The 7 Most Terrifying Pirates From History

By Eric Yosomono and Jean Flynn

Captain Bartholomew Roberts With Two Ships, artist unknown.
Courtesy of WikiMedia Commons.

As I’ve mentioned a few times (herehere and here), I’m a huge fan of I love them because they’re hilarious, but also because they seem to have three or four people on staff dedicated solely to writing historically themed articles, and those three or four people always manage to inform me about things I didn’t know while making me laugh so hard I can’t breathe. Excellent combination. Please be aware, this article contains bad language and humor some might find offensive.

Between Johnny Depp and numerous sports logos, pirates have become cartoon characters in modern culture. It’s easy to forget that the real thing did exist, and that in many cases they were much more badass than the Hollywood version.

Don’t take the word “badass” the wrong way; these men were unspeakably violent, often mass murderers and slaveholders. They were pirates, real pirates, not goofy caricatures. Here’s proof.

#7. Francois l’Olonnais Eats a Fucking Heart, Holy Shit

French pirate Francois l’Olonnais really, really hated Spain. Early in his pirating days, l’Olonnais was almost killed by Spanish raiders, and instead of reconsidering his career choice and becoming a dairy farmer or something, he decided he would spend the rest of his life on an anti-Spain rampage. He let them know exactly what he intended by beheading everyone in the crew of a Spanish ship except one man, sending him back with this message: “I shall never henceforward give quarter to any Spaniard whatsoever.”

That was just the beginning, though. Considering what happened next, it looks like those beheaded Spaniards were actually the lucky ones.

Having made a reputation for himself, l’Olonnais raised a pirate fleet of eight ships and hundreds of men and proceeded to terrorize the coast of South America, sacking Spanish-ruled cities, capturing treasure ships returning to Spain and generally being a huge pain in the ass to anything Spain-related. Presumably he also killed his fair share of Portuguese sailors during this time, because really who can tell the difference?

However, the situation was reversed when l’Olonnais himself, returning from pillaging the coast of Venezuela, was ambushed by a much larger force of Spanish soldiers. With his pirate buddies being blown to pieces left and right, l’Olonnais narrowly managed to escape and somehow captured a few Spanish hostages along the way. The problem now was that l’Olonnais and the other survivors needed to know which way to escape so they didn’t run into more Spanish ships, which they weren’t in any condition to fight. What to do?

Easy: l’Olonnais drew his sword, sliced into one Spanish prisoner’s chest, pulled out the heart with his hands and 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.’”

While we wouldn’t recommend you use this technique the next time you need directions to the nearest Taco Bell, in this case it apparently worked like a charm. The pirates escaped safely. So if you were wondering what happened to all the heads of the decapitated Spaniards we mentioned earlier … well, let’s just say the whole crew dined like kings for like a week.

#6. Jean Laffite Tells King George to Suck It

Jean Laffite, despite his effeminate name and Frenchness, was an honest to goodness pirate king. He led an entire pirate island in Louisiana, capturing ships and smuggling stolen goods into New Orleans. He was so successful that when the Governor of Louisiana offered a $300 price for his capture (back when 300 bucks was half the national budget) Laffite responded by offering a $1,000 reward for the capture of the governor.

The media and the authorities painted Laffite as a dangerously evil mastermind and mass murderer, the Osama bin Laden of the 1800s, if you will. Apparently his reputation spread across the Atlantic, because in 1814, Laffite was approached by the British and handed a letter signed by King George III himself, promising citizenship and landholdings if he joined their side. Also, if he refused they would tear his little island to pieces, and sell it for scrap. Laffite said he needed a few days to think about it … and ran straight to New Orleans and warned the Americans that the English were coming.

You see, the United States may not have been a very big fan of Jean Laffite, but Laffite was apparently a huge fan of the U.S. of A.

Even though he wasn’t American, Laffite watched the new country with great admiration and ordered his entire fleet never to attack an American ship. The one time a pirate disregarded his order, Laffite killed the guy himself. He was also known for treating captured crew well and sometimes returning their ships if they weren’t fit for pirating. Laffite was a hero among the people of New Orleans, since his smuggling operation allowed them to buy stuff they otherwise couldn’t afford.

