David must have felt pretty lonely staring down Goliath with no one to back him up. David was just a young boy. Goliath was a mountain of a man, a head taller than any of the Israelites, and a fearsome fighter. Each day, he would venture out from Philistine lines to challenge any Israelite who would dare face him to a battle to the death. Each day, for 40 days, no man would dare risk his life. Then one day, David, the youngest of 7 brothers, took matters into his own hands and challenged Goliath to a duel. To this duel David brought only his sling and five stones from a nearby creek. He managed to strike Goliath in the head—or, if a modern translation is to be believed, the knee—and bring him to the ground. He then beheaded him and took his sword.

The moment that Caravaggio chooses to show here depicts two kinds of isolation—David’s in victory and Goliath’s in defeat. The battle for David represents an ascension of sorts, as it is this moment that shows that David is the rightful king of Israel. He stands alone as the only man brave enough to stand down the giant. For the deceased, the tortured expression on his face says it all. Additionally, Caravaggio’s rather personal touch adds a third dimension of isolation to this painting. The head is Caravaggio’s own. Goliath’s tormented expression parallels Caravaggio’s attitude at the time, as he was exiled and seeking a pardon and repatriation by Cardinal Borghese. David with the Head of Goliath, along with two other paintings, was created as a part-apology, part-bribe to convince Borghese to let him back into Rome. Tragically, he died on a ship on his way back to his home city, but his testament to pain and loss remains.