10 Gruesome Facts About the Real Pirates of the Caribbean

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Piracy is as old as the sea itself … or at least since there’s been some loot to be plundered. But the pirate legacy has since been high-jacked by Hollywood and romantic fiction. And pirates have been told as being faintly noble, selfless, independent, and with a great degree of charm. But the real pirate story is much darker. Pirate life was nasty, brutal, and – especially – short. And for a brief moment in time, each of these lives terrorized the oceans and demanded the attention of the navy. Mercy and honesty were rarely in any pirate’s vocabulary. Today we’ll be taking a look at what made the real pirates the most feared “predators” on the high seas.

10. Blackbeard’s Reign of Terror

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Born sometime around 1680, Blackbeard’s real name was probably Edward Teach. Some documents, however, refer to him as Edward Thatch or even Edward Drummond, and he is believed to have been either from Bristol, New York, California, Philadelphia, or even as far away as Denmark. Not much is known about his origins, it would seem. But regardless, he became among the most notorious pirates to have ever terrorized the Caribbean and the American East Coast. From a very young age he went to sea and served on an English ship during the War of the Spanish Succession by privateering along the Spanish Main. With the end of the war in 1714 he, like many others, turned to piracy.

Initially serving under another pirate who later retired, Blackbeard became captain in 1717, and commandeered a French merchant vessel which he renamed Queen Anne’s Revenge. He fitted it with 40 cannons, made it his flag ship, and together with three other smaller vessels (sloops) under his command, Teach plagued the West Indies and the Atlantic coast. In May 1718 he blockaded the Charleston harbor in South Carolina for four days, plundering several ships trying to get in or out, and held the local magistrate and his son for ransom. He then headed north, where he ran two of his vessels aground, the Queen Anne’s Revenge included, marooning most of his crew, in order to get a larger share of the loot. Having the governor of North Carolina in his pocket, he was secured a pardon under the royal Act of Grace and retired himself.

His best weapon of all was fear. He made himself appear ferocious, like a psychopath addicted to violence. He always had at least six loaded pistols, a cutlass, and a musket with him, and wore a big feathered tricorn on his head. He sported a huge black beard in which he would tie hemp and light it during battle. Together with lit cannon fuses tied under his tricorn, those who saw him fighting said that he “looked like the devil” with his fearsome appearance and the smoke cloud around his head.

Regardless of his retirement, he was soon back at sea. The governor of Virginia then put a bounty on his head and on November 21, 1718 a small group of men ambushed him and nineteen others within an inlet on Ocracoke Island, in North Carolina. Following a fierce battle the following day, Blackbeard was dead. He was reportedly shot five times and stabbed more than twenty times before being finally decapitated. His head was hung from a pike in Bath, the town he was supposed to retire in. Blackbeard’s reign of terror lasted a little over 2 years, even though he was among the most feared pirates of the 18th century.

9. The Privateers and Buccaneers

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At first glance, the words pirate, privateer, and buccaneer seem to mean the same thing. And while this is true to a certain extent, there certainly are some differences. For instance, privateering made use of private ships for attacking foreign vessels under the approval of a country’s government. In a sense, piracy in the Caribbean started off as privateering under the British government. As early as the 16th century, many private English ships carried letters of marque, entitling them to attack, loot, sink or capture ships belonging to all enemy nations – especially Spain. They would then give part of the spoils to the government, while the rest they would keep for themselves. However, while the state stood only to gain from these private contracts, the privateers, if captured by the enemy, would be tried as pirates and swiftly executed.

The most famous privateer was Francis Drake. In 1567 he made one of the first English slaving voyages, bringing African people to the New World, and was the first Englishman to circumnavigate the globe. In 1577, under secret orders from Queen Elizabeth herself, Drake went around South America, plundering Spanish ports on the undefended Pacific coast. And thanks to his cunning he even managed to take over and plunder the Cacafuego (“fires**tter”), officially Nuestra Señora de la Concepción, a huge Spanish galleon, filled to the brim with Inca treasure. On his return to England, he was knighted by the Queen. However, he would be one of the few privateers who would actually do what he was intended to. Bolstered by Drake’s accomplishments, many others would try to find the same fame and riches; a standard that would never be achieved again. In time, these would-be privateers would descend to the level of blood-thirsty opportunists, operating under false flags, killing witnesses and betraying their own nations and crewmates.

