Zheng Shi, the most successful pirate of all time

Updated: Mar 11, 2020

#womaninamansworld #imperialchina #zhengshi

Let's talk about Zheng Shi, The Pirate Queen. Who was she and how did she end up commanding a confederation of pirates? We don't know all the facts for sure, but one thing is true: Zheng Shi was without a doubt the most successful pirate of all time.

Welcome to the first episode of "Chinese History: Legendary Figure Painting." As a formidable female pirate and incredibly gifted businesswoman, Zheng Shi -- the main subject of my painting called The Pirate Queen -- is the stuff of legends. In this video, I share fascinating tidbits culled from her life that I discovered while searching for reference materials.

If you enjoy learning about this kind of stuff, do let me know so I'll be sure to keep it up. And if you have any suggestions or ideas, I'd love to hear them as well. Thanks and enjoy.


It's mid-November 1809. In an alliance of last resort, the Chinese and Portuguese have come together to take down the most formidable confederation of pirates the world had ever seen. The Portuguese have bl­ockaded a fleet of pirate ships in the narrow Humen Strait along the Pearl River Delta. Their targets? Pirate confederation leader Zheng Shi and her second-in-command, military strategist, adopted son, and lover. Yeah, it's a little weird, what little we know of this woman. But all the same, this is the fascinating story of hands-down, the most successful pirate of all time.

Hi everyone, I decided to start sharing stories about the subjects featured in some of my art in these new episodes called Chinese History: Legendary Figure Painting, because what I realized is that as I go about researching my subjects and finding reference materials, I always stumble upon something fascinating about the person or time period that gets me excited about painting, and I hope it helps you understand a little bit of background about the subject as well.

As is probably always the case, the story I'm about to share is a mix of fact and lore, as very little is really known about the Pirate Queen, Zheng Shi. First, let's take a look at the time period. Now, most of the photographs featured here were taken in the late 1800s, some 50 to 60 years after Zheng Shi had already retired. But they do give us a sense of what life might have been like during the Qing Dynasty, and the years in which she lived after she gave up her piratical career.

Zheng Shi came from the lowest rungs of society. Even though Canton was home to the most rich and powerful members of Chinese society, it was also home to some of the most desperate and destitute. As the only port through which almost all foreign countries were allowed to trade, Hong Kong and towns along the Pearl River thrived with merchants, traders, warehouse owners, and government officials. But, the wealth gap between the haves and have nots was immense. Floating slums made up of boats strung together became the home for fishermen, prostitutes, and other lower class citizens -- more commonly known as, "boat people." And this is where historians first find any record about our Pirate Queen.

Some time in the late 1790s, Zheng Shi was working as a prostitute in a floating brothel, known at the time as flower boats, not unlike this one pictured here. The prostitution industry at this point was highly developed in Southern China. At the time, daughters were considered a liability to families. You feed them, clothe them, raise them, and marry them off -- taking a dowry with them, and you never see them again. They essentially become members of another family. So, it was not uncommon at the time for daughters of poor families to be sold to richer households to work as servants or slaves, or as was probably Zheng Shi's case, sold to brothels.

So you're probably wondering how a prostitute became a pirate queen. Well, Zheng Shi managed to catch the eye of an infamous pirate at the time -- then commander of the Red Flag Fleet and the pirate confederation, Zheng Yi. He came from a long line of pirates, as piracy was back then, a family affair. But, he really set himself apart by turning the world of ragtag, competing pirate boats that were constantly at risk of killing each other off into a well-oiled, military coalition with himself at the top.

Historians aren't really sure if Zheng Yi was simply infatuated with her, or whether he married her for her genius in business and trade, but in the end, the marriage was rumored to have been a full partnership, as Zheng Shi refused to marry him unless he gave her 50% control and stake in all of his operations.

So let's just do a recap here, we have a young prostitute who (1) not only receives an offer of marriage from an infamous pirate who could basically take whatever he wants, she (2) demands half of his empire, and (3) he actually agrees. They married in 1801, but only six years later, Zheng Yi apparently died, having drowned in a tsunami, leaving the commanding position over the pirate coalition up for grabs.

The most logical successor would have been Zheng Yi's adopted son, Zhang Bao Zi who he groomed from a fisherman to become a well-liked, charismatic and effective pirate in his own right. But, this prospect didn't go over well with Zheng Shi. She manages to secure not only Zhang Bao Zi's vote for herself to become to next leader of the pirate confederation, they become lovers as well. Once members of Zheng Yi's extended pirate family also supported her, the other fleets fell in line behind her as their next leader.

I think it's hard for someone like me, even in the modern era to understand how it was possible for a woman to have amassed this much power among a group of predominantly male outlaws, but this is part of the surprising thing about looking back in history and seeing such an example of female leadership.

At the time that Zheng Shi was operating during the Qing Dynasty, it was highly uncommon for women to take an active role in society. This was the era in which foot binding was everyday practice for any family in polite society. Confucianism as a social philosophy relegated women to a very small, supporting role in family life. Women really couldn't do much at all. But, among the margins of Chinese society, where people had to struggle to survive, foot binding was a luxury families could not afford. This is a photo of a boat woman during the Qin Dynasty and just compare her with a lady of the same time period.

