From Captivity To Terrorism: The Unlikely Rise of a Legendary Pirate

Before L'Olonnais became one of the most legendary pirates in history, he was known as Jean-David Nau, and was born in 1635 to a penniless French family in a small seaside town. Because they were poor, his parents sold him as a slave to a sugar plantation in Martinique when he was just 15 years old. He was soon carted off to the Spanish-run island of Hispaniola (now known as Haiti and the Dominican Republic) where he endured endless hours of backbreaking work as an indentured servant with no compensation whatsoever for his efforts. These dark years galvanized his hatred of the Spanish who whipped, abused, and generally mistreated him for about nine long years before eventually releasing him.

In keeping with most men of his station, he was expected to become a farmer or something similar, which he instantly dismissed as being a colossal waste of time. Instead, he struck up with a bunch of shady Frenchmen wearing animal skins known as Boucaniers. He thoroughly enjoyed hunting wild pig and cattle and smoking their flesh over an open fire, until he finally realized he could be doing the exact same thing to those vile Spaniards and probably getting paid for it. Thus, his life as a privateer began.

The young man who was once Jean-David was ready to reinvent himself, taking on the more dashing name of L'Olonnais and moving to the French-controlled island of Tortuga in 1660. As a hot destination for scurvy men looking for booty of all kinds, the town was rife with disease-ridden "working girls," parlors, and plenty of trouble, all of which L'Olonnais took full advantage. Before long, he had signed on to a shipload of buccaneers who were primed to ravage the high seas in search of conquest, riches, and bloody revenge.

As a brutal member of the crew, he was known to be unforgiving and particularly fond of slicing random pieces of flesh from those his disliked, that is unless he chose to cut out their tongue instead. Once the Governor of Tortuga took stock of his natural abilities, L'Olonnais was awarded his own ship. He took on a slightly more respectable tone as captain, even bringing a priest onboard to bless his men. But when a surly heckler interrupted the prayer, L'Olonnias wasted no time in firing his weapon at the unruly mate and tossing him overboard.

While L'Olonnais was notorious throughout the West Indies for his depravity, his actions sometimes shocked even the most wretched among him. As he and his men set out to attack Puerto Cabellos and San Pedro, those pesky Spaniards seem to best him at every turn. Facing ambushes on all sides, his crew was soon diminished to almost nothing until he finally managed to turn the tides of the battle and capture the few remaining enemies.

Once in his gasp, they were mercilessly questioned about their knowledge of his tactics, but of course, the captives betrayed nothing. Frustrated by their lack of response, L'Olonnais drew a knife from his belt, cut out the heart of a pleading Spaniard, and began to gnaw on the bloody organ. Appalled and titillated, his crew cheered their victory but, given their diminished numbers and one remaining ship, assumed their adventures had come to an end, at least for a bit. But L'Olonnais, drunk with rum and bloodlust, was completely unfazed by their lack of manpower and readily pushed them forward to the next conquest.

It's important to note that L'Olonnais was technically not just any old pirate - he was a privateer with an official letter from the French government legally empowering him to plunder any Spanish galleon he came across. He saw himself not as a common thief but as a man liberated to work on his own account, no matter what that may be - answerable to no one but himself. With this license to kill, he was more than just a pirate; he was a French-sponsored terrorist who was free to whatever the hell he wanted, as long as it meant disrupting the transfer of wealth from the New World to Spain. And, without a doubt, he excelled at this mission, killing anyone who opposed him and happily licking the blood from his sword.

In the eyes of the Spanish, L'Olonnais was a force to be reckoned with. During the War of Devolution between 1667 and 1668, he launched many successful attacks against the Spanish, taking on the reputation of a notoriously frightening killer. Many men threatened by his opposition claimed they would rather die under his sword than be taken prisoner and forced to suffer the grueling torture for which he was famous. 

But his brutal wrath was not without backlash, and he stumbled on some bad luck in 1667 when he sailed into some stormy weather, and found himself shipwrecked off the western coast of the Yucatan. Even though he and most of his crew survived the ordeal, they were immediately set upon by the Spaniards on land who massacred the majority of his men. Seeing his chances were nil, L'Olonnais quickly rolled in the blood and sand, burying himself below the piles of dead bodies until the coast was clear. Then, disguised as a Spaniard, he made his way to Campeche where his unsuspecting enemies were celebrating his legendary death, and with the help of some slaves, made his way back to Tortuga where he instantly found new men and two small ships. The privateer was back in business.

Before long, the Spaniards were hip to his escape and figured out L'Olonnais was not dead after all. In their fury, a crew of pirate-hunters set out to destroy his crew and his ship, taking him alive so he could be tortured and killed at a later date. Similarly, his hatred of the Spanish had reached epic proportions, so he sailed to Cuba where he hoped to sack the town of Cayos. Even though the governor of Havana had established a 10-gun warship off the coast to defeat him, L'Olonnais deftly captured the enemy vessel by rowing right up to it in the dead of night, boarding it, and beheading every man on board, except one. That lucky soul was given a hand-written message to be delivered to the governor: I shall never henceforward give quarter to any Spaniard whatsoever. And he kept his promise.