Buccaneers, on the other hand, were mostly felons, many of them facing capital charges. They were former sailors who’d jumped ship, or servants who ran away from their contracts working the sugar plantations on the many Caribbean islands. The word derives from the native “buccan,” which refers to a wooden framework used for smoking or slow-roasting meat over a fire. The first buccaneers used these buccans to prepare meat and sell it to sailors. But later, they turned to piracy, operating from the jungles. Whenever there was a ship close by, a handful of buccaneers would jump into a small rowing vessel and board the unaware ship. In the beginning, the island of Hispaniola (present day Haiti and Dominican Republic) was a major buccaneering base. They were later chased off the island by the Spanish and became pirates, operating from the island of Tortuga and Port Royal in Jamaica. They, too, would later be hired in the service of the crown.

8. Pirate Weapons

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The above mentioned buccaneers made good use of the Buccaneer Musket. It was a large and heavy gun, measuring almost 6 feet in length. They used it initially for hunting boar on the islands, but also to shoot the helmsman off an enemy deck some 300 yards away. The buccaneers were really good shots, and became the masters of small arms; the first who gave them any real attention. Firing these guns continuously as they were rowing towards their target, they would disable the ship and prepare it for their boarding. The flintlock pistol was another weapon of choice, desired for its light weight and small size. It was ideal for boarding enemy ships, and pirates usually carried more than one since it was good for only one shoot before needing reloading. That’s why Blackbeard carried six with him at all times.

Pirates also made use of the Blunderbuss. It was loaded with a handful of pistol balls and when it was fired it created absolute devastation over a broad area of decks. It had a massive recoil and had to be fired from the hip. Otherwise, it would break the shoulder. Grenades were also used extensively by pirates. Basically a spherical-cast hollow iron ball about 5 inches in diameter, loaded with 5 ounces of gunpowder, the grenade had a wooden fuse sealed with wax. Once lit, it took about 6 seconds to explode. Pirates and buccaneers would throw these onboard an enemy vessel just before boarding it, creating utter chaos and devastation. However, all of these firearms were one-shot weapons, so the backbone of any boarding action was the cutlass. Used for both thrusting and slashing, the cutlass was short so it wouldn’t become a hindrance on a crowded deck. Pirates sometimes used both cutlasses and boarding axes, among other swords or knives, as melee weapons.

7. Hooks for Hands and Wooden Legs

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When thinking about a pirate, it’s almost impossible not to imagine him without either an eye-patch, a hook for a hand, or a wooden stump. And knowing the nature of their business, the weapons they were using (and which were used against them, as well), it’s no surprise so many of them had these, let’s say, “prosthetics.” But the real reason for why so many had missing limbs has more to do with infection than the many wounds they were subjected to. For instance, musket balls had the nasty habit of taking a piece of fabric with them when passing through its victim. And while doctors may have been able to take out the ball, the piece of cloth most likely stayed behind. This in turn caused the wound to fester, and many were subject to gangrene.

With no anesthetics or antiseptics, they were aware that if the limb was not amputated it would “mortify,” as they called it, and they would die in severe pain. So, the only effective method available was to chop off the limb. The way they went about it was to strap the injured to a table, have a few men hold him down, give him a good shot of rum, and then put a strap of leather in his mouth to stop him from screaming so much. Then the “doctor” would tie up his leg or arm, in order to stop the bleeding as much as possible. Next he’d take a sharp knife and start cutting the skin and muscle above the wound. When he reached the bone, the doctor would take a saw and cut that, too. The whole procedure would take between 30 to 60 seconds, depending on the doctor’s skill. Finally he’d tie off the arteries, put a dressing on, and off the limping pirate went. But not even this ensured the patient’s survival, and many still died after the procedure.

6. Captain Charles Vane – Years Active: 1716-1720

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As we said before, pirate life was brutally violent and extremely short. A good example was Charles Vane, a notorious pirate, contemporary and friend to the infamous Blackbeard. His pirating days began in 1716 and in 1718 he became a captain himself. He was renowned for his violence and ill temper, being hated even by his own crewmen. He is one of the few pirates who didn’t accept the King’s pardon, and in a mere four years after his “career” began, he would be hanged. After a mutiny aboard his ship, he was left behind on a small sloop together with a few loyal comrades. In a hurricane, he would miraculously survive, being washed ashore on a small fishing island. However, the man who found him there recognized him and brought him to justice.

