Who is Caravaggio’s black-winged god of love? What does this masterpiece reveal about the rogue genius? Art and design

TThe boy howls as his head is thrown down, a huge thumb pressing his cheek as his father’s strong hand holds him by the neck. This is the Sacrifice of Isaac, and I see it in the Uffizi Gallery in Florence, and I feel distressed by the way Caravaggio has so frighteningly transformed the face of this suffering child from the biblical story. It seems that Abraham, commanded by God to kill his son, could break his neck with just one blow. However, Abraham’s preferred method is to use the silvery gray knife he holds in his other hand, preparing to cut Isaac’s throat. One thing is for sure – whoever pretended to be Isaac in this amazing work was a great actor. Not only is there fear, shock, and pleading in his dark eyes, but there is also sadness that his guardian could betray him so completely.

When I stand in front of the painting, I know that this is a real face, an accurate record of a young model, because the same boy—recognizable by his disheveled hair and almost black eyes—appears in two other Caravaggio paintings. In each of them, this richly expressive face steals the show. In John the Baptist, he looks mischievously out of the shadows as he embraces a ram. In Cupid the Triumphant, smiling with the cruelty he learned on the streets of Rome, his black feathery wings devilish, he is a naked child who runs riot in a wealthy household.

Victorious Cupid, which goes on display this week at the Wallace Collection in London, is considered the most embarrassing masterpiece of all time. You feel completely thrown looking at it. Cupid, the god of love whose arrows fill people with often painful desire, is depicted as a very real being, brightly lit, inverted objects including stringed instruments, a music manuscript, a tablet shield, and an architect’s T-square. This pile of objects deliberately resembles the mathematical and architectural equipment spread across the floor in Albrecht Dürer’s engraving Melencholia I — except here, the dismal chaos is caused by a smiling Cupid and the mayhem he can unleash.

Before painting this painting, around 1601, Shakespeare wrote: “Love sees not with the eyes, but with the mind, and therefore the winged Cupid is painted blind.” But Caravaggio’s Cupid is not blind. He looks directly at you. That face—the mocking, red-cheeked one, staring with impudent confidence as he struts naked—is the same face that screams in horror at Isaac’s sacrifice.

When Michelangelo Merisi da Caravaggio painted his three portraits of the same funny-looking child in Rome at the beginning of the 17th century, he was the most popular religious artist in a city ablaze with the Catholic Renaissance. “The Sacrifice of Isaac” shows why he is required to adorn churches: he can take a Biblical story that has been depicted many times before and make it so fresh, raw, and profound that the horror seems to be happening right in front of you.

However, there was another side to Caravaggio, which emerged as soon as he arrived in Rome in the winter of 1592, as a painter in his early twenties with no teacher or patron in the city, only skill and daring. Most of the paintings brought to the attention of the Holy City were not holy at all. What may be the oldest works hanging in the National Gallery in London. A young man opens his crimson lips in a scream of pain: as he reaches out his filthy fingers for the cherry, he is attacked instead. The Boy Bitten by a Lizard is sensuality amidst misery: you can see Caravaggio’s gloomy room reflected in the murky waters of the glass vase.

The boy wears a pink flower in his hair – a symbol of the sex trade in Renaissance art. Venetian artists, such as Titian and Palma Vecchio, depicted courtesans holding flowers, and in a work that was destroyed in World War II but identified through photographs, Caravaggio depicted a famous courtesan, Filde Melandroni, holding a pose to her chest. The message of all these floral connotations is clear: sex is for sale.

What are we to make of Caravaggio’s sensual depictions of boys—and one boy in particular? It’s a question that has divided its translators ever since it achieved great fame in the 1980s. The complicated historical truth is that the artist was neither the exotic hero that Derek Jarman presented, for example, on screen in his 1986 film Caravaggio, nor was he quite so religious, as some art historians claim, that his Boy with the Basket of Fruits is actually a portrait of Jesus.

His early paintings feature explicit sexual propositions or displays. It is as if Caravaggio, then a penniless young painter, sympathized with the sex workers in Rome, selling himself to survive. At the Uffizi Museum, with this idea in mind, I turn to another early work, the 1596 masterpiece Bacchus, in which the god of wine stares at you coldly as he begins to untie the black ribbon of his robe.

A few years after Bacchus, what could have prompted Caravaggio to paint Cupid Triumphant for the art collector Vincenzo Giustiniani, when he had finally become almost respected in prestigious church commissions? This unholy pagan god revives the sexual provocations of his early works but in a more intense and difficult way. Half a century later, its secret became clear: it was a portrait of Caravaggio’s lover. British traveler Richard Symonds saw Cupid Triumphant in about 1649 and was told that his subject had “a body and a [Caravaggio’s] He has a boy or a servant who has slept with him.” This boy’s name was Sekou.

