Ching Shih, The Former Prostitute Who Became The Greatest Pirate Who Ever Lived

Hayley Milliman

Hayley Milliman
Content Lead

In September 1809, two Portuguese ships pulled out of the port at Macau. The ships left after nightfall, loaded to the brim with cannons, rifles, men, and a very specific mission: stop the notorious Red Flag Fleet, which had ruled China’s seas unchecked for years.

At the head of the Red Flag Fleet was the most powerful pirate in history, and sorry, Blackbeard, we’re not talking about you.

We’re talking about Ching Shih, a female prostitute turned pirate who became the leader of a fleet of tens of thousands of men before she was 35.

Badass Bitch Ching Shih is the coolest pirate we know. Sorry, Jack Sparrow.

Started From The Bottom…

Never one to turn down an opportunity, Ching Shih made the most of her time in a floating brothel, like the one pictured above. She used her position to learn secrets about the wealthy and powerful.

We don’t know a ton about Ching Shih’s early life. We don’t even know her birth name – “Ching Shih” basically translates to “widow of Ching.”

What we do know suggests that Ching Shih’s childhood and early adulthood were not great. She was born in the Guangdong province of China in 1775 and as a young adult made her living as a prostitute in a floating brothel in Canton. There are few accounts of her time in the brothel, and Ching Shih herself rarely spoke about it. Regardless, Ching Shih would later be a pioneer in the treatment of women and, more specifically, female prisoners once she came into power. More on that later, though.

Eventually, Ching Shih’s beauty caught the attention of a pirate named Zheng Yi, who commanded the Red Flag Fleet. There are various accounts of how Ching Shih and Zheng Yi ended up married – some say he ordered a raid to plunder the brothel and steal Ching Shih away, some just say he was like, “Hey, let’s get married.” Either way, he met Ching Shih and knew he had to marry her.

Irrespective of how strong Zheng Yi’s proposal game was, we know that Ching Shih herself was already a boss ass bitch.

She accepted Zheng Yi’s marriage offer, with two big stipulations: she had to have power in the Red Flag Fleet, and Zheng Yi had to split all his plunder with her. Zheng Yi, recognizing that Ching Shih was really f***ing awesome, agreed, and the two were married.

Under the dual leadership of Zheng Yi and Ching Shih, the Red Flag Fleet did some serious growing up. In just a few short years, the fleet grew from 200 ships to 600 ships and made alliances with other powerful pirates in the area. Everything was sailing along just fine until Zheng Yi died, six short years after his marriage to Ching Shih.

Never one to miss an opportunity, Ching Shih took her husband’s death in stride, consolidating power and assuming control of the Red Flag Fleet. Ching Shih summoned the fleet captains to her (some of whom had tried to run away after Zheng Yi’s death) and threw down a challenge: either they could try to escape, and probably die, or they could serve under a woman and become the baddest fleet the world had ever seen.

Now, we imagine that scene went a little something like this:

Ching Shih laid out her terms to the fleet captains. The pirates looked at each other slowly and then back at Ching Shih. After a long pause, the biggest and burliest of them said something like, “I’m in,” and the rest followed suit. Ching Shih, a light salty breeze tossing her hair, raised an eyebrow and said, “Let’s get to work, boys,” as the violins swelled.

Or you know, something like that.

A Code Worth Fighting For

If you saw one of Ching Shih’s ships approaching, you probably wanted to start moving very quickly in the other direction.

Ching Shih was unlike any leader the Red Flag Fleet had ever had. For starters, she had a vagina. She was also quiet, calculating, and smarter than all of the other pirates put together.

Her first act as ruler of the Red Flag Fleet was to marry her husband’s lover and adopted son (yes, you read that right), Cheung Pao Tsai (also known as Chang Pao or Cheung Po), whose name translates roughly to “Cheung Pao the Kid.”

Cheung Po had been Zheng Yi’s right-hand man before the latter’s death and was well-respected throughout the Red Flag Fleet. Despite their relationship status of, “it’s complicated,” Ching Shih knew that Cheung Po would be a powerful ally. Ching Shih seduced and married Cheung Po soon after Zheng Yi’s death, gaining a new husband and a loyal lieutenant in one fell swoop.

