When Women Turn Pirate: Famous Female Pirates of the High Seas

The traditional "Jolly Roger" of piracy

Anne Bonny, Charlotte de Berry and Ching Shih are but a few of the names of famous female pirates who sailed the high seas in search of adventure and plunder.

Anne Bonny Pooh-Poohs the Creature Comforts of an Easy Life to Become a Pirate Rogue

It might readily be supposed that piracy is strictly a male domain. But, in fact, the ledgers of history are filled with a surprising number of piratical accounts featuring swashbuckling piratesses, or female pirates.

How or why did women enter this dangerous, disreputable, high-stakes, rum-swilling male domain and become pirates?

In the case of Anne Bonny, she could have lived a comfortable if uneventful life under the roof of her rich plantation-owning father. She instead chose to live a life fraught with danger and bloodshed — much of it innocently shed, which is an uncomfortable reminder to those of us who may be tempted to glorify the exploits of pirates in general.

Perhaps when Anne Bonny wanted to become a pirate, she would have had a conversation with her old man in his drawing room that ran something like this:

“Papa, I’ve decided to run away with Jack Rackham and become a female pirate.”

Her father, livid and perhaps dropping from the mouth his rich-man’s cigar on the hearth rug, would have said, “You want to be a female — what? Young lady, you’ve got precisely one minute to retract your statement, or, so help me God, I’ll disinherit you on the spot!”

“I might have supposed you wouldn’t understand, Papa. Life to me is intolerably boring, and I won’t suffer another day under your roof. Goodbye then.”

“Why, you ungrateful, impudent, wild young thing! Come here. You’re not too old for my riding crop. Now where did I leave it?”

“It’s right behind you on the mantelpiece where you left it. You’re so forgetful these days. I do hope you’ll be able to get on well without me.”

“Wicked creature! Is this the misery you bring to your father in his old age? And who will inquire after my health when you’re gone?”

“It’s no use, Papa. I’ve made my decision. Jack and I are sailing with the evening tide — er, in a stolen vessel, I might add; but it’s just the sort of roguish life that appeals to me and which you’ll never understand. Don’t try to look for me.”

In fact, Anne Bonny’s father did look for her a few years later after she’d lost her last battle and was imprisoned. Though there is no documented evidence to say so, it is widely believed that when Anne was about to face the hangman, her old man — that same one who could not understand her decision to turn pirate — discreetly saw to it, whether through money or influence, that she was set free.

Ching Shih: From Prostitute to Big-Cheese Pirate Extraordinaire

Ching Shih, or Cheng I Sao, was a no-quarters-given pirate who went by the pirate book. She never met a pirate rule she didn’t like to have enforced.

In the year 1801 the working-girl prostitute Shi Yang (later to become known as Ching Shih) had the good fortune to marry Cheng I, also known as Zheng Yi, who happened to be in possession of a rather large pirate fleet. Now, as all the world probably knows, a large pirate fleet usually means that you can have your way where rich merchant ships are concerned. To this end, Ching Shih took full advantage.

At the time of her husband’s death to a gale in 1807, Ching Shih was in command of over 400 ships and up to 80,000 men. Later, she was in command of an unheard of 2,000 pirate ships– definitely a number to write home about. To suggest that she was anything other than a major player, in fact, the major female pirate player in history, would be duh-faced folly.

Scheming, crafty devil that she was, she was able to consolidate her power further by marrying her stepson, Chang Pao, just after acquiring the fleet.

As an early proponent of women’s rights, and with the authority to enforce what she would, Ching Shih was uncompromising when it came to matters of the flesh. If a crewman of hers was found to have had his way with a captured woman, even if it was not against her will, he would be executed. And, for good measure, the woman would be thrown overboard with a weight attached.

The Chinese fleet attempted to destroy Ching Shih’s pirate fleet but was never able to get the job done. In fact, the clashes often resulted in Ching Shih further enlarging her fleet with captured ships that had belonged to the Chinese fleet.

An amnesty for Ching Shih seemed the best solution for both sides. Ching Shih, with her amnesty in hand, was able to retire in 1810. She lived a long and prosperous life, with a lovely brothel (old habits and inclinations die hard) and gambling house helping to supplement her income as she lived to a respectable old age.

Charlotte de Berry, Resisting the Improper Advances of a Certain Captain, Responds As Any Girl Would: She Beheads Him and Becomes a Pirate

There is some doubt as to whether Charlotte de Berry was a fictional character or not, but there is no doubt she was the subject of more than one lurid penny-dreadful story in bygone centuries. In any event, her story begins in the year 1636, when she was born. It seems that when her man went to sea, de Berry decided to follow him dressed as a man herself. Her husband ended up getting killed off the coast of Africa after a run-in with another ship, and she herself was captured. The capturing captain of that ship, who must have noticed that the curves in her clothing were all wrong for a man, decided that here was an opportune chance for some hanky-panky. De Berry, however, was of a different mind and succeeded in removing the captain’s head with a sword or knife.

Having wiping her blade clean, de Berry then addressed the crew. With a decidedly feminine voice coming from a person previously thought to be as much a man as any of them, she would have easily caught their attention. Though she did not possess the customary pedigree of a prototypical pirate, she nonetheless possessed a commanding presense.

Addressing the crew, she would have said something like, “Listen, lads and all ye who have formerly suffered under a cruel master. If ye have no objections to sailing under one who is female, I hereby take control of this vessel. And — oh, yes — this is now a pirate ship.”

Under de Berry’s leadership the ship and crew enjoyed a successful run doing what pirates do best as they raided along the coast of Africa.