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Why This Macabre Painting Meant Life or Death for Caravaggio

An artwork that turns pain into compassion

8 min readOct 2, 2025

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Detail of ‘David with the Head of Goliath’ (c.1606–10) by Caravaggio. Oil on canvas. 125 × 101 cm. Galleria Borghese, Rome, Italy. Image source

If there was ever an artist immune to the call of the sedate life, then it was the Italian painter Caravaggio.

His volcanic temper was forever getting him into trouble.

For instance, when he slammed a plate of artichokes into a man’s face whilst working as a waiter. And the time he beat a man with a stick at 3 o’clock in the morning.

But the gravity of these episodes paled in comparison to the night of 29th May 1606.

The location was Rome. Caravaggio and three other companions arrived at a pallacorda court in the Campo Marzio — pallacorda was a Tuscan ballgame similar to tennis. According to reports, the posse was there to settle a gambling debt with a local gangster named Ranuccio Tomassoni. The dispute soon turned into a brawl, whereupon Caravaggio, who often carried weapons, reached for his dagger. Tomassoni was killed. Since the injury was to his groin, historians have since speculated that Caravaggio had intended to castrate his foe, positing that the dispute was actually over a local prostitute, Fillide Melandroni, one of Caravaggio’s female models over whom Tomassoni acted as her pimp.

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