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Ching Shih and The Story of Gay Pirates

Ching Shih

Very little is known about the early life of Ching Shih, there wasn’t much documentation and if there was most of it wasn’t in English. But thanks to Dian Murray, the fact we even know who she is, is because of Dian and her book “Pirates of the South China Coast 1790-1810” which covers her exploits.

Who was Ching Shih

So Ching Shih was Cantonese and was born in 1775, in Guangdong. It’s believed she was a sex worker who quickly rose through the ranks in a brothel in Guangzhou. She was famous for using her incredibly effective “pillow talk” to influence men to get what she wanted.

She did this until 1801, when she married Cheng Yi, who was a well-known pirate and the formidable commander of the Red Flag Fleet. Cheng Yi could trace his family pirating roots to being connected to the Ming dynasty.

The Ming Dynasty was the ruling dynasty of China between 1368 to 1644.

Sources differ on why he married 26 year old Ching Shih, some argue that it was purely a business move intended to consolidate power, and others say that it was because he became just so infatuated with her beauty and loved her dearly.

But what the sources don’t mention is that it was SHE who, flat out REFUSED to marry him, unless she became a full and equal partner in the business, with 50% shares. (She had some cahoonas on her thats for sure!!)

Meeting Ching Yi

So they agreed to marry, and Ching Shih got involved fully in her husband’s piracy, solidifying her place in the large pirate fleet and organising a coalition with many other large Cantonese pirate fleets. She became known as Ching Yi Sao (which basically translates to Wife of Ching Yi). In records she is called Zheng Shi, Madam Ching, and many other variations on her name, which all meant wife or widow of Ching Yi.

You may of heard of this badass woman pirate before and thinking “It sounds so familiar??!” Well… in ‘Pirates of the Caribbean. At World’s End’ she appeared with the name “Mistress Ching”.

Ching Yi used his reputation and naval strength to bind former rivaling Cantonese pirate fleets into a unified alliance and Ching Shih would use secrets she learned as a sex worker to wield influence over wealthy and politically connected power players in the area.

Soon they unified many small groups of pirates into one massive fleet, in fact a federation of 70,000 men and 400 junk ships. Their coalition consisted of six fleets known by the colours of blue, red, green, black, white and yellow.

Their Growing Fleet

So during their marriage, Cheng Yi adopted an adult son, Cheung Po Tsai, his legal heir, and they also had later two more biological sons.

Sadly though, Cheng Yi died. Maybe it was dodgy, suspicious, or maybe not, some reports said that he sailed directly into a storm and drowned, but that seems unlikely. Either way, because of his death, that initially left Ching Shih in a bit of an awkward position, although she was co-leader and 50% of everything was in her name, she was female, so that along with the fact that she was a female pirate, was a very rare phenomenon.

Cheng Yi’s adoptive son and heir, Cheung Po Tsai, was originally intended to inherit control over the Red Flag Fleet. Unlike in Western countries, the adoption of adults was a common practice in China at this time, this was to establish a kinship basis for further interaction between families.

mistress ching
Mistress Ching as portrayed in Pirates of the Caribbean: At World's End

Where’s the Gay you’re asking?

Well… so Cheung Po Tsai was more than just Ching Shih’s step-son, the young pirate had also been Ching Yi’s lover!

PIRATES ARE GAY!!! (Although I don’t suggest being a lover with your adoptive son….)

So in the 17th century, the pirate world lived in parallel to the traditional one, and homosexual couples may have been the norm, not the exception. The gays, and society around them, at this time were oddly impartial when it came to same-sex civil partnerships and they even had health insurance!

Of course, technically, it was illegal to engage in form of gay sex in many navies – Britain’s Royal Navy punished ‘sodomy’ or ‘buggery’ with lashes and even hanging. In reality, a lot of captains found homosexual relationships useful on board as they reduced tension and increased the bond between men.

Pirates would often recruit their crew from merchant or military ships they attacked. A lot of these crew members were already engaged in gay sexual acts so it was a lot easier to lure someone over with the promise of not being hanged for having sex with the same-sex. Also, piracy was seen as a release from the wider restrictions of society’s other sexuality and gender based rules.

For any women pirates, they were allowed to be androgynous and wear trousers! Women who wanted to be known by a different name whether female or male, was also accepted.


