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Ching Shih: A Prostitute Who Became History’s Deadliest Pirate

Interestingly, the most successful pirate ever was an Asian woman

When you hear the word “pirates” you undeniably end up thinking of proficient fierce men whose life stories have mesmerized millions of teenagers and adults alike for several centuries now. Names like Blackbeard, Henry Morgan and Sir Francis Drake may ring a bell in the minds of several reader’s of history. These men were considered to be the most successful pirates of all time. 

Contrary to these popular ideas, the most successful pirate-lord in recorded history was not any of the previously mentioned American or European men. Instead, she was an extraordinary Asian woman who is known today by the name Ching Shih, which simply translates to ‘Ching’s widow’. Her saga is nothing less than an exhilarating rag to riches story. At the height of her power, she commanded over 800 large ships, 1000 smaller vessels and over 70,000 pirate crew, comprised of both men and women.

In comparison, the over-hyped Blackbeard at his peak commanded a laughable 300 ships and few thousand pirate crew.

Ching Shih’s humble beginnings

Ching Shih was born as Shih Yang, in 1775, in the poverty-ridden society of Guangdong province, in China. Akin to many of the women of this period, on attaining puberty at the tender age of thirteen, she was forced into prostitution in order to supplement her families income. She worked in one of the floating brothels, also known as flower boats, in the Cantonese port city. These boats would sail along the nearby coast with the customer on board. Back then, the Chinese perceived that the rocking of the boat added an entirely new dimension to sexual pleasures and enhanced the overall experience.

In a short span of time, young Ching Shih had become the talk of the town, due to her striking beauty, poised nature and lavish hospitality. This attracted several high profile customers, which included courtiers of the royal palace, army military commanders, rich merchants visiting the port city, and many more. Apart from this, very little is known about her early life, given her humble origins.

Destiny finds its way

In the year 1801, Zheng Yi, a notorious pirate commander of the infamous Red Flag Fleet, encountered Ching Shih in the Cantonese port and was enthralled by her beauty. No sooner he visited the floating brothel and met Ching Shih, expressed his feelings and asked her to marry him. At this juncture, Ching Shih asserted that she would marry him only if “she was granted fifty per cent share over his monetary gains and a partial control over his pirate fleet.” This episode indicates that she did not want to end up as eye candy for her husband for the rest of her life. Drowned in his love for her, Zheng Yi invariably agreed to her conditions and got married to her. The veracity of this chain of events is often debated today. A group of historians claim that Zheng Yi had ordered his men to abduct Ching Shih from the brothel, forcibly marrying her.

Well, either way, it was Ching Shih who benefited the most from their union and her encounter with Zheng Yi is often considered to be her stepping stone to greater glory which in turn got her etched into history as one of the most successful pirates in recorded human history.

The “Red Flag Fleet” thrives

Under the joint command of Zheng Yi and Ching Shih, the Red Flag Fleet began to grow and prosper like never before. The fleet grew from 200 ships, at the time of their wedding, to 1800 ships, in the next few months.

Immediately after joining her husband, Ching Shih implemented some strong reforms and constituted the code of laws to be strictly adhered by all the crew. A select few have been stated below:

Pirates who gave unauthorized orders or those who refused to follow orders were executed on the spot without a chance to justify themselves.

All seized goods had to be presented for inspection. If any pirate was found hiding or under-reporting goods, a part of their body was chopped off depending on the scale of the crime.

  • Loyalty and honesty were greatly appreciated and worthy pirates were rewarded generously, thereby setting an example for the others.
  • Female captives needed to be treated respectfully. They were segregated based on their looks. The weak, pregnant, and unattractive ones were freed as soon as possible.
  • The attractive women captives were held back for ransom. The pirates were given the freedom to marry these attractive women under mutual consent.
  • Infidelity and rape were treated as a serious offence. These offenders were immediately hanged. In the case of consensual pre-marital sex, both the offenders were executed. In a few cases, the man was castrated and the woman was banished from the fleet.

Apart from these, several economic reforms were sanctioned, keeping in mind the happiness of the crew as an expression of gratitude towards them. This resulted in many of the pirate groups of the region merging themselves unconditionally under the banner of the Red Flag Fleet, which resulted in it becoming the largest pirate fleet on the face of the planet.

Meanwhile, unable to conceive a future heir, the pirate couple decided to adopt a young fisherman who was in his mid-twenties named Cheung Po, from a nearby coastal village. This meant that Cheung Po became the second in command to Zheng Yi and the most respected crew after him and Ching Shih. This move puzzled many of the crew members as to why the pirate couple chose to adopt a fully grown man. The answer to this is a bit kinky for reasons you’ll shortly read ahead.

