The 7 Most Terrifying Pirates from History

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

greenmodels

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."

Wikipedia
"Yeah, we sorta got that from the beheadings, thanks."

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?

paulinespiratesandprivateers
Assuming they're all Spanish because they're having siestas is an odd point to make at 2 a.m.

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.'"

nmm.ac.uk
"Also, morale is down for some reason. What gives?"

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 Lafitte Tells King George to Suck It

Wikipedia, Wikipedia

Jean Lafitte, 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) Lafitte responded by offering a $1,000 reward for the capture of the governor.

Wikipedia
"In fact, what the hell, bring me six governors. And an elk."

The media and the authorities painted Lafitte 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, Lafitte 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. Lafitte 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 Lafitte, but Lafitte was apparently a huge fan of the U.S. of A.

thepirateking
The first libertarian.

Even though he wasn't American, Lafitte 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, Lafitte 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. Lafitte was a hero among the people of New Orleans, since his smuggling operation allowed them to buy stuff they otherwise couldn't afford.

wessweb
"This cloth will be great after all the blood has been washed off."

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 Lafitte's men if they agreed to assist the U.S. Navy -- which, at the time, consisted of a fraction of the ships in Lafitte's personal pirate fleet.

Wikipedia
It's stuff like knowing how to count that makes a good president.

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

Wikipedia, airbournecombatengineer

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.

Wikipedia
Proof that, at one point, our nation had its priorities straight.

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."

Wikipedia
"After that time I cut my fucking arm off, of course."

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.

thebirdman
Decatur, seconds before shooting his attacker in the face.

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.

Wikipedia
"I'm 97 in homicidal years."

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

thepirateking

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.

Getty
"No, it's OK, Blackbeard. I'll do the pirating while you stand there looking like an idiot."

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.

Getty
"We only got up to the 'yo ho ho' bit."

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."

SheGotTheBeat
"We're making a surprise rum cake for Jonesy's birthday. The surprise is the gunpowder."

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.

thepirateking
Proof that the Peter Principle also applies to piracy.

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.

Recommended For Your Pleasure

To turn on reply notifications, click here

490 Comments

The Cracked Podcast

Choosing to "Like" Cracked has no side effects, so what's the worst that could happen?

The Weekly Hit List

Sit back... Relax... We'll do all the work.
Get a weekly update on the best at Cracked. Subscribe now!