resides in it, and in what way it is given life and food.

Anatomical study of a woman, ca. 1508-1510.

Both the psychological and physical mysteries of motherhood would motivate two of Leonardo’s late paintings, the Saint Anne, Mary and Jesus now in the Louvre, and the Leda and the Swan, now lost except for copies by his assistants and others. The origins of the Saint Anne are still shrouded in mystery, as Vincent Delieuvin, the author of a major 2012 exhibition at the Louvre, attests. It may have originated as a commission by King Louis XII; as a painting for the Servite monks of the Santissima Annunziata in Florence; or simply as a further development of all of these initiatives. Significantly, Leonardo kept the painting with him until his retirement and death in Amboise, in France. Another painting he kept in his personal possession until the end is the Louvre Mona Lisa.

Perhaps this Mona Lisa, a second version based on the original portrait of Lisa del Giocondo, should be seen in this same context: Leonardo’s interest in maternity and the creative forces of nature. That he would produce two versions of the same painting is by no means unusual. Throughout his career, Leonardo (together with his assistants) would paint multiple versions of The Virgin of the Rocks, The Madonna of the Yarnwinder and the Saint Anne, to name a few, arguably to compensate for the fact that Leonardo’s workshop (in contrast to his competitors) produced only a small number of originals.

The Louvre Mona Lisa, ca. 1508-1515

As several scholars have noted, the enigmatic landscape of the Louvre Mona Lisa seems to illustrate Leonardo’s idea that the human body has analogous forms in nature. “Even though a man is composed of earth, water, air and fire,” Leonardo wrote, “his body resembles that of the earth; and as man has in him bones, the framework of his flesh, so the world has its rocks, the supports of the earth.” It therefore seems plausible to think that the Louvre Mona Lisa is the culmination of Leonardo’s growing interest in the symbiosis between motherhood and nature, and the idea that both stem from a common source: the mystery of creation. If this assumption is correct, then the Louvre Mona Lisa is no longer a portrait in the true sense, but rather an allegorical meditation on womanhood as the font of life, in harmony with the awesome, Genesis-like depiction of Creation around her.


So the inevitable conclusion is that Leonardo painted two portraits of Mona Lisa: one, the Isleworth (or Earlier) version of 1503-1507, as a commissioned likeness of Lisa del Giocondo; and two, the Louvre version of 1508-1515, as Leonardo’s depiction of the unfathomable mysteries of motherhood and human life.

For more information about the book The Mona Lisa Myth (2013), please visit or


i Serge Bramly, Leonardo: The Artist and the Man, 106. Leonardo would later describe this technique in his Treatise on Painting.

ii Codex Urbinas 110v.

iii Frank Zöllner, “Leonardo’s Portrait of Mona Lisa del Giocondo,” Gazette des Beaux-Arts, 121 (1993): 115-138.

iv Feldman, Stanley, et al., Mona Lisa: Leonardo’s Earlier Version. Zurich: The Mona Lisa Foundation, 2012; p. 66.

v Otto di Guardia 147, 19-20, as cited in Pallanti, Giuseppe. 2006. Mona Lisa Revealed: The True Identity of Leonardo’s Model. New York: Rizzoli.67.

vi The full title of the book, first published in 1550 and rereleased in an expanded edition in 1568, is Le Vite de’ più eccellenti pittori, scultori e architetti (Lives of the Most Eminent Painters, Sculptors and Architects). The paragraph reads: “Leonardo undertook to execute, for Francesco del Giocondo, the portrait of Mona Lisa, his wife; and after toiling over it for four years, he left it unfinished; and the work is now in the collection of King Frances of France, at Fontainebleau.

vii The original text of Vespucci’s handwritten note reads: “Apelles pictor. Ita Leonardus Vincius facit in omnibus suis picturis, ut enim caput Lise del Giocondo et Anne matris virginis. Videbimus, quid faciet de aula magni consilii, de qua re convenit iam cum vexillifero. 1503 8.bris,” in Veit Probst, “Rätselhafte Mona Lisa: Wer ist die geheimnisvoll lächelnde Dame auf Leonardo da Vincis Bild?” in UniSpiegel (Heidelberg: University of Heidelberg, 2008).

viii For more information about the Battle of Anghiari project, please see the new study by Margherita Melani, The Fascination of the Unfinished Work: The Battle of Anghiari (CB Edizioni, 2012).

ix Fernando “the Spaniard,” properly known as Fernando Yañez de la Almedina, would shortly thereafter return to his native Spain and execute a portrait of St. Catherine of Alexandria (1510), whose features betray the influence of the first Mona Lisa. The painting is currently in the Museo del Prado in Madrid.

x At some universities and colleges, autopsies for educational purposes—using the bodies of paupers and executed criminals—were limited to one per year, underscoring the delicacy of what Leonardo was doing at the Santa Maria Nuova. See Katharine Park, “The Criminal and the Saintly Body: Autopsy and Dissection in Renaissance Italy,” Renaissance Quarterly 47, no. 1 (Spring, 1994), 8.

xi The number of thirty cadavers, “both male and female,” is provided by Leonardo himself, based on an account of Antonio de Beatis, secretary to Cardinal Luigi d’Aragon, who paid a visit to Leonardo at the Chateaux de Cloux on October 10, 1517. Biblioteca Nazionale Vittorio Emanuele III, Naples, MS X F.28, f 77