Before his death however, in April 1718, Vane and his men came upon a sloop somewhere in the Bahamas and attacked it. They violently beat the crew, stole everything onboard, and chose one man, Nathaniel Catling, to be hanged. He remained suspended until everyone believed him dead, and the pirates brought him down. He somehow survived, but seeing this, one of the pirates hacked him across the collarbone with his cutlass. Vane and the other pirates then set the ship on fire and left. However Nathaniel Catling not only survived a hanging and a slash to the neck, but also escaped to describe the events in an official deposition. In a similar incident, Vane had someone tied to the bowsprit, while they were burning his eyes with matches and holding a pistol in his mouth. Vane was forcing him to tell what valuables were hidden onboard.

5. Edward Low – Years Active: 1721 – 1724

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Edward Low got his notoriety of being a psychopath first, and a pirate second. He made his fleet in Nova Scotia, where he managed to capture 13 fishing vessels, and then he moved south to the more lucrative Caribbean. As his pirating career went on, his infamy grew. A few surviving victims recalled his brutal nature where he often chained, mutilated, burned, and even forced some of his captives to eat the heart of their captain. In one particular incident, Governor John Hart described as Low was attacking a ship from Portugal bound for Brazil. As they were being boarded, the captain of the Portuguese vessel dropped a bag of gold into the ocean to keep the pirates from taking it. Seeing this, “Low cut off the said Master’s lips and broiled them before his face, and afterwards murdered the whole crew being thirty-two persons.”

Due to his increasingly violent nature, both against his victims and his own men, in 1724 the crew mutinied and left him marooned on an island. What eventually happened to him is a matter of speculation. Some believe he was found by the French who, after discovering who he was, had him hanged in Martinique. Others believe he managed to escape and lived out the rest of his days somewhere in Brazil.

4. Henry Morgan, King of the Buccaneers – Years Active: 1655-1682

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Henry Morgan is one of the successful few who managed to live to the ripe old age of 53, and die of tuberculosis, and not by hanging or decapitation. And he did so by staying somewhere in the gray area and not going full on “black,” as many other privateers or buccaneers did back then. Throughout his life he acquired a reputation as a remarkable leader and a fearsome conqueror. He sacked the city of Puerto Principe in Cuba, Puerto Bello in Panama, the towns of Maracaibo and Gibraltar in present-day Venezuela, as well as the city of Panama (which he completely burned to the ground). For his many victories for the English crown against the Spanish, Morgan was honored by the King and promoted to deputy governor of Jamaica.

Nevertheless, a pirate is still a pirate even if he’s made governor. The sacking of all of those Spanish settlements weren’t done solely for the glory of England. The booty Morgan collected from all of them made him a very rich and highly influential man. In the city of Maracaibo, he and his buccaneers tortured many citizens in order to find the hidden valuables. In Porto Bello he burned the private parts of his women prisoners and even roasted a woman alive on a stove, in order to get the information he so desperately desired. In Gibraltar they tortured a man by placing four stakes into the ground and tied him by his thumbs and big toes. They then pulled and pushed at the cords with all their strength. If this wasn’t enough, the pirates then placed a 200 pound stone on his belly and lit some palm leaves, burning his entire face.

3. Montbars the Exterminator – Years Active: 1668 – 1670s

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A French buccaneer, Daniel Montbars got the appellative “Montbars the Exterminator” from the Spanish, against which he was renowned for acting violent to the extreme. Born to a wealthy family, he was well educated and raised as a gentleman. He developed a deep hatred for the Spaniards after learning of their savage treatment of the indigenous people in the New World, and would become a fierce enemy of the Spanish Empire throughout his career. In 1667 he left France for the West Indies together with his uncle, where they served in the Royal French Navy. Their vessel was later sunk by the Spanish and his uncle perished.

Montbars then moved to Tortuga and joined the buccaneers, where he became a captain. He distinguished himself during an attack against a Spanish galleon where, “Montbars led the way to the decks of the enemy, where he carried injury and death; and when submission terminated the contest, his only pleasure seemed to be to contemplate, not the treasures of the vessel, but the number of dead and dying Spaniards, against whom he had vowed a deep and eternal hatred, which he maintained the whole of his life.” He attacked and set ablaze many Spanish strongholds and settlements across the Caribbean, giving no quarter to his enemies. One of his most famous torture methods was to cut open the abdomen of his prisoners, nail his large intestine to a post, and then force the poor man to dance away from it, all the while “beating his backside with a burning log.”

