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Black Flags & Black Hearts: The Truth About the Caribbean Pirates

Updated on August 7, 2019

Notable Pirates In Fact & Fiction

Real Life Pirates
Famous Fictional Pirates
Edward "Blackbeard" Teach
Captain Hook
Francois "Bane of Spain" l’Olonnais
Long John Silver
Edward Lowe
Jack Sparrow
Bartholomew "Black Bart" Roberts
Sinbad the Sailor
Francis Spriggs
Captain Flint

A Pirates Life Was Not For You!

Walking the plank was a walk in the park compared to the ruthless tactics employed during the “Golden Age of Piracy” Yo Ho (A Pirate’s Life For Me) was released in 1967 by Disney and didn’t it sound like a fun thing to be? Johnny Depp’s swooning performance in Pirates of the Caribbean was exciting and filled with adventure; he got the women, the loot, and answered to no-one. Also, who didn’t love Muppet Treasure Island? Yes, Tim Curry was a real shyster but he had nothing on guys like the sadistic “Black Bart”. Even the recognizable skull and crossbones flag hoisted on the mast of many a pirate ship is known as the “Jolly Roger”. It’s the ultimate misnomer as there was nothing ‘jolly’ about the life of a Pirate. Now, I’d like to apologize in advance to the Pirate Community for pulling back the curtains and showing you what a “real” pirate was all about.

The "Disneyfication" of Pirates

A common trait among pirates was their propensity for torture; they weren’t Robin Hoods. Many of these “freebooters” would stop at nothing to grow their fearsome reputation. Having an infamous reputation was good for business and would turn even the most hardened sailors into obsequious snitches. The more atrocious the better, with the ultimate goal of frightening the life out of grown men , at the mere mention of names such as “The Bane of Spain”. The one thing Disney and Hollywood proper got right was the foul and disgusting appearance of these seafarers that were on par with their brutal tactics. Scars, sores, dirty dread-locked hair, unkempt beards, missing limbs, and eye-patches were all part of the ‘look’. Now lets look at some anecdotes of some particularly vicious pirates that will surely shiver your bones.

Black Bart

Ah, good old Black Bart. Bartholemew Roberts started as a deckhand on a slave ship before it was captured by pirates and forced to join the crew of captors. Reluctant at first, Bart quickly became seduced by the lifestyle and turned out to be one of the most successful pirate captains in history---capturing an estimated 400 ships! Tired of his marauding, the countries of Barbados and Martinique put together a joint task force with two heavily-gunned warships dispatched to take him out. This attempt was fruitless but they did however manage to kill at least 20 of his crew members, enraging Bartholemew who swore vengeance. He changed his flag to himself standing on top of two skulls with the letters ABH & AMH under the image which stood for, “A Barbadians Head” and “A Martiniques Head”. He eventually captured the governor of Martinique and he was promptly hung and left hanging there for months as a warning to those who would cross him. In another act of brutality, he set fire to a slave ship that failed to surrender to him (after politely asking), with 80 enslaved Africans still shackled on board...all 80 slaves were either roasted alive or drowned as the ship sank. The Royal Navy caught wind of this massacre and sent a warship that destroyed Bart’s ship, killing him in the process. The fearsome pirate was hit with grapeshot to the neck(a particularly brutal way to die) , but was weighed down by his loyal crew and tossed overboard into Davy Jones’ Locker, before the British could claim their prize.

The Bane of Spain

Francois l’Olonnais should be placed in the evil hall-of-fame, if they ever had one. When he was just a young boy, his own parents sold him as an indentured servant only to become a freeman after fulfilling his contract. The bitterness he carried from such a tragic upbringing was certainly a factor in the sadism he’d exhibit throughout the course of his life. Eventually, Francois became a buccaneer (essentially a state-sponsored pirate) for his native France---attacking, looting, and destroying Spanish ships. After being shipwrecked near the coast of Mexico, he and his crew were attacked by a party of Spanish soldiers killing nearly every stranded pirate...except for one. Francois played dead by dousing himself in the blood of the deceased and pulling their still-warm bodies on top him to blend in. The Spaniards left, and he made his way to the island of Tortuga (a safe haven for pirates) and gathered together a new band of pirates under his wing. They held an entire town hostage and demanded ransom from Spain, but were met by a ship sent to kill him instead. Francois captured and beheaded the entire crew save for one, and had him deliver a harsh warning to the Spaniards, “I shall never henceforward give quarter to any Spaniard whatsoever." Basically, if I see a Spaniard or a Spanish warship , ‘they’re good as dead’.

One of Francois more particularly cruel exploits, he and a fellow buccaneer set sail from Tortuga with a fleet of eight ships and 440 pirates to ransack the Spanish province known as “Maracaibo” which is modern day Venezuela. After overtaking a fortress thought to be impenetrable, Francois and his men began to pillage but discovered that most of the town’s residents had fled and hid their gold. This did not make l’Olonnais a happy camper. The residents were tracked down and tortured mercilessly and carried out personally by the man himself. Some of his methods included continuously slicing portions of flesh off the victim until they could take it no longer, burning them alive, and tying strong and thick rope called “woolding” around the victims head and tightening it until their eyes popped out of their heads! When word of his attack reached the seedy island of Tortuga, his nasty reputation grew, and was given the nickname “The Bane of Spain” for his efforts. When criminals and scoundrels find you appalling enough to coin a nickname for you---you must be a special kind of scum!

