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Rogier van der Weyden was appointed official painter to the city of Brussels in 1436. His work for the city included paintings on the theme of justice for the court room of the town hall. Besides his official work, he was commissioned to do a large number of portraits, usually by distinguished patrons at the Burgundian court (Duke Philip the Good, his son Duke Charles the Bold, Philip de Croy, "Le Grand Batard de Bourgogne", Francesco d'Este, Nicolas Rolin etc.). He was a talented painter of portraits, who looked beyond the incidental details of his subjects.
This painting is the right wing of a diptych. The left wing - now in the Henry E. Huntington Library, San Marino - represents the Virgin with Child.
Philippe de Croy (1435-1511) was a member of the most distinguished Burgundian nobility; in 1457 he was chamberlain to Philip the Good, he was administrator of Hainault in 1456-1465, and finally, in 1473, he became a knight of the Order of the Golden Fleece. He would have been about 25 in this portrait. Van der Weyden portrayed him as a refined and pious man. The fact that he is depicted at prayer supports the notion that this male portrait originally formed the right-hand part of a diptych.
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