A catastrophe strikes

Just six years into their marriage, in 1807, Ching Shih’s life took a sudden tragic turn, Zheng Yi passed away in the backdrop of a devastating storm off the coast of Vietnam. Their adopted son Chang Pao was instated as the leading commander of the Red Flag Fleet and the pirate queen Ching Shih’s confidant.

Amidst this tragedy, there was an internal rift for power amongst the power-hungry captains of partnering ships. The future of the Red Flag Fleet was in danger. In the nick of time, Ching Shih managed to secure command of the fleet and win the support of factions loyal to Zheng Yi, including his nephew and cousins, by utilising a few cunning business tactics. Soon after, the power-hungry traitors were captured and executed in public to set an example and deter any future possibilities of a coup.

Following this situation, stricter disciplinary measures and code of laws were implemented and the lawbreakers were hacked to death instantly regardless of their rank.

A startling subterfuge

Less than two weeks after the tragic death of her husband the pirate queen announced that she was getting married to her adopted son, the commander of the Red Flag Fleet. It is said that she had shared an illegitimate relationship with him for a very long time, which is also the reason why she was not conceiving from her first marriage. It was under her influence that credulous Zheng Yi had adopted the young fisherman and declared him as his willful heir.

Ching Shih’s absolute domination

Under the leadership of Ching Shih, the Red Flag Fleet set off to capture new coastal villages and flaunted total control and domination over the South China Sea. This came as an addition to the trouble British and French colonisers faced, as their ships were regularly plundered by the pirates.

The Red Flag Fleet was no sooner operating its businesses at an enormous scale. Not a single ship moved in the South China Sea without the knowledge of Ching Shih’s army. Entire coastal towns worked for them, supplying them with food, goods, and other provisions. Ships that wanted to cross the South China Sea were taxed by the pirates. If they refused, they were attacked and plundered immediately.

Nevertheless, the Chinese dynasty desperately wanted to put an end to all this. So, the novice Mandarin navy vessels were sent out to confront the Red Flag Fleet in the South China Sea and destroy them. Just a few hours into the battle, the Mandarin navy was starting at a humiliating defeat. Ching Shih used this opportunity and announced that the Mandarin crew would not be punished if they joined hands with the Red Flag Fleet. So, just like that, the Mandarin navy was absorbed by the pirates and the Qing dynasty lost a huge part of their navy.

Calls it off under the right conditions

The Emperor of China was enraged to think that a woman was controlling such an enormous amount of the land, sea, resources, and people that belonged to him. So, in an attempt to ink a peace deal with the pirates, the emperor offered an amnesty to all pirates of the Red Flag Fleet, hoping to terminate Ching Shih’s reign over the sea.

Meanwhile, the Red Flag Fleet came under the attack from the Portuguese navy. The Portuguese navy had already been defeated twice before. However, this time things were different, they had come prepared with superior ships and weapons. This gave the Portuguese an upper hand and the Red Flag Fleet was unable to retort back with an attack of the same intensity, they were being slaughtered by the Europeans in their own backyard.

Ching Shih recognised the fact that there was no point in persisting, the Portuguese navy was ruthlessly destroying her fleet. So she readily accepted the amnesty offered by the Chinese emperor. The entire crew of the Red Flag Fleet was forced to surrender. The emperor allowed pirates to take home all the loot that had been accumulated over the years without facing any major repercussions and moreover several pirates were granted jobs within the Chinese bureaucracy. Ching Shih’s adopted son and later husband Chang Pao became the captain of Qing’s Guangdong navy. In 1813, she welcomed her first child, a son named Cheung Yu Lin, followed by a daughter whose whereabouts have been long lost in history.

In 1822, her second husband lost his life at sea, after which she relocated to Macau along with her children, and opened a gambling house with all the wealth she had acquired at sea. She was also involved in trading salt. Towards the end of her life, she opened a brothel in Macau, this episode made sure that her story ended in a complete circle from where it all had begun.

Retires peacefully into that good night


It’s quite ironic that after all the trouble she had caused, she died peacefully in her sleep at the age of “sixty-nine”. She did not die as just another exploited prostitute, instead, she seized every opportunity and made the most of it, such that it made a positive impact on her life.

Despite all the violence and illegal activities surrounding this story, Ching Shih’s life conveys a beautiful and poetic message as to how a pitiable young teenager forced into prostitution went on to command the largest fleet of ruthless pirates and also managed to subdue the mighty emperor of the Qing dynasty.

If there’s one thing that this chapter in history has taught us, it is that a determined woman is unstoppable and possesses the power to rewrite history, I hope you enjoyed this post and as always have a chilled day from the Viking

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