Portrait of alof de wignacourt and his page, 1608 by Caravaggio

Caravaggio here toned down and 'improved' certain physical peculiarities discernible in Portrait of Alof de Wignacourt and His Page: the ear is less pointed, the nose less pronounced and the skin less wrinkled. But he also transformed its restless, brooding and pessimistic quality into a more extrovert, 'sergeant-majorish' characterization which combines physical with mental alertness and stresses the public side of the Grand Master's powerful personality. Wignacourt, one of the outstanding Grand Masters, had joined the Order in 1564 at the age of seventeen and distinguished himself at the Great Siege of Malta of 1565.

But despite the notable achievement of being responsible for building the Malta aqueduct and sponsoring several successful, if inconsequential, expeditions against the Turks, the superficial splendour of his rule concealed the Order's substantial decline by the early seventeenth century, both in terms of military power and ecclesisatical jurisdiction.