The Greatest Pirate That Ever Lived

Meet Zheng Yi Sao--From Flower Boat Girl to Queen of Her Own Fleet

Apr 15, 2023

I’m very pleased to share a HistoryCraft profile by Valorie Clark, creator of Unruly Figures, a Substack that “celebrates history’s biggest rule-breakers.”

Enjoy this riveting story!

In the South China Sea in the 18th century rose a formidable naval power: Zheng Yi Sao and her enormous pirate army.

She was probably born around 1775 and named Shi Yang at birth, though we don’t know much about her early life. She grew up just as a time of prosperity in China spiraled downward into trouble.

The 18th century had seen rapid population growth, and the empire was politically stable. Trade with Britain and other European powers was especially strong, meaning that exports of silk, porcelain, and tea were at an all-time high. Money was pouring into China, and ships weighed down with incredibly valuable cargo were sailing in and out of Canton, in Southern China, at an incredible rate.

Though things looked good for the emperor, life for the average person was getting worse. The growing population meant resources were getting scarce, and the Emperor didn’t notice until it was too late. Professor Ronald C. Po in “You’re Dead to Me” pointed out that “a dangerously unequal distribution of wealth and a sudden increase in the cost of living” was hurting regular people throughout China at the close of the 18th century.

This led to the phenomenon of piracy as a seasonal job: During high fishing seasons, sailors worked legitimate jobs fishing. When the fish migrated, and that work wasn’t as available, they turned to piracy to make ends meet. At the dawn of the 19th century, our heroine’s future husband, Zheng Yi, and his sailors became pirates. They started stealing silks, spices, and gold, and were soon making enough money that their one ship became a small fleet.

Meanwhile, the bustling trade in the port of Canton led to a unique job opportunity for women: Flower boats. In these floating brothels, women entertained men with music, dancing, drinking, and sex.

Shi Yang worked in one of these flower boats. It’s unclear what her role was on board–many assume she was a prostitute. Whatever she did, she began liquoring up some of the wealthier clients on board and getting secrets out of them. She then traded those secrets to other wealthy people. This gave her some extra money and probably increased her power on this ship.

In 1801, when Shi Yang was in her mid-twenties, Zheng Yi spotted her flower boat. Legend has it that on this day, Zheng Yi was already a wealthy pirate. His first wife had died, so he was searching for a new one. He sent a few of his men to her flower boat to kidnap the most beautiful women on board so he could make one his wife. When the women were brought to him, Shi Yang clearly outshone them all, so he immediately proposed to her. When she was untied and ungagged so she could answer him, she flew into a rage and lunged at him, trying to claw his eyes out.

This display of ferocity only endeared Zheng Yi to her, and he begged her to marry him. He promised her jewels and silks and a life of luxury if she agreed. She looked around at his sumptuous captain’s room and said she would marry him if he gave her half his ships and wealth. He accepted, so she accepted, and the two were wed. This is where she gets her historical name–Zheng Yi Sao just means “wife of Zheng Yi.”

There’s some debate about the timing, but at some point, this power couple adopted a teenager named Chang Pao. Why they adopted is up for debate; possibly Zheng Yi Sao couldn’t give birth, and the couple wanted a son to inherit their pirate kingdom. (Piracy in China was often a family business in a way that European piracy was not.)

In 1805, the couple marshaled their large crew into a confederation of pirates. They created six fleets, each with a commander. Zheng Yi captained one, and the captains of the other fleets reported back to him. In the background, Zheng Yi Sao was the one actually running everything. Violent and merciless, the fleet was soon considered unstoppable. It grew in response; soon, the couple had at least three hundred ships sailing under the combined command of all their fleets, and each ship could hold over a hundred people–this totals over thirty thousand men under their command.

They attacked ships with little distinction. If it was a Chinese ship, they press-ganged the crew into service, and they sold the stolen goods to European merchants at a discount. European sailors were usually treated okay and ransomed back to their governments quickly. They also began to attack actual military fortresses, overwhelming them through sheer numbers. From the fortresses, they would steal cannons, cannonballs, and gunpowder for use in the rest of their naval conflicts.

It’s unclear how, but Zheng Yi died in November of 1807. He was either thrown overboard and drowned during a typhoon, or he was killed by a cannonball during the fighting. In Chinese seafaring culture, when a spouse died, it wasn’t uncommon for the remaining spouse to take over their responsibilities. But the stakes were higher than the average for Zheng Yi Sao due to the sheer wealth and power of the fleet. She quickly secured the support of two of her late husband’s leading commanders for her to become the ruler of the fleet.

However, she also realized that she needed another figurehead like Zheng Yi. She promoted their adopted son, Chang Pao, to captain of the strongest fleet. Then, to secure her position, she married him, despite being his adoptive parent. With this binding, he couldn’t easily turn on her.

