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The young man with very short curly hair, dressed in black, is sitting in prayer towards the left. He is in the corner of a room with a view through a window left and right over a hilly landscape at a lower level. In the left foreground in a kind of fortified inner garden are the Virgin and Child under a lean-to roof, flanked by two angels, one of which is playing a lute. Joseph is drawing water in a jug. The background shows the silhouette of Bruges seen from the Minnewater. In front we see the Minnebrug (bridge) between the two towers, while at the back loom the towers of Our Lady's Church and probably St Donatian's Church.
The portrait was ascribed to Memling until the beginning of the 20th century, when the hand of the Master of the Legend of St Ursula was recognized. Since then this attribution has generally been accepted as correct. Technically it is one of the most carefully painted portraits by this contemporary of Memling. Although related to the latter's portraits, the conception here is definitely different. Not a full landscape, but two views on either side, draw the eye into the depth. The lighting too is not at right angles with the surface of the painting, but frontally onto the head and hands, which creates stronger shadows. Both of these distinguishing marks are typical of this minor master. Owing to the size and the red colour of the reverse, the Virgin and Child of the Fogg Art Museum was assumed to be the portrait's counterpiece. This connection has not yet been proved but is quite possible. The nature of the decorative inscriptions on the reverse point in this direction.
The sitter was identified as Ludovico Portinari, nephew of Tommaso and brother of Benedetto and Folco, whose portraits were painted by Memling. Ludovico was appointed in Florence in 1479 as the successor to his other uncle Accerito.
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