Wait, There's More...

It doesn’t end there...In what would be the last expedition for “The Bane of Spain”, he set sail for the Honduran mainland with a crew of 700 pirates with the predictable goal of raping, pillaging, and ransacking everything in his wake. However, his plans were quickly foiled after a large force of Spanish soldiers ambushed him and his men, with Francois and a small number of his men narrowly escaping with their lives by retreating into the nearby jungle. Somehow, Francois was able to capture two Spanish soldiers and demanded they show him an escape route. The next action he took was one of the more heartless(no pun intended) acts of cruelty I’ve ever come across in literature or otherwise. Alexandre Exquemelin, author of one of the most important ‘sourcebooks’ on 17th century piracy, described the details of what happened next better than I ever could: "He drew his cutlass, and with it cut open the breast of one of those poor Spanish, and pulling out his heart with his sacrilegious hands, began to bite and gnaw it with his teeth, like a ravenous wolf, saying to the rest: I will serve you all alike, if you show me not another way.” It’s safe to say the other captive was beyond horrified and showed l’Olonnais a direct route to the Honduran city known as San Pedro. Determined to finish the job, Francois and his small crew tried an attack but were repelled and forced to retreat back to their ship. They were unsuccessful at dislodging their ship from shore, so they headed inland on foot to find food. In a textbook example of karmic justice, they just so happened to run into a native tribe and were quickly captured. About the demise of l'Olonnais, Exquemelin wrote that the natives, “...tore him in pieces alive, throwing his body limb-by-limb into the fire and his ashes into the air; to the intent no trace nor memory might remain of such an infamous, inhuman creature". A fitting end I would say to such a horrid character.

'Lowdown' Edward Lowe

Edward Lowe didn’t need a spine-tingling nickname to strike fear in mariners around the world. The son of notorious thieves, he followed in his parents footsteps by engaging in theft and burglary at a young age. Interestingly enough, he tried to play the game straight for awhile as a rigger, but eventually grew tired of his captain and shot at him over an argument about rations. He fled the ship with several other men and stole a ship of his own, murdering a man in the process. Clearly , there was no turning back and Lowe and his crew hoisted up the black flag. The first instance of Lowe’s outstanding cruelty happened on one of the first ships he captured. Two Portuguese passengers were murdered by being dropped from the sails onto the deck over and over until they expired in a heaping mass of blood and shattered bones. On another ship, the cook was burned alive, and on a different ship he personally murdered a crew of 53 people with just his cutlass. Growing more and more sadistic, he developed a personal favorite method of torture that saw the victims hands tied behind their back with rope placed between each finger. Lowe would then set fire to the rope causing the flames to slowly burn the victims flesh down to the bone. His magnum opus of barbarity, however, happened after the captain of a freshly captured Portuguese ship dropped a bag of 11,000 gold coins into the sea---rather than hand it over to the pirates. Lowe became so enraged that he sliced off the guy’s lips, broiled them, and then forced him to eat them before murdering the entire crew of 32 men. This act shocked even his own men, who would later go on to describe him as a ‘maniac’ (you think?...)

Like many men that taste the sweet nectar of power, he became increasingly unhinged and brutal. Torturing captives became a standing operating procedure for Lowe and his crew; eventually the crew refused to carry out Lowe’s torturous orders and organized a mutiny. They cast him on his way in a ship containing no provisions, with the hopes that the evil ship-captain would starve to death. Unfortunately, the details of his fate remain unknown.

Famous vs. Infamous

You’re probably now asking yourself, ‘Where’s the mention of the most famous pirate of them all, Blackbeard?” Well, part of the impetus of writing this article is to dispel the rumors and set straight the record of pirate myths & truths, so here you go. Believe or not, Blackbeard was not that bad of a guy! Yes, he did have an intimidating appearance with the big dark beard and the story of him lighting fuses under his hat to frighten his enemies is true, but there is no known account of his ever having harmed or murdered those whom he held captive. He wasn’t a cold-blooded marauder; on the contrary, Edward Teach (real name) was a calculated & shrewd captain that avoided the use of force, instead relying on his frightening look to cajole ships to part with their loot. As a matter of fact, Teach commanded his vessels with the consent of their crews! The man known as “Blackbeard” should never be placed in the same company with the likes of pirates such as “Black Bart”.

Now You Know the Truth

The aim of this article wasn’t to ruin the fun and mystique surrounding the Caribbean pirates. I will admit that I’m a fan---who hasn’t dreamed of going back in time and joining a rag-tag group of close-knit brothers singing songs, drinking beer, sailing the ocean blue, and climbing a mast with a knife clenched between your teeth and raising your flag on an enemy ship? It was a high octane lifestyle that I’d liken to that of an outlaw motorcycle club. Unadulterated freedom is what drew us in as children and I simply wanted to shine some light on the true nature of many of these so called “freebooters”. Next time you cross paths with a kid in a pirate costume or a Jack Sparrow impersonator on Hollywood Blvd, do me a favor and try not to get into a historical argument about the moral indignity of glorifying the pirate lifestyle. You know the truth, but pirates are fun and let's keep it that way.


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