The Woman Who Ruled The South China Sea by J. L. Bleakley

Most stories start at the beginning. I should warn you now, this woman’s story isn’t like most others. History has preserved nothing of her birth or childhood. There isn’t even an official record of her real name. In later life, she chose her own name, “Ching Shih”.

Ching Shih’s footprints first leave their imprints on history’s pages aboard the Flower Boats of Canton, China in 1801.

The Flower Boats were floating brothels exclusively for the wealthy elite in China. The girls who worked on these boats were bought at age 5 or 6 from poor families for as little as $5. They were trained until the age of 12 when they would start working. Ching Shih would have spent her childhood being educated and taught how to be courteous and engage in conversation with powerful men. Unbeknownst to her, this was the skill that years later would save her life.

As a possession of the Flower Boats, her daily life was no more than a business transaction. The future was bleak for girls like her. In the name of beauty, their feet were bound, hindering their movement. Years of this left them deformed and unable to work or even carry out menial tasks once the Flower Boats were done with them.  Those who didn’t become diseased and die, or sold for a steep price to an admirer, were reduced to begging on the streets for the rest of their days.

Ching Shih was smart, resourceful, and observant. She watched how the business was run and gained an understanding of managing the accounts. She had nothing to her name but she was preparing, quite possibly with no idea what for. It was in those murky flower boats where Ching Shih honed the skills that she would need to face up to the most powerful men in her part of the world.

In 1801 she crossed paths with the pirate ZhéngYi. This wasn’t your typical tale of boy-meets-girl. It was a mutually beneficial and highly successful business partnership.

When setting the scene for this buccaneering meet-cute, history is, at best, hazy. There are enough versions of this meeting to rival One Thousand and One Nights. But all these retellings tend to loosely fall into one of two scenarios. The first claims Zhéng Yi sent his pirates to raid the Flower Boats and Ching Shih was brought to him along with the rest of the loot. The second suggests she had worked her way up the ranks to Madame and Zhéng Yi was a regular. Even if we don’t know exactly how the meeting happened, we do know the outcome.

Zhéng Yi asked Ching Shih to marry him and she said yes if she had co-ownership of his fleet and an equal share of the plunder. It was a bold request of a pirate who could kill her on the spot. Here’s the crazy part, he agreed!

Zhéng Yi came from a long line of career pirates and commanded a fleet of 200 vessels. He set himself a notch above his predecessors by becoming involved in political intrigue. Already having made a name for himself on the waves of the South China Sea, he began to extend his reach and influence onto land.

This could explain why he chose Ching Shih and why he agreed to her terms. The Flower Boat’s clients reached all the way up the political ladder. Ching Shih possessed an arsenal of information that made her incredibly valuable to a man like Zhéng Yi, but secrets gleaned from pillow-talk wasn’t all she had to offer. Here was a woman intelligent enough to easily converse with China’s most powerful men, intuitive enough to figure out their weaknesses, resourceful enough to make herself indispensable, and savvy enough to form a business agreement that gave her power, wealth and security, all with the fearlessness to demand it of China’s most feared pirate at the time. Zhéng Yi knew how valuable Ching Shih was, but more importantly, so did she.

In just three years the couple combined Zhéng Yi’s notorious reputation and Ching Shih’s business brain to rally more members, doing the unthinkable and uniting various small pirate gangs into one united pirate army. They were a force like China had never seen - The Red Flag Fleet.

No doubt Zhéng Yi felt invincible. In 1807, at the height of his career and after just 6 years of marriage, disaster struck. Zhéng Yi drowned in a typhoon. Suddenly Ching Shih was alone with business growing faster than she could have anticipated and over 20,000 pirates to control.

Legally, because of her pirate prenup, she was the sole leader of the largest pirate fleet in history. The wealth the Red Flag Feet had acquired was staggering and at that moment Ching Shih was the woman who held the purse strings. This was possibly the most dangerous moment of her life but she wasn’t about to back down. To strengthen her position of leadership she began a relationship with her late husband’s protégé, Cheung Pao. By marrying him, Ching Shih eliminated the most likely contender for her title as fleet commander.

With her leadership now indisputable she had to enforce her power. How does any pirate control their crew? With a pirate’s code. In true Ching Shih fashion, hers was like no other. Her rules were strict with severe punishments and covered not only the conduct on board, distribution of wealth, and loyalty to the fleet, but also the pirate’s love lives. The lengthy list can be condensed into four main rules:


  1. Pirates who refused to follow orders from their superiors or who gave unsanctioned orders of their own were beheaded immediately.
  2. All goods plundered had to be registered before it was divided amongst the fleet. The ship responsible for the goods received 20% while the rest was put in the communal pot and distributed. If any pirate was found stealing more than their share or not registering their captured booty they were whipped. A second offence cost them their head.
  3. Deserters or pirates taking an unauthorised leave of absence, if found, were removed of their ears and paraded in front of their crew as an example.
  4. Female captives were completely off-limits to the pirates. They were to be unharmed and ransomed. Unattractive women were released and sent back to their homes, free of charge. Any pirate who crossed the line with one of their kidnapped beauties was beheaded. Marriage to a captive, however, was allowed but if the pirate was unfaithful to his bride he lost his head.


Whatever her pirates may have thought of the unusual code they respected and obeyed it, with amazing results.  The Red Flag Fleet grew in numbers, power, and comradery. They’d found a woman worth fighting for and she demanded honour amongst her thieves. Word of Ching Shih’s success rippled through the waters of the South China Sea. The Flower Boat runaway had blossomed from an ambitious girl into the leader of the most organised, untouchable criminal organisation of her time. The Chinese Emperor, Portuguese Navy, and East India Company all tried and failed to bring her down. The view from the top was spectacular but Ching Shih had already learned from her late husband’s untimely passing that when you’re standing on top—the only way is down.

Whether by the sword, the ocean’s wrath, or capture and execution, one thing was for certain: if you lived a pirate, you died a pirate. That is until Ching Shih changed the rules of the game. The Red Flag Fleet had become a nuisance the Emperor was desperate to put an end to. Ching Shih saw an opportunity. In an unprecedented move, with the same boldness she approached Zhéng Yi with nine years previously, she stood before the Chinese Emperor. Once again she negotiated for her life with the confidence of a woman who knew her capabilities. Her terms were clear. She would end her criminal enterprise and retire the Red Flag Fleet if she and her men were granted immunity and she was allowed to keep her wealth and maintain her power and influence. If those demands weren’t high enough she also threw in a high paying job for her new husband in the Navy. Unbelievably, like Zhéng Yi, the Emperor accepted her terms.

From a nameless girl to the most successful pirate in history, Ching Shih charted her own course in life exceeding every expectation and defying the cards life had dealt her. Ching Shih settled down with her husband, opened a gambling house, and lived out her days raising her family and living comfortably until she died peacefully in her sleep, aged 69.