Women have not always been welcome aboard ships, since they were said to bring bad luck — or, more likely, disputes amongst the male crews. The Cantonese pirate Ching Shih, however, is exception to that tradition: she led a powerful pirate fleet and terrorized the Southern Seas in the early 19th century.

Shih Yang probably did not expect such an exraordinary fate for herself. Born in the poor districts of Guangzhou, China, she turned to the world’s oldest occupation to survive off buccaneers’ carnal appetite… At the time, lots of pirates swarmed across the South China Sea (Hong Kong and Macau being their headquarters), trading part of their bounty for the prostitutes’ services. Shih Yang worked in a floating brothel set near the Pearl River, the main artery of Guanghzou, where prostitution had become a flourishing business. She was fifteen years old.

Pillow-talking her way out

Teenage Shih Yang still would not complain. Her situation was far from desperate: her notorious beauty caught the eye of a rich and powerful customer base. The prostitutes’ nest turned into a web of intrigues where power, wealth and intelligence overlapped. Pillow-talk with her regular Johns granted Shih Yang with what she needed: secrets and money. Soon enough, she secured herself a better social position.

In 1801, 26-year-old Shih Yang married Cheng I, a pirate with a growing reputation and a 200-junk fleet. Good enough: for the Cantonese prostitute, this meant switching a life of slavelike misery with one featuring exciting sea adventures. She nevertheless negotiated firmly with her new partner the terms of the nuptial agreement. She would run 50% of the fleet and crew, and join the ranks of the Red Flag Fleet under the title of vice-captain.

The newlyweds did not plan on honeymooning and steering away from the piracy business. It was too lucrative to put aside. So they decided instead to widen the crew, recruiting small pirate gangs across the South China Sea. The strategy paid off: in a few months, the Red Flag Fleet grew to 40,000-60,000 men. This was enough to frighten the Chinese Empire, worrying it would disrupt trade along its busy shores… And powerful European countries, too, feared that their business ties with China would be severed.

The Black Widow

In November 1807, Cheng abruptly died — perhaps swallowed alive by a typhoon off the coast of Vietnam — and the command of the massive Red Flag Fleet fell into the hands of his widow. Could one of the most powerful pirate crews of all time be spearheaded by a woman? Ching Shih (“Cheng’s widow”) would not give her pirates the opportunity to doubt it: to consolidate her power and her men’s loyalty, she introduced a harsh set of measures aimed at disciplining her crew. First rule: one who disobeys his superior’s orders shall have his head cut off. The same fate awaited one who helped himself into the communal fund or was found guilty of bad treatments towards captive women.

The Cantonese pirates flying red flag also took a share in the local, almost-legal business: they emitted documents to grant the safe passage of fishermen, handled salt trade in the area, established customs houses along the coast… As if they were competing with the Chinese civil servants! Ching Shih knew what she was doing, and her strategical insight proved decisive for the success of her cause. Until…

Parlay?

At that point, the Cantonese pirates were more than a thorn in the side of the Chinese governement and other maritime authorities — they also bullied both Portuguese and British armadas, although they ranked amongst the mightiest across the world… Prejudiced countries thus sided forces and formed an alliance to discourage further pirate attacks. On April 18, 1810, Ching Shih successfully negotiated general amnesty for her men. Here again, her bargaining thinking proved useful: most pirate officers were offered further employment in government offices, and the rank-and-file men were encouraged to join the Imperial Army.

Back on solid ground, Ching Shih could have opted for a safe, well-paying government job and be satisfied with the lifelong pension she was given; she didn’t. The leopard can’t change its spots. Her piracy profits fueled Macau’s underground economy — prostitution and gambling, mostly — since illegality was more lucrative than ever. Eventually, the Cantonese captain passed away in 1844, aged 60 (twice the life expectancy of the time!) at the height of her fame and fortune. But her main success was undoubtedly switching from an objectified-woman statute in Cantonese bordellos to respected captain of one of the mightiest pirate fleets of all time.

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