Caravaggio was in Malta by July 1607. He had gone there, according to Bellori, because he 'was eager to receive the Cross of Malta which was usually given as an honour to notable persons for merit and virtue'. Whatever his motives, he was probably introduced to the island through Ippolito Malaspina, Prior of the Order of the Knights of St. John in Naples and a relative of Caravaggio's Roman patron, Ottavio Costa. While on the island Caravaggio is known to have painted at least two portraits of Alof de Wignacourt (1547-1622), the French Grand Master of the Order from 1601.
One of them depicts Wignacourt standing and in armour and is now in the Louvre, the other showed him in robes and seated, a picture possibly represented by a copy surviving at Rabat, Malta. The present work has only recently been attributed to Caravaggio by Mina Gregori and interpreted as an unidealized 'study' for the Louvre portrait, which it resembles in the pose of the head and torso. The attribution to Caravaggio seems indisputable on technical grounds, and the identification of the sitter is also convincing. Even if we choose to define the work as a study, however, it is certainly neither unfinished nor merely a sketch, for the rather summary handling of some passages, such as the left hand, as well as the tendency of the reddish-brown ground to show through in several places, are features common to other late works.