Portrait de Laurent II de Médicis, duc d'Urbino

The young man in the gold-trimmed coat is Lorenzo de' Medici, Duke of Urbino, grandson of Lorenzo the Magnificent and the man to whom Machiavelli addressed The Prince a few years before Raphael painted him. His uncle, Pope Leo X, had made him duke and was steering him toward a French marriage. Raphael's portrait was tied to exactly that. Made around 1518, it was sent to France to show off the bridegroom to the family of Madeleine de la Tour d'Auvergne. The wedding went ahead, and a daughter followed who would one day be Catherine de' Medici, queen of France. Lorenzo himself did not last long. He was dead by 1519, in his twenties, worn out by illness. The painting then dropped out of sight for centuries and resurfaced only recently, selling at auction in 2007 for a record price.