2. Francois L’Olonnais – Years Active: 1660-1668

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While on the subject of psychotic Frenchmen, let’s take a look at Montbars’ predecessor, Francois L’Olonnais, another Spanish-hating buccaneer. His real name, however, was Jean-David Neu, but he also went by “Flail of the Spaniards.” He was born in France around 1635, where he was sold to a master who took him to the Caribbean. In 1660 he joined the buccaneers stationed in Saint-Domingue and his reign of terror began. In 1663 he survived a shipwreck where all of his crewmates died, and when the Spanish came to investigate, he covered himself with his crewmates’ corpses and smeared himself with their blood to appear dead. He then dressed himself as a Spaniard, released some slaves and escaped on some small canoes. On his way to Tortuga he and his small crew destroyed an entire Spanish ship and left only one man alive to tell the story.

From Tortuga, L’Olonnais launched an attack on Maracaibo and Gibraltar, hunted down the people trying to escape through the jungles, then raped, tortured and murdered everyone. In another raid on the town of Puerto Cabellos, he “ripped open one of the prisoners with his cutlass, tore the living heart out of his body, gnawed at it, and then hurled it in the face of one of the others, saying, ‘Show me another way, or I will do the same to you.’” He wanted to find a safe route to San Pedro, another Spanish port-city close by. In 1668 his small fleet was finally captured and destroyed by the Spanish. He managed to escape the onslaught by running into the jungle. There, however, he was captured by natives who ripped him to pieces while still alive and then burned him. Some rumors go as far as saying that he was eaten by cannibals.

1. Olivier Levasseur – Years Active: 1716-1724

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Okay, let’s move out of the Caribbean for this last one. Olivier Levasseur, aka La Buse (The Buzzard) was a French privateer in service to the French crown during the War of the Spanish Succession (1701–1714). After the war he was ordered to return home, but instead joined a pirate company in 1716. The Buzzard decided to try his luck in the Indian Ocean, on the Western coast of Africa. He and some other famous pirates like Edward England or John Taylor raided and plundered ships and ports in the region, going as far as razing to the ground the slaver port of Ouidah, in present-day Benin. From 1720 they began operating from the island of Sainte-Marie, just off Madagascar.

Taylor and Levasseur later marooned England on the island of Mauritius on the account of him being too humane with his prisoners. The Buzzard’s favorite torturing method was the “woolding.” In order to extract information he’d take a length of rope, which went around the head of his prisoners, and with a stick he would tighten it little by little. If the captive didn’t divulge his secrets, or if he had none, the rope would be twisted so much his eyes would pop out of their sockets. Levasseur called it, “the rosary of pain.”

In any case, the two pirates managed to accomplish one of piracy’s greatest exploits. Without even firing a single cannon, they captured the Portuguese great galleon Nossa Senhora do Cabo (Our Lady of the Cape). This ship was carrying the treasures of the Patriarch of the East Indies, and the Viceroy of Portugal, who were both onboard, on their way home to Lisbon. Since the galleon went through a severe storm, the crew had dumped all of its 72 cannons overboard, preventing the ship from capsizing. The booty was huge, consisting of many bars of silver and gold, countless chests full of golden coins, jewels, pearls and other valuables, as well as many religious artifacts. And among them was also the Flaming Cross of Goa made of pure gold, inlaid with diamonds, rubies and emeralds. It was so heavy, it required three men to move it to Levasseur’s ship. This treasure-trove made all the pirates rich beyond their wildest dreams.

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In 1724 he sent an emissary to discuss an amnesty on his behalf. But since the French government wanted a sizable chunk of his loot (estimated at over £1 billion), he instead settled down in secret somewhere on the Seychelles archipelago. Eventually he was captured and hanged in 1730. While he was at the gallows, he threw a necklace into the crowd while yelling, “Find my treasure, the one who may understand it!” The necklace contained a cryptogram of 17 lines. The hidden message proved too hard to figure out, and to this day his immense treasure is still hidden away somewhere.


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1 Comment

  1. Actually, mercy and honesty were PRETTY DAMN HIGH in most pirates vocabulary. Blackbeard, Ching Shih, Calico Jack, Anne Bonney, Charles Vane and many if not most other pirates had strict policies against harming prisoners and non-combatants, and dishonesty between pirates was a great way to lose a hand. In fact, the only famous pirates who didn’t practice extreme mercy were Benjamin Hornigold and William Kidd, who both became pirate hunters, Grace O’Malley and Henry Morgan, who were both privateers, not pirates, and Black Bart, who worked as a slave traders before taking up piracy.

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