This is Biagio d'Antonio's most distinguished portrait, and was painted in around 1470. Its sculptural quality is indebted to the sculptor and painter Verrocchio, who had a deep influence on artists of Biagio's generation. In the background Biagio shows the valley of the Arno river with the city walls and cathedral of Florence.

The cocky sitter—to judge from his appearance no more than fifteen or sixteen years old—stands before an extensive landscape and stares confidently at the spectator. He is unidentified, but the view of the walled city of Florence in the middle ground on the left indicates that he was Florentine. He may even have been a member of the Niccolini family, since the portrait was sold from the Niccolini palace. If the Niccolini owned property in the countryside to the east of Florence, the prominent rolling hills behind the sitter may allude to their land holdings.

Parents usually commissioned portraits of their sons to commemorate important occasions, such as their leaving their homeland to work in distant cities. In this portrait, however, the sitter's pose has been interpreted as evidence that the painting is posthumous, on analogy with a carved relief of the deceased Filippo Brunelleschi (1377–1446) in the cathedral of Florence showing the great architect as if he were alive, standing in a similar attitude, bare-headed, with his left arm akimbo and his right hand holding the end of a chaperon, or cowl hood, the rest of which hangs down his back. Given the naturalness of the youth's pose, however, it is hard to believe it had such a specific meaning: as they walked through the streets of Florence, countless young men must have held their hoods this way.

When the portrait came on the art market, it was given to Botticelli (Berenson 1925), an indication of its high quality. The attribution persisted until Roberto Longhi, in an expertise of 1937, recognized it as a work by Biagio d'Antonio, a prolific Florentine painter whose historical identity was not established until the 1930s. Biagio d'Antonio was a contemporary of Botticelli (1444/45–1510), and like the young Botticelli he was influenced by Andrea del Verrocchio (1435–1488). Biagio was one of the team of artists including Botticelli, Cosimo Rosselli (1440–1507), Perugino (active by 1469–died 1523), Domenico Ghirlandaio (1448/49–1494), and Luca Signorelli (active by 1470–died 1523), who decorated the side walls of the Sistine Chapel in 1481–82. Not only did Biagio paint one of the main murals, the Parting of the Red Sea, he also executed secondary scenes in Ghirlandaio's Calling of the First Disciples and Rosselli's Last Supper.

Biagio's talent for portraiture is evident in the dozen or so animated faces he painted in the Sistine Chapel and in the three donor portraits he made of Niccolò Ragnoli, his wife, and son in the large altarpiece for the church of San Michele in Faenza (Philbrook Museum of Art, Tulsa, Oklahoma), a documented work of 1476. The present picture is one of three surviving autonomous portraits by Biagio, all of them bust-length portrayals of young men standing before landscape backgrounds. The other two are Portrait of a Boy (National Gallery of Art, Washington), set before an unusual landscape with jagged mountain peaks, and Portrait of a Young Man Wearing a Red Cap (Alana Collection, Newark, Delaware), set before a meandering river valley landscape. The MMA portrait is the earliest: reflecting Verrocchio's sculptural style, it probably dates from about 1470.

[2011]

The painting support is a single poplar board approximately 2 cm in thickness, with a mild convex bow. The x-radiograph reveals extensive worm tunnels made by wood-boring insects, and in the past the panel was thinned slightly on the reverse—exposing some of the tunnels—in order to stabilize it. In addition to weakening the wood support, this condition also caused damage to the ground and paint layers and a rather uneven picture surface due to collapsed tunnels.

The painting was prepared with white gesso-type ground. Traces of freehand incisions and a barbe from an original engaged frame are seen at all edges, within a border of originally unpainted (though now heavily overpainted) wood. Infrared examination [see Images] reveals that much of the composition was laid in with underdrawing applied with a brush. The underdrawing (describing contours, features, folds in the clothing, and the hills in the landscape on the left) was initially carried out in a very dilute and fluid medium that shows only minimally in the infrared image. This initial drawing was then reinforced with bodied black paint, applied very boldly, in select areas: the facial features and ear, contours of the face, neck, proper right hand, and proper right shoulder. The artist adjusted the position of the proper right side of the neck, the ear, and the contour of the proper right shoulder during this process. Some of the strong black secondary lines of underdrawing show through the paint where it is worn or has become more transparent over time, particularly around the nose, top of the chin, and below the proper left eye. Infared examination also reveals that the artist made changes to the position of the proper left hand, which was painted mostly if not entirely, over the red lake coat.

