The Female Prostitute That Rose to Become One of the Most Powerful Pirates in History and Whose Armada Took on the Chinese, British, and Portuguese Navies… and Won

Today I found out about the prostitute that rose to command a huge armada that controlled the South Chinese Sea and the Guangdong province.

While female pirates weren’t uncommon off the coast of Asia in the 18th and 19th centuries, one woman stood above them all.  Her birth name isn’t known, but this Cantonese pirate went by the name Ching Shih (also, by Zhèng Yi Sao, “wife of Zhèng”, and Zhèng Shì, “widow of Zhèng”.  For the purpose of this article, I’ll just refer to her as Ching Shih to avoid any confusion.)

Ching Shih was born sometime around 1775 (the exact date isn’t known).  At the age of 26, she found herself working as a prostitute in a floating brothel in Canton.  While there, she caught the eye of Zhèng Yi, already a successful pirate with a small fleet of ships at his command, known as the “Red Flag Fleet”.  Exactly how the two ended up together is disputed.  Some historians hold that Zhèng Yi sent a raid to plunder the brothel and asked his men to bring back his favorite prostitute, Ching Shih, for his portion of the loot, while others claim he simply went there himself and proposed that they wed, which she only agreed to after he consented to give her equal share of his plunder and to allow her to help run the organization.  Whatever the case, once married, Ching Shih did indeed begin helping  Zhèng Yi run the Red Flag Fleet.

During the next six years, their fleet grew initially from about 200 ships to 600 with some key alliances, including forming the Cantonese Pirate Coalition with pirate Wu Shi’er, and then to 1700-1800 ships by 1807, as more and more pirates flocked to their banner.  Unfortunately for Zhèng Yi, on November 16, 1807, he found himself caught in a typhoon and didn’t manage to survive the ordeal.

Rather than step aside, handing over the organization to someone else, Ching Shih convinced Zhèng Yi’s second in command, 21 year old Chang Pao, to support her in taking over the Red Flag Fleet.  Chang Pao was the son of a fisherman and had actually been captured by Zhèng Yi when Chang Pao was just 15.  He was then forced into the life of a pirate.  He quickly gained favor in the eyes of Zhèng Yi due to his intelligence, bravery, and skill in a fight and was adopted by the pirate captain and Ching Shih as a son and made second in command of the fleet.

With Chang Pao leading their troops in raids and the like, Ching Shih focused on the “business” side of things, continuing to plan military strategy and also to govern and grow the organization into something that went beyond just partnered pillaging pirates.  At the Red Flag Fleet’s peak in 1810, she commanded about 1800 ships, both big and small; 70,000-80,000 pirates (about 17,000 male pirates directly under her control, the rest being other pirate groups who agreed to work with her group, then female pirates, children, spies, farmers enlisted to supply food, etc.); controlled nearly the entire Guangdong province directly; held a vast spy network within the Qing Dynasty; and dominated the South Chinese Sea.

She didn’t just rely on looting, blackmailing, and extortion to support her troops either.  She setup an ad hoc government to support her pirates including establishing laws and taxes.  Because she controlled pretty much the entire criminal element in the South Chinese Sea, she also was able to guarantee safe passage through it to any merchants who wanted to pay.  Of course, if they didn’t pay, they were fair game for her pirates.

In order to manage her ruffians and get them all to do what she said without question, she setup a strict system of law within the Red Flag Fleet which basically equated to, “You don’t follow the rules or I think you aren’t and you get your head chopped off.  No exceptions.”  Specific laws included:

  • If you disobey an order, you get your head chopped off and body thrown in the ocean.
  • If you steal anything from the common plunder before it has been divvied up, you get your head chopped off and body thrown in the ocean.
  • If you rape anyone without permission from the leader of your squadron, you get your head chopped off and your body thrown in the ocean.
  • If you have consensual sex with anyone while on duty, you get your head chopped off and your body thrown in the ocean and the woman involved would get something heavy strapped to her and also tossed in the ocean.
  • If you loot a town or ship of anything at all or otherwise harass them when they have paid tribute, you get your head chopped off and your body thrown into the ocean.
  • If you take shore-leave without permission, you get your head chopped off and body thrown into the ocean.
  • If you try to leave the organization, you get your head… ha, just kidding, in this case you get your ears chopped off.
  • Captured ugly women were to be set free unharmed.  Captured pretty women could be divvied up or purchased by members of the Red Flag Fleet.  However, if a pirate was awarded or purchased a pretty woman, he was then considered married to her and was expected to treat her accordingly. If he didn’t, he gets his head cut off and body thrown in the ocean.