So how did the U.S. respond when he warned them about the English? Why, by raiding his island and locking up his men, figuring he was full of shit. It wasn’t until badass future president Andrew Jackson stepped in and pointed out that New Orleans wasn’t prepared for a British attack that the authorities agreed to release Laffite’s men if they agreed to assist the U.S. Navy — which, at the time, consisted of a fraction of the ships in Laffite’s personal pirate fleet.

It’s a good thing, too, because the pirates were pretty much the only reason New Orleans didn’t fall to the British, which would have been a huge strategic victory. New Orleans could have given the British a place to gather their forces before attacking the rest of the country. Think about it: The U.S. might not even exist today if it weren’t for this unwashed French “terrorist.”

#5. Stephen Decatur: All-American Pirate

Stephen Decatur doesn’t really fall into the stereotypical image of a pirate, in that he was actually a respected U.S. Navy officer. Decatur was the youngest man to reach the rank of captain in the history of the navy, which sounds like a bullshit line of expository dialogue from an unbelievably stupid Hollywood film trailer. But in this case, it happens to be true. He was also the first American celebrated as a national military hero who didn’t play a role in the American Revolution — hell, they even put his face on $20 notes.

So how did he get to be so famous? Why, by pulling off some of the most epic (and bloody) sea raids of all time.

For example, when the USS Philadelphia was captured by Tripolitan pirates in 1803, the 25-year-old Decatur gathered a group of men, disguised them as Maltese sailors and infiltrated the enemy harbor armed only with swords and pikes. Did they recover the ship? Nope — they overtook the entire crew without losing a single man and set it on fire just so the pirates couldn’t use it. Admiral Horatio Nelson, the same man who had his arm removed so that he could get back to battle, called the raid “the most bold and daring act of the age.”

But wait, there’s more. Later, as Decatur was returning from seizing another ship with a crew twice as large as his, he learned that his brother had been shot while fighting the pirates. Even though the whole crew was exhausted from the latest raid, Decatur turned around and chased the enemy ship, which he and 10 other men proceeded to board.

Disregarding everyone else, Decatur, a Liam Neeson-like machine of vengeance, went straight after the man who shot his brother and killed him. The rest of the crew eventually surrendered, leaving Decatur with 27 prisoners and 33 dead pirates in a single day.

Again: he was 25.

#4. Blackbeard’s Mentor, Benjamin Hornigold, Just Didn’t Give a Shit

Benjamin Hornigold was the Emperor Palpatine to Blackbeard’s Darth Vader. While his protege went on to become the most famous pirate of all time, Hornigold went on to become a footnote in hundreds of books with the word “Blackbeard” on the cover. Still, for our money, Hornigold is where it’s at, even though you’ve probably never heard of him before.

Hornigold started his career of piracy in the Bahamas with little more than a few canoes. A few years later, he had a huge fucking 30-gun warship, possibly the most heavily armed in the area. This made sailing over to merchant ships and stealing their goods and booze extremely easy. So easy, in fact, that he apparently did it just for shits and kicks. Which leads us to the story that, to us, is Benjamin Hornigold in a nutshell:

Hornigold overtook a merchant ship in Honduras and the only thing he demanded was everyone’s hat. He explained to the puzzled crew that his pirates got drunk and lost their hats the night before, then took off without stealing anything else.

This was not an isolated incident. Another time, a captured crew reported that Hornigold let them go having taken “only some rum, a little sugar, powder and shott.”

Sadly, it looks like his crew didn’t share his priorities. Hornigold always considered himself a “privateer” rather than a pirate, and to prove it he refused to attack British ships. His men didn’t share this delusion and eventually deposed him, with a good part of his crew and ships going to that asshole Blackbeard. Who subsequently lost his head.

Hornigold eventually retired as a pirate, but rather than simply moving to a condo and taking up golf (or whatever the 18th century equivalent of that was), he accepted a royal pardon and became a pirate hunter — being tasked with chasing some of the same guys he used to run with.

#3. William Dampier, Science Pirate

Englishman William Dampier was a bit of an overachiever. Not content with being the first man to circumnavigate the world three times and becoming a celebrated author and scientific explorer, he also had a little hobby: raiding Spanish settlements and plundering other people’s ships. All in the name of science, of course.

