10 Historical Pirates Hollywood Should Actually be Writing About

So many things wrong with this picture… Copyright goes to Warner Brothers Pictures.

I’m writing about something a little different today at LAS. Instead of a story or Doctor Who discussion, I’m going to combine three things that I love- writing, history, and lists.
So sit tight, grab some rum, and set topsail: things are about to get all historical up in here. (Oh, and there’s some historically accurate violence to follow.)

If you just so happen to be one of the 98.7% of Americans  who own a TV, you’ve probably seen a couple hundred ads for the movie Pan. Despite big talent (director Joe Wright is one of my favorite directors) the big budget blockbuster is quickly getting recognized as one of the biggest flops of 2015. Among the littany of reasons listed for its failure: A bloated script, CGI overkill, and accusations of whitewashing the cast. None of these things were why I was turned off from watching. I didn’t watch because, for some reason, the movie’s writers decided to make Blackbeard the movie’s villain.

Trivial? Yeah. Strangely specific? Maybe. Unreasonable? No.

Blackbeard has now been used as a villain or main character in Crossbones, Pirates of the Caribbean 4, and Pan. In Pirates he’s described as the pirate all pirates fear. In Pan he’s the tyrannical leader of Neverland. In Crossbones he’s pretty much a Pirate King/mob boss. And here’s the problem: He was none of these things. He was not an exceptionally successful pirate, nor a particularly violent one, nor was he at all a leader of pirates. He in fact served under an unofficial “pirate mayor”. And perhaps it’s a little ridiculous to expect fantasy movies to get their pirate history right… okay it is ridiculous to expect that. But the fact is there are so many real-life pirates far more interesting than Blackbeard, and there’s a wealth of potential stories Hollywood is leaving untapped.

And before the list starts: Shoutout to Black Sails for having a pretty accurate portrayal of plenty of real life pirates not named Blackbeard.

1: l’Ollonais

Character archetype: Diabolical villain

Francois l’Ollanais was one of the most violent pirates of all time. He possessed a fiery hatred of the Spanish, and did not make any effort to hide it. Have you heard of the town of Gibraltar, Venezuela? You most likely haven’t. That’s because in 1667 l’Ollanais attacked it with a fleet of six ships and ~800 men and destroyed it so thoroughly it never recovered. Even today, it’s only a fraction of the size it was before l’Ollanais destroyed it. The sack yielded gems and gold from the Spanish treasure fleet (gems and gold being things ol’ Blackbeard never touched) and killed thousands. l’Ollonais was a particularly cruel torturer. While Blackbeard never physically injured any captive of his, l’Ollonais was fond of a great number of… uh, creative methods of interrogation. The most infamous moment of torture being when he cut out the heart of a still-alive Spaniard, and, before the poor man died, took a bite out of his heart. He was messed. Up. He also died a death as violent as his life. He was roasted and eaten by cannibals living in modern day Campeche. Yikes.

2: Black Sam Bellamy

character archetype: Antihero/freedom fighter

Okay, maybe audiences wouldn’t exactly flock to a story as violent as l’Ollonais’s unless it was written by Tarantino. Black Sam Bellamy provides a chance for the movie industry to tell the story of one of piracy’s good guys.

Bellamy is a distinct figure in pirate lore, forgoing wigs for his own long black hair and having a very generous approach to the operation. If you had to get captured by some historical pirate, you’d want it to be Black Sam. A merciful captor, he would release captives and his ship was one of the most democratic of all pirate ships.(Most pirate ships were democratic operations to some degree.) Bellamy likened himself to Robin Hood, and is quoted as saying “they rob the poor under the cover of the law, and we plunder the rich under the protection of our own courage.” Safe to say Sam Bellamy would be feeling the Bern right now.

His crowning moment came in 1717, when he captured the slave ship Whydah. He found a fortune in gold and valuables, and if the value of the slaves on board is counted, it was the richest prize in pirate history. I, however, would not count it, both out of the moral greyness of the notion and the fact that Bellamy did not sell any of the slaves. He allowed them to join his crew if they liked, so they could fight against the nation that put them in bonds. The few who did not wish to become pirates were freed.

Bellamy became captain when the crew of his ship mutinied against their former captain, Benjamin Hornigold, who did not want to attack English ships. The crew deemed him more worthy of captaincy than Hornigold’s first mate, who was, you guessed it, Blackbeard.

3: Roche Braziliano

Roche Braziliano, probably thinking about how much he hates the Spanish

Character archetype: Consumed by vengeance

Braziliano is a fascinating character study, however not much is known about him, allowing potential writers much more artistic license towards his story than others. He apparently had a vendetta against Spain. Spain was a popular target among pirate captains for its great wealth at the time, but Braziliano’s attacks appeared personal. Think Inigo Montoya meets Walter White. (You’re welcome, whatever tv channel/movie producer sees this idea.) Like l’Ollonais before him, he was brutally effective at torturing his captives, tearing off fingernails or burning them alive. He was captured twice by the Spanish, escaping both times. The most appealing part of him as a possible character is that his story is open ended. He simply disappears from record in the 1670’s, with no nation ever claiming to have killed him. With this story and personality, he becomes a perfect fit for what Joe Wright wanted in Pan. A tyrannical pirate with an open-ended story.

