This Painting Helped Him Get Away With Murder

This piece is called David with the Head of Goliath by Caravaggio. You might look at it and wonder if that is a movie star holding a severed head, but this painting was actually created in the 1600s. It is a self-portrait of the artist as a decapitated head, sent as a bribe in hopes of securing a pardon after he committed a murder.

Throughout human history, many people have existed on this planet. Among them, a small fraction fall into the category of genuinely terrible people, and an even smaller fraction could be considered artistic geniuses. When those two circles overlap, you find the tiniest sliver of the population: people who are artistically brilliant but also extremely morally questionable.

That is where you find Michelangelo Merisi da Caravaggio. You could call him a sociopath or any other name you want, though you should not say it to his face unless you want a plate of food thrown at you or risk physical mutilation. Caravaggio was a volatile man, and to understand his final masterpiece, we must look at the story that inspired it.

The painting is based on the famous biblical account of David and Goliath. The Israelites were at war with the Philistines, who boasted a giant warrior named Goliath. He challenged the Israelites to single combat, but no one dared to fight him because he was nine feet tall and undefeated. Eventually, a young shepherd named David volunteered to face him with only a sling and a few stones.

First Samuel 17 describes what happened next: David reached into his bag, took out a stone, and slung it at the Philistine. The stone sank into Goliath’s forehead, and he fell face down. David then took the giant’s own sword and cut off his head. The passage notes that David was brought before King Saul while still holding the giant’s head, which is the exact moment Caravaggio captured.

In the painting, David stands at the entrance of Saul’s tent, showing off his trophy. David is carved out of the darkness by a harsh, dramatic light. He grips Goliath’s sword with his right hand, and in his outstretched left hand, he dangles the severed head by a fistful of dark, matted hair.

Artists had been depicting this story for centuries, almost always as a triumphant victory where a young hero stands bathed in glory. But in Caravaggio’s version, there is no celebration. The background is a suffocating, impenetrable wall of black. Although David just became a national hero, he does not look triumphant; he looks like he feels deep sorrow for his enemy.

Blood flows from Goliath’s neck, his jaw is slack, and his eyelids hang heavy over eyes drifting in different directions. His furrowed brow directs our attention to the spot where the stone struck him. But Caravaggio did not paint a random model as Goliath; he painted himself.

Why would an artist paint himself as a decapitated head? At the time he created this, Caravaggio was not just an artist; he was a wanted murderer and a fugitive with a bounty on his head. He was using this painting as a desperate plea—a get-out-of-jail-free card sent to those in power.

Caravaggio’s life was a chaotic mess of violence and instability. If he was sick, he would visit a local barber-surgeon, the same man who would cut his hair, balance his humors, and stitch his wounds, often with the help of leeches. It is a relief that those medical practices are firmly in the past, yet today we face the modern challenge of finding the right doctor.

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Caravaggio came to prominence after the High Renaissance. You can think of the High Renaissance as the peak of the era, when Leonardo, Michelangelo, and Raphael lived and worked simultaneously. After such an intense period, the art world seemed to suffer from a collective hangover, leading to the movement known as Mannerism, which was strange and uncertain.

Caravaggio, however, changed everything. The people in his paintings look like individuals you might pass on the street. He used a technique called tenebrism, which created dramatic contrasts of light and shadow, making his scenes look cinematic. He took sacred biblical stories and made them feel as though they were unfolding right in front of the viewer.

He painted his friend Mario in Boy with a Basket of Fruit, and he painted himself as Bacchus, the god of wine. Notably, he painted the Bacchus self-portrait while recovering from being kicked by a horse. He also created Boy Bitten by a Lizard, a painting much more provocative than one might expect from the era.

Caravaggio was adept at pushing the limits of what was acceptable in both his art and his personal life. Even before he arrived in Rome, he had legal trouble. One biographer, who knew him later in life, wrote a vague but damning account of a murder involving a prostitute, a tough guy, and a slain policeman.

