Female Pirates Who Were Every Bit as Fearsome as Blackbeard

Grace O’Malley

Think all pirates were rough-and-ready men who took to the seas to escape poverty? Think again! Grace O’Malley was none of these things. In fact, she was born into Irish nobility, the daughter of southern Irish chieftain and wealthy sea trader. As befits such a young lady, she received a fine education, learning Latin and, just as importantly, how to run an estate.

However, it was not her books that fascinated young Grace, but the sea. Such was her desire to sail, she famously cut her own hair and dressed as a boy in a failed attempt to get a job on one of her father’s vessels. The exploit may not have got her on a boat to Spain, but it did earn her the nickname ‘Grainne Umhaill’ (or ‘cropped hair’), which would stick for the rest of her life.

In 1546, Grace was married, though for politics instead of love. Her union with Donal, the son of another chieftain was certainly useful, and fruitful, too, producing three children. It was, however, quite short-lived. Donal was killed while out hunting, just one of many victims of the clan warfare that plagued Ireland during the sixteenth century. Grace was to be heartbroken again soon after. Following the death of her husband, she took a sailor for a lover, but he too was killed, this time by members of the MacMahon clan. Grace vowed revenge.

Under her command, her crew attacked a MacMahon clan stronghold, killing the men involved in her lover’s slaying. But even then her thirst for vengeance was not sated. Grace married again, with her union with Iarainn Bourke, or ‘Iron Richard’, giving the two families almost complete control of the seas off southern Ireland. But within a year, the couple were divorced. Showing her tactical awareness, Grace took the Burke stronghold of Rockfleet Castle, giving her a key advantage as she took to the seas to ward off English ships. According to most accounts, Grace was a skilled and fearless leader of men in naval battle, repelling the old enemy as the Tudor monarch tried to exert greater influence over Ireland, and fending off attacks from rival Irish clans.

So powerful did Grace O’Malley become that the English plotted to kidnap her two sons. They succeeded but did not break her. Instead, she boldly went straight to London in person, meeting face-to-face with Queen Elizabeth I. She convinced the monarch to not only let her sons go but to remove the hated Sir Richard Bingham from Ireland (according to legend, she had a dagger hidden on her person just in case the talks didn’t go so well).

Despite this woman-to-woman agreement, Grace returned home to Ireland and continued to support the campaign for Irish independence, going back on her word to Elizabeth. The last years of her life were dedicated to this cause. Her death at Rockfleet Castle in 1603 removed a huge thorn from the side of the English.

Pirate Queen Teuta of Illyria

However powerful it became, Ancient Rome didn’t always get its own way. This was certainly the case in the Adriatic Sea, where they never quite managed to tame the Illyrians, a small but strong nation, feared and respected for their sea-faring prowess. But not for them the life of trade. Instead, under the strict rule of King Agron, the Illyrian people preferred to attack trade ships and ports, pillaging whatever they could and getting fat and rich off the profits.

King Agron loved nothing better than joining in piracy and then partying with the crews of his ships afterward. So fond was the monarch of enjoying the spoils of war that, after learning that his forces had recorded a famous victory over the Aetolians, he literally drank himself to death. His second wife, Teuta, was required to step in and rule over the Illyrians until Argon’s son Pinnes was old enough to assume his destiny.

As it turned out, Teuta was every bit the warrior her deceased husband was. Almost straight away she got busy upsetting her nation’s neighbors, giving her royal approval to her subjects’ pirating raids. Not only did this help keep her people wealthy, it also allowed her to expand her kingdom, most notably with the capture of the island of Corcyra after the Battle of Paxos. Control of this island meant control of the main trade routes between mainland Greece and Greek cities in Italy. While the Roman Republic might have been happy to look the other way in the past, now it felt threatened and decided to act.

Rome sent two ambassadors to meet with Teuta, hoping to convince her to put an end to her people’s piracy in the Adriatic. They severely underestimated their adversary. The Queen declared piracy to be a legitimate business, put one of the ambassadors to death and imprisoned the other. When news of this reached Rome, the Senate declared war on Illyria. The year was 229 BC.

