Who exactly was Caravaggio's black-winged god of love? The secrets that masterpiece reveals about the rogue artist

A young lad cries out as his head is forcefully held, a large digit pressing into his face as his parent's powerful palm grasps him by the throat. That moment from The Sacrifice of Isaac visits the Uffizi Gallery, creating unease through the artist's chilling portrayal of the suffering youth from the biblical narrative. It seems as if Abraham, instructed by the Divine to sacrifice his son, could snap his neck with a single turn. Yet the father's chosen approach involves the metallic steel blade he grips in his other palm, prepared to cut the boy's throat. One certain element stands out – whomever modeled as the sacrifice for this astonishing piece displayed extraordinary acting skill. There exists not only dread, shock and begging in his darkened gaze but also deep sorrow that a guardian could betray him so completely.

He adopted a familiar scriptural story and transformed it so vibrant and visceral that its horrors seemed to happen directly in view of you

Viewing in front of the painting, viewers recognize this as a real face, an accurate depiction of a adolescent model, because the same youth – identifiable by his disheveled hair and almost black eyes – features in several other paintings by the master. In every instance, that highly expressive visage commands the scene. In Youth With a Ram, he peers playfully from the shadows while holding a ram. In Victorious Cupid, he smirks with a toughness acquired on Rome's alleys, his black plumed wings sinister, a naked adolescent creating riot in a affluent residence.

Amor Vincit Omnia, presently exhibited at a London gallery, constitutes one of the most discomfiting masterpieces ever created. Observers feel totally disoriented looking at it. Cupid, whose darts fill people with often agonizing longing, is portrayed as a very real, brightly lit unclothed figure, standing over overturned objects that include musical instruments, a musical score, metal armour and an builder's ruler. This heap of items resembles, intentionally, the mathematical and architectural equipment strewn across the ground in Albrecht Dürer's engraving Melencolia I – except here, the gloomy mess is caused by this grinning Cupid and the mayhem he can unleash.

"Affection sees not with the vision, but with the soul, / And thus is winged Love depicted blind," wrote Shakespeare, just before this work was created around 1601. But the painter's Cupid is not unseeing. He stares directly at the observer. That countenance – ironic and ruddy-faced, staring with brazen assurance as he poses unclothed – is the same one that shrieks in fear in Abraham's Test.

As Michelangelo Merisi da Caravaggio created his multiple images of the identical unusual-looking youth in Rome at the dawn of the 17th century, he was the highly celebrated religious painter in a city enflamed by religious renewal. Abraham's Offering demonstrates why he was sought to adorn sanctuaries: he could take a scriptural narrative that had been depicted many occasions previously and make it so new, so raw and physical that the horror seemed to be happening directly before the spectator.

Yet there was another side to Caravaggio, evident as quickly as he came in Rome in the winter that concluded the sixteenth century, as a artist in his early twenties with no mentor or supporter in the city, just skill and boldness. Most of the paintings with which he caught the sacred city's attention were everything but holy. What may be the absolute first resides in the UK's National Gallery. A youth opens his crimson lips in a scream of pain: while reaching out his filthy fingers for a cherry, he has rather been bitten. Youth Bitten by a Reptile is eroticism amid poverty: viewers can see the painter's gloomy chamber reflected in the cloudy waters of the transparent vase.

The adolescent wears a pink blossom in his hair – a symbol of the erotic trade in Renaissance art. Northern Italian artists such as Titian and Palma Vecchio portrayed prostitutes grasping blooms and, in a painting lost in the WWII but documented through photographs, Caravaggio represented a renowned woman prostitute, holding a posy to her chest. The message of all these botanical signifiers is clear: sex for sale.

How are we to make of the artist's erotic depictions of boys – and of one boy in particular? It is a question that has divided his interpreters ever since he gained widespread recognition in the 1980s. The complex past reality is that the artist was neither the queer icon that, for instance, the filmmaker put on film in his 1986 movie Caravaggio, nor so entirely pious that, as some artistic historians improbably assert, his Boy With a Basket of Fruit is actually a portrait of Christ.

His initial paintings do offer overt sexual suggestions, or even propositions. It's as if the painter, then a destitute young creator, aligned with Rome's sex workers, selling himself to survive. In the Florentine gallery, with this idea in consideration, observers might look to an additional initial work, the 1596 masterpiece Bacchus, in which the deity of alcohol stares calmly at you as he starts to untie the black sash of his robe.

A few years following the wine deity, what could have driven Caravaggio to create Victorious Cupid for the artistic collector the nobleman, when he was finally becoming nearly respectable with important ecclesiastical commissions? This profane pagan god revives the sexual provocations of his early paintings but in a more intense, unsettling manner. Half a century afterwards, its secret seemed clear: it was a representation of the painter's companion. A English traveller viewed Victorious Cupid in about the mid-seventeenth century and was told its figure has "the physique and countenance of [Caravaggio's|his] own boy or assistant that laid with him". The name of this adolescent was Francesco.

The artist had been dead for about 40 years when this account was documented.

Crystal Richardson
Crystal Richardson

A passionate cultural historian and writer based in Genoa, specializing in Italian art and urban heritage.