Five Real-Life Pirates to Inspire your Next Character

real-life pirates

by Amanda Mae Downey

Real-life pirates weren’t the nicest guys and gals. They didn’t have peg legs or happy parrots on their shoulders. They were actually kind of sick, and as you know, us writers love taking inspiration from sick people. Maybe that says something about us.

Captain Blackbeard and his vessel, the Queen Anne’s Revenge have inspired depictions like that in the television series Black Sails and the 2016 novel Blackhearts by Nicole Castroman. Blackbeard is an interesting pirate, but there are hundreds of pirates (or in this case, five) that deserve some quality air-time and I’m here to give it to them.


Samuel Bellamy

Samuel Bellamy
Portrait of Samuel Bellamy || {{PD-US-unpublished}}


Samuel Bellamy was a regular English lad who served for the Royal Navy as a teen. Then he travelled to Cape Cod and met a woman named Goodie Hallett. The details about her age, marital status, and real name are historically iffy, but the general idea was that her parents didn’t like him. This caused the ever so reasonable Sam Bellamy to turn to a life of piracy. Once he became wealthy, he figured he could run away with his love.

Bellamy really committed to the whole pirate gig from 1716 to 1717. He captured over fifty ships and earned the name “Black Sam”, a reference to a black powdered wig he wore. During Bellamy’s year of sailing the seas as a piratical style icon, Goodie gave birth to his son and hid the child in a barn, assuming that it might survive the winter there. Unfortunately for Goodie, she vastly misunderstood proper child care, so upon the son’s death, she was exiled from Cape Cod. Bellamy died en route to Cape Cod, where he wouldn’t have even found Goodie.

Character Inspiration:

Sam Bellamy, possibly because of his motivations or because of his start in the Royal Navy wasn’t actually a horrible guy, you know, for a pirate. He was often described as the “Robin Hood of the Sea”. His motivation for being a pirate is what’s interesting about him. It’s also a lesson in picking unique motivations for villains or antiheros besides just wanting to watch the world burn.

Black Sails

Calico Jack and Friends

Calico Jack
Woodcut of Calico Jack from  A General History of the Pyrates (1725) || {{PD-US}}

Calico Jack is famous for other people’s success, and since he was the captain of so many other notoriously successful people, we’ll just talk about his life of playing second banana from the years of 1718 to 1720.

He was originally shown-up by his first mate, Karl Starling, who designed the Jolly Roger flag. That was a hugely important design, but Calico Jack did manage to do one really important thing, too. He dethroned the cunning Captain Charles Vane, a cruel pirate captain operating out of Nassau.

After this success though, Calico Jack met none other than Anne Bonny, an Irish woman and the wife of a governor. She and Jack had an affair and ran away together, stealing a new ship in the process. On their travels in search of a new crew, they came across a man by the name of Mark Read. He joined the crew and happened to  develop quite the affinity for Anne. As he and Anne got closer, he came clean about himself. Mark Read was actually Mary Read, who was using her dead brother’s name to get work. Mary Read was no pushover though, when one man said he was uncomfortable having her on the ship, she made him even more uncomfortable by stabbing him.

Calico Jack ended his life of inadequacy by being hanged in the British Isles. Both Anne and Mary escaped the death sentence by claiming to be pregnant, but sources tend to disbelieve at least Mary Read, if not both of them.

Character Inspiration:

Not everyone can be the hero of their own adventures and protagonists that constantly get shown up by other people are interesting to write about. Calico Jack was also friends with some pirates that could inspire stories of their own.

François l’Olonnais

Francois l'Olonnais
Illustration of François l’Olonnais in The History of the Bucaneer of America || {PD-US}}


You want a bloodthirsty pirate? Fine. Here’s François l’Olonnais, a creep if there ever was one.

François was active for an entire eight years, from around 1660 to 1668. He was the creative sort and he spent most of his time in the Spanish Main. When he went to Tortuga though, he got extra creative. After pillaging and terrorizing locals, he would also take hostages back to his ship and torture them. I don’t want to get into details, but he made keelhauling look like a flu shot.

After leaving Tortuga, François nearly died in Honduras, but made it to Panama alive. In an elegant twist of fate, François l’Olonnais became the dinner of the local cannibalistic tribe, the Kuna.

Character Inspiration:

François l’Olonnais makes a fantastic villain, but turning the tables and allowing someone as brutal as him to inspire your main character is another idea. Let’s remember that pirates weren’t nice guys. Pirates were criminals with stolen ships instead of fast cars. So if you’re going to write about a pirate character, you’ll have to commit to making them a little gritty.

Pirates of the Caribbean

Ching Shih

Ching Shih
Madame Ching as seen in History of the Pirates of all Nations || {PD-US}}

Not all piratical women disguised themselves as men or ran away with already established male captains. While we like to give Blackbeard the famous role, Ching Shih is actually considered the most successful pirate in history bar none.

She spent only a few years actively pirating in the South China Sea. The dates are unclear, but this was during the mid or early 1800’s, several decades after the golden age of piracy had come to an end. Most knew her as Madame Ching, but at the height of her career, it was very rare to even come across her. She had a fleet of 300 ships and tens of thousands of men devoted to her service.

Early on, Ching Shih was a prostitute until she was captured by pirates. Through her capture she learned the business. She married Cheng I, another pirate. The marriage was simply a 50/50 share of Cheng I’s current career, until he died and Ching Shih took over completely. Ching Shih married Cheng I’s kind-of-adopted son, Cheung, after he died. With such a deceptively similar name, I’m sure no one noticed how strange that was.

Character Inspiration:

Talk about a savvy underdog. While I make it sound like Madame Ching got all the candy, it definitely wasn’t an easy road to the top. She had to eat a few vegetables along the way. Characters that struggle to success are always interesting to read about because conflict drives the story.

Stede Bonnet

Stede Bonnet
An Engraving of Stede Bonnet in A General History of the Pyrates || {{PD-US}}


Often known as “The Gentleman Pirate”, Stede was simply a wealthy landowner with an intolerable wife before 1717. In fact, things were alright. He had a lot of money and a lot of land. Unfortunately, Stede couldn’t handle the fact that he hated his wife. After much contemplation, he realized that the only sensible solution was for him to bite the bullet and turn to piracy.

So he did. He got himself a ship and named her the Revenge. Bonnet knew zilch about sailing, so he had to hand over the reins to the up-and-coming Blackbeard who ended up recycling Stede’s totally unique and totally threatening ship name. Stede worked with Blackbeard for a while until his crew abandoned him for the Queen Anne’s Revenge. After that, he got a license to become a privateer, but that didn’t even save him from being hanged on two counts of piracy in 1718. I bet Lady Bonnet got a kick out of that.

Character Inspiration:

No matter how you tell the story, The Gentleman Pirate was just that—a wealthy man who wanted a new life. A character that doesn’t like the hand he’s been given is a classic, but often overlooked character. We usually see characters with already established roles whose conflict arises due to their jobs or piratical misdoings. Turn it around!

Pirates of the Caribbean

Today, we’re so entranced by pirates because they led dramatic, dangerous, and romantic lives—and that’s not just a fictional trope! Taking inspiration from or writing about real people is a huge part of historical fiction. In fact, Anna wrote a post on how to write characters like this. So go forth and take inspiration from these real-life pirates for your next character. There are some things that you just can’t make up.

What real-life pirates do you find the most interesting? Are they any other notorious pirates that should be on this list?

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