Zheng Yi Sao: the pirate queen who defied an empire

The next part in our series on female pirates is all about Zheng Yi Sao, also known as Ching Shih, the commander of the Guangdong Pirate Confederation. The first article in the series examines the lives of Anne Bonny and Mary Read and you can read it here.

In the 19th century, a figure emerged from obscurity to dominate the humid waters of the South China Sea. Zheng Yi Sao rose from the margins of society to command one of the largest and most disciplined pirate fleets in history. Blackbeard, who is often regarded as the most legendary pirate of all time, commanded four ships and 300 pirates. Zheng Yi Sao, on the other hand, commanded 1,800 ships and around 80,000 pirates. That’s not just a fleet, that’s a floating, lawless kingdom.

Not only did Zheng Yi Sao successfully control a vast network of pirates - impressive enough in itself - she brought the mighty Qing dynasty to its knees. Even the way her pirate career ended is remarkable. Not bad for someone who started out as an impoverished sex worker in a Cantonese brothel. Throw in a complicted relationship with her “adopted son” and her story becomes all the more memorable.

From brothel to black sails

Like many low status women, Zheng Yi Sao’s early life is not well-documented. She was born as Shi Xianggu around 1775 in Guangdong Province, where the bustling ports were magnets for merchants, smugglers, imperial agents, and pirates alike. Shi worked at one of the area’s many floating brothels, known as flower boats, where she traded in more than just sex. She quickly developed a reputation for extracting secrets from her high-ranking clients and it's said that this business acumen is what drew the attention of Zheng Yi, a formidable pirate captain from a family with deep ties to maritime crime.

Whether their initial connection was romantic or transactional remains unclear but we do know that Shi negotiated her way into the heart of Zheng Yi’s operations. Not content with the status of a pirate’s wife, she is said to have demanded a 50% stake in his pirate business before agreeing to marry him. Zheng Yi agreed and the two married in 1801. Shi Xianggu became Zheng Yi Sao - literally, ‘Wife of Zheng Yi’ - but she was far more than a figurehead.

They spent a year enjoying life on the high seas, doing standard pirate stuff. But a pirate’s life is never a quiet one. In 1802, Zheng Yi’s cousin was captured and executed by the Vietnamese imperial forces. Rather than let his cousin’s fleet dissolve or go it alone, Zheng Yi absorbed it into his own ranks. It was a logical step, but not without consequences: infighting inevitably broke out between the various factions. Eventually, thanks in part to Zheng Yi Sao’s political savvy, the disparate groups were unified into one super swashbuckling organisation - the Guangdong Pirate Confederation.

Building a pirate empire

The confederation was organised into six fleets, each known by the colour of its flag. The largest and most powerful was the Red Flag Fleet, under the command of Zheng Yi. It was a tightly-run crime operation that extended its reach across the South China coast, disrupting trade, raiding towns, and demanding protection money. The Qing navy were powerless to stop them. But no king rules forever. In 1807, Zheng Yi suddenly died when he fell overboard during a storm. Tradition dictated that command of the confederation pass to a man but this is where things got a little weird…

Rewind a few years. Zheng Yi is doing his thing, raiding, being piratey and at some point, he kidnaps a young man called Chang Pao. Chang Pao turns out to be a pretty good sailor, so much so that Zheng Yi makes Chang Pao his protege and his second-in-command. In fact, both Zheng Yi and Zheng Yi Sao were so fond of Chang Pao that they later adopt him, officially making him Zheng Yi’s successor. It may seem strange to us that a grown man was adopted but that’s not even the half of it. Zheng Yi and Chang Pao were also in a sexual relationship. It may give contemporary readers the ick but adoption of adult men was not unusual when power needed to be transferred outside of traditional inheritance lines. Nor was it uncommon in pirate circles for older captains to take junior pirates as lovers.

Back to 1807 and command of Zheng Yi’s fleet passes to Chang Pao. Zheng Yi Sao, however, had other plans. You see, Chang Pao wasn’t just sleeping with his adoptive father…he was also in a sexual relationship with his adoptive mother, Zheng Yi Sao. Just two weeks after Zheng Yi’s death, Zheng Yi Sao married Chang Pao, securing not only personal loyalty but the inheritance too. Official reports at the time make it clear who was really in charge. One Qing official wrote that "Chang Pao obeyed Zheng Yi Sao’s orders and consulted her on all things before acting." In effect, Zheng Yi Sao assumed command of the entire pirate confederation, with Chang Pao acting as her subordinate and captain of the Red Flag fleet.

