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the influence of his family in the Grand Duchy of Florence. In the portrait he is dressed for winter, in a thick black monastic habit with a white long-sleeved shirt underneath. A large, eight-pointed cross of the Order of St John gleams on his chest in the half-dark. The habit marks him out as a Grand Cross of the order, the highest rank to which an elite Knight of Justice could rise. Martelli was indeed a member of the Venerable Council, an ally of Wignacourt and Malaspina. He had been appointed the order’s Prior of Messina in 1606,57 and was regarded in Medici circles as something of a phenomenon: as late as 1618, when Martelli was in his eighty-fifth year, the Grand Duke of Florence would appoint him General of Artillery in Tuscany. There is a strong sense of his formidable character in Caravaggio’s portrait, even a hint of hero-worship about it. As a child, thanks to the plague, he had known few men on whom to model himself. A man like Martelli may have awoken in him not only admiration, but something resembling the emotion of filial respect.

By November or December, Caravaggio was painting the Grand Master himself. According to Bellori he depicted Wignacourt both seated and standing with a page, but only the second picture survives. It can be seen in the Louvre. The painting is somewhat damaged but remains none the less an impressive essay in a type of grand manner portrait originally pioneered by Titian in his work for the Spanish royal family more than half a century earlier. It is a more old-fashioned, stiff, conservative work of art than the portrait of Martelli, which may be a reflection of Alof de Wignacourt’s unbending sense of his own importance. Instead of a monastic habit the Grand Master wears an ornate suit of mid sixteenth-century armour, a deliberate anachronism intended to evoke the glorious past, and in particular the heroism of the Great Siege. Bellori says the portrait was actually hung in the knights’ armoury, where the similarly ornate armour of Jean de la Valette was also displayed, which must have reinforced the association. He holds the baton of high office in his gauntleted hands.

Wignacourt had a prominent wart on the left side of his nose, which Caravaggio has been careful to shroud in shadow. The Grand Master looks off to one side, but his look, unlike that of Martelli, is neither introspective nor retrospective. He looks to the future with necessary vigilance, the guardian of Christendom’s frontline with Islam. While Wignacourt strikes a slightly creaking pose of authority, his adolescent pageboy enters the scene, stage right, with an expression of cool wariness in his wide and curious eyes. He holds the Grand Master’s helmet against his downy cheek, allowing its plumes to caress the side of his face. The pageboy’s identity is unknown, but a possible candidate is Alessandro Costa, son of Caravaggio’s patron Ottavio Costa. He had travelled to Malta on the same flotilla as the artist, entering Wignacourt’s entourage of pages on his arrival. Within the conventions of state portraiture, he represents innocent youth, in contrast with Wignacourt’s wise old age. But his presence also adds an irregular, unexpected frisson of eroticism to the scene. Caravaggio’s evident interest in the boy threatens to unbalance the composition.

By all accounts, Wignacourt was delighted by the portrait. The artist’s biographers are unanimous in asserting that Caravaggio received the cross of the Order of St John as a direct reward for the Grand Master’s portrait. Wignacourt may even have discussed the matter with him during sittings for the picture. If so, he would have made Caravaggio aware that there was a considerable stumbling block to the conferment of the honour. Having abolished the Knighthood of Magistral Obedience, the only kind for which Caravaggio might have been eligible, Wignacourt would have to appeal directly to Pope Paul V for permission to reinstate it: he was obliged to seek papal support whenever going beyond the letter of the order’s statutes. That is exactly what he did.

On 29 December 1607