It’s possible that Western art history wouldn’t have been the same without Sandro Botticelli. With members of the influential Medici family as his top patrons, Botticelli received many high-profile commissions, some of which are considered the Renaissance movement’s best achievements. Throughout the latter half of the 15th century, he produced secular portraits of Florentine elite, as well as religious and mythological scenes that defined a new era of artistic achievement. On the occasion of Sotheby’s sale this week of Botticelli’s rare single-figure portrait, A Young Man Holding a Roundel, which is expected to become one of the most expensive Old Masters artworks ever sold at auction, here is a guide to the artist’s career and seminal works.
Born in Florence around 1444–45, Alessandro di Mariano di Vanni Filipepi, also known as Sandro Botticelli, came from humble beginnings. His father was a tanner who placed a young Sandro under the apprenticeship of a goldsmith. But Botticelli’s preference for painting would lead him to the first stage of his artistic career when he was still a teenager. In the late 1450s, he entered the studio of the artist Fra Filippo Lippi, whose expressive figures and pale hues influenced Botticelli’s mature works. Botticelli also studied with other leading Renaissance painters like Antonio Pollaiuolo and Andrea del Verrochio, whose sculptures emphasized human anatomy in a way that would later appear in Botticelli’s art.
It was the Medici family that would go on to help mint Botticelli’s reputation. By the mid-15th century, the Medicis’ political and financial clout in the Republic of Florence established the family as the region’s de facto authority. Botticelli’s ascendant star rose alongside the reign of Lorenzo the Magnificent, who cultivated an elite circle of humanist scholars, art patrons, and bankers.
The family would go on to figure in the making of one of Botticelli’s earliest masterworks, Adoration of the Magi (1475–76), which was commissioned for the Gaspare di Zanobi del Lama altar at the church of Santa Maria Novella. Featuring a frontal view of the religious scene, the painting includes portraits of the three magi, whose faces are based on the visages of Medici family members. Also included is a portrait of the artist on the far right facing the viewer—a gesture toward his ties to the political family. Following the Pazzi conspiracy in 1478, which resulted in the assassination of Giuliano de’ Medici, Botticelli was commissioned to paint a commemorative portrait of the deceased leader above the Porta della Dogana in Florence.
A Prestigious Commission: The Sistine Chapel
As part of his landmark 1550 book Lives of the Most Excellent Painters, Sculptors, and Architects, art historian Giorgio Vasari wrote an account of Botticelli’s early career, focusing on the period before the artist took on painting commissions for Florentine churches, launching him to prominence. As Vasari tells it, in 1470, Botticelli established his own workshop, and by 1480, he had reached the apex of his career. In 1481, alongside artists Domenico Ghirlandaio, Cosimo Rosselli, Pietro Perugino, and others, Botticelli was among the several Italian painters hired to decorate the Sistine Chapel, as commissioned by Pope Sixtus IV. The exchange was a product of the Lorenzo de Medici’s diplomacy, which some historians have described as an attempt by the statesman to secure an alliance with the Pope. Positioned opposite the Papal throne, Botticelli’s painting, Temptation of Christ, portrays Christ’s various triumphs over a disguised Satan, as described in the Gospel of Matthew. As in his other religious paintings, Botticelli inserts homage to his patron here. The top left of the scene is a forest filled with oak trees, which would have been read as being symbolic of the powerful Della Rovere family to which Pope Sixtus IV belonged. At the center, the temple of Jerusalem is painted as the facade of the Chapel of Santa Maria in Traspontina of the Church of Santo Spirito in Sassia in Rome, a nod to the Pope’s church renovation project in 1475.
During the 1480s and ’90s, as Renaissance artists grew in prominence, Botticelli produced two of his most famous works: Primavera (ca. 1480) and the Birth of Venus (ca. 1485). Both feature mythological subjects that embody the values that took hold in Italy at the time. Many of those beliefs were derived from humanism, an intellectual movement that placed an emphasis on classical literature, philosophy, and science with the hope of moving toward a purer form of Christianity. Taking cues from images produced by ancient Greek artists, The Birth of Venus features a central female figure modeled on the sculpture Venus pudica. Famously, the image shows the goddess arriving on the shore of Cythera amid white-capped waves and floating flora. Many of Botticelli’s figures have naturalistic-looking bodies that were anatomically correct, but here, the artist took a different tack, slightly elongating Venus’s chest and using her form toward more expressive means.