She didn’t just restrict herself to sea battles either.  She used her numerous shallow-bottomed boats to good advantage along rivers to raid towns along the way, including defeating any armies that came against her.  For instance, two towns once banded together, raised an army, and sent it against her forces.  The Red Flag Fleet won the battle and she subsequently marched her army to the two towns and ransacked them, including beheading every male found there.

Now, a pirate controlling a large portion of the Emperor’s land and subjects didn’t sit well with him.  As such, he raised a fleet of ships to attack Ching Shih’s fleet.  Unfortunately for him, Ching Shih was also a brilliant military strategist and rather than running from the Emperor’s armada, she sailed out to meet it with her fleet, which defeated the armada quite easily.  Not only this, but she managed to steal 63 of the large ships sent against her and convinced most of the surviving crews to join her… by letting them choose between being nailed to the deck by their feet and then beaten to death or becoming members of the Red Flag Fleet and celebrating the victory with the rest of the pirates.  Needless to say, she found herself with plenty of replacements for the pirates she’d lost in the battle.  As for the Admiral of the fleet sent against her, Kwo Lang, he committed suicide before he could be captured by Ching Shih.

The attacks on her fleet didn’t stop there.  However, now without a fleet large enough to take her on alone, the Qing Dynasty government enlisted the aid of the super-power British and Portuguese navies, as well as many Dutch ships, paying them large sums for their help.  These combined forces waged war on Ching Shih’s organization for two years with little success.  She won battle after battle until finally the Emperor decided to take a different tack.  Instead of trying to defeat her, he offered her and most of her organization amnesty.

Ching Shih initially rejected the terms of the amnesty treaty.  However, in 1810 she unexpectedly showed up at the home of the Governor General of Canton with the intention of working out a peace treaty.  The deal that she struck was that the fleet would disband, including giving up most of their ships, and in return, they would nearly all be granted amnesty and allowed to keep any loot they had acquired during their time as pirates.  The exceptions were 376 of her crew of which 126 were executed and the other 250 received some punishment or other for their crimes.

All the rest got off scot-free and as part of the agreement any who wanted it were to be allowed to join the military, including her second in command and now husband, Chang Pao.  He was given command of 20 ships in the Qing Dynasty navy to command.  Ching Shih was also given money to distribute to her crew to help offset the cost of them switching from a life at sea, to one in the mainland.

As for Ching Shih herself, she negotiated the rights to keep the fortune she’d accumulated and acquired a noble title, “Lady by Imperial Decree”, which entitled her to various legal protections as a member of the aristocracy.  She then retired at the age of 35, opening a gambling house/brothel in Guangzhou, Canton, which she managed until her death at the age of 69.  During this time, she also became a mother to at least one son and a grandmother.  One can only imagine the bedtime stories she told her son and grandchildren.

So not only was she arguably the most successful pirate of all time, but unlike pretty much every other famous pirate in history, she also managed to escape being executed or punished in any way for her crimes and retired extremely wealthy and a member of the aristocracy.  The Dread Pirate Roberts has nothing on her.

If you liked this article and the Bonus Pirate Facts below, you might also like:

Bonus Pirate Facts:

