Throughout history men have placed themselves in positions of authority but every now and then a woman temporarily breaks through the testosterone ceiling and takes charge. Piracy is no exception. Following are a few interesting women who, for at least a part of their lives, were successful pirates.
Zheng Yi Sao
She was born Shi Yang in 1775 in China. In 1801 she married a pirate, Zheng Yi and became Zheng Yi Sao (wife of Zheng Yi, but I’m going to continue calling her Shi Yang, because reasons). Her husband Zheng Yi was born into the pirate life, his father and grandfather both having been pirates, so Shi Yang married into a family business. Her husband was leader of a pirate confederation; several large fleets of pirates banded together, creating a navy larger than any nearby government, so large it was essentially a business corporation.
It’s interesting reading the various sources regarding the marriage. Several sources (probably citing each other) describe Shi Yang as “brothel madame”, or a prostitute, and at least two sources describe her as nefarious and powerful in her own right through secrets she learned during pillow talk. Her husband is often described as infatuated or seduced and the marriage is considered one of convenience between business partners. One source even claims that the marriage contract included Shi Yang getting 50% of her husband’s piracy business.
In truth, there is virtually no evidence she worked as a prostitute. The accusation of prostitution against a woman of influence is common in ancient history, both occidental and oriental. I direct you Mary Magdalene for a western example.
In 1807, her husband died, however sources disagree about how he died. It was either in a storm, falling overboard in an accident, or killed by his wife (of course). Shi took control of the fleet, consisting of about 200 ships and between 20,000 and 40,000 men and by 1809 the fleet had grown to over 500 ships.
Sources are quick to point out that her trusted lieutenant was her stepson (he had been captured by her husband in 1797 during a raid, adopted by her husband and eventually became a leader of the largest fleet). Her stepson, Zhang Bao, was also her lover and eventually she married him, and if that sounds a little icky, they were only about 5 years apart in age.
Under Shi the pirate confederation became much more active with numerous battles with government fleets and raiding of ports. Despite many attempts, authorities were never able to defeat her navy except in small battles and Shi was always able to recover quickly from these defeats. Then in 1810, things changed.
In 1810, Shi negotiated her surrender (and I use the term loosely). The sources diverge on why things changed, but the general consensus is that she was in such a powerful position and the governments were so desperate to stop piracy that she was able to negotiate form a position of power.
A second explanation was growing disenchantment under her command. The commander of the one of the other fleets in the confederation, the Black Fleet, had fought a naval battle with Zhang Bao (commander of the largest fleet, the Red Fleet) and in January 1810 had surrendered his fleet to authorities in exchange for becoming a senior commander with the government. This former Black Fleet commander was now a pirate hunter.
Regardless of the reasons for her surrender, Shi was able to secure for herself and her pirates a complete pardon. Her men were given food, wine and money, her husband Zhang Bao was able to keep a private fleet of 20 to 30 ships, and Shi herself was given a large piece of land.
Shi retired to build and run a successful gambling house, dying peacefully in 1844 at the age of 68, outliving her second husband, Zhang Bao by 22 years.
Most pirate lives didn’t end as happily as Shi Yi’s did. And most were definitely not as long. Here are three examples of women who became pirates and died young.
Rachel Wall
She was born in Pennsylvania, but eventually moved to Boston where her husband convinced her to join him as a pirate. Together they stole a boat and began preying on shipping around the New England coast. A typical ploy was to pretend the boat was damaged and Rachel would stand on deck imploring passing ships to assist her. When they had pulled alongside, the crew of Rachel’s ship would attack the ship giving aid. Between 1781 and 1782 they successfully stole from at least 12 ships, killing at least 24 sailors in the process.
Eventually, her husband and most of the crew were killed in a storm. Rachel survived, made her way back to Boston and worked as a servant for a number of years, but a life of theft was one she could not give up. She frequently went down to the docks at night, boarded ships and stole from them while the crew slept. She was convicted of highway robbery after attacking a young woman and stealing her shoes, belt, and bonnet. During her trial she insisted that she be tried as a pirate and not as a “common thief”. Rachel Wall was convicted and hanged in 1789 at the age of 29, having been found guilty of highway robbery; her pirate life lasting about 2 years (although her life as a thief lasted much longer). She holds the dubious distinction of being the last woman executed in the U.S. state Massachusetts.
Rabbit Hole
Pedantic corner, actually. Massachusetts is generally described as a state but its official name is the Commonwealth of Massachusetts. Along with Pennsylvania, Kentucky and Virginia they are the answer to the nit-picky question of “How many states are there in the United States?” While most would answer 50, in the course of the research for this blog I read no less than three papers that argued the correct answer is 46 since the aforementioned four are commonwealths not states.
It’s question and answers like this that make pub trivia a nightmare, and I look forward to pompously correcting someone in the future.
End Rabbit Hole
Anne Bonny and Mary Read
Anne Bonny’s background is unknown. The first mention of her comes from an 1724 book, A General History of Pyrates. Born in Ireland, she moved to the Bahamas and became a member of the crew of pirate John Rackham, along with Mary Read who appears to have joined around the same time. I’m suspecting that John Rackham may have been a lady’s man.
Again, nothing is really known of Mary Read’s background, and her first mention is in the same book as Anne Bonny’s.
From late August to mid-October 1720, Rackham and his crew, including the two young ladies, preyed upon shipping around the Caribbean. Captured in October 1720 by a former privateer turned bounty hunter, Rackham and his male crew were executed. Anne and Mary, however, both claimed to be pregnant and were spared, although they remained in jail. Mary died in jail in April 1721 of unknown causes.
Anne’s fate is murkier. There is no mention of her after the trail, although there is a burial register for an Ann Bonny in December 1733. No family is listed and she was buried without a ceremony, in the same parish where Anne Bonny’s trial took place. It could be the same person, but it is impossible to know for certain.

Rabbit Hole
In the process of researching Anne and Mary, I discovered a whole universe of drawings, art work and stories about the two female pirates. A disturbing amount of the male authored stories portray them as lovers, and rather blood thirsty. Despite being active for only 2 months several stories describe one or both as “Pirate Queens” commanding feared flotillas flying flags of death (that was a fun sentence).
In A General History of Pyrates, there is one passage referencing the trial of Anne and Mary in which the author of the book states they were lovers. There is no other reference anywhere to their relationship. In spite of that they are considered by some to by icons of early LGBTQ+ culture. “
“They lived determinedly and followed their hearts – both in being pirates and seeking their own destiny but also following their desire to love each other – when society demanded marriage” Professor Kate Williams.
I would like to point out that that she can only make such a statement by referencing A General History of Pyrates, which is considered less history and more fan fiction with the author taking considerable artistic licence (noted even at the time of publishing by contemporary biographers).
In fact, A General History of Pyrates (it’s full name is A General History of the Robberies and Murders of the most notorious Pyrates) is considered to be the template by which all following pirate fiction is based. Among the things mentioned that later became stereotypical of pirates; The Jolly Roger flag with the skull and crossbones design, the idea of missing legs and eyes, a parrot and the feathered trichome hat.
End Rabbit Hole
Enough for today, have a good week!
Next week, I got a traffic ticket in Italy!

