Long before Kiera Knightly and Penelope Cruz ever swaggered across the deck of the Black Pearl, a small group of fierce female pirates ruled the seven seas. They turned to piracy to escape the entrapments of civil society, to protect their people, to defend their legacy and to follow their true loves.
These women embodied bravery, loyalty and an unceasing sense of adventure. They heard the sea’s call and answered it with a rallying cry that put fear in the hearts of even the staunchest soldiers.
1. Cheng I Sao
Cheng I Sao, which literally means “the wife of Cheng”, was working as a prostitute when she caught the eye of a young pirate captain. When she married Cheng I in 1801, Cheng I Sao struck him a deal: She would accept his proposal on the condition that he make her an equal partner in his piratical ventures.
It was, with little doubt, the best decision Cheng I ever made.
By the time Cheng I passed away, the couple had managed to amass a fleet of over 400 ships. After her husband’s death, Cheng I Sao took over the entirety of the pirate fleet, using her shrewd business skills to grow the fleet further until it included over 1,500 ships and 80,000 men.
Knowing that the pirates would not respond to direct female leadership, Cheng I Sao put her adopted son, Cheng Pao, in charge of the fleet. She then married him.
While her new husband took care of the every day workings of the fleet, Cheng I Sao focused her efforts on orchestrating a huge network of spies and smugglers to supply her fleet with food and information.
This fierce female pirate is also infamous because of the articles her men sailed under. Cheng I Sao’s pirate code was unusually harsh: Raping a female captive was punishable by decapitation and any deserters would lose their ears.
Attempts by the authorities to stop Cheng I Sao’s fleet resulted in bitter defeat after bitter defeat until the government lost so many ships they were forced to commandeer private vessels to chase the pirates.
Eventually Cheng I Sao and her crew were offered amnesty by the government, a bargain that the piratess knew she could not refuse.
After retiring with Cheng Pao to run a successful brothel, Cheng I Sao finally died at the ripe old age of 69.
2. Grace O'Malley
Known today in her native Ireland as Granuaile, Grace comes in a close second to Cheng I Sao as one of the fiercest female pirates of all time.
Born to a seafaring family that traded, fished and fought throughout European waters, Grace’s veins ran blue with saltwater.
Though Grace married Donál O’Flaherty at 16, it was clear from the start that she was not prepared to take up the traditional wifely duties that would have been expected of her. Grace became more powerful than her husband and eventually commanded the unquestioning loyalty of her clansmen.
Grace made a devious profit by descending on sluggardly merchant ships and offering them safe passage for a price. If they refused to pay, their safe passage ended there and then.
When Donál died during a skirmish against a neighbouring clan, Grace quickly avenged his death and took control of their island castle. The castle had been known as Caislean-an-Cullagh (the Cock’s Castle) because of Donál’s arrogant pride. After Grace’s swift retribution, however, the castle became known as Caislean-an-Circa, or the Hen’s Castle.
Denied the property that was rightfully hers by her own sons, Grace moved her operations to Clare Island. From her island fortress she could continue her piratical escapades with the help of her loyal followers.
After several more years filled with legendary adventures and romances, Grace married Richard-an-Iarainn, or Richard the Iron, with whom she bore one son. Supposedly Tibbot was born at sea and, when the ship was attacked the very next day, Grace leapt on deck to fight, cursing her useless crew who could not go a day without her guidance.
As the English took control of Ireland, Grace found herself under constant bombardment by the new Governor of Connaught, a man named Richard Bingham who was intent on destroying her and her clan. Tired of his relentless harassment, Grace eventually wrote to Queen Elizabeth I, beseeching her to end the injustices against her, and allow her to fight against the Queen’s enemies.
The Queen responded with a series of questions but, just as Grace responded, Bingham arrested her son and brother. This was the final straw for Grace and she set sail for England to lay her case before the Queen herself.
So it was that the Queen of England and the Pirate Queen of Ireland met in the summer of 1593. Apparently, the two women each saw a great deal of themselves in the other and Queen Elizabeth commanded Bingham to leave Grace and her family alone.
Grace retired to one of her castles and passed away in the same year as Queen Elizabeth.
3. Mary Read
Mary Read’s life was unusual from the moment she was born. Mary’s father and brother died within months of each other, forcing Mary’s mother to disguise her as a boy to ensure the continued financial support of Mary’s paternal grandmother.
Going through several career changes, Mary met her husband while she was a cross-dressing soldier in the army. She confessed her gender, her love and married her comrade only for him to die a few months later.
Mary took to the seas following her husband’s passing but, as luck would have it, the Dutch merchant she was aboard was captured by pirates. The nefarious crew was commanded by non other than the pirate captain Jack Rackham, also known as Calico Jack, and his first mate, Anne Bonny.
Mary was on board the ship for several months before she and Anne discovered that they shared the same secret. Probably the only two cross-dressing pirates to ever cross paths, the two became fast friends.
Though the pirate crew was eventually captured by the authorities, Mary and Anne went down with their boots on, fighting even while their male crew members cowered below decks.
After daring her shipmates to fight like men, Mary fired a few shots into their midst, killing at least one man.
Mary escaped death by hanging by claiming to be pregnant. Unfortunately her pregnancy could not save her from the ravages of a fever and she died while still in prison.
4. Anne Bonny
The illegitimate daughter of a lawyer, Anne and her father moved to South Carolina after the details of the affair became public.
Even as a teen, rumours abounded concerning the girl’s strong temper: She was said to have stabbed a servant girl and severely injured a young man who tried to molest her.
Anne eventually fell for a low-life pirate named James Bonny whom she married. In fact, Anne was still married when she met Jack Rackham. After trying to get her marriage annulled unsuccessfully, Jack and Anne took to the seas together.
When Mary joined the crew, the three became inseparable until the very end.
Like Mary, Anne escaped the death penalty because she was pregnant, an excuse Jack could not make use of.
It is said that Anne was allowed to see Jack one last time before he was hanged and her final words to him were: “I’m sorry to see you here, but if you had fought like a man, you need not have hanged like a dog.”
Anne’s own fate is unknown but it is certain that she did not die in prison.
This 9th century Goth princess was a woman of fierce conviction who had little regard for social conventions.
Supposedly a young woman of untold beauty, Alfhild’s father protected his daughter’s virtue by keeping her locked inside under the guard of two poisonous snakes. Any man who wished to seek her hand in marriage had to first make it past her scaly guardians. If any potential suitor failed, he was to be decapitated and his head displayed on a stake before the castle.
Needless to say, when Prince Alf became the first man to make it past the snakes using his own cleverness and resourcefulness, it was expected that Alfhild would take his hand. Apparently, however, the newly freed princess had her own plans.
Alfhild quickly turned to piracy, apparently becoming successful enough in her raids that several expeditions were sent to stop her. Finally Alf himself was sent to capture the Goth piratess.
Alf’s crew fought until his lieutenant crossed swords with the princess herself. Before unleashing his final blow, the soldier’s sword knocked her helmet off and the prince got his first look at his princess. According to legend, that glance was enough to send him into a passion and the battle ended there and then when he scooped her into his arms.