A lot of what we know about piracy today is actually from the Buccaneers age. This age of piracy was from the 1650s to the 1730s and Buccaneers were created on the island of Hispaniola, in the Caribbean. Which today, is known as Haiti and the Dominican Republic.

These had been Spanish Colonies previously, but by 1605 it had been abandoned by the colonisers. So these areas became a haven for runaway slaves, mutinous soldiers, sailors and protestants who fiercely opposed the Catholic Spanish. They all came here and sheltered together.

There weren’t many women, so it was nearly an entirely male society, so they would live in same-sex couples. They would initially hunt pigs and cattle that would roam the island which they would roast on a wooden barbecue which was called a “Boucan”, earning them the name “Buccaneers”, they would also sell the hides and meat to passing ships.

The Spanish government worked hard to wipe out the buccaneers by destroying the animals they hunted. But this just made them turn to piracy in an attempt to survive. Eventually this persecution forced them off the island and onto a much smaller and barren, but more defensible island of Tortuga, off the north coast of Hispaniola. (Which links back to the film Pirates of the Caribbean.)

Tortuga was split between French and English colonies, which worked out, because they both hated the Spanish too! But they weren’t biggest fans of the Buccaneers, and they definitely didn’t like the whole “gay sex” thing.

So the French had a plan for that. The governor Jean Le Vasseur arranged for up to 1,650 female prostitutes and petty criminals to be shipped from Paris to the island. Which the buccaneers were not opposed to, and so they just started having sex with both men and women and had a great old time!

So they created a whole new pirate community that started their very own society, with new standards and principals, like universal healthcare.

Pirate Society

So it was up to captains like privateer (which is a state sponsored pirate) Captain Henry Morgan to draw up contracts with their crew before an attack.

Pirate compensation:

  • If they lost a foot or a hand in battle, they would receive 600 pieces of eight as compensation.
  • Both legs were worth 1,800 pieces of eight
  • 200 pieces of eight were compensation for losing one eye,
  • And 2,000 pieces of eight would be awarded they became totally blind.

They also had their version of Gay marriage, their same sex unions were called Matelotage, those in a matelotage shared all possessions, were called a ‘matelot’. They also inherit and choose to take punishment on the others’ behalf.

Their relationship was treated with solemn respect and would not be interfered with by other crew members.

But this wasn’t the only freedom allowed within the pirating world. Back to the small number of women who joined the pirates, a lot of those would live their lives as men. Whether this was because they ‘had to’ or maybe they were happy to do so, identifying as what we would now identify as non-binary or transgender; we will never know fully as they didn’t have that kind of identification back in those days.

Mary Read and Anne Bonny are the most famous female pirates. Whilst both went outwardly as male, they didn’t just seem to just solely identify as male, this is because how they would refer to each other.

The real Ching Shih

So Anne Bonny’s father had stolen her away from his wife’s family when she was young and dressed her as a young boy called Andy to aid the disguise. She grew up with a temper and she was stabbing people by 13 years old. She fled to the Bahamas and that’s where she began to hang with the pirates.

Mary Read on the other hand who would go by the name Mark, was said to have dressed as a man to get ‘honest’ work at sea. But that went tits-up when pirates took a ship she was working on and forced her into joining them.

She swapped ships onto the one that was owned by pirate Captain John ‘Calico Jack’ Rackham, where she saw and began being seduced by Captain John’s lover at the time, Bonny, yes that’s right, Anne Bonny. This made John a little put out, and nearly made Mary walk the plank but Anne persuaded him not to, and instead suggested they could just have threesomes together!

They then went onto stealing a ship from Nassau, the capital of the Bahamas, recruited the crew and captured many other ships around Jamaica. They were having a great time shagging each other, getting treasure, until…

On the 15th November 1720, Calico Jack’s crew were having a rum party on board when a pirate hunter cornered them and stormed their ship! A lot of the men were too drunk to fight back. Only Anne, Mary and one other pirate were able to fight. They single handedly took on the hunters and apparently Mary was NOT happy they disturbed the party and on top of that got very angry that the pirates were not defending themselves, so started shooting at her own crew members.

Eventually though, the pirate hunters beat them and Captain John was sentenced to death and Anne’s last words to him were “Had you fought like a man, you need not have been hang’d like a dog”. Anne and Mary escaped immediate execution because they were both pregnant with HIS babies!