Women at the bottom rungs of everyday life were expected to work, and it was no different whether you lived on a fishing boat, a flower boat, or a pirate ship. Zheng Shi had proven herself as a shrewd business woman as Zheng Yi's wife, and now with her adopted son supporting her as second in command, there really was no stopping her. Still, she had to control anywhere from 20,000 to 80,000 pirates and coordinate 300 to 1,000 junks in a fair and organized manner. Just to give you a Western reference point, the infamous Blackbeard commanded only 300 pirates and a few ships, so by comparison, Zheng Shi had to fill some pretty big shoes.

One of the first things she did was enact a strict code of laws. Everyone was subject to them, no exceptions. The cost of breaking a code was almost always punishable by cutting off the offender's head and tossing their body in the ocean. For example, a ship's loot must be registered with the fleet. The ship takes a 20% cut with the remaining going into a collective fund, and any pirate giving his own orders without permission or disobeying a superior order was beheaded immediately. The code also protected women in particular. If a pirate raped a female capitve, he'd be beheaded as well. If he had consensual sex with a female captive, then both parties would be beheaded. What's more is marriage was allowed. Pirates could marry with permission, but he was required to be faithful to her and honor his wife accordingly.

Under Zheng Shi's rule, the fleet flourished in the most sinister way possible. Even though Zheng Shi is remembered now as somewhat of a lovable villain slash folk hero, it's important to remember that she and her men were still ruthless pirates who terrorized not just the rich, but also everyday people, fisherman, villagers just trying to make a living. The pirates not only extorted protection money from the government and foreign trading ships, they demanded it from towns and if anyone resisted, they would raze it, burning everything to the ground, sparing no one – man, woman, or child – killing them by the thousand, decorating banyan trees with their victim's heads and setting people on fire. The only way you could save yourself from their wrath was to pay up.

Now the Chinese, Portuguese, British navies all made attempts to stop Zheng Shi, but their campaigns met with limited success. The pirate confederation would regularly thwart any plans to stop them, and it wasn't until a combination of more modern naval technology from the Portuguese, bad weather, and confederation in-fighting that hinted to Zheng Shi that her star was waning. Which leads us to the beginning of this story, where Portuguese and Chinese naval forces have Zheng Shi and Zhang Bao Zi's Red Flag Fleet cornered in the Humen Strait in November of 1809. If you consult Chinese imperial or Portuguese records, the combined naval forces bombarded the pirate ships, sank dozens of enemy junks and killed more than a thousand pirates.

However, according to an English merchant officer Richard Glasspoole, who was on board with the Red Flag Fleet as Zheng Shi's captive at the time awaiting ransom at the time, “not a single [pirate] vessel was destroyed.” The navy had even sent burning fire boats loaded with explosives into the bay in order to set fire to the trapped pirate flotilla, but the pirates were able to divert them all to shore, put out the fires, and requisition the boats for their own uses. As the wind shifted, those same fire boats that remained in the bay ended up hurting the Portuguese, allowing the pirates to escape. Nevertheless, it was overly apparent that Chinese ships were at this point completely outgunned by foreign ships – an advantage that the British would exploit in the Opium Wars not long afterwards.

Not only that, the pirate confederation seemed to be getting too large for a single commander to maintain absolute control. It's said that the confederation's Black Flag Fleet was supposed to have aided Zheng Shi's Red Flag Fleet during the battle in November 1809, but they were a no show and defected to the imperial Chinese government in exchange for amnesty. The cracks were already beginning to show in Zheng Shi's empire. So, at the height of her power in April of 1810, Zheng Shi made a bold maneuver and agreed to retire. She purportedly went to Canton and met the Governor General at his residence, she was unarmed and accompanied by a delegation of seventeen women and children family members of her pirates.

The terms of the surrender were as follows: Surrender their junks and weapons, and they could keep their ill-gotten plunder. Those who were willing could join the army or navy. Zhang Bao Zi became a Lieutenant and was allowed to keep a personal fleet of 20 junks – supposedly for trading salt. Zheng Shi was made a lady, and had her mother-son relationship with Zhang Bao Zi annuled, so the two were formally married as well. On April 20, of the more than 17,000 pirates who formally surrendered, only 60 were banished for two years, 151 were permanently exiled, and 126 were executed. The meager 2% that were punished either did some really terrible things or maybe Zheng Shi had it out for them. We don't really know.

So you probably want to know how it all ended for the lawless couple now turned law-abiding citizens. Well, Zheng Shi and Zhang Bao Zi settled in Canton where they had a son and probably a daughter. Zhang Bao Zi ultimately became a Colonel and died at the age of 36 in 1822. Zheng Shi herself enjoyed her new found title and ran a highly profitable gambling house, living well into her 60s and died in 1844, surrounded by her family. So that's the basic story of the most successful pirate of all time, a true villain and queen of the high seas, Zheng Shi.

I hope you enjoyed learning about her as much as I did, and included my reference materials below in the description. Just a final word, I hope to make more of these videos, so please let me know if you have any thoughts, corrections, or even ideas for future videos, too – in a comment below. I promise to read and respond as soon as I can. Thanks for watching.

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