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Few figures in history are as feared and fascinating as Ching Shih (also known as Shi Yang, Zheng Yi Sao, Shi Xianggu, and Shek Yeung), a woman who rose from humble beginnings to command one of the largest and most powerful pirate fleets the world has ever seen. Operating in the South China Sea in the 19th century, she took over her husband's fleet after he died, turning it into a fearsome and powerful empire. 

Early life

Ching Shih was born to a working-class family in China's Guangdong province in 1775. She began her working life as a sex worker in a floating brothel before marrying the pirate leader Zheng Yi. When he died in 1807, she took leadership of his fleet, becoming a pirate queen. She proved to be a capable commander and exceptional strategist. 

Red Flag Fleet

Ching Shih's fleet, known as the Red Flag Fleet, grew from 200 ships when Ching Shih and Zheng Yi first got together to 1800 ships, making it the largest pirate fleet in the world. Under her leadership, the fleet flourished and dominated the South China Sea, raiding ports, terrorizing merchants, and effectively controlling maritime trade routes in the region. 

Ching Shih enforced strict codes of conduct among her crew: theft of booty from fellow pirates was punishable by death, desertion was forbidden, and women on board were treated with respect. Marital infidelity and abuse of female captives was cause for execution. On the other hand, good deeds, loyalty, and honesty were rewarded.

Ching Shih vs. China

Being the largest pirate fleet is bound to attract attention, as it did for Ching Shih. The Chinese Qing Dynasty wanted to put an end to her power, so the Mandarin navy was sent to confront her fleet.

However, they were no match for Ching Shih and his band of fearsome pirates. She had them cornered within hours, but instead of killing them all, she promised the Mandarin crew safety if they joined the Red Flag Fleet. As a result, her fleet multiplied while the navy shrank.

Historic retirement

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In 1810, Ching Shih famously retired from piracy without meeting a violent end, an extremely rare feat for a pirate. The emperor of China, humiliated that he was being outsmarted and out-muscled by a woman, negotiated a peace deal with her. The deal allowed her and her crew to retain their loot and avoid prosecution, on the condition that they abandon piracy. Much of her crew was even able to secure jobs within the Chinese military. 

A wealthy woman, Ching Shih, relocated to Macau and opened a casino and a brothel, and also got involved in the salt trade. She lived peacefully until her death at the age of 69 in 1844, surrounded by her children. Some of the gambling businesses existing in the area today are said to be run by her descendants. 

Defying societal expectations, Ching Shih built one of the most formidable fleets in history and maintained power in a dangerous and chaotic world.

She remains the most successful pirate ever, female or male, not just in terms of wealth or ships, but in influence, legacy, and the respect she commanded from allies and enemies alike.