The painter had been dead for about 40 years when Symonds heard this. Similar tales have circulated about Italian artists in the past. Sculptor Donatello was allegedly obsessively in love with one of his apprentices, which makes sense if you’ve ever seen a nude bronze David. But was the story just a way to justify the Donatello statue’s overtones? Giorgio Vasari, the painter and historian, even spread rumors that Leonardo da Vinci “had as his assistant the Milanese Salai, who was exceedingly beautiful in grace and beauty, and had fine locks twisted into braids, with which Leonardo was very pleased.”

Was Caravaggio Secco’s painting a myth? No – because, as we have seen, the boy in this painting was the usual model for the painter in the early seventeenth century, as befits his presence in the artist’s home, as both apprentice and servant. In all three paintings he has an incredible presence and individuality – performing, one might almost say, in front of the camera, but in reality in front of his master. In two of the paintings, he was completely naked.

But the most intimate is John the Baptist. As John cradles a curly-horned ram, he sits on a red blanket lined with white pillows and cozy fur, his body streaked with light that catches his legs and shoulders while his penis is in shadow, though still visible. It’s supposed to be wild but it looks more like a bedroom, a room he looks at from a relaxed state, without feeling awkward at all. Meanwhile, the ram looks at it, and gets absorbed in it. Could this beloved face depict Caravaggio himself as the demonic, horned monster?

This certainly fits with the way Caravaggio’s enemy, the artist Giovanni Baglioni, saw him. In 1602, this far less talented rival painted Sacred and Profan Love, a response to Cupid the Triumphant, positioning himself as the Christian antithesis to Caravaggio’s demonic excesses. Baglioni depicts the angel of sacred love alternating between a red-bodied devil with features of Caravaggio and a “catamete.” The angelic savior looks lovingly upon the young man while the Caravaggio-faced devil fumes at being deprived of the object of his lust. It is a wicked parody of the triumphant Cupid who makes a grave accusation: Caravaggio is a sodomite and Cupid is his victim.

Caravaggio replied. He and his friend, the artist Orazio Gentileschi, published crude poems about Baglioni in the streets of Rome, accusing him – justifiably – of being a bad painter. Baglioni, in turn, accused them of defamation and took them to court. Gentileschi stated in his testimony that Caravaggio had recently visited his home to borrow a pair of bound wings, supposedly those worn by Victorious Cupid.

Caravaggio lost the case and faced further charges of violent crimes, until he was forced to flee Rome after killing a man in 1606. But his unbridled genius inspired an artistic movement across the continent. His radical and brutal style, his stark use of light, and his harsh everyday stories captured the imagination of young artists across Europe, from Orazio’s daughter Artemisia Gentileschi to Georges de la Tour, Diego Velázquez and the Caravaggisti of Utrecht. And of course, there was the Sicco del Caravaggio, as he became known.

Whatever Caravaggio did with Secco – we will obviously never know – he trained him to become a painter. Simmonds refers to the Cupid archetype as an artist in his own right: “Ceco del Caravaggio is well known among painters.” Cecco’s Interior with a Young Man Carrying a Recorder, in the Ashmolean Museum in Oxford, includes a skillful collection of objects, including fruit and musical instruments, very much in the mode of Caravaggio. What’s more, Caravaggesque is a vessel containing water in which we see distorted reflections, echoing the boy bitten by a lizard.

Should we know the private lives of artists? Vasari thought so. For some experts on Baroque art, the idea that Caravaggio wandered around Catholic Rome bragging about his sinful life is unbelievable — but his paintings do just that. What we can’t do is call him gay or queer in any comfortable sense. The past is another country and they wished there differently. The latest serious historical scholarship on male sexual relations in early modern Italy shows that despite church and court prohibitions, there was a lot going on.

Historian Michael Rock found that during a 70-year period in the 15th century, 13,000 men in Florence—a city with a population of 40,000—were accused of sodomy. Those who are convicted are usually fined, and often “offended” again. But the prevailing tradition is that mature men desire younger males: Leonardo with Salai, Caravaggio with Secco. As Caravaggio’s English contemporary Christopher Marlowe reportedly said: “Those who do not love tobacco and children are fools.” This strange and disturbing country of the past is what Caravaggio thrusts in your face.

Even in that world, Caravaggio was close to the edge, and there his art flourished, on the edge of danger. His “boy” exposes Sekou in ways that openly challenge the Church and has called Baglione out on it. Caravaggio is like the devil, Baglioni’s response to Cupid says: he is the embodiment of sin.

Four hundred years later, the great painting that would join Wallace’s collection might be better understood if we simply used that old word, “sin.” Caravaggio’s paintings tremble and evoke sin—the supposed sinful pleasures of sweet grapes, red wine, and sex. He came to see himself as a great sinner. He was: a murderer who spent his last years on the run, trying to atone with his art.

His quest for redemption, through painting altarpieces in southern Italy, plunged him into self-inflicted daydreams. He painted his face on the severed head of Goliath that the boy David was carrying. It is a haunting and haunted face: Caravaggio imagines himself being punished even after death, his eyelids drooping, his mouth open, as his head is held high by the young avenger. For his sins.