And sometime around 1482, Botticelli completed the allegorical scene Primavera, which is believed to have been commissioned by Lorenzo di Pierfrancesco de’ Medici (a cousin of the politician and top arts patron) on the occasion of his wedding to Semiramide Appiani in May that year. Here, Botticelli’s figures are inspired by classical poet Lucretius’s “De Rerum Natura” and Ovid’s “Fasti” Roman festival calendar. Venus is again the central figure in this work, here representing marriage and fertility; her son Cupid is shown blindfolded and pointing an arrow of desire toward the Three Graces, which are symbolic of the virtues Chastity, Beauty, and Love. At the far left of the painting, Mercury clears wintry clouds away with his staff to ring in the beginning of spring, and to the far right of the painting Zephyrus, the west wind, pursues Chloris, initiating her transformation into Flora, the goddess of spring. The painting merges tropes derived from Gothic religious painting with the classical ideas favored by the humanists that were percolating during the early Renaissance. As scholar Lilian Zirpolo argues in Botticelli’s Primavera: A Lesson for the Bride, the work may have been meant to instruct a Medici bride about a woman’s role in marriage. Both paintings are currently held in the Uffizi Gallery in Florence, where they are among the two top attractions at the museum.
Though his mythology-inspired works are among the best known of his oeuvre, Botticelli completed a number of single-figure portraits as the genre became established in Northern Europe. Only eight portraits by the artist are known to exist, with most held in international museum collections. Among the most widely known of them is Young Man Holding a Medal of Cosimo de’ Medici (ca. 1474). With Flemish painting accessible through global trade, elements from those canvases were soon adopted by early Italian Renaissance artists. Drawing on the invention of Hans Memling’s work, which features a central figure set against a landscape, the Botticelli portrait offers a look at the Florentine humanist elite. The roundel the figure is holding is an emblem used in portrait painting to commemorate the dead or religious virtues.
Housed at the National Gallery of Art in Washington, D.C., another example of the sort, a portrait of Giuliano de’ Medici (ca. 1478–80), depicts the recently killed younger brother of Lorenzo. A dove in the foreground and an open window in the back, each symbols of death, are thought to commemorate the figure’s passing. Botticelli also broke with convention, continuing to push at the genre’s boundaries once more with Portrait of a Young Man (1480), now owned by the National Gallery in London. In this picture, the youthful subject is shown head on, his whole face in view—a deviation from the usual composition of Italian portraits of the era, which featured sitters turned away slightly from the viewer, leaving their faces partly unseen.
Primavera and The Birth of Venus are often considered Botticelli’s masterpieces, but in fact, the artist produced a greater volume of devotional subjects than mythological scenes. The Cestello Annunciation, which the artist completed in 1489 for Guardi family chapel in the monastery church of Cestello, is among his masterworks in that vein. Set before a grassy countryside, influenced by Flemish landscape painting, and taking place in a walled interior, the painting, which is now owned by the Uffizi, depicts the biblical episode in which the archangel Gabriel descends from heaven to tell the Virgin Mary she will carry the child of God. Botticelli emphasizes the drama of the moment, showing each figure in motion.
Another key religious scene in Botticelli’s oeuvre, this one made in circular format known as a tondo, is the Madonna of the Magnificat, in which the Virgin Mary pens the Magnificat, a Christian hymn in an open book, with the infant Christ on her lap, as as two angels crown her. Botticelli’s patrons may appear once more here—some historians argue the Madonna was made in the image of Lucrezia Tornabuoni, Piero de’ Medici’s wife. Paintings such as these are now considered highly valuable. In 2013, another widely known painting of the same imagery came up on the market. The Rockefeller Madonna, once owned by John D. Rockefeller, Jr., sold at Christie’s for $10.4 million.
Amid the Medici’s exile, which lasted until 1512 when the family resumed power, the final phase of Botticelli’s life coincided with a change in Florence’s political climate. With the city experiencing political turmoil, Botticelli’s late-career period was defined by his allegiance to the Italian friar and religious reformer Girolamo Savonarola. As the artist’s following of Savonarola’s moralistic teachings and condemnation of Florentine excess deepened, his style changed. By 1500, the artist focused his artistic output on devotional subjects, creating The Mystical Nativity (1500–01), merging the story of Christ’s birth and return at the end of the world into one canvas. According to scholars, the picture, which is now owned by London’s National Gallery, marks a return to medieval painting conventions. By Vasari’s account, Botticelli’s work fell out of favor during this period, although other contemporaneous records suggest that Botticelli remained a prominent figure in Florence, continuing to work for the younger Medici branch up until 1497. Botticelli died in 1510, with the Medicis still removed from power. From then on, his work went relatively unnoticed until renewed interest came in the 19th century.