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Ancient Rome

When pirates kidnapped Julius Caesar (and lived to regret it very briefly)

A young and cocky Caesar fell into the hands of the Mediterranean pirates, became their best friend, promised them between laughs that he would crucify them all… and, once free, kept his word to the letter · Aegean Sea, around 75 BC

23 May 2026 · 15 min
A young Julius Caesar in a toga smiles defiantly with arms crossed, surrounded by armed pirates on a ship's deck in the golden Mediterranean light

This is one of the best stories in all of antiquity, and the astonishing thing is that almost nobody knows it. It is about a conceited twenty-something, brilliant and dangerously sure of himself, who falls prisoner to a band of pirates, spends his captivity treating them like servants, promises them, splitting his sides with laughter, that he is going to crucify the lot of them, and then, once free, hunts them down across the Mediterranean and keeps his promise with a coldness that makes your hair stand on end. Oh, and the twenty-something was called Julius Caesar. Yes, that Julius Caesar. Come with me, dear readers, to meet the future master of Rome when he was still a kid with an outrageous amount of nerve.

A young man with airs, bound for Rhodes

The year was roughly 75 BC. Julius Caesar was then a young man of about twenty-five, still a very long way from being the conqueror of Gaul and the master of Rome. He belonged to a patrician family fallen on hard times, he had enormous political ambitions and, above all, a self-esteem the size of an aqueduct. Like every well-bred young Roman worth his salt, he was travelling east to perfect the art of oratory, essential for success in Roman politics.

His destination was the island of Rhodes, where he meant to study with a famous master of rhetoric. So he boarded a ship and set sail across the Aegean. What young Caesar did not expect was that this sea was infested with a fearsome plague: the Cilician pirates, so called because they came from Cilicia, on the coast of present-day Turkey. Those pirates were the scourge of the Mediterranean, assaulting ships, sacking coasts and kidnapping wealthy travellers for ransom. And a Roman patrician travelling with a retinue was a luxury morsel.

The kidnapping and the most extraordinary ransom

Near the small island of Pharmacusa, the pirates boarded the ship and captured Caesar. For them, the perfect client: young, rich, of an important family. They reckoned his worth and demanded a ransom of twenty talents, a considerable sum. And here comes the first delicious detail of this story, the one that defines the character.

Because Caesar, instead of being terrified or relieved, was offended. Only twenty talents? For him? He burst out laughing and told his captors they had no idea whom they had captured, that he was worth a great deal more, and that they should ask for at least fifty talents. You read that right: the kidnapped man scolded the kidnappers for asking too little money, and demanded that they raise his own ransom. The pirates, astonished, gladly accepted (more money for them). Caesar sent his companions off to the nearby cities to gather the fortune, and stayed behind himself as a hostage, almost alone, among the band of outlaws. Thirty-eight days of the most peculiar captivity were beginning.

The captive who ruled over his captors

What happened during those nearly six weeks is one for the frame. Because Caesar did not behave for a single day like a frightened prisoner. He behaved as if the pirates were his personal escort and he the chief. He took part in their games and physical exercises as if he were one more of them, but giving orders. When he wanted to sleep and the pirates made noise, he ordered them to be quiet, and they, bewildered, obeyed.

But the best detail is the literary one. Caesar, who fancied himself a great orator and poet, wrote poems and speeches during his captivity and then read them aloud to the pirates, expecting admiration. And when those rough outlaws failed to applaud his verses with the enthusiasm he considered they deserved, Caesar insulted them to their faces, calling them illiterates and uncultured barbarians incapable of appreciating genius. Picture the scene: a kidnapped man calling his armed-to-the-teeth kidnappers ignorant for not appreciating his poetry. That lad had a fine pair of something, very well placed indeed.

Julius Caesar, young and in a toga, recites his poems with a theatrical gesture to a group of bored and bemused pirates in the ship's hold, lit by a lantern
Caesar reading his verses to the pirates, who did not applaud enough

The promise that sounded like a joke

And amid all those eccentricities, Caesar had a habit he repeated over and over, always with a grin from ear to ear. He warned them, laughing, of what he intended to do with them the moment he got his freedom back.

He would throw it in their faces, hugely amused, without the slightest disguise, something like:

«Laugh now, my friends, enjoy yourselves. Because the moment I am free, I will come back for you, I will capture you all and crucify every last one of you.»

The pirates roared with laughter. To them it was the height of comedy: the conceited boy they had grown fond of (because, it must be said, they liked Caesar, he was fun and easy-going) joking with his little crucifixion routine. They saw it as the likeable bragging of a kid with too much gift of the gab. They had become almost friends, after all. How could he be serious? Poor fools. They had understood absolutely nothing. When Caesar smiled and promised to crucify you, he was not joking: he was informing you.