Brothels were the center of social life for many artists in Rome. An underground economic system developed where painters exchanged their finished works for the services of models they could not otherwise afford to pay. If the artist became famous, the model could sell the painting as a way out of the profession.

Because of this, the most successful sex workers often modeled for the greatest painters. This dynamic should have caused conflict with the church, which commissioned much of the art, but nothing about Caravaggio’s world followed typical logic. He painted the biblical story of Judith beheading Holofernes, using a sex worker named Fillide Melandroni as his model.

Fillide’s pimp, a man named Ranuccio Tomassoni, likely felt uneasy about this arrangement, as every hour Fillide spent posing was an hour she was not earning him money. Meanwhile, Caravaggio enjoyed prowling the streets of Rome at night, armed and dressed in black.

Caravaggio understood that Rome’s most powerful men needed art, which gave him a degree of immunity. He believed he was untouchable, even going so far as to test that theory with violent outbursts. It was an open secret that he was involved with his studio assistant, Cecco, who modeled for him in various compromising positions.

A rival painter named Giovanni Baglione hated Caravaggio so much that he created a painting to insult him, portraying Caravaggio as the devil caught with a young Cupid. Since sodomy was illegal at the time, Baglione was essentially accusing Caravaggio of a serious crime.

Caravaggio’s response was to write a series of vulgar poems about Baglione and circulate them throughout Rome. He called him names like “Johnny Testicle.” Baglione sued him for libel, won, and Caravaggio was thrown in jail.

His history of violence continued to escalate. In 1604, he ordered a plate of artichokes at a tavern. When he asked the waiter which were cooked in butter and which were cooked in oil, the waiter told him to smell them to find out. Caravaggio reacted by smashing the plate into the server’s face, cutting open his eye.

In 1605, he got into an argument with a notary named Mariano Pasqualone over a woman named Lena, who was a courtesan and model. A few days later, Caravaggio snuck up behind the notary in the street and struck him in the back of the head with a hatchet.

These incidents were merely a glimpse into a pattern of disregard for the law. Everything came to a head on May 28, 1606, when Fillide’s pimp, Ranuccio, met Caravaggio at a tennis court to settle their differences. Tennis courts were the preferred location for sword fights at the time.

During the fight, Caravaggio sliced Ranuccio’s femoral artery, causing him to bleed to death. Caravaggio claimed he was not trying to murder him, but rather that he intended to castrate him and missed. It is a bizarre and tragic story.

Some historians believe Caravaggio was actually a part-time pimp himself, which would explain the conflict over models and his recurring legal issues. When the news of Ranuccio’s death spread, authorities issued a capital sentence, meaning anyone could kill Caravaggio without legal repercussions, and a bounty was placed on his head.

Caravaggio fled the city with Cecco. It was during this period of exile that he created David with the Head of Goliath. He intended it as a gift for Cardinal Scipione Borghese, the Pope’s nephew and a powerful art collector.

This is likely why David’s face shows such disgust; it was an emotional appeal to the Cardinal, suggesting that if he did not remove the bounty, he might regret the loss of the artist. Some believe the model for the painting was Cecco, while others argue that David is a self-portrait of a younger, innocent Caravaggio.

If that theory is true, it transforms the painting entirely. The inscription on David’s sword is often interpreted as an abbreviation for a Latin phrase meaning “humility kills pride.” The painting represents a man confronting the wreckage of his own life.

There is a theory that many artists of this period were violent because of lead poisoning from their paints, which can cause paranoia and sudden outbursts. They would drink alcohol to mitigate the symptoms, which only worsened the effects.

David with the Head of Goliath was delivered to Rome and successfully helped secure a papal pardon for Caravaggio. However, the artist would never live to receive it. Caravaggio died on July 18, 1610, at the age of 38, likely of sepsis or lead poisoning.

Given how he lived his life, it is a miracle he survived as long as he did. Caravaggio remains one of the greatest artists of all time, and his status allowed him to commit horrific acts that would have seen anyone else executed much sooner.

Perhaps that is why this painting feels so different from his others. It freezes him forever in a moment of profound desperation, begging for a pardon he would never live to see.