Female Pirates Who Were Every Bit as Fearsome as Blackbeard

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.