The Illyrian War was not exactly a close-run contest. Rome sent a huge force, some 20,000 men on 200 ships, across the Adriatic. Faced with such a foe, Teuta’s generals quickly surrendered, and their pirate Queen was forced to retreat. After a brief siege, Teuta herself surrendered, signing a treaty that forced her to recognize the rule of Rome, to give up most of her lands. Her tyranny of the seas was over. What became of Teuta after her defeat to Rome is not known. According to some sources, the Queen, so distraught at her loss of power, threw herself off a mountain, a fittingly dramatic end to such a colorful life.

Mary Read

Cutlass in hand, a pair of daggers around her waist and a battleax in reserve as she boarded yet another ship: Mary Read was not to be messed with, as her enemies learned the hard way. Sailing alongside Calico Jack Rackham and Anne Bonny, she epitomized the so-called ‘Golden Age of Piracy’, wreaking havoc on the Caribbean Sea and leaving this world as dramatically as she entered it.

The future swashbuckler was born in 1685, the illegitimate child of a sea captain’s widow. Given the circumstances of her birth, Mary’s mother was keen to keep it secret. Since she had a son who had recently died, she decided to raise Mary as a boy, fooling friends and even family. The ruse was so effective, in fact, that Mary was able to find employment, first as a footboy and then, even more improbably, as a sailor in the British Navy.

In her female guise, Mary met a Flemish soldier. The two were married and Mary gave up her sea-faring ways to settle down as an innkeeper in the Netherlands. But her domestic bliss was short-lived. Her husband’s untimely death tempted her back into service, this time for the Dutch Navy. However, this was a time of peace, and so, seeking adventure and fortune, she soon quit and jumped on a boat heading to the West Indies.

Ever the rebel, Mary joined the rest of her crew in mutiny, and soon joined with small-time pirate John ‘Calico Jack’ Rackham and his partner-in-crime Anne Bonny. Mary succeeded in fooling everyone with her male disguise. So much so, in fact, that Bonny soon found herself attracted to her new crewmate, forcing Mary to tell the truth. The three then enjoyed great success targeting smaller vessels in the Caribbean, until one night, when they were drunk from celebrating a heist and the British Navy caught up with them off the coast of Jamaica.

Led by feared pirate hunter Captain Jonathan Barnet, the British had the element of surprise, and the pirates were almost all too drunk to put up a fight. Mary Read did, however, refuse to be taken without a struggle. According to lore, she killed one of her crewmates to encourage the others to resist, but to no avail. All were captured and sentenced to hang.

As with Anne Bonny, Read claimed that she was with child, sparing her the hangman’s noose, but not prison. It was here, behind bars in Spanish Town, Jamaica, that she caught a fever and died in April 1721.

Cheng I Sao

At the height of her powers, Cheng I Sao commanded more than 300 pirate ships and an estimated 20,000 men. What’s more, she had good relations with fellow pirate leaders and between them, they had a huge outlaw armada at their disposal. Quite simply, Cheng I Sao was one of the most remarkable people ever to set sail under the Jolly Roger. And her accomplishments are even more astonishing given her humble origins.

Though next to nothing is known about Cheng’s early years, what is known is that she was born as Shi Xianggu, in Guangzhou, southern China, in 1775. As a young woman, she turned to prostitution but was hardly a victim. Using her charms, she quickly learned how to take advantage of men, getting to know their secrets and using this knowledge to her advantage. One of the men she got to know and win the respect of was Cheng I, a local businessman who belonged to a long line of pirates.

Whether it was pure love, or whether Cheng I saw the chance to make use of Shi Xianggu’s wiles for his own ends, the pair were soon married. The most profitable partnership in piracy history was born. For six years, the duo oversaw the expansion of the Cheng piracy empire, with his militaristic aptitude and her people skills ensuring that they controlled almost all the South China Sea. Then, in 1807, Cheng died. But, rather than stepping aside, his grieving wife took on the business herself. Cheng I Sao (literally translated as ‘Cheng’s Widow’) was born, and she was only getting started.

