Who was Francois L’Olonnais, you ask? He was not only a real, living historical figure, but he was also the most ruthless and fearsome pirate to ever sail under the black flag. And given the overall brutality of 17th-century life on the high seas, that is one hell of a claim. Born in France and sold into indentured servitude at a young age, his early sufferings were largely captured in the pages of The Buccaneers of America by the Dutch writer Alexandre Oliver Exquememlin, first published in 1678. His accounts are both first hand and based on stories from the survivors of his crew, providing a rare glimpse into the fascinating details of the French presence in Hispaniola and the shrewd strategies and navigation of history’s greatest debauchers. It was through these popular writings the world was able to see the true intrigue, greed, and recklessness of the Spanish Main and the sordid buccaneers who ruled the politics of the sea.

It is said the dark years of L’Olonnais’s early life are what led him to such an appetite for destruction, eventually propelling him to the top of the criminal food chain. Through years spent on nefarious enterprise and wickedness, L’Olonnais eventually evolved into more than just a pirate—he became the bane of the Caribbean and one of the most deadly figures to ever capture the attention of seafaring history. He was a badass marauder who dominated the Golden Age of Piracy—not because he was clever or sadistic or fearless or dashing, but because he embodied all those characteristics—while still managing to pull in more booty than any other privateer in seafaring history. Nicknamed the “Flail of Spain” for the uncontrollable fear he provoked in others, his life as an adventurer bent on treasure, destruction, and revenge left a bloody wake through the Caribbean and gave his name legendary status.

Before L’Olonnais became noticed as one of the most memorable 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. Out of financial desperation, his parents sold him into slavery on a sugar plantation in Martinique when he was just 15 years old. He was then shipped off to the Spanish-run island of Hispaniola (now known as Haiti and the Dominican Republic) where he could really get to work, enduring endless hours of backbreaking work as an indentured servant. He received no compensation whatsoever for his labor and was stuck in a brutal environment without his family or the hope of a future. This dark period galvanized his hatred of the Spanish who whipped, abused, and generally mistreated him for several years before they finally released him into the wide world. At this point, he was still just a  young man, without money, education, or prospects.

In keeping with most men of his station, he was expected to become a farmer or something similar, a possibility he instantly dismissed as being a colossal waste of time. Instead, he struck up with a shady collection of rogue Frenchman, pirates, servants, and escaped African slaves, most of whom wore animal skins and called themselves Boucaniers. These guys knew how to live— hunting wild pig and cattle and smoking the fresh meat over an open fire, and they lived on their own terms. But even though this way of living appealed to his inner rebel, L’Olonnais still had burning embers of hatred in his heart for the Spanish who had imprisoned him, and he would rather see their naked, bloody bodies hanging over an open fire. Based on what he knew, there must be a way to earn some easy money while exacting his precious revenge.

Jean-David, the young man who had only tasted the bitter end of life, was ready to reinvent himself and soon assigned himself the more dashing name of L’Olonnais. Moving to the French-controlled island of Tortuga in 1660—a wild destination for scurvy men looking for all sorts of booty—he soon discovered a town rife with disease-ridden prostitutes, brothels, and plenty of trouble to explore, all of which he took full advantage. The Buccaneers had created a base of operations in Tortuga where they could easily ambush Spanish ships headed home and loaded with treasures of gold, silver, and other precious materials. It wasn’t long before L’Olonnais had signed on as well, ready to ravage the high seas and take back the rich of Spanish who had dominated this area of sea trade since 1494 when the Treaty of Tordesillas gave them (along with Portugal) sole control of the Americas. The Spanish were sending their ships out to gouge the precious metals from the earth of the New World, thereby making themselves the wealthiest and most powerful country in Europe, and L’Olonnais was ready to make a dent in this ambition. Of course, the Spanish did everything in their power to drive the Buccaneers and other settlers out of this area which was so close to their beloved Hispaniola, but this effort only solidified their ranks and their universal need for vengeance.

