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

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.

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.

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.