How a Chinese Prostitute Became One of the Most Successful Pirates in History

How a Chinese Prostitute Became One of the Most Successful Pirates in History

Stephanie Schoppert - July 7, 2017

By the 19th century, the Golden Age of Piracy was over. The life of a pirate was harder, navies were sent out to stop pirates from disrupting trade, Kings were no longer supportive of privateers and able-bodied sailors were being pulled toward respectable jobs instead of the life of a pirate. And yet, in the midst of the great decline of piracy, one would manage to become what many call the most successful pirate in history. Ching Shih went from being a prostitute to having 40,000 pirates at her command in what is one of the most incredible stories ever told on the seven seas.

Ching Shih was born Shih Gang Xu in 1775 and she grew up in the province of Guangdong. When she reached a certain age, she took up work as a prostitute in a floating brothel. How long she was a prostitute and what her early life was like is largely a mystery. It was not until 1801 that her life took a drastic change as she caught the eye of the pirate Zheng Yi who commanded a fleet that was known as the “Red Flag Fleet.”

Zheng Yi or Cheng I belonged to a family of successful pirates that could trace their criminal roots to the mid-seventeenth century. He had spent his life reuniting several rival Chinese pirate organizations and had hundreds of ships and thousands of pirates under his command. Some records say that Zheng Yi wanted Shih Gang Xu for her beauty and others relate that he had heard of her keen business savvy. As a prostitute, Shih Gang Xu had learned secrets about a number of her wealthy and politically connected clients and used that to wield power over them.

How a Chinese Prostitute Became One of the Most Successful Pirates in History
A Chinese Junk ship sailing under a red flag. Pirates were known to sail under a red flag. Ancient Origins

Not only is it unclear why Zheng Yi was so intrigued by Shih but also it is not clear how he became married to her. Some accounts suggest that he raided the brothel and took her as a prisoner and then requested her hand in marriage. Others say that he simply asked her for hand. But Shih did not readily agree to the marriage. Instead, she said that she would only agree to marry Zheng Yi if she was given power in his fleet and an equal share of the loot the fleet took in.

Zheng Yi agreed to Shih’s conditions and the two were wed. Their marriage and their life of piracy together was quite successful. Zheng Yi’s fleet grew from 200 ships to 1,800. Zheng Yi used his reputation to continue to unite Cantonese pirate fleets to sail under him and unite together. By 1804, Zheng Yi and Ching Shih were in command of a very formidable force and one of the most powerful pirate fleets in all of China. Their success and time as a couple was cut tragically short when Zheng Yi perished in 1807 during the Tay Son Rebellion in Vietnam.

How a Chinese Prostitute Became One of the Most Successful Pirates in History
Chinese pirates attacking a trade ship.

At the time of Zheng Yi’s death, the armada had tens of thousands of pirates and almost 2,000 ships. With her husband dead, Ching Shih had two choices either return to a life of prostitution or take on her husband’s role instead of his second in command. Chang Pao was designated as second in command and set to take over for Zheng Yi. He was also the adopted son of Zheng Yi and Ching Shih. With the support of Chang Pao, she started maneuvering herself into a position of power within the fleet.

She started to build relationships with her rivals in order to recognize her status and authority. With the support of the most powerful members of her husband’s family, she played on the loyalties of the fleet captains. She reminded them of their loyalty to her husband and found ways to make herself essential to the other captains within the fleet. She also started something of a romantic relationship with Chang Pao to secure her position. Chang Pao had also been the lover of her husband.

Once she was secure in her position as leader of the fleet, she got to work implementing changes. She put together a code of laws that all of the pirates in her fleet abided by. However, some sources suggest that it was Chang Pao that issued the code. The code consisted of several regulations that dictated how everything was to be done within the fleet. The first regulation was that anyone issuing their own orders or disobeying the orders of Ching Shih would be beheaded on the spot. Second, no one was to steal from a public fund or village that supplied the pirates.

How a Chinese Prostitute Became One of the Most Successful Pirates in History
Ching Shih

The third regulation required that all goods taken as booty had to be presented for group inspection. It was registered by a purser and the fleet leader then distributed the booty. The original seizer took 20% and the rest was placed into the public fund. The fourth regulation required that actual money was given to the squadron leader who would use the money to purchase supplies for unsuccessful ships as well as give a small amount to the seizer.

There were also regulations for the treatment of women. A pirate could take a woman prisoner as a wife but he had to be faithful to her. Women who weren’t desired by the pirates were ransomed or released. Any pirate who raped a woman was put to death. If a pirate had consensual sex with a woman captive both the pirate and the woman would be put to death. Punishments for pirates who disobeyed orders ranged from flogging to quartering. Anyone caught leaving without permission had their ears cut off and were then paraded around the squadron.

The code made a fleet of pirates that was almost unmatched on the seas. They were so fearful of the code and punishment that they would do anything to avoid punishment. They would be “intrepid in attack, desperate in defense, and unyielding even when outnumbered.” While it may have been a strict code it allowed Ching Shih to have a pirating career that was unparalleled by even some of history’s most well-known pirates.

How a Chinese Prostitute Became One of the Most Successful Pirates in History
Junks in Canton circa 1880. It was said that Ching Shih commanded 1,800 of these. Atlas Obscura

Soon Ching Shih and her fleet established a hegemony over the coastal villages and in some cases, they even imposed levies and taxes on the settlements. Reports state that Ching Shih robbed towns, markets, and villages from Macau to Canton. Ching Shih’s fleet was so large that it was able to defeat any attempt to stop it. Qing dynasty Chinese officials tried to stop her. The Portuguese Navy and the British Navy also tried but all failed to bring her down.

In 1809, she captured Richard Glasspoole, an officer with the East India Company. He and seven other British sailors from The Marquis of Ely were taken prisoner. He wrote down much of his experiences and what he learned during his time with the female pirate captain. She became known as “The Terror of South China” as people would share tales of her cruelty and punishments of any who opposed her. She punished anyone who tried to resist her by nailing their feet to the deck of her ship and beating them.

When it became clear that it was not possible to defeat Ching Shih by force the Chinese government tried a different tactic. In 1810, they offered amnesty to all pirates. It was a deal that Ching Shih could not refuse although there was some negotiation with official Zhang Bai Ling. It was part of the deal of amnesty that pirates would kneel before the government officials and surrender their loot. This was unacceptable for Ching Shih. Ching Shih took matters into her own hands and walked into Zhang Bai Ling’s office unarmed to negotiate terms.

In the end, she was able to keep all the loot she had acquired during her time as a pirate. In order to settle the issue of kneeling, a unique arrangement was made. Ching Shih and Chang Pao decided to wed with Zhang Bai Ling as witness. As part of the ceremony, Ching Shih and Chang Pao had to kneel before Zhang Bai Ling and give thanks. This was a roundabout way of getting them to comply with the order to kneel as part of their surrender. She remains one of the few pirates to ever be able to retire and keep all of her ill-gotten gains, which is largely the reason why she is considered one of the most successful pirates in history.

It was in this way that she ended her very short but extremely lucrative career as a pirate. She used her riches to open a gambling house in Canton and had a son with Chang Pao. Chang Pao died at the age of 36 of unknown causes leaving Ching Shih alone to run the gambling house until her death in 1844 at the age of 69. The story of Ching Shih has been retold in film and books, including the third Pirates of the Caribbean film which portrayed Mistress Ching.