In a move worthy of a Roman emperor, Cheng installed her deceased husband’s number two, a man by the name of Chang Pao, as the head of her formidable navy. And while he took to the seas to plunder what he could get his hands on, she worked behind the scenes, building up alliances with other pirates and extending the business into other areas, including extortion and blackmail.

But perhaps Cheng’s most remarkable achievement was her creation of a set of pirate laws. Realizing she needed to instill some discipline into an armada that now stretched to 1,500 ships, she laid down her laws. Any sailor flying under her Red Flag would be beheaded for disobeying an order. Thieves would also lose their heads. What’s more, she also changed the rules with regard to captives. Women deemed too old or ugly were set free, while young and attractive females were auctioned off among the crews. Business was booming, but her list of enemies was growing.

With the Chinese Navy, as well as the British and the Portuguese on her tail, she quickly accepted a deal from her homeland: In exchange for her freedom, and that of most of her men, she would leave her piracy life behind. Remarkably, unlike so many pirates, Cheng lived to a fine age, becoming a grandmother and respected businesswoman. She even enjoyed a peaceful death, dying in her sleep at the age of 69 in 1844.

Rachel Wall

Rachel Schmidt’s childhood was far from idyllic. She was born to a devoutly religious family in Carlisle, Pennsylvania in the year 1760. Her family owned a farm, but a life living off the land held no appeal to young Rachel. Instead, she found herself instinctively drawn to the city’s waterfront. The docks were no place for a young lady on her own, however, and one day she was attacked. But, so the legend goes, a man by the name of George Wall came to her rescue. The two were soon besotted with one another and, while Rachel’s mother objected to the union, got married. Luckily for the bride, George owned a boat…

After George returned from one of his many trips to sea, he finally persuaded his wife to join him on a voyage. She readily accepted, and along with a motely crew and their loves, the couple set sail on a schooner. Soon, however, their funds ran out. Should they return to shore? Rachel could go back to her job as a house servant perhaps. But George had a better idea: Why don’t they become pirates instead?

Whether Rachel accepted the proposals enthusiastically or if she needed convincing, nobody knows for sure. But before long, she was not only a crew member of a pirate ship but was playing a crucial role in targeting its victims. She would play the ‘damsel in distress’, standing up on deck alone and calling at passing boats for help. Should a vessel come to her aid, the pirates would storm the ship, kill all its occupants and steal whatever they could get their hand on. In all, it’s estimated that between 1781 and 1782, George, Rachel and their crew captured 12 boats, stole thousands of pounds in money, and killed as many as 24 people.

She might have gotten away with it, too, had it not been for her own arrogance and greed. Once their spree was over, the outlaw couple returned to dry land and Rachel resumed life in domestic service, this time in Boston. But she couldn’t help herself: She would frequently go down to the docks and, if she saw something she liked, would steal it for herself. She was finally caught trying to steal a fancy bonnet and hauled before the judge on a charge of robbery.

On the dock, Rachel requested that she be tried for piracy. She admitted her crimes but maintained she had personally never killed anyone. Despite her pleas, she was found guilty of piracy and sentenced to death, aged just 29. She holds the distinct honor of being the last woman to be hanged in the State of Massachusetts

Jeanne de Clisson

In the midst of the Hundred Years War between England and France, just the name ‘The Lioness of Brittany’ was enough to strike fear into the hearts of French sailors. And for good reason. Jeanne de Clisson was every bit as ruthless as any male pirate, though her background could not have been more different to the average outlaw.

Jeanne – or, to give the lady her full title, Jeanne Louise de Belleville, de Clisson, Dame de Montaigu – was born in 1300 to a noble family in Brittany, northern France. As was the custom for the aristocratic youth of the time, she was married off aged just 12. The youthful union produced two children and lasted for 14 years until the death of her nobleman husband. A short-lived second marriage followed and then Jeanne got married for a third time to a wealthy Breton trader by the name of Olivier de Clisson.