Free, and with a very clear agenda

At last the fifty talents of the ransom arrived, gathered in the city of Miletus. The pirates collected, kept their side of the bargain and set Caesar free, safe and sound, on dry land. For them, a tidy bit of business and case closed. Goodbye to the likeable lad of the verses and the funny threats. On to the next thing.

But Caesar, the moment he set foot on land, did not waste a single second. He did not go off to celebrate, nor to continue his journey to Rhodes, nor to give thanks for being alive. He went straight to the port of Miletus, hastily gathered a few ships and some armed men at his own risk (he held no official post that allowed him to, but that sort of thing never bothered him much), and threw himself out to sea after his former captors. The day's agenda had a single item, and it was not exactly to forgive.

The hunt

And here the pirates made their final mistake: they were still sitting pretty, anchored near that same island of Pharmacusa, dividing up the loot, without imagining what was coming for them. Why would they flee? The matter was settled, they had been paid, all at peace.

Caesar fell upon them by surprise. He captured most of the band without much trouble, recovered his fifty talents into the bargain (the clever devil even took back the ransom money) and seized the rest of their booty as a prize. Those men who a few days earlier had laughed at the boy's jokes were now his prisoners, in chains, beginning to suspect, far too late, that perhaps the «jokes» had not been so much of a joke. Caesar took them ashore and locked them up in a prison in the city of Pergamon, to await what he had always promised them.

A fleet of Roman war galleys with oars and sails pursues the fleeing pirate ships across the sea at sunset, near a rocky Aegean island
Caesar raised a fleet in Miletus and hunted down his former captors

The governor who hesitated and the Caesar who did not

Here a very Roman bureaucratic obstacle arose. The authority to try and punish those criminals belonged officially to the Roman governor of the province of Asia, a certain Junius. So Caesar went to him to have him order the execution of the pirates. But the governor began to stall and to drag his feet. The reason? He had set his eye on the loot and the prisoners: he thought he could make good money selling them as slaves rather than executing them. Greed, as you know, muddies everything.

Caesar was not a man to wait for an indecisive official to make up his mind while he calculated profits. He lost patience. So he did what he did best: take the initiative on his own, without asking permission. He returned to Pergamon, where he had the pirates locked up, and set about personally fulfilling the promise he had made them so many times between laughs. If official justice hesitated, Caesar's justice did not.

The promise kept (with a touch of «mercy»)

Caesar ordered all the pirates crucified. All of them. Exactly as he had announced over and over during his captivity, while they split their sides believing it a jest. The likeable bragging of the boy of the verses turned out to be, word for word, an advance death sentence. Forewarned is forearmed.

But the story has one last detail, and it is the one that turns it into a small masterpiece on this man's character. It turns out that Caesar, deep down, held a certain fondness for them: during the captivity they had treated him rather well, without abusing him. So he showed them a gesture of «clemency», a touch of gratitude. Crucifixion was an atrocious and very slow punishment: the condemned could take days to die, in agony and torment. Well then, Caesar ordered that, before nailing them to the cross, their throats be cut. A quick and clean death, to spare them the prolonged suffering. That was his thanks for the good treatment received: cutting their throats first so they would not suffer on the cross.

Pause a moment to savour the lesson, dear reader. To Julius Caesar, that was a compassionate gesture, almost tender. «I am going to crucify you, yes, because I promised it and because you are pirates; but since I rather liked you, I'll kill you quickly first so it won't hurt.» If that was his version of mercy, you can well imagine how he handed out cruelty.

The portrait of a dangerous man

This anecdote, told to us by ancient historians such as Plutarch and Suetonius, is much more than an amusing curiosity. It is a perfect psychological portrait of the man who, decades later, would conquer Gaul, cross the Rubicon and make himself master of the Roman world. It was all there already, in that kidnapped twenty-something: the absolute self-confidence, the charisma that won him even the affection of his enemies, the contempt for rules and hierarchies when they got in his way, the ability to act on his own over the heads of authority, and that implacable coldness that let him smile at a man and plan his death at the same time.

The pirates made the mistake of judging Caesar by his likeability. They saw a charming, joking lad, and did not realise that behind that smile lay an iron will that did not know how to bluff. It is one of the great lessons of history: beware of men who threaten you laughing, because sometimes the ones who smile the most are the ones who joke the least.

The Mediterranean of pirates, corsairs and vengeances served over the waves is a setting I am passionate about, and to which I devoted my book «Malta 1565», where fearsome corsairs like Dragut ply that same sea centuries later. If that world of sea, daring and blood fascinates you, you will find it in its pages. History as it was never told to you.

✠ Recommended reading ✠

Malta 1565 · The Great Siege of Malta

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✠ David S. Matrecano
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