No one knows just what happened to Braziliano. Most likely he ended up caught in a storm and went down with his ship. But who knows? Maybe he ended up on some magical island to start his career over, only to be upended by some flying boy and a bitchy faerie.

4: Ms. Cheng

Character archetype: Mob boss

Jumping hemispheres to the South China Sea, I introduce to you Ms. Cheng. Remember that epic battle between the British and assembled pirate fleets at the end of Pirates of the Caribbean 3? It is closer to reality than you may have expected. While Ms. Cheng operated about a century after her fictionalized counterpart, her pirate fleet was absolutely massive. The low estimate for her total manpower is 20,000 men. The high: 80,000 all told. She inherited a fleet of between several hundred and one thousand ships, larger than any navy on earth at the time, and was never defeated in a battle. Her fleet fought off both the British and Chinese navies and actually possessed large areas of land. She was every bit as violent and brutal as some of her male counterparts, ruling in a very un-democratic way. Her code was strict, calling for beheadings if someone in her crew was caught sleeping with a woman.

Ms. Cheng’s career, unlike almost every other pirate in history, ended well. She simply walked into the office of a Chinese official and negotiated a “surrender” which involved her keeping her entire stash of loot. She was able to retire and live out the rest of her natural life in peace. Not bad… not bad.

5: Jean Lafitte

Character archetype: Anti-hero/mob boss

Jean and Pierre Lafitte ran a smuggling business in Louisiana in the early 1800’s, a century after piracy’s golden age had ended. Despite being artifacts of another time, the brothers managed to set up a very successful smuggling operation in Barataria Bay.Lafitte’s story is a chance to show the more strategic side of piracy. It’s not going to be particularly action packed, instead it’s going to rely on tension and political games as the Lafitte brothers outsmart adversaries. (Certainly more House of Cards than Black Sails.) Like Bellamy, Lafitte was generally merciful to his victims, often returning their ships to them. After robbing them of their loot, of course.

The climax to Lafitte’s story comes in 1815: shortly after the American navy finally defeated his haven and put a stop to their operations, the British army arrived to invade New Orleans. He was given two offers, to either fight with the invading British or to help protect the city in exchange for a full pardon. Lafitte accepted the American offer, and he and his men became American heroes, fighting alongside a motley crew of native americans, militia, and professional soldiers to defeat the British. Come on, Hollywood! You love American heroes! There’s one right here just waiting for a miniseries!

6: Calico Jack Rackham.

Anne Bonny and Calico Jack as they appear in Season 1 of “Black Sails.” Why the costume designers didn’t give Jack more colorful calico to wear, I don’t know

Character archetype: Lovable rogue

Number six on the list is the pirate perhaps most accessible to the average movie audience, because his name and personality is already partially represented in the form of the most famous fictional pirate of all time: Jack Sparrow. While hardly the most successful pirate, Rackham’s flamboyant personality and colorful career makes him a perfect candidate for a blockbuster. Calico Jack was obsessed with women and clothing, wearing a coat made from the same colorful material as his nickname. His crew also contained the only two known female Caribbean pirates: Anne Bonny and Mary Read. The producers of Pirates of the Caribbean went as far as to make his flag the flag of the Black Pearl.

Rackham also nicely falls in line with many expected pirate tropes: His crew’s ultimate demise came when the men of the ship got shit-faced drunk and were thus unable to put up a fight when a British warship stumbled across them. The women, however, did put up a fight. Upon his execution, Anne Bonny is also credited with one of the best historical quotes relating to piracy: “Jack, if you had fought like a man, you needn’t be hanged like a dog.”

Speaking of…

7. Anne Bonny

Character archetype: Femme fatale

Tomahawk-wielding, fearless, and by all accounts stunningly beautiful, Anne Bonny was Jack Rackham’s non-exclusive lover and by all means his equal. Her gender, unique choice in weaponry, beauty, and ferocity make her a character almost impossible to get “wrong” as long as she’s written accurately. There’s always a place in fiction for women like her, whether it’s Brigid O’Shaughnessy in The Maltese Falcon or Rita Vrataski in Edge of Tomorrow. And to the entertainment industry’s credit, Anne has fared better than many of the men. She’s in Black Sails, League of Legends, and Assassin’s Creed IV. 