Her power secured, she turned her attention to making the fleet more efficient. First, she established a passport system. Merchants had long paid the pirates for protection, but her formal passport system helped everyone track who was up on their dues. We say “passport,” but it’s clearly a protection racket–merchants would pay for a certificate of safe passage before going out on their journey, which would guarantee them safety from Zheng’s pirates as well as Zheng’s protection from other pirates.

Then, Zheng Yi Sao went a step further: She basically invented subscription services! Merchants could buy safe passage one journey at a time, or they could buy an annual passport, which cost more upfront but was less expensive in the long run. And it worked–humans have always loved a bargain. It was kept quiet at the time, but even the British East India Company was paying her protection fees to ensure their ships would leave Canton safely. Zheng Yi Sao began selling these passports to coastal towns, too, so entire towns were both exempt from being pillaged and also protected by her pirates from other threats. In these towns, she set up passport offices where people could go to get their papers without sailing out to find her. She was essentially her own separatist government unto herself at this point.

Meanwhile, she realized there was money to be made somewhere else: Salt. In southwest Guangdong province, there were around 20 salt farms, where salt was harvested and then shipped out for sale. She began attacking the fleet that transported the salt, stealing it to sell at a profit. Before she set her eyes on them, the Chinese government had about 270 salt ships; pretty soon after she decided she wanted to be in the salt business; she had 266 salt ships under her control and the government had 4. To be clear, the same people who had been on board these ships before were still on board these ships; they were just doing things on Zheng Yi Sao’s terms now instead of the government’s. It was a hostile corporate takeover.

Unfortunately for the Chinese emperor, the navy was not at its best. It was not fun to be a member of the Chinese Navy at this time. The highlights were terrible food, aggressive punishments, and poor pay. They couldn’t get recruits, and the people they did manage to recruit tended to die or defect. So, though the Emperor wanted to stop Zheng Yi Sao from stealing the entire salt industry, the Navy was too weak to do much. Of course, the weaker they were, the easier for Zheng to steal their ships and recruit their sailors. By 1805, the pirates outnumbered the Chinese Navy 3:1.

Next, Zheng Yi Sao set her sights on inland cities. By 1809, the coastal cities had mostly paid her off, and the Navy was all but defeated, so Canton became her next target. She had her pirates post a notice registering their imminent attack, which sent the city into a complete panic. Their reputation for violence has spread far and wide, so it was an effective intimidation tactic: People fled or joined her. Since her attack on Canton had gone smoothly, she did the same thing in Macau a few weeks later. While there, she stole a ship belonging to the Portuguese governor of Timor, plus five American ships, and blockaded a Thai diplomatic mission.

Other countries began to see that her pirate fleet could no longer be politely ignored and paid off. They began to see her as a separatist government destabilizing the region; she was no longer just a nuisance but a rebel.

The Chinese Emperor went to the Americans, the English, and the Portuguese and asked for aid in defeating Zheng Yi Sao. In return for aid, the European and American powers asked that China open up more ports to trade. (This would lead directly into the Opium Wars, a disaster for China.) But they were unsuccessful. Even though everyone sent in their best to deal with her, Zheng Yi Sao’s pirate fleet was able to defeat them all handily.

So the Emperor took a different tack: divide and conquer. He sent people to approach individual squadrons of Zheng Yi Sao’s fleet and offer them a military pension if they retired from piracy. The commander of the Black Fleet retired first, and it was a domino effect from there. The pirates retired in droves.

Some commanders might have been offended by what they saw as desertion. Not Zheng Yi Sao. Instead of clinging to the past, she decided she was ready to retire too.

In 1810, she walked into the governor general’s headquarters in Canton, ready to make a deal. Surprised but relieved, the government in Canton tentatively accepted her resignation. They entered negotiations, but talks stalled over disagreements about who would own the ships going forward. Zheng Yi Sao retreated to her ship, promising to return to running her merciless pirate army if they couldn’t meet her halfway.

After letting them stew for a few weeks, Zheng returned to the governor general's headquarters. She reoffered her resignation, re-entered negotiations, and secured a safe retirement for thousands of pirates in her crew in just two days. Many of them were even offered military positions, probably because they were better at being a navy than the imperial navy was. Never before and never again was there a large-scale pirate surrender like this!

Zheng Yi Sao retained around thirty ships, which she used to create a merchant fleet. She also got to keep most of the money she’d stolen. This is a happy ending if any historical figure has ever had one.

But of course, she couldn’t totally give up her life of crime. In the 1840s, she opened an infamous illegal gambling house. She also might have been involved in opium smuggling, despite using her legitimate business to help the Chinese government fight smuggling.

Around 1844, Zheng Yi Sao died in Macau at 69, rich and in control of her life. Piracy continued in the South China Sea, but her success as the Pirate Queen was never surpassed. She’s often remembered as the greatest pirate that ever lived.

Have a nice weekend,

Neal