Pirates have always been fascinating. From Blackbeard to Sir Francis Drake, it seems people can’t get enough of historical figures who looted for treasure and were fierce fighters. You wouldn’t want to cross them unless you wanted to walk the plank.

But one story that has remained in the background is the one of Ching Shih, a female Chinese pirate leader who became known as the “Princess of the Chinese Seas.” She embodies all of the characteristics associated with pirates. It was rare for a woman to be so skilled at commanding a ship, but Ching Shih was not an average woman. She was a free woman, which was unusual for the early 19th century.

Learn more about Shih and her fascinating tale as a female pirate. She was a force to be reckoned with and she wouldn’t hesitate before sending you to walk the plank. Ahoy, matey!

Starting out as a prostitute

Not much is really known about Ching Shih’s early life. Born Shih Yang in 1775 in the Guangdong province of China, she worked as a Cantonese prostitute in a floating brothel in Guangzhou eventually becoming a madame. Later in her life, Shih barely spoke about her experience as a prostitute—perhaps wanting to forget that part of her life. However, she would later serve as a pioneer in improving the treatment of women, particularly female prisoners.

Qing Scroll - Piracy of the South China Sea
Qing Scroll – Piracy of the South China Sea / triotriotrio / Wikimedia Commons

In 1801, Shih married a notorious pirate, Zheng Yi (Cheng I), who commanded the Red Flag Fleet. This was her escape from prostitution. There are various stories about how her marriage actually came about. Some accounts explain Yi ordered a raid to plunder Shih’s brothel and steal her away, but others say he merely proposed to her.

Regardless of how it happened, when she accepted his offer, she had two major stipulations: she had to assume 50-percent control over his Red Flag Fleet, and he had to split all his plunder and treasure with her. She wanted an equal share, and she got exactly what she wanted.

This was only the beginning of their incredible partnership as not only husband and wife, but also as dual pirates of the Chinese Seas.

Shih and Yi’s success as pirates

No one should have underestimated the power team of Shih and Yi. Following their marriage, Shih participated fully in Yi’s piracy life. In just a few short years, the Red Flag Fleet grew from about 200 ships to 600 ships, and the husband and wife duo made alliances with other powerful pirates in the South Asian area.

The fleet was so renowned that the Daoguang Emperor granted Yi with the title of “Golden Dragon of the Imperial Staff,” officially promoting him to the rank of a prince. This would make Shih a princess, as well. Shih probably couldn’t have dreamed about this happening to her when she was working as a prostitute.

Yi was a force to be reckoned with. He skillfully used military assertion and his new rank to bind former rivaling Cantonese pirate fleets into an alliance. By 1804, the Red Flag Fleet was one of the most powerful in China.

During their marriage, they adopted a son, Cheung Po, as Yi’s fully legal heir. Shih also bore two sons: Cheng Ying Shih and Cheng Heung Shih. Things were going well until a tragic accident changed everything Shih knew.

Shih sought the support of various members of Yi’s family, including his nephew (Ching Pao-yang) and his cousin’s son (Ching Ch’i). The more help she had, the more she was able to grow the Red Flag Fleet.

On November 16, 1807, Yi was unexpectedly killed in Vietnam. Shih was suddenly a widow with three children, who had to maneuver her way into her husband’s leadership position.

While most people would be intimidated and scared of this position, Shih accepted it with her head held high. She took on the family business and announced, “Under the leadership of a man, you have all chosen to flee. We shall see how you prove yourselves under the hand of a woman.”

Shih already demonstrated a different leadership power than her husband. While Yi was brash and loud, Shih was quiet, and she carefully calculated the fleet’s plans. She cultivated personal relationships in order to convince rivals to recognize her status and authority. She also began an intimate relationship with her adopted son, Cheung Po, and placed him as head of the fleet.

Additionally, Shih sought the support of various members of Yi’s family, including his nephew (Ching Pao-yang) and his cousin’s son (Ching Ch’i). The more help she had, the more she was able to grow the Red Flag Fleet. It seemed to work for her because the fleet eventually gained tens of thousands of fierce pirates.