L’Olonnais was a quick study in brutality and developed a fondness sadistic measures. As a crew member, he would gladly slice off random pieces of the enemy’s flesh—starting with the hand, then the arm, and moving to the face— until his victim bent to his will or died, making the process last for days. Or sometimes, he just cut out their tongues.These, among many other violent exploits, were well-documented in Exquemelin’s novel, and apparently drew the attention of the Governor of Tortuga as well who was always in the market for new Buccaneers to harass the Spanish and invade their treasure. Once hired to captain his own small, ten-gun ship, L’Olonnais did not receive any official pay but was essentially given a crew of 20 men and a license to seek and destroy his enemy, taking whatever treasure he could find.

in 1667, L’Olonnais took on the more respectable role of captain, and even though this did nothing to lessen his violent ways, he took the position seriously. When the priest brought on board to bless the ship was interrupted by a surly heckler, L’Olonnais pulled out his musketoon, shot the man between the eyes, and threw the unruly mate overboard. And while this type of impulsive behavior was not unheard of among pirates, L’Olonnais became notorious throughout the West Indies for having the ability to shock even the most wretched of onlookers.

Once settled as captain, his ship set out to attack Puerto Cabellos and San Pedro, but the clever Spaniards seemed to best him at every turn. As L’Olonnais and his men traveled through the Mona Passage, an area between the east coast of Hispaniola and Puerto Rico, they had been firing on a large Spanish trading vessel for some time but could not seem to get the leg up. Facing ambushes on all sides, L’Olonnais’s crew took a major hit, dwindling to almost nothing, that is until they managed to turn the tide and finally capture the ship. Once in his grasp, the remaining Spanish sailors were mercilessly questioned about their knowledge, but of course, the captives betrayed nothing. Enraged by their stoicism, L’Olonnais drew a knife from his belt, cut out the heart of a pleading Spaniard, and began to gnaw on the bloody organ. Both appalled and titillated, his small crew cheered their victory and the brutality of their leader, assuming this would be the end of the voyage. But L’Olonnais had no intention of quitting, and drunk with rum and blood lust, he scoffed at their lack of manpower, forcing them to push-off into yet another conquest.

It may seem curious why L’Olonnais felt so empowered to venture forth despite the obvious dangers. And in this way, it’s worth noting that L’Olonnais was 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 encountered. As a result, he saw himself not as a criminal but as a man liberated to work on his own account, no matter how deplorable—answerable to no one but himself. With this license to kill, he was more than just a pirate; he was a French-sponsored terrorist empowered to use any means necessary to reach his goal, just 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, who generally looked down upon Buccaneers as mere annoyances, L’Olonnais was a force to be reckoned with. During the War of Devolution between 1667 and 1668, L’Olonnais launched several successful attacks against the Spanish, taking on the reputation of a notoriously frightening killer and a master torturer. Many of his enemies claimed they would much rather die under instantly his sword than be taken a prisoner and forced to suffer the grueling torture for which he was so famous. His techniques included burning his victims, slicing out their tongues, skinning them alive, or employing his favorite practice of “woolding,” where a rope tied around a victim’s head would be slowly twisted in the back and tightened until the poor man’s eyes were literally forced out.

But the luck of L’Olonnais sometimes gave out, like the time 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 and a few other survivors made their in wooden boats to Campeche where his unsuspecting enemies were celebrating his legendary death. Although there is some historical discrepancy on this account, it is known he escaped with the help of some slaves and made his way back to Tortuga where he regained his hold on two ships. The privateer was back in business.

Before long, the Spaniards 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. Near Cay Largo, the Spanish sent a patrol boat complete with an executioner to capture and hang any pirates they found, but it appeared L’Olonnais would not be so easily found. Under the cloak of darkness, he and his men rowed up to the 10-gun warship, climbed aboard, and beheaded every man except one. That lucky soul was given a hand-written message to be delivered to the Governor of Cuba reading: I shall never henceforward give quarter to any Spaniard whatsoever, and I have great hopes I shall execute on your own person the very same punishment I have done upon them you sent against me. Thus I have retaliated the kindness you designed to me and my companions. And if there was one thing L’Olonnais would do, it would be to keep his promise.

L’Olonnais was creatively brutal in his tactics, but he was also extremely clever, said to be one of the first Buccaneers who organized land attacks. Not only did he fire on ships, but he was known to hop off into port and bring the fight right to the ground, shocking and horrifying the citizens of whatever town he barraged.