What makes Anne Bonny so infinitely “writable” is that, like Braziliano, no one knows what became of her. There is no record of her after 1720. Perhaps she returned to her wealthy plantation owning father in the colonies, perhaps she resumed her life as a pirate, perhaps she settled down somewhere and kept to herself. A writer can take Anne Bonny’s personality and story and take it anywhere. And it’s not hard to make it work; after all, she’s the ultimate pirate badass. Your move, Hollywood.

8. Richard Taylor and Olivier Levasseur

Character archetype: Whatever One Eye Willy is.

One of the most interesting tidbits about Golden Age piracy is that the best place to haunt if you really wanted to strike it rich was not the Caribbean, but Madagascar. Richard Taylor was one of these Madagascar pirates, and commanded a fleet of three ships. Olivier Levasseur served as captain to one of these ships, the Cassandra. Together, in 1722, they captured a Portuguese treasure ship called Nostra Senora de Capo. It was the final capture in Levasseur’s seven year career, and was all any pirate ever needed. Get ready for some gigantic numbers:

A conservative estimate for the treasure’s total worth is $1,540,000. The highest total estimated value? $2,320,665,000. That’s 2 billion. Or approximately 0.5 Donald Trumps.

The minimum individual share for each pirate, if the high estimate is correct: $11,603,325.00

In addition to the gold and other forms of currency, Levasseur also took home a golden cross, inlaid with rubies and diamonds, supposedly so heavy it required three men to carry it. If true, it is by far the largest instance of thievery in history. And here’s the kicker: Levasseur may have actually buried part of it.

While Richard Taylor was able to do what so few pirates ever did, and retire with his share of the wealth, Levasseur was captured and executed in 1730. He used his last words to toss a coded manuscript into the audience and say “find my treasure, he who may.” To this day, rumors persist of the greatest treasure in history hidden somewhere in Madagascar. Go crazy, authors.

9. Black Bart

Character archetype: eccentric villain

Bartholomew Roberts, otherwise known as Black Bart, was the most successful pirate of the Golden Age. Interestingly, he didn’t choose the thug life pirate life. He was a sailor on board a merchant ship captured by a pirate named Howell Davis, and forced into piracy. However, about a month after getting forced into piracy, Davis was killed and in a rather unexpected move, the crew elected Roberts as the new captain.

He captured 400 ships (easily 10x as many as that other guy) in three years. (which is ancient in pirate years.) He terrorized two hemispheres, getting bored of the Caribbean and eventually sailing to the west coast of Africa in pursuit of treasure. Among his most violent acts: he attacked a French warship (not because he wanted loot, but because he considered himself at war with the rest of the world) and hanged a governor from the masts of his own ship. He also enacted a terrible vengeance upon the Portugese island of Principe to avenge the captain he succeded. But what makes Bart so interesting from a writing perspective is that he is the most unique male character in pirate lore.

Reports conflict a bit here, but it’s said that he was a teetotaler, banning rum on board his ship and having a cup of tea every morning. In a time where most pirates were non-practicing protestants, he was a devout Catholic, wearing a golden cross around his neck and holding Sunday mass every week. (Imagine that, a bunch of rowdy pirates essentially in church on a boat.) Like Rackham, he had an obsession with fine clothes, opting for a crimson coat and fancy hat. He was a mercurial leader, sometimes forgiving, sometimes merciless. But most of all, he relished conflict. He’s quoted as being disappointed when a fleet of merchants simply abandoned ship and let him steal them without a fight. Even his enemies were in awe of his boundless courage and bravado.

Bart has the potential to be an extremely interesting character. A deeply religious man pressed into a life of crime, who ended up becoming one of the best in the world at it. He’s an extremely capable villain with a distinct personality that shatters several pirate cliches, and his boast of war against the world is one of the most badass of all time.

10. Captain Mission

Rounding out the list with a bit of a cheat, as Captain Mission was most likely fiction, despite being named in the same book as our primary source on many other pirates in this list. However, it is a bit ridiculous to ask Hollywood to get their pirate history accurate when making movies about flying ships, mermaids, and barnacle-encrusted tentacle-faced undead sailors. So instead of providing a real life story to translate to screen, I’m concluding this list to an alternative to Blackbeard as he’s being used in modern film- as this sort of ultra-powerful king of pirates.

Mission is said to have been the leader of a “pirate nation” in Madagascar known as Libertalia. The residents of Libertalia came from a mix of countries, and so they created their own unique language, blending english, french, dutch, and others, and all of them called Mission captain, though Libertalia operated as a democracy. They were jerks with hearts of gold, targeting slave ships in particular and freeing the africans on board.

TL:DR: Get your pirate shit together, Hollywood.

Cordingly, David.  Under the Black Flag.  Random House, 2013.


Johnson, Charles.  A General History of the Most Notorious Pyrates.


Cordingly, David (1999) Life Among the Pirates: the Romance and the Reality


Special thanks to Dr. Ken Fox of Exeter University

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