The painting appears to be mainly in tempera, but with some glazes in oil (no analysis has been undertaken). The overall effect of the paint is lush and resonant which, together with the strong composition and characterization of the young man, gives the portrait a powerful and engaging presence. The once-green copper glazes used in the landscape have darkened to brown. There is paint loss due to collapsed worm tunnels and to abrasion in the past, notably in cheeks, neck, parts of the jacket, the proper left hand, and the top of the sky. However, the painting reads well due to the skillful reintegration of these damages in a past conservation treatment.

[Extracted from the examination report by Charlotte Hale, 2010]

marchese Eugenio Niccolini, Florence (as by Sandro Botticelli; sold to Grassi); [Grassi, Florence, until 1925; sold to Lugt]; [Frits Lugt, Amsterdam, 1925; sold to Kleinberger and Lucerne Fine Arts Co.]; [Kleinberger, New York, 1925; sold for $100,000 to Friedsam]; Michael Friedsam, New York (1925–d. 1931)

New York. The Metropolitan Museum of Art. "The Michael Friedsam Collection," November 15, 1932–April 9, 1933, no catalogue.

New York. The Metropolitan Museum of Art. "Florentine Paintings in the Metropolitan Museum," June 15–August 15, 1971, no catalogue.

Berlin. Bode-Museum. "Gesichter der Renaissance: Meisterwerke italienischer Portrait-Kunst," August 25–November 20, 2011, no. 26.

New York. The Metropolitan Museum of Art. "The Renaissance Portrait from Donatello to Bellini," December 21, 2011–March 18, 2012, no. 26.

"Col. Friedsam Buys Famous Old Masters." Art News 23 (July 18, 1925), pp. 1, 3, ill., as by Botticelli, about 1470.

Bernard Berenson. Letter to Mr. Kleinberger. May 2, 1925, calls it "probably the earliest of all Botticelli's known portraits".

Bernard Berenson. Letter to Kleinberger. March 31, 1925, considers it "perhaps [Botticelli's] earliest portrait".

Bernard Berenson. Letter to Michael Friedsam. May 31, 1925, considers it the earliest of Botticelli's known portraits and dates it somewhat before 1470.

"Another Botticelli for America." International Studio 81 (September 1925), p. 467, ill., as by Botticelli, about 1470.

Bernard Berenson in The Michael Friedsam Collection. [completed 1928], pp. 73–74, attributes it to Botticelli, calls it an early work, and suggests that it may represent a member of the Niccolini family of Florence.

Raimond van Marle. "The Renaissance Painters of Florence in the 15th Century: The Third Generation." The Development of the Italian Schools of Painting. 12, The Hague, 1931, p. 46, fig. 11, attributes it to Botticelli.

Bernhard Berenson. Italian Pictures of the Renaissance. Oxford, 1932, p. 105, lists it as by Botticelli.

Bryson Burroughs and Harry B. Wehle. "The Michael Friedsam Collection: Paintings." Metropolitan Museum of Art Bulletin 27, section 2 (November 1932), pp. 35–36, no. 58, assign it to the Florentine school and date it to the last quarter of the fifteenth century.

Bernhard Berenson. Pitture italiane del rinascimento. Milan, 1936, p. 90, erroneously as "Ritratto di giovine donna".

F. Mason Perkins. Letter. March 24, 1938, attributes it to Botticelli.

Harry B. Wehle. The Metropolitan Museum of Art: A Catalogue of Italian, Spanish, and Byzantine Paintings. New York, 1940, pp. 42–43, ill., calls it Florentine and dates it to the third quarter of the fifteenth century, observing analogies to the work of Verrocchio, Pollaiuolo, Castagno, and Ghirlandaio.

