According to James Dennistoun, this small portrait on panel was in the collection of Giuseppe Crosti, an artist in Città di Castello who seems to have acquired it in Urbino. Dennistoun, author of Memoirs of the Dukes of Urbino, published in 1851, bought the panel from Crosti in 1838 and had it restored in the studio of Giovanni di Colombo in Rome. The panel was subsequently in several more collections including that of Thomas George, Lord Breadalbane Morgan, that of Baillie-Hamilton, and in the London collection of Leopold Hirsch. In 1934 it was acquired for the Thyssen-Bornemisza collection.
Both the identity of the sitter and the attribution have been debated since Crowe and Cavalcaselle drew the panel’s attention to a wider group of experts in 1870. In Dennistoun’s day the panel had an inscription on a parapet whose authenticity was widely questioned. It stated that the image was a portrait of Raphael aged six, painted by his father Giovanni Santi. When the painting was restored in 1963 it was determined that this inscription was later and it was removed. The painting was, however, published as a work by Giovanni Santi by Raimond van Marle when it was in the Hirsch collection and by Melozzo da Forlì in two catalogues of the Thyssen-Bornemisza collection following its acquisition. Berenson suggested that it was by Evangelista da Pian di Meleto, a pupil of Santi, then later attributed it to Santi. In 1964 Hendy considered it to be by Piero della Francesca, an attribution that various other authors accepted.
With regard to the sitter, the only hypothesis to date is that of Brinton, published by Hendy and in the catalogues of the Thyssen collection, but with reservations. Brinton based his identification on the similarity between this painting and the medal of Guidobaldo by Francesco di Giorgio of 1483. Guidobaldo di Montefeltro, who was born in 1472 and died in 1508, was the son of Battista Sforza and Federigo da Montefeltro, Dukes of Urbino, whose portraits by Piero della Francesca are in the Uffizi in Florence. Heir to the dukedom, Guidobaldo is depicted as a child in his mother’s arms in The Communion of the Apostles by Justus de Ghent in the Galleria Nazionale delle Marche and holding the ducal sceptre, next to his father, in paintings attributed to Pedro Berruguete in Urbino.
The Musée du Louvre has a portrait of Sigismondo Malatesta by Piero dated 1450 which repeats the composition of this panel: the sitter is in strict profile with pale flesh tones modelled to convey a great sense of volume. The handling of the light as it falls on the bust against the black background contributes to this effect. This simple image, in which the sitter is depicted without any accessories, may according to Hendy be a portrait made for Guidobaldo’s father who was absent during these years campaigning against Lorenzo de’Medici.