Every picture or every artifact has its own history, which is sometimes very difficult to trace especially when till 1550 many artists did not sign their works. It used to be thought that the portrait of Ginevra de Benci was commissioned between 1474-1478 by a member of de Benci family, possibly by her father Amergo de Benci, who was a director of the Geneva branch of the Medici Bank and a wealthiest Florentine after the Medici, or as a wedding-portrait by her husband Luigi de Bernardo Niccolini. However, the newest studies narrowed the commission date to 1466-1468. They also brought us a lot of new information about the circumstances of the commission and about the commissioner himself. The recently discovered indications, Bembo-related manuscripts in Eaton College Library, strongly suggest that the commissioner was Bernardo Bembo, a Venetian ambassador and diplomat, close friend of Giuliamo de Medici. For the first time he met Ginevra on January 28, 1475, at the giostra (kind of carrousel) of Giuliamo de Medici in Florence. At the time of giostra Ginevra was at the age of seventeen, witty, beautiful, rich and married to a cloth-trader Luigi. Bernardo Bembo was in his early forties, with a wife and a son, and a mistress, and a love-child somewhere else in his life, but he threw himself in a "Platonic" affair with Ginevra. It was within the conventions of the day to have a cavaliere servante, but there is strong evidence that their relationship was not only strictly "Platonic".
After the childless death of Ginevra in 1520 it became the property of Niccolini family in Florence. It is also known that between 1478 and 1733 the portrait was shortened and may have originally include her hands as was shown in Leonardo's "Study of Hands" (1473, the Windsor collection). From 1733 it became the property of prince Carl Eusebius of Lichtenstain. In 1967 it was bought by Ailsa Mellon Bruce Foundation and placed in the Gallery of Art in Washington, were it can be seen.

The cost per square centimeter of paint of the portrait of Ginevra de Benci is the greatest in the history of collecting. Why is this portrait so precious, so significant? Maybe because the paintings by Leonardo da Vinci are so rare. Sure, it can be a good reason, but not only one. This Leonardo's work, as many other works by him was not signed. Author's authenticate expertise are quite expensive and time consuming. We know from contemporary sources and from Leonardo himself, that someone from the circle of de Benci family in Florence commissioned such a portrait. On the base of this information it was rather easy to identify the sitter - Ginevra de Benci - whose first name means juniper (ginepro) and the juniper bush can be seen on the background of the portrait. Also on the background the laurel and palm, the emblem of the commissioner, Bernardo Bembo, is shown enclosing the spring of juniper. Furthermore, the portrait reveals Leonardo's incomparable technical skill characteristically for Leonardo. There are passages such as the modeling of the lips, which Leonardo never surpassed in delicacy. The alabaster smoothness of the Ginevra's face was a desired effect that Leonardo accomplished by smoothed the surface of the paint with his own hands. Such value transitions are miracles of technique, and Leonardo was the first painter to have the perfect control of his medium necessary to make light and shade merge imperceptibly.

In his drawings, Leonardo several times compares curls of hair to swirling water. The ringlets that frame Ginevra's face resemble cascading whirlpools. These curls are so like Leonardo's rendering both of hair in his other paintings and of water in his drawings as to be a virtual signature. Lastly there are Leonardo's colored reflections discussed at length in his "Treatise on painting". In Ginerva's portrait such reflected colors reverberate through the painting and course the flesh to glow as if, like the moon, it reflected some hidden radiance.

One more the most important reason, is that it is the first psychological portrait ever painted and one of the first the three-quarter or frontal view of the sitter. Leonardo's tremendous innovation was developed in his four portraits of women where each woman express different mood: the earliest Ginevra withdrawn sadness or melancholy, the next Celicia Gallerani appealing wistfulness, the portrait of Lucrezia Crivoli withdrawn happiness, and the last the Mona Lisa mirthless amusement. Of these, the most original is the enigmatic melancholy of Ginevre de Benci. Leonardo's sensibility shows us her beautiful, melancholic, alabaster face framed by little cascades of curly, glossy hair. Her eyelids are heavy, her gaze abstracted, her beautiful eyes are looking into a distance but they do not seem to see. She seems to be listening to the sounds of her thoughts. The reason of her melancholy is unknown, but it is possible that beneath it the real heart that gets broken is hidden. Sadness has rarely been represented in portraiture before the seventieth century, and even then the tragic view of life was usually conveyed by portraits of men, not of woman.