With Cheung Po’s help, Ching Shih grew the Red Flag Fleet until it had tens of thousands of pirates. She was a shrewd and regimented pirate lord who held her underlings to an extremely strict code of ethics, which she required each ship to display in a common area.

Cheung Chau, the island where Cheung Po supposedly stashed a sh*tload of treasure.

Here are the rules that pirates in the Red Flag Fleet had to follow:

  • Ching Shih is boss. If you disobey her orders or dare to give your own, you lose your head.
  • Booty belongs to the fleet. Anything you claim as booty during an attack has to be turned over to your superior. If you f*ck up once, you’ll be whipped. If you f*ck up twice, you die.
  • Stay on your ship. If you leave without permission, you’ll lose your ears (because you weren’t using them to listen to your orders). If you do it again… you guessed it, you die.
  • Don’t rape women. If you rape a female captive, you’ll be down one head (your own, in case that wasn’t clear).
  • Consent is sexy. So is commitment. So you want to have sex with a woman? Cool, but you have to marry her first and you have to mean it. Because if you cheat on her, you’ll regret it. Not for long though, because you’ll be beheaded. Want to have sex with a woman who’s not your wife? Too bad. You don’t get to. If you do, well, you guessed it. You die.

Ching Shih’s code was harsh, revolutionary, and extremely f*cking effective. Under her leadership, the Red Flag Fleet was unstoppable. She ruled the seas from Macau to Canton, plundering coastal towns, markets, and villages, lining her pockets and getting more and more ships and men to join the Red Flag Fleet.

Her reign continued, largely unchecked, until the Battle of the Tiger’s Mouth in 1809.

Every New Beginning Comes From Some Other Beginning’s End

A map of Tiger’s Bay, where the Portuguese navy was finally able to piss Ching Shih off enough to retire.

Cut back to those two Portuguese ships.

By 1809, the Chinese, the Portuguese, and the British (all of which had sea trading interests in the area where Ching Shih and the Red Flag Fleet were operating) were sick of Ching Shih’s shit. They were losing to her, a lot, and her dominance was getting in the way of their whole keep-all-the-money-for-themselves operation.

In the past, each country had tried to take on the Red Flag Fleet individually and lost almost every time. So, the three powers teamed up to take down Ching Shih.

The Portuguese knew that Ching Shih wouldn’t go down without a fight, so they loaded their ships with as much firepower as possible and set out to meet the Red Flag Fleet, which was under the command of Cheung Po.

Sources are conflicting about what happened next. Some say that the Red Flag Fleet’s small junk ships (that’s not a commentary on their quality, they were actually called junk ships) were no match for the heavy artillery of the Portuguese and the fleet was defeated. Others say that Ching Shih went to the Emperor of China to ask for amnesty. Still others say that the Emperor of China himself went to Ching Shih to grant clemency. Regardless of what actually happened, the Red Flag Fleet was defeated.

But how did Ching Shih take her fleet’s defeat?

Like a badass bitch, obviously.

Instead of simply giving in, Ching Shih refused to go quietly and spent months negotiating with the Chinese government. The end result? Ching Shih didn’t surrender. She retired.

And she retired pretty handsomely, too. Ching Shih got amnesty for most of her men, herself included. She negotiated an even sweeter deal for her adopted son-turned-husband Cheung Po, who became an officer in the Chinese Navy.

And all that booty Ching Shih had accumulated over the years?

She kept it.

This kind of “retirement package” was basically unheard of – after all, Ching Shih had spent years stealing from not one, but three, of the largest naval powers at the time and plundering villages up and down China’s coast. To walk away with no prison time, a fat stack of cash, and no lasting consequences was shocking.

It seems like nothing was impossible for Ching Shih.

Not one to fade off into obscurity, Ching Shih took the money she had earned and opened a gambling house. She lived for another thirty years and died at age 69, a wealthy, comfortable, and well-respected badass bitch.

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