By all accounts, theirs was a happy partnership, with the couple welcoming five children into the world. However, history got in the way of true romance. The early 1300s saw the crowns of France and England at war, with Brittany caught in the middle of the bloody conflict. Olivier sided with the French against the English, but that didn’t stop rumors emerging that he had switched to the other side. Learning of such rumors, King Philip VI ordered Olivier to be tried for treason. After a sham of a trial, he was beheaded. What’s more, his body and head were sent to different parts of France to be publicly displayed, a shame usually reserved for common criminals rather than members of the nobility. Jeanne was not only grief-stricken but humiliated and angry. She vowed to have her revenge.

And how better to get back at King Philip of France than to sell all her land and build her own mini-army? At first, she and her loyal men attacked French soldiers in Brittany, but this soon got too risky, so she took to the seas. Here, in the English Channel, flying under black sails and black flags, her small fleet would attack any French ship they came across. When they captured a vessel, all the crew were butchered, with the exception of one or two men, who were sent back to France to spread the word that the ‘Lioness of Brittany’ had struck again.

For some 13 years, Jeanne fought the French, first as an independent pirate and then in alliance with the English. She even continued after her nemesis Philip VI died, and only gave up the pirating life to marry an English noble and settle down. While some might say she got her revenge, the Lioness of Brittany never did manage to get hold of the man who started the rumors against her beloved Olivier.

Mary Wolverston

During the reign of Elizabeth I, the coastal waters of Great Britain were a dangerous place for a vessel to be, particularly any carrying valuable cargo. And the southwest of England, in particular, was a hotspot for piracy and smuggling, thanks in no small part to the countless harbors, coves and hidden beaches that dot the shoreline here. It was here that Mary Wolverstone plied her illegal trade.

Little is known about the early life of Mary, but it is known that she was born in the county of Suffolk around 1525. The history books describe her father Philip Wolverstone as a ‘gentleman pirate’. And while young Mary might have shunned the family profession for a short while, when her first marriage ended with the untimely death of her husband, she was soon following in her father’s footsteps.

Her chance came through her second marriage to Sir John Killigrew, an outwardly respectable Member of Parliament and landowner based in what is now modern-day Cornwall. However, like many politicians of the time, Sir John was often greedy and willing to break the law to get what he wanted. Part of his vast estate included Pendennis Castle, a fortification dating back to the time of Henry VIII. Control of the castle meant control of a huge natural harbor, something Sir John, with the help of his wife Mary, took advantage of.

The criminal couple would order raids on boats coming into their harbor, bribing local officials into keeping quiet about their illicit activities. While Sir John was adept at spotting ships with bug bounties, Mary loved handling the booty. Some of the treasure she stored in the basement of Pendennis Castle, and some she buried in its large gardens. The partnership was highly successful and hugely profitable, and Mary might have gotten away with it had she not let greed get the better of her.

In the winter of 1582, Mary heard rumors that a Spanish vessel carrying great treasures had docked not far from her base. Despite the fact she was now in her 60s, she sensed an opportunity and ordered her men out to sea. In the raid, a Spanish sailor was killed, something even the friendly local officials would struggle to hush up. Mary was accused of organizing the raid and also found guilty of fencing treasures obtained through piracy. The punishment for such a crime was, of course, the death penalty.

Mary, however, escaped the executioner’s ax after her son paid a huge bribe to the magistrates. She would eventually receive a royal pardon from Elizabeth I, and lived out her last years in relative obscurity. The exact date and place of her death remain unknown.

Sayyida al-Hurra

If you were captaining a ship through the Mediterranean Sea in the early sixteenth century, you’d definitely be hoping to steer clear of Sayyida al Hurra. The pirate queen controlled almost every square mile of the western part of the sea, enriching herself through the plundering of treasure and capturing of slaves. Not bad for a lady who was originally expected to play the role of a quiet, submissive and doting wife.

