Ching Shih
(1775-1844)
Princess of the Chinese Seas
In 1809, the Chinese government sprang a trap. They were gunning for a group who’d taken control of its southern waters, the Red Flag pirate fleet. Blockading them in a bay, the authorities laid siege to the pirates for three straight weeks with an overwhelming amount of firepower. In the end, the Red Flags strode out through a graveyard of government ships, largely unscathed. At the head of the Red Flags stood one of the most fearsome pirates in history — Ching Shih, a former prostitute turned leader of over 70,000 men.
Getting accurate information on Lady Ching is a bit difficult. Nobody knows much of her early life. Even the name Ching Shih isn’t her own — it translates to “widow of Ching”, her late husband and commander of the Red Flags before her. We do know that before her husband died, he (and by extension, his fleet) was so renowned that the Emperor gave him the title “Golden Dragon of the Imperial Staff,” effectively promoting him to the rank of prince — and thus, one could argue, obliquely making her a princess.
“Under the leadership of a man you have all chosen to flee. We shall see how you prove yourselves under the hand of a woman.”
She was a leader unlike any they’d had before. Where her husband had been brash and loud, she was quiet and calculating. Soon into her rule, she took a charismatic man named Chang Pao as her husband and installed him as head of the fleet. This proved a savvy move for a number of reasons. Chang Pao had been her husband’s right hand man (and lover… and adopted son… yeah, it’s a bit weird), and was widely respected among all the pirate fleets. Moreover, he was an illiterate fisherman’s son (he’d been taken by the pirates as a child and received little to no schooling), and likely easy to manipulate.
Under Chang Pao’s name (and Ching Shih’s guiding hand), many unruly pirate fleets united under the Red Flag banner, eclipsing the size of all other pirate groups. Every single ship, no matter how small, was given an edict from Ching Shih to display in a common area. This outlined an incredibly hardcore code of conduct:
- Ching Shih okays all attacks beforehand. Disobey, and you’re beheaded.
- You give all loot to your superior, who distributes it afterwards. Disobey once, you’re beaten severely. Disobey twice, you’re dead.
- Don’t desert your post or take shore leave without permission. Disobey once, we cut off your ears (since you clearly weren’t using them) and parade you around. Disobey twice, you’re dead.
- Rape a female captive, better believe that’s a beheading.
- Have consensual sex with a female captive without permission, you’re headless and she’s taking a swim with a lead weight.
- If you want to have sex with a female prisoner, you take her as your wife. You are faithful to her. You treat her well. Or we take your head.
- Oh, and don’t use the word “plunder.” Instead, say “transferring shipment of goods.” It just sounds nicer.
It is telling that one of the primary sources on Ching Shih’s life was a Westerner she’d imprisoned for three months while setting up his ransom.
Under the leadership of Ching Shih, the Red Flags were unstoppable. As previously remarked, the government (with the help of the Portuguese) made a concerted effort to isolate and kill her in late 1809. That didn’t happen. When the government sent “suicide boats” — ones loaded up with straw and explosives, set on fire, and launched at the pirates — the Red Flags extinguished the flames, repaired the ships, and incorporated them into the fleet. In the end, the pirates lost 40 people and lost not a single ship. The leader of the government expedition falsified the reports to make himself look better and later committed suicide in shame.
Eventually, the government’s persistent interference became too troublesome for even Ching Shih, and she put up her swords — but here, too, her genius shines through. Instead of merely negotiating amnesty by informing on her shipmates, she spent months bargaining with the government. The end result: she actually retired. The government gave over a big chunk of cash, cancelled all warrants for her, and made Chang Pao lieutenant in the Chinese navy. One of his first acts? Using the government forces to destroy their old pirate rivals.
According to most sources, Ching Shih spent her final years running a brothel and gambling den. She died at age 69, a wealthy and widely-respected woman.
Art Notes
- They’re all wearing silk robes, as the leaders of the fleet would be at this point in time. Chang Pao (seen on the left) is in purple, as was his habitual dress style.
- The ship they’re on is a Chinese junk, with requisite red flag on top.
- She’s wielding two period-accurate Chinese scimitars, although whether she actually did much swordplay is a matter of some debate.
- Tied up on screen right is a British admiral, a callback to the fact that much of what we know about her came from one of her captives.
- She’s signing her actual name on the scroll.
If you were a Patreon backer,
you'd be seeing some cool stuff right here.
Next Time on Rejected Princesses
What? You SAID you were thirsty, Cyrus.
Login with Patreon


These are all so awesome! Love them all! Can you do Kurmanjan Datka next? Pleeeease? I’m in Kyrgyzstan where’s she’s a big fucking deal because, well, she was a badass.
There are hints each week for who the next princess will be. The current hint is “This notable resident of Flinders Island has a name – and a story – that reads like a tragic opera.” So… probably not Kurmanjan Datka. But she is on the list.
Cool! Reminds me of Grace O’Malley.
Has she broken her back, or was her backbone made out of rubber?
That bizarre 90-degree angle is actually her leg.
I get it, I can’t draw. Thanks y’all. :) It’s on the docket to be redrawn.
not really an error in the article, but ive always thought it telling that among historians, that when successfull and powerfull pirates gets brought up, ching-shih is almost never brought up, or when she is, she’s often ranked far below where she should be, considering that all in all, she was undoubtedly the most powerfull and among the richest pirates the world has ever seen.
she controlled a fleet of, at its height 70000+ men, more than several modern nations have proffesional soliders. she took on the powers of the portugese and chinese empires of the time, both nations have massively powerfull navies and crushed them. then after a life of asskicking, she forced an empire she had plundered for years to give her and her men amnesty for their crimes and then retired peacefully and rich as sin.
all of this should mean that she’s the greatest pirate ever to live, yet she’s far more obscure than pretty much any carribean pirate of any renown, even though the most powerfull of those, Bartholomew Roberts didnt have one tenth of that power behind him and died fighting the authorities.
hell, here’s Forbes list of the top earning pirates in history http://www.forbes.com/2008/09/18/top-earning-pirates-biz-logistics-cx_mw_0919piracy.html and she despite actually retiring with most her wealth isnt even mentioned.
in other words, despite being history’s greastest pirate, she doomed to obscurity because she’s 1. a woman and 2. asian.
Grace O’Malley could totally outsail and outpirate that [sexist slur redacted] any day of the week. But then, she actually has disney princess-esque cartoons.
https://www.youtube.com/watch?v=RR-iI0ioKyI
Hi there,
Thank you for commenting, but, as you can imagine, using sexist slurs is not allowed on this site. And there is certainly plenty of room for both Grace O’Malley and Ching Shih to be great historical figures. The awesomeness of one does not detract from the other.
No but she did defeated fleets of the chinese and portugese navies and survived, survived suicide boats and repaired and added them to her fleet. Pretty much made the government her botch and retired,unlike most pirates, and lived happily and rich. So. Also, she was a woman in charge in a time where women werent respected period. So who cares about a rubber back? Its a rubber back. Whoopdee do
inspiration for her was Mistress chang
people are jealous of the truth sad to say! 1. yes 2. perhaps but even chinese dont want to remember there ancestors Mao told all chinese to destory family records everything and I mean everything
the woman on movie way too old, since she retire at her age of 35 on the history book.
yeah