How A Prostitute Terrorized the British and Portuguese Empire

Screengrab from: Disney's Pirates of the Caribbean  

In 1800s, a Chinese prostitute could not be defeated, neither by Qing dynasty Chinese officials nor by Portuguese or British bounty hunters.

We’ve unknowingly seen her in several books, novels, video games, and films about piracy, including the Pirates of the Caribbean. Due to her tremendous influence and achievements as a pirate, she is widely accepted to be the most successful pirate in history.

Ching Shih a Cantonese prostitute married Cheng Yi, a notorious pirate, in 1801.

Together, Cheng Yi and Ching Shih formed a massive coalition from unifying small gangs into a federation of 70,000 men and 400 junk ships. Their coalition consisted of six fleets known by the colors of blue, red, green, black, white, and yellow. By 1804, this coalition was a formidable force and was known as the Red Flag Fleet.

However, Cheng Yi died on Nov. 16, 1807. Ching Shih took control of her late husband's pirate fleet and by 1809, she commanded over 800 large junks and 1,000 smaller ones. She also commanded over 70,000 men and women in her pirate crew. She commanded the Red Flag Fleet and controlled South China’s seas.

With the great force she has, she needed someone to assist her, but also accepted and respected by her pirates. She later married her adopted son, Cheung Po Tsai, who is also a lover of her late husband.

The fleet under Cheng Shih’s command established hegemony over many coastal villages, in some cases even imposing levies and taxes on settlements. According to Robert Antony, Ching Shih "robbed towns, markets, and villages, from Macau to Canton." But the fleet generally preyed on ships belonging to the British, Portuguese, and the Qing Dynasty.

Terry Breverton in his book A Gross Of Pirates: From Afhild the Shield Maiden to Aftweyne the Big Mouth, even described the fleet had a “constitutional-monarchy-style government, with Madame Ching as queen; a council whose member she selected; and a prime ministerial position, held by her lover/husband Cheung Po” 

In 1809, Ching Shih captured Richard Glasspoole, an officer of the East India Company ship The Marquis of Ely, and later become among the witnesses who foretold the great pirate story of Madame Ching Shih.

In order to unite the great vast fleet, Cheng Shih started issuing code laws. According to Glasspoole, the code was very strict and was strictly enforced.

Taken from the book: A Gross Of Pirates: From Afhild the Shield Maiden to Aftweyne the Big Mouth

As a woman leader, Ching Shih imposed a set of different rules for female captives. Pirates who raped female captives were persecuted. Most women captives were either released or ransomed, but most pirates would make them concubines and wives.

In September and November 1809, Ching Shih and Cheung Po Tsai fleet suffered a series of defeats inflicted by the Portuguese Navy at the Battle of the Tiger's Mouth and there was no way they would be able to hold out forever. In their final battle in the Naval Battle of Chek Lap Kok 1810, they surrendered to the Portuguese Navy on January 21 and later accepted an amnesty offered by the Qing Imperial government to all pirates who agreed to surrender, ending their career and allowed to keep the loot money and treasures that same year.

She later opened gambling houses, ran cartels of smugglers and smuggled opium. She died in her sleep, aged 69.

In 2007, in Pirates of the Caribbean: At the World’s End she was portrayed as Mistress Ching, one of the nine Pirate Lords.

Due to Chen Shih’s indomitable spirit, she inspires a lot of people, especially women today, who are still seen by some as second-class citizen and not capable of being a leader.