One of the most notable things that Zheng Yi Sao did was to implement new codes of conduct for her pirates. Some of the codes we often read about - such as those banning the mistreatment of women - were actually thanks to Chang Pao. However, some of Zheng Yi Sao’s rules were:

• Anyone caught giving their own orders or disobeying a command was immediately decapitated.

• Stealing from the villagers who supplied the fleet was punishable by death.

• All bounty had to be registered with the quartermaster before being distributed by the fleet leader.

• A pirate could keep 20% of his bounty but the rest went into a communal treasury.

• Casual hook-ups without Zheng Yi Sao’s permission were punishable by death - beheading for the man and drowning for the woman.

With literally thousands of pirates under her control, it’s no surprise that Zheng Yi Sao ruled with an iron fist. Under her command, piracy was not a chaotic smash-and-grab enterprise; it became a business. Zheng Yi Sao ensured that loyalty was tied to fear but also to shared interest.

Over the next few years, the Guangdong Pirate Confederation dominated the South China Sea. Much of what we know comes from Richard Glasspoole, an employee of the East India Company who was kidnapped in 1809 and held for months in the hold of one of Zheng Yi Sao’s ships. Glasspoole described the pirates wearing human heads around their necks as trophies and flogging Chinese prisoners to death if they refused to join the fleet. He claimed that she had 80,000 pirates under her control - that’s more than the population of my home town!

The emperor strikes back

But Zheng Yi Sao’s success was a double-edged sword. Her power made the Qing dynasty look impotent and in 1808, they decided enough was enough. They launched a major naval offensive to crush her but let’s just say it didn’t go as planned… Utilising her superior knowledge of the coastline, Zheng Yi Sao lured the Qing navy into narrow, shallow waters, where their larger ships struggled to manoeuver, and used smaller, faster ships in ‘hit-and-run’ style attacks. When the smoke cleared, her fleet had grown once again, thanks to the defecting Qing sailors she welcomed into her ranks.

Frustrated by their inability to quell Zheng Yi Sao’s fleet, the increasingly desperate Qing dynasty did something unthinkable for a Chinese government: they turned to outsiders. The Portuguese and Britain’s East India Company both had a vested interest in removing pirates from the South China Sea, so they agreed to help out. For a while, it looked like even this new coalition wouldn’t be enough. Several battles followed but Zheng Yi Sao continued to dominate.

However, the real threat came from within.

The pressure from the combined imperial and foreign forces began to wear down the Guangdong Pirate Confederation and cracks developed. The leader of the Black Flag Fleet, Guo Podai, grew increasingly resentful of Chang Pao and his closeness to Zheng Yi Sao. In a moment of supreme pettiness, he refused to support Chang Pao’s Red Flag Fleet against the Portuguese. In return, Chang Pao attacked the Black Flag Fleet. This is exactly what Zheng Yi Sao had tried to avoid. The fragile unity of the confederation collapsed because of a pissing match between two captains.

The final gambit

Realising that his card was marked, Guo Podai decided to surrender to the government in exchange for a full pardon. A massive chunk of Zheng Yi Sao’s fleet evaporated overnight, leaving her exposed both to enemy attack and further defections. But where other pirate leaders would have fought to the bitter end, Zheng Yi Sao proved once again to be the ultimate pragmatist. Recognising the shifting tide, she negotiated directly with the Qing authorities and in a bold and theatrical gesture, she marched into the office of the governor-general of Canton with a cohort of pirate women and children and struck a deal. Relieved that this pirate super-fleet would no longer be a problem, the Qing dynasty granted full pardons to Zheng Yi Sao and her crew. Many, including Chang Pao, were absorbed into the imperial navy - ironically transforming from pirates to pirate-hunters.

Although it feels like Zheng Yi Sao had lived several lifetimes by this point, she was actually only 35 years old when she retired from piracy. She received land as part of her settlement and established a successful gambling house. She and Chang Pao had two children before his death in battle at 39. Zheng Yi Sao lived out her remaining years in quiet prosperity, dying at the age of 69.

This is all the more astonishing when we consider the fate of other notorious pirates, such as Blackbeard or Calico Jack, who ended their careers in blood and spectacle. Zheng Yi Sao, by contrast, not only walked away unscathed but reinvented herself yet again, this time as a legitimate businesswoman and mother. Her rule over the Guangdong Pirate Confederation was more organised and arguably more effective than the local governments of her time. It allowed her to do what many pirates could not: play the game and win.

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