  • Another famous female pirate was Anne Bonny.  Born to a family that eventually became quite wealthy, she went against her father’s wishes and married a poor sailor/pirate.  Now disowned by her father, she moved to the Bahamas around 1715 where she became acquainted with various pirates, in particular Captain John “Calico Jack” Rackham.  She became his mistress and left her husband for the pirate life.  Taking part in the fighting and looting, this red-headed beauty quickly gained the respect of her fellow pirates. (I wonder how a red-head at sea in the Bahamas without sunscreen managed to survive the sun.  My red-headed wife required near hourly doses of the thickest/strongest sunscreen money can buy to remain un-crisped in the few weeks we spent in the Bahamas).  In any event, in October of 1720, the ship she was on was attacked, with most of the crew drunk or asleep, leaving Bonny, Read (another female pirate), and one other unknown pirate to try to fight off the invading troops.  They failed and supposedly Bonny’s last known words about her lover, Captain Rackham, were “…if he had fought like a Man, he need not have been hang’d like a Dog.”
  • Although sentenced to die, Bonny and the other female pirate, Read, were initially spared as they were both pregnant.  They were to be executed after they gave birth.  Read, however, died shortly thereafter in prison of some unknown sickness.  Bonny was never executed and seems to have lived to a ripe old age, dying around 1782. It isn’t exactly known how she got off, but it is thought her father intervened on her behalf (he is known to have done so before in other instances where she was arrested), using his connections with various merchants and businessmen in the Bahamas to secure her release.  Evidence by her descendants suggest she then was returned to her father and married off to Joseph Burleigh a year later and subsequently had 10 children by him, along with the one by Captain Rackham, and lived to the ripe old age of 80.  Again, I bet she had fascinating bedtime stories that she told her children.
  • Another female pirate mentioned above was Mary Read, comrade of Anne Bonny.  Due to being born illegitimately, Read’s mother began dressing her as a boy nearly from birth to take the place of her dead legitimate older brother.  This allowed her mother to continue receiving the inheritance due to her dead son.  Read continued to dress as a boy until grown and found her way as a crewman aboard a ship.  Not liking that, she switched and joined the British military, again still disguised as a man.  She didn’t begin dressing as a woman until she married a Flemish solder and took up residence running “The Three Trade Horses” Inn in the Netherlands.
  • Unfortunately for Read, given how the rest of her life turned out, her now comfortable life was interrupted by the death of her husband at which point she began impersonating a man again, once again joining the military.  After a while she got tired of this and so traveled to the West Indies at which point her ship was taken by pirates and she was coerced into joining their ranks.  A few years later, in 1720, she  joined the crew of Captain Rackham and Anne Bonny, though still with everyone thinking she was a man.  She was discovered to be a woman by Bonny when Bonny started to fall for her. The two then became even closer, once Bonny knew she was a woman, and Rackham became jealous.  When Rackham tried to murder Read, he too was let in on the fact that she was actually a woman.  From there, she sometimes dressed as a woman and sometimes as a man, depending on the circumstance.
  • The two went on pirating together until they were captured as described above.  Read subsequently died in prison either before or during childbirth.  As there is no record of her baby or the birth, it is thought she died of some sickness before giving birth.
  • When first married, Chang Shih and Zhèng Yi sailed to Vietnam and took part in the Tay-Son rebellion, but their faction was defeated and they left shortly thereafter.
  • The third Pirates of the Caribbean movie features a character based loosely on Ching Shih named “Mistress Ching”.
Expand for References
Share the Knowledge! FacebooktwitterredditpinteresttumblrmailFacebooktwitterredditpinteresttumblrmail
Print Friendly, PDF & Email
Enjoy this article? Join over 50,000 Subscribers getting our FREE Daily Knowledge and Weekly Wrap newsletters:

Subscribe Me To:  | 


  • Interesting article. I just think the title is not proper… Could have been something more like “The woman who started as a prostitute and become one of the most powerful….”, since saying “The Female Prostitute” implies that she was born as a prostitute and stayed a prostitute in any case.

  • Were it not for the fact that this is even a NAUTICAL history article, I would not mention this pet peeve: it is NOT take a “different tact”, it is take a “different TACK” – as in *sailing*.
    ( see: )
    Otherwise – very interesting.

  • Honestly you might be better off replacing the word prostitute with sex worker to avoid the confusion.

    As Daryl Lang sums up: “The word prostitute, as a noun, carries the person’s entire identity in one word and casts someone as an object for sale. The phrase sex worker describes a human being performing a task for money.”

    • Sex worker is a Vegas & Reno thing and fairly modern, an attempt to obfuscate in the same vein as calling casinos gaming places……………a rose by any other name.
      NOAA is even playing the name game………….there are no storms anymore, just weather events.

      Confucious said: “The beginning of wisdom is to call things by their proper name.

      We are so silly.

  • Great article though, I never knew any of this. Fascinating woman.

  • Interesting article. I would like to know more. Could you post your sources?

  • Melody Lanzatella

    She is my spirit animal, if you will.

  • is it just my everything acting up or are half the sources broken links?