Pop culture demands that all pirates be toothless hobos who talk like fucking idiots, but Dampier was the exact opposite of that: he didn’t just respect the English language, he actually expanded it. The Oxford English Dictionary cites Dampier’s writing over a thousand times, since he provided the first written example for words like “barbecue,” “avocado,” “chopsticks” and hundreds of others.

Dampier has been called the first natural historian of Australia — he was the first person ever to describe things like the “large hopping animal” and the “midget bear with a fondness for humping trees”[citation needed]. Dampier’s contribution to Western culture is so massive that Darwin based his work on evolution off of his observations and Gulliver’s Travels specifically mentions how awesome he is.

His most badass moment has nothing to do with science or literature, though. In 1688, when his first trip around the world was almost over, Dampier told his crew to eat a dick and voluntarily marooned himself off the coast of Thailand, otherwise known as “the middle of fucking nowhere.” He grabbed a native canoe and sailed off on his own, showing up in England three years later, completely penniless, carrying nothing but his journals … and, um, a tattooed slave prince.

At this point he published his first book, which was an immediate success, also making a little money on the side by showing off his new friend.

#2. Black Bart Dishes Out Some Sea Justice

In the 17th and 18th centuries, sailing with the navy or on a merchant vessel was a shitty, shitty job. The conditions were miserable, and if you did anything to piss off the officers of the ship, punishment was brutal and often deadly. The job was so harsh that nobody wanted to do it, so the navy and the merchants would literally kidnap people out of the ports and force them to work on their ships. Shockingly, this was later proven to not be such a fantastic way to engender the loyalty of one’s crew.

Bartholomew Roberts (or “Black Bart”) was a reluctant pirate himself, which didn’t make him any less good at his job. Roberts happened to be working in a slave ship that was captured by pirates — when the pirates “asked” the crew to join them, he looked at his measly salary and figured, “Why the hell not?” Also, there’s a pretty good chance they threatened to kill him if he didn’t. Roberts quickly became the pirate captain’s trusted confidant because of his intelligence and navigation skills. When the captain was killed, Roberts (who had only been with the pirates for six weeks) was elected as the crew’s new leader, reportedly stating “Better being a commander than a common man.”

Roberts went on to become a legendary pirate on his own merits, but apparently he never forgot where he came from: After capturing a ship and before taking his pick of the booty, he would ask the captured crew whether or not they were treated well by the captain and officers. If any of the commanding officers or the captain received complaints, he’d slice and dice them to the cheers of those they mistreated. This was actually a common practice among some pirates, some of whom used more elaborate forms of punishment, like making the torturers run in circles for 10 minutes while the men stuck forks, knives and compasses into their butts.

Roberts, a civilized man, eventually forced his crew (the same crew who captured him months earlier) to agree to a strict 11-point code of conduct, including articles like no gambling for money, no women on board, lights go out at 8 p.m., keep your shit clean and “If any man rob another he shall have his nose and ears slit, and be put ashore where he shall be sure to encounter hardships.”

#1. Barbarossa Says Fuck It, Starts Own Nation

When you look at movie or TV pirate captains, they’re always lucky if they have one ship and a few dozen men to follow their orders. It turns out some real-life pirates had it slightly better than that. Ottoman pirate Hayreddin “Redbeard” Barbarossa didn’t just have his own fleet — he had his own damn country.

Barbarossa started out as a legitimate merchant sailor in the 16th century, but was forced to flee the Eastern Mediterranean after backing the wrong candidate for sultan. Becoming a pirate, he started attacking Christian ships around what’s now Tunisia until his enemies took his base, leaving him homeless once again. Tired of getting kicked out of countries all the time, Barbarossa went ahead and started one for himself: the Regency of Algiers (present-day Algeria, Tunisia and parts of Morocco). He did this by pledging alliance to the Ottoman sultan and getting in return enough ships and weapons to blow the shit out of whoever lived there before him.

How big of a deal did this guy become? Let’s put it this way: At one point, Barbarossa single-handedly defeated the combined forces of Venice, the Vatican, Genoa, Spain, Portugal and Malta during the Battle of Preveza (1538), and by “single-handedly” we mean it was just him and 122 ships he commanded.

Courtesy of
Image: Captain Bartholomew Roberts With Two Ships, artist unknown, courtesy of Wikipedia.

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