At this point, L’Olonnais was at the height of his prowess, sailing from Tortuga to Maracaibo (in what is now Venezuela) with at least 600 fellow pirates aboard eight different battleships. But L’Olonnais soon realized the harbor was protected by 16 cannons, so he covertly docked along the coast and rowed several canoes up a small river to attack the port from the land side and completely blind sided the enemy who expected an approach by sea. After a three-hour gun battle, his men captured the 16-gun fort and descending on the town. But Maracaibo had been warned of the piracy on the horizon and was largely empty at this point. Nonetheless, L’Olonnais rounded up whoever he could find in the woods and tortured them to reveal the hidden wealth of the city. According to one account, “it was the custom of L’Olonnais that, having tormented any persons and they not confessing, he would instantly cut them to pieces with his hanger and pull out their tongues.” Most of them died in agony, unable to offer him the prize he had hoped for, so he held the deserted town for a ransom of silver, silk, and jewels. He received a ransom of ten thousand pieces of eight to spare the city, at which time he sailed back to Maracaibo and demanded another twenty thousand, which he also received. Upon his return to Tortuga, he was regarded as a hero and a pirate of the highest order, having seized a bounty worth an estimated 260,000 pieces of eight, or Spanish dollars.

After his attack in Maraciabo, the enemy had been brought to their knees and L’Olonnais was free to move on to his next big thing—the Spanish Main. By this time, he had 700 fearsome crewmen under his command, and he and set sail, plundering along the coast of Central America and sacking what is now Honduras. Although he captured a Spanish galleon off Trujillo, he was not finding the amount of treasure he envisioned, and this put his fellow captains in a funk. To make matters worse, the crew took to land under the orders of L’Olonnais and were ambushed, and some accounts say it was at this time that the fearsome captain ripped the heart from the chest of his devious guide and took a bite to show his displeasure. Soon learning a Spanish treasure ship was on its way, the crew decided to wait, but the boat eventually showed up three months later with no treasure at all.

Many of L’Olonnais’s men became grumpy at this sequence of losses and decided to take off in another direction, leaving him alone with his one ship and crew of just 400. But L’Olonnais was a savage, unfazed and unafraid, and headed south towards the Mosquito Coast of Nicaragua where he managed to run ship aground. Setting up camp on the shore, he and the ship’s survivors \started building new boats with salvaged materials while L’Olonnais lead the others along the San Juan River hoping to attack a small native village for food. Shipwrecked and starving, L’Olonnais’s men approached a small village with the hopes of raiding it for food and materials. But alas, it would seem L’Olonnais had finally run out of luck, as the natives surrounded the Buccaneers, shooting them with poisonous arrows, capturing the immortal captain whom they burned alive, cut into pieces, and ate.

These natives were no stranger to L’Olonnais, as they had long considered him an enemy. Consuming his flesh was a symbolic gesture to prove they had finally vanquished him from the earth. It is believed various ethnic groups in the Caribbean during this time did practice cannibalism as a way to ritualize the death of an enemy and declare war on their soul. The personal accounts of Christopher Columbus recount these native people as savages who hung body parts in their villages and regularly engaged in cultural cannibalism, but modern scholars agree these reports were based largely on fear and minimal knowledge of their spiritual beliefs.

Considering the extent of his overall depravity and senseless violence, many historians believe L’Olonnais was not just a cruel pirate, he was insane. Although his feud with the Spanish was likely justifiable in his own mind, his treatment of innocent citizens and native inhabitants was so savage, it bordered on the deranged actions of a sociopath. It is believed his time as a slave, abused and tortured on a regular basis, may have pushed into a mental break that stole his ability to reason and sent him to a place of darkness that was only fed by his unusual lifestyle and opportunity for murderous enterprise. With no accountability or legal repercussions, he was free to act on these impulses, often receiving financial and social rewards as a result. Unlike the confines of today’s world, L’Olonnais lived in a private kingdom of his design—beholden to no one—and driven by nothing more than his own piercing anger, the sharpness of his cutlass, and the bracing ocean air, this impressive pirate traded bondage for bounty.

And the rest is history.