Sadly though, a fever got hold of Mary and she died from it in prison. Anne however escaped, and was never captured again.

The gay history of pirating is very rarely told. But it’s definitely there!

But I bet you’re wondering about Ching Shih?

Well, although many things about pirating remained the same in the East as it was in the West. The biggest difference was that there was no stigma on women being on board a ship, or being bad luck for the ship.

In Southern China, male and female couples lived together on the water, sharing in the work equally. From fishing to pirate ships, women worked alongside men, and the captain’s wife often succeeded her husband in the event of his death.

In Ching Shih’s case though, she was going to have a big job trying to take control of so many outlaws. So first on her to-do list was to neutralise the threat of her husband’s lover / adopted son, and she did this by what? MARRYING HIM!

Yep, she really did that! She took Cheung Po as HER lover and maneuvered herself back into power. Ching Shih’s control over the pirate fleet at that time was absolute, which was because this time, it wasn’t a 50-50 split with her new husband. Instead this time, it was ALL hers, which enabled her to rule unopposed but also because of her insistence that all pirates under her command respect very strict pirate code. That pirate code had three main rules and several secondary ones, and all of them influenced pirate sailors into the tight-knit group that was very organised and tough to beat.

The pirate code rules of Ching Shih’s fleet were:

  1. Pirates who gave unsanctioned orders or who refused to follow orders were executed on the spot.
  2. Stealing from the “public fund” of captured goods or money or raiding villages that supported pirates was punishable by death.
  3. All captured goods, money or slaves had to be presented for inspection. The rewards were handed out in a predetermined way.
  4. It was absolutely prohibited to have sex or rape female captives. Pirates could marry pretty captives if they had means to support them and be faithful to them, but rest were either ransomed or freed.
  5. Various other offenses were punishable by flogging, ironing, quartering and mutilation (this was almost exclusively performed on deserters).

With her very savvy business mind, she ruled from the Yellow Sea to the Straits of Malacca. Since the turn of the 19th century, poverty in China was on the rise, Ching Shih was like the Chinese female version of Robin Hood and instead of just plunging ships for some treasure and scraps, she turned her sites on wealthy towns. Then she would charge them a fee to stop pirates coming back, going onto redistributing some of that wealth back to the poverty stricken areas of China.

This earned her loyalty and more importantly, a supply of food, recruits and clean water.

Ching Shih became one of the richest people on the planet at that time and and the largest pirate fleet ever seen.

The Power of Ching Shih

An East India Company employee named Richard Glasspoole was captured by Ching Shih’s pirates in September 1809 and held him until December of that year. In his account of the ordeal, he estimated that there were 80,000 pirates under Ching Shih’s command and some 1,000 large junk and 800 smaller junks and rowboats.

Let’s compare that to good old, Blackbeard. Who only commanded 4 ships and 300 pirates within the same century.

Ching Shih was so rich, she even started up a pirate bank and dealt out pirate pension plans! She was doing ALL this by just her early 30s!

The size of her fleet allowed her to take on entire nation’s navies, squaring up to the Chinese, British and Portuguese. The Chinese really tried to stop her, but she sank 63 chinese warships in just ONE battle, so the rest of the chinese sailors fled, convinced she had some kind of magic!

The one thing that really cements the fact that Ching Shih was the best pirate of the time was that did ALL this and got off in the end, completely scot free!

In 1810, at the age of 35, she accepted an offer of amnesty from the Chinese government. Which meant she got a full pardon for her crimes and was allowed to keep all the money she made and on top of all that she even was allowed to set up a fund to help pirates transition from piracy to civilian life.

There isn’t much information on what happened after her deal with the Chinese government, there were a few stories. One was she married a governor and lived the rest of her days in a quiet, rich lifestyle. The other one is that she ran a brothel and gambling house until her death. Or that she may have run a massive land-based smuggling operation.

Maybe she did none of those things, I guess we’ll never really know.

What we do know is that she lived until 1844 and died at the age of 69 surrounded by her children and grandchildren and a TON of money!

So that is the story of Ching Shih, and the great Gay history of pirates!

My sources were:

Shannon Halliwell (She/Her)
Latest posts by Shannon Halliwell (She/Her) (see all)

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