Roberto Salvini. Tutta la pittura del Botticelli. Milan, 1958, vol. 1, p. 69, pl. 133 A [English ed., New York, 1965, part 2, p. 77, pl. 133a], rejects the attribution to Botticelli and calls it the work of an imitator, whose style resembles that of Jacopo del Sellaio and Raffaellino del Garbo.

Bernard Berenson. Italian Pictures of the Renaissance: Florentine School. London, 1963, vol. 1, p. 37.

Gabriele Mandel in The Complete Paintings of Botticelli. New York, 1967, pp. 88–89, no. 35, ill., gives an incorrect provenance.

Federico Zeri with the assistance of Elizabeth E. Gardner. Italian Paintings: A Catalogue of the Collection of The Metropolitan Museum of Art, Florentine School. New York, 1971, p. 146, ill., attribute it to Biagio d'Antonio, relating it to his "Portrait of a Boy" in the National Gallery of Art, Washington, and dating it to the same time, about 1480.

Burton B. Fredericksen and Federico Zeri. Census of Pre-Nineteenth-Century Italian Paintings in North American Public Collections. Cambridge, Mass., 1972, pp. 28, 523, 607.

Everett Fahy Harvard University. Some Followers of Domenico Ghirlandajo. New York, 1976, p. 207, attributes it to Biagio d'Antonio.

John Pope-Hennessy and Keith Christiansen. "Secular Painting in 15th-Century Tuscany: Birth Trays, Cassone Panels, and Portraits." Metropolitan Museum of Art Bulletin 38 (Summer 1980), pp. 16, 37, figs. 31–32 (color, overall and detail).

Charles Sterling. "Fouquet en Italie." L'Oeil no. 392 (March 1988), pp. 26–27 n. 16, fig. 5, attributes it to Biagio d'Antonio and dates it about 1480.

Everett Fahy. "The Argonaut Master." Gazette des beaux-arts, 6th ser., 114 (December 1989), p. 287.

Nicoletta Pons. Botticelli: catalogo completo. Milan, 1989, p. 104, no. 174, ill., gives an incorrect provenance.

Roberta Bartoli. Biagio d'Antonio. Milan, 1999, pp. 38, 91, 187, 191, 202, no. 18, ill.

Miklós Boskovits in Italian Paintings of the Fifteenth Century. Washington, 2003, p. 593 n. 18, suggests that this work and the "Portrait of a Man" (ca. 1460–65; National Gallery of Art, Washington) attributed to Piero del Pollaiuolo might both be commemorative portraits because of their similarity to Buggiano's sculpted commemorative portrait of Brunelleschi (Duomo, Florence), noting that all three depict the sitter bare-headed, with his head covering thrown over his right shoulder and the end held in his right hand.

Eleonora Luciano in Italian Paintings of the Fifteenth Century. Washington, 2003, pp. 132–33 n. 18, finds it closely related to Biagio's "Portrait of a Boy" (National Gallery of Art, Washington) of about 1475–80, but calls the MMA picture more advanced compositionally and so dates it after the Washington picture.

Dóra Sallay and Vilmos Tátrai in Botticelli to Titian: Two Centuries of Italian Masterpieces. Exh. cat., Museum of Fine Arts, Budapest. Budapest, 2009, p. 130, see a close relationship between the modelling of the head and that of Saint James in "The Virgin and Child Enthroned, with Five Saints and Two Angels" (Szépmuvészeti Múzeum, Budapest), attributed to the workshop of Verrocchio.

Keith Christiansen in The Renaissance Portrait from Donatello to Bellini. Exh. cat., Bode-Museum, Berlin. New York, 2011, p. 124.

Everett Fahy in The Renaissance Portrait from Donatello to Bellini. Exh. cat., Bode-Museum, Berlin. New York, 2011, pp. 132–34, no. 26, ill. (color) [German ed., "Gesichter der Renaissance: Meisterwerke italienischer Portrait-Kunst," Berlin, 2011, pp. 133–34, no. 26, ill. (color)].