Who exactly was the dark-feathered deity of love? The insights that masterpiece reveals about the rebellious artist

The young lad cries out while his skull is forcefully gripped, a large thumb pressing into his cheek as his parent's powerful palm holds him by the neck. This scene from The Sacrifice of Isaac appears in the Florentine museum, evoking distress through Caravaggio's chilling portrayal of the tormented youth from the biblical account. The painting seems as if Abraham, commanded by the Divine to kill his son, could break his spinal column with a solitary twist. Yet the father's preferred method involves the silvery steel knife he holds in his other hand, ready to slit the boy's neck. A definite element remains – whoever posed as the sacrifice for this breathtaking piece demonstrated extraordinary expressive ability. Within exists not only fear, surprise and begging in his darkened gaze but also profound grief that a protector could abandon him so completely.

He took a well-known scriptural tale and transformed it so vibrant and raw that its terrors appeared to happen right in front of you

Viewing before the painting, observers recognize this as a real countenance, an precise record of a young model, because the same boy – identifiable by his tousled hair and almost dark eyes – features in several other paintings by the master. In every instance, that richly expressive face commands the composition. In John the Baptist, he gazes playfully from the darkness while embracing a ram. In Victorious Cupid, he grins with a hardness learned on Rome's alleys, his dark feathery appendages sinister, a naked adolescent running chaos in a well-to-do residence.

Amor Vincit Omnia, presently displayed at a London gallery, represents one of the most discomfiting artworks ever created. Viewers feel completely disoriented gazing at it. Cupid, whose arrows inspire people with often painful desire, is shown as a very real, brightly illuminated nude form, straddling overturned items that comprise musical devices, a musical score, metal armour and an architect's T-square. This heap of items resembles, intentionally, the mathematical and construction gear strewn across the ground in Albrecht Dürer's engraving Melancholy – save in this case, the melancholic disorder is caused by this smirking deity and the mayhem he can unleash.

"Affection sees not with the vision, but with the mind, / And therefore is winged Cupid depicted sightless," penned Shakespeare, shortly prior to this work was produced around the early 1600s. But Caravaggio's Cupid is not blind. He stares directly at you. That countenance – sardonic and ruddy-cheeked, staring with brazen confidence as he struts naked – is the same one that shrieks in terror in The Sacrifice of Isaac.

When the Italian master created his three portrayals of the same unusual-looking kid in the Eternal City at the start of the 17th century, he was the most acclaimed sacred painter in a city enflamed by religious renewal. Abraham's Offering reveals why he was commissioned to decorate churches: he could adopt a biblical story that had been portrayed numerous times before and render it so new, so raw and visceral that the terror seemed to be occurring immediately before you.

Yet there was a different side to Caravaggio, evident as soon as he arrived in the capital in the cold season that concluded 1592, as a artist in his initial 20s with no mentor or supporter in the urban center, only skill and boldness. The majority of the paintings with which he caught the holy city's attention were anything but holy. That could be the absolute earliest hangs in London's art museum. A young man parts his crimson mouth in a scream of agony: while reaching out his dirty digits for a cherry, he has instead been attacked. Youth Bitten by a Reptile is sensuality amid squalor: observers can see Caravaggio's gloomy room mirrored in the cloudy waters of the glass container.

The boy sports a pink flower in his hair – a symbol of the sex trade in Renaissance art. Venetian artists such as Titian and Palma Vecchio portrayed prostitutes grasping blooms and, in a painting lost in the WWII but documented through photographs, Caravaggio portrayed a famous woman prostitute, clutching a posy to her chest. The message of all these floral indicators is obvious: intimacy for purchase.

What are we to interpret of the artist's sensual depictions of youths – and of a particular boy in particular? It is a inquiry that has split his commentators ever since he achieved mega-fame in the twentieth century. The complicated historical reality is that the artist was neither the queer hero that, for example, Derek Jarman presented on film in his twentieth-century movie about the artist, nor so entirely pious that, as some art scholars unbelievably claim, his Boy With a Basket of Fruit is actually a portrait of Christ.

His early paintings indeed offer explicit sexual suggestions, or even offers. It's as if Caravaggio, then a penniless young artist, identified with the city's sex workers, offering himself to survive. In the Florentine gallery, with this thought in consideration, observers might look to another early creation, the sixteenth-century masterpiece Bacchus, in which the god of alcohol gazes coolly at you as he starts to untie the dark sash of his robe.

A several annums following Bacchus, what could have motivated Caravaggio to paint Victorious Cupid for the art collector Vincenzo Giustiniani, when he was finally becoming almost established with prestigious ecclesiastical commissions? This profane pagan god revives the sexual provocations of his early paintings but in a more intense, uneasy way. Half a century later, its hidden meaning seemed clear: it was a representation of the painter's companion. A British visitor viewed Victorious Cupid in about the mid-seventeenth century and was told its subject has "the body & face of [Caravaggio's|his] owne youth or assistant that slept with him". The identity of this boy was Francesco.

The artist had been deceased for about 40 annums when this story was documented.

Matthew White
Matthew White

A tech enthusiast and business strategist with over a decade of experience in digital transformation and startup consulting.