Ching Shih’s strict code of conduct

While her rules seem harsh, Shih knew exactly what she had to do to lead the Red Flag Fleet. During her time as a leader, the fleet was unstoppable.

As a leader, Shih organized a strict Code of Conduct for the Red Flag Fleet. These rules were strictly enforced unless you wanted to be punished.

The rules were, as followed:

  • Ching Shih was the boss. Anyone who gave their own orders or disobeyed Shih was beheaded on the spot.
  • No one was to steal from the public fund that supplied the pirates.
  • All loot was given to their superior, who then distributed it. If the pirates disobeyed once, they were beaten. If they disobeyed again, they were killed.
  • No one should have deserted their post. If they disobeyed once, their ears were cut off. If they disobeyed again, they were killed.
  • If they raped a female captive, they were beheaded.
  • They must have married a woman before having consensual sex with her. If they mistreated her or weren’t faithful to her, yes, they were beheaded.

While this seems harsh, Shih knew exactly what she had to do to lead the Red Flag Fleet. During her time as a leader, the fleet was unstoppable. They ruled the seas from Macau to Canton, plundering as many coastal towns, markets, and villages they could find. But this doesn’t mean she didn’t run into problems.

Problems with the Chinese government

In January 1808, the Chinese government tried to overtake Shih’s power of the Chinese Seas. With the help of the Portuguese Navy, the government sent “suicide boats” loaded with explosives, but Shih’s Red Flag Fleet always extinguished the flames, repaired the ships, and carried on their regular plundering business.

It seemed Shih could not be defeated. However, in September and November 1809, Shih’s fleet suffered a few defeats by the Portuguese Navy during the Battle of the Tiger’s Mouth. This marked the beginning of Shih’s decline as a great pirate. During her fleet’s final battle in the Naval Battle of Chek Lap Kok on January 21, 1810, she surrendered to the Portuguese Navy, promptly ending her career.

After the defeat, repercussions were swift. Sixty of Shih’s 17,318 pirates were banished, 151 exiled, and 126 were put to death. The remaining pirates had to immediately surrender their weapons. Cheung Po negotiated a deal with the Qing dynasty government, and he became a captain of the Qing’s Guangdong Navy fleet. As for Shih, well, the final years of her life were probably less exciting as her years as a plundering, looting pirate.

Ching Shih’s retirement

In her later years, Shih kept herself busy during her retirement by serving as an advisor to Lin Zexu, the Chinese head of state and governor.

Shih’s retirement was something to envy. It was unheard of for someone to walk away as a known pirate without serving any prison time or having long-lasting consequences. She also had so many earnings that she never had to work again.

In retirement, she also asked the governor of Guangdong, Zhang Bailing, to dissolve her adopted mother and son relationship with Cheung Po so they could officially and legally be married. Even though this would be unheard of in 2020, Bailing granted permission and was a witness to their marriage ceremony.

Afterward, Shih decided to retire. The Chinese government canceled all warrants for her arrest. In 1813, Shih gave birth to a son with Po, Cheung Yu Lin. She later gave birth to a daughter with an unknown birth date and name.

Ching Shih’s final years

Shih became a widow for a second time when Po died at sea in 1822. Knowing she had to do something to earn a living and provide for her family, Shih moved everyone to Macau to open a gambling house and brothel. Her life came full circle.

In her later years, Shih kept herself busy during her retirement by serving as an adviser to Lin Zexu, the Chinese head of state and governor, while he was battling the British Army during the First Opium War in 1839. Shih knew how to be a fierce leader, which is exactly what was needed.

In 1844, Shih died peacefully in her bed in Macau, surrounded by her family. She was 69 years old, but she probably lived longer than she thought she would while she was a plundering pirate.

In the end, she was wealthy, highly respected, and a comfortable woman who achieved more than she could have possibly anticipated.

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