Sayyida al Hurra was, the history books tell us, born in the year 1485 in Granada, Spain, to a wealthy Muslim family. When the Spanish Catholic Monarchs Ferdinand and Isabella re-took the city, her family were forced to move to Morocco, where she received a full education until being married off to a friend of her father at the age of just 16. Luckily for her, her new husband happened to be the governor of the city of Tetouan and, when he died in 1515, she took on the role. She even stayed in the position after she re-married, this time to the King of Fes. But, she was not simply content to sit in her palace all day. Sayyida still felt deep, burning anger at her family’s forced to escape from Granada. She plotted revenge on her Christian enemies.

Using her status and connections, she reached out to Heyreddin Barbarossa in nearby Algiers and proposed an alliance. Under the agreement, she would engage in piracy in the western part of the Mediterranean, while he enjoyed the spoils of the eastern seas. The deal worked out extremely well for both parties. Thanks to her family’s wealth, Sayyida was able to build up a strong fleet and used it to target both Spanish and Portuguese ships. Any treasure on board, she kept. However, she was open to returning captured crewmen to their native countries, providing a heavy ransom was paid, of course.

Sayyida was widely respected, both by her allies and her enemies. A successful and highly lucrative raid on Gibraltar in 1540 further cemented her reputation as one of the most feared pirates in all of the Mediterranean. For almost three decades, she oversaw hundreds of raids, amassing a huge personal fortune through the taking of treasure and slaves, and is now regarded as one of the most notable women in the history of the Islamic world.

However, while her family connections may have helped kickstart her career as a pirate, so too did family matters bring the good life to an end. In 1542, her son-in-law rose up against her, successfully removing her from power and condemning her to live her final years powerlessly and impoverished. She died in self-imposed exile in the summer of 1561.

Jacquotte Delahaye

Sure, lots of pirates had cool nicknames. But did any ever have a moniker as intriguing as that of Jacquotte Delahaye? Probably not. Her nickname, “Back from the Dead Red” hints at just how fascinating her life was, even if relatively little is actually known about it.

What is known for sure is that Jacquotte was born in modern-day Haiti in around 1600. According to the legend, her mother died in childbirth and her father was brutally murdered when she was just a young girl. She was then left alone to care for her disabled brother. Since there were very few professions open to adventurous and strong-willed ladies at that time, Jacquotte turned to piracy and, before too long, she was making a name for herself on the Caribbean seas.

In partnership with another female criminal, Anne-Dieu-le-Veut from France, she put together a small ragtag crew and targeted small boats, plundering their treasure. This did not sit well with other pirates, and soon a price was put on her head. In a bid to get them off their back, while at the same time escaping the authorities, Jacquotte faked her own death. But retirement held little appeal and soon she was back out on the open seas.

Like many of her female counterparts, Jacquotte tried to pass herself off as a man. However, her striking beauty and flowing bright red hair easily gave her away. Soon, then, she gave up the pretense. She was “Back from the Dead”, and quickly returned to leading hundreds of outlaws and dozens of boats. She even managed to establish a “freebooter republic”, taking over a small Caribbean island. It was here, so the legend goes, that she died, defending her pirate utopia from attackers.

With her unbeatable combination of beauty and bravery, Jacquotte Delahaye inspired countless tales over the years. Some even maintain that she herself was a work of fiction. Certainly, unlike many pirates, there is no real historical evidence confirming her existence. But where’s the fun in that?

Where did we find this stuff? Here are our sources:

“Rachel Wall, New England’s Only Lady Pirate”. New England Historical Society.

“The Revenge of Anne and Mary”. Rebecca Simon. Medium. Oct 9, 2019

“How Two 18^th Century Lady Pirates Became BFFs on the High Seas”. Hadley Mears, Atlas Obscura, September 2015.

“Ireland’s pirate queen: Twelve fascinating facts about the legendary Grace O’Malley”. Aidan Lonergan, The Irish Post, July 2017.

“The Swashbuckling History of Women Pirates”. Lorraine Boissoneault. Smithsonian.com, April 2017.