The Portrait of a Young Man Holding a Roundel (also known as Portrait of a Young Man holding a Trecento Medallion^[1]) is a painting attributed to Sandro Botticelli. Due to its style it has been estimated to have been painted around 1480.^[2] The identity of the portrait's subject is unknown, but analysts suggest it could be someone from the Medici family, as Lorenzo de' Medici was one of Botticelli's main benefactors.^[3]

The painting, thought to have been completed c. 1480, is believed to represent the beauty ideals^[4] of Renaissance Florentine high society.^[5] The young man's tunic is of a simple, fine quality with a blue color very rare at the time.^[6] The work was painted in tempera on poplar wood^[7] with a width of 38.9  cm and a height of 58.7  cm.^[1] The figure of the bearded saint in the trecento medallion^[8] was added after the portrait was completed and is believed to be an original by Bartolomeo Bulgarini, also known as the "Ovile Master".^[8] The medallion is very similar to other works by Bulgarini^[9] with a presumption that it was originally trimmed from a rectangular trecento.^[10] The young man is portrayed in front of a window frame in which the artist has fashioned a series of color planes.^[8] The inner frame is a uniform grey color, and appears to have a bright blueish tone to the left with a darker grey one in the right so the colors seem to change from left to right.^[8] One of the young man's fingers, supporting the medallion from below, rests on a bright grey strip at the bottom of the painting. The hand acts as a repoussoir that provides the illusion that the medallion is in another level within the painting.^[8]

The first modern record of the painting was in 1938, when it was owned by Baron Newborough of Caernarvon.^[1] At the time, the art dealer Frank Sabin^[2] visited the Newborough estate and appraised the painting's value.^[1] Lord Newborough was ignorant of the true value of the painting, so Sabin managed to buy the piece for a relatively low price.^[1] Art historians assumed that the painting came into the possession of the Newborough family when the 1st Baron Newborough, Thomas Winn, lived in Florence, Italy between 1782 and 1791.^[2][1]

Sabin sold the portrait to the collector Sir Thomas Merton in 1941 for a five-figure sum.^[2] During Merton's ownership the portrait was first described as a work by Botticelli.^[1] The attribution to Botticelli was doubted later, as prominent monographs on Botticelli did not include the portrait as one of his.^[9] Currently a majority of the art historians accept the attribution to Botticelli.^[2] While the Merton family owned the portrait, it became the subject of a poster for a Royal Academy of Arts Exhibition of Italian Art in 1960.^[11] In 1982, Merton's descendants sold the painting for £ 810,000 at an auction at Christie's.^[2]

After Sheldon Solow bought the piece in 1982,^[12][2] the portrait was loaned to major museums including the Metropolitan Museum of Art in New York, the National Gallery in London, and the Städel Museum in Frankfurt,^[3] where it was displayed in a Botticelli exhibition in 2009–2010.^[2] In January 2021, the portrait was sold at an auction at Sotheby's New York for more than US$92.2 million^[13] to a Russian-speaking collector.^[14] The price for the painting was the highest paid for a Botticelli and the highest for an Old Master work since Leonardo Da Vinci's Salvator Mundi sold in 2017.^[15]

• List of works by Sandro Botticelli