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Blackbeard, Edward Teach, had a veritable fleet compared to most pirates. But in terms of sheer numbers, he was absolutely dwarfed by the leader of this confederation. Cheng I Sao was able to command more ships and men than almost every nation's navy during her time. Instead of just trying to carve out a place for herself in a patriarchal society, she turned the whole thing on its head and had the Empire of China at her mercy. Think you had to be captain of a ship to become a pirate? You're only half right. 

Cheng grew up with dreams far from piracy, but her skill at business would lead her to become the captain of the largest pirate fleet in history. How did someone rise from absolutely nothing and become the most dangerous woman to sail the seas? Let's find out how this queen commandeered enough ships to be considered a nation of her own.

The Rise of a Maritime Matriarch

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Even before she became a pirate queen, Cheng I Sao worked as a merchant on the floating brothels of Canton. She understood early on that information was power, using contacts throughout the criminal underworld to gain her influence. In 1801 she impressed none other than Cheng I, the Pirate King himself, with her quick mind and canny business sense. They quickly married though it was less a romance and more of a partnership. Cheng Sao negotiated a fifty-percent stake in her husband's empire from the onset.

Her husband died unexpectedly in 1807, which many pirates believed would result in infighting between lieutenants trying to take over command. Cheng I Sao quickly moved to ally herself with her husband's strongest allies, his top lieutenants and his adopted son, Cheung Po Tsai. She had never been tested commanding thousands of pirates before but went on to outplay the male-dominated pirate world at its own game. The Red Flag Fleet stayed intact under her leadership and grew more fearsome with each raid.

It's impressive that she went from the right hand to the unstoppable leader of over 1,800 ships and an estimated 80,000 pirates. She had little time to take power, but what Cheng I Sao did was earn the respect of an ocean's worth of pirates who weren't used to taking orders from women. Leading that many men must have taken some sort of charisma, sure. But I think it really came down to understanding what made humans tick.

Discipline and the Dreaded Pirate Code

To keep this enormous pirate crew organized Cheng I Sao developed some rules. Laws that were downright terrifying. Cheng maintained a strict pirate code which outlawed her crew from issuing commands (unless they were ordered to by Cheng) or stealing from the ship's treasure. You were publicly executed on the spot if you were found guilty of these crimes.

Cheng also created laws that defended prisoners who were female from harassment.

Cheng I Sao ran her pirates like a well-oiled machine and expected her crew to be disciplined. She maintained a central treasure dock akin to a large corporate bank we might use today. Any stolen goods were logged and recorded. Eighty percent of stolen goods were reverted back to the fleet as a general fund to repair and resupply ships that may have been damaged or ran low on materials. No single ship would go hungry if another was fed.

The Ultimate Exit Strategy

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Desperate for assistance in regaining control of their waters, the Chinese government called on both the British and Portuguese navies to assist them in destroying the Red Flag Fleet. Even against some of the most technologically advanced warships on the planet at the time, Cheng I Sao's pirates managed to win a number of decisive battles, thanks largely to their intimate knowledge of local waters. That being said, she was intelligent enough to know that she couldn't take on several world powers indefinitely.

What really sets Cheng I Sao apart from other pirates is that she realized this and opted to negotiate a surrender while she was still on top. Striding unarmed into the office of the Governor-General of Canton in 1810, she negotiated a surrender in 1810 that was really more of a total victory for herself and her pirate army. She basically told the Emperor she didn’t care by demanding a full pardon for herself and her men as well as permission to keep the spoils of their pirating careers.

Not only did she receive promises that her pirates would be given positions in the Chinese military, she would also be given a noble title herself. Cheng I Sao retired from piracy with her hard earned fortune and lived out the rest of her days running a gambling house (and occasional smuggling operation) in Guangzhou. Rather than being hung up for pirates like so many of her predecessors, Cheng I Sao passed peacefully in her sleep at the age of 69.