The date 1514 is just visible on the letter carried by the sitter, although the words are illegible. The melancholy mood of the painting is underlined by the inscription on the parapet which reads, in primitive French, ‘who loves well is slow to forget’.

The unknown young man wears the Maltese Cross of the Order of Saint John. It has been suggested that he may be Giulio de’ Medici, from the ruling family of Florence. In 1513 Giulio’s cousin Giovanni de’ Medici became Pope Leo X and made Giulio a Knight of Rhodes. The Knights lost Rhodes to Sultan Suleiman the Magnificent in 1523 and stayed in Rome, Viterbo and elsewhere while seeking a new base. After he was elected Pope Clement VII in 1523, Giulio was personally responsible for establishing the Knights on the island of Malta in 1530.

In 1514 Franciabigio was working for the Order, painting a fresco of the Last Supper in the refectory of their Convitto della Calza in Florence.The prioress of the convent, Sister Antonia, was a Medici. She is identified by an inscription on the fresco at the lower left, and the wine jugs on the table are painted with the Maltese Cross and the arms of the Medici. It is possible that she also commissioned this portrait as a memento of her relative.

Giulio de’ Medici’s mother was Fioretta Gorini (Fioretta is a diminutive of Antonia); his father Giuliano de’ Medici was assassinated a month before his birth. He was only legitimised and his parents’ marriage recognised in September 1513 (by Leo X). One theory is that Sister Antonia may have commissioned both the portrait and the fresco to commemorate this long awaited legitimisation as part of the Medici family.

Franciabigio’s portraits are among his finest works for their immediacy and psychological intensity. The composition and pose of the sitter here recalls in reverse Franciabigio’s Portrait of a Man with Gloves (Uffizi, Florence), also signed and dated 1514. In that painting Franciabigio experiments with a new approach to ordering the sitter’s features – his eyes, the line of his mouth and tilt of his head all lie parallel to the angle of his cap. This approach is reused and perfected in the Portrait of a Knight of Malta, suggesting that it was completed after the Uffizi portrait.

The painting is influenced by the work of Andrea del Sarto, with whom Franciabigio was friends and shared a workshop. From Sarto he adopted the soft smoky shadows of the face, the smouldering melancholy expression seen in the almost contemporaneous Portrait of a Young Man, and the pose of his nearly contemporary portrait of a woman known as Lucrezia (Prado, Madrid). However, the composition ultimately derives from portraits painted by Raphael during his period in Florence, which had a significant impact on other artists working in the city, such as Ridolfo Ghirlandaio and Rosso Fiorentino.

The inclusion of a parapet is a feature common to Venetian portraits of this period. It is used to set the figure back in pictorial space and to neatly crop the lower part of the body. Franciabigio takes the illusion a step further and allows the knight’s sleeve to hang over the edge of the parapet into our space, which again recalls the art of Venice, particularly the pose of Titian’s Portrait of Gerolamo (?) Barbarigo of about 1510.