Ching Shih was born around 1775 in China and became a prostitute in Canton, a province in southwest China, before marrying a pirate leader, taking over his fleet, and growing it until it was able to destroy a combined fleet of Chinese, British, and Portuguese navy ships as well as Dutch mercenary vessels.
Then she accepted amnesty from the Chinese government and walked away with her ill-gotten fortune and a title as Chinese nobility.
Ching attracted the eye of Zheng Yi Sao — a pirate leader with a fleet of a few hundred ships — when she was 26 years old and working as a prostitute. Zheng became smitten with her and either proposed to her in the brothel or ordered her abducted in a raid. (Both stories have been passed forward in the years since the incident.)
Either way, Ching agreed to marriage with a couple of specific requirements, the most important one being that she gain some control over the fleet and a share of its profits.
For the next six years, Ching and Zheng managed the "Red Flag Fleet" together. But Zheng died in a tsunami, leaving Ching in the dangerous position of being a woman atop 600 ships and their crews of outlaws.
Ching quickly struck an accord with Chang Pao, Zheng's lieutenant and former slave who was granted control of the fleet. Ching and Chang built a new power structure for the Red Flag Fleet and grew it quickly.
Ching focused on the business dealings of the fleet and Chang led the troops in combat. They employed shallow-bottomed boats that attacked coastal villages and conducted raids in rivers while larger junks, the premiere war-fighting and commerce ship in the area at the time, raided merchant shipping and fought the Chinese navy.
The really revolutionary part of their partnership was Ching's economic foresight. She extorted protection payments on a larger scale than most others and she formed a network of farmers, fisherman, and spies to keep the fleet well supplied and informed. Eventually, Ching took over control of the entire Red Flag Fleet from Chang.
The criminal network grew until it consisted of over 1,700 ships and 80,000 pirates. The bulk of the ships were still in the Red Flag Fleet, but many ships were assigned to subordinate commanders who ran the Black, White, Blue, Yellow, and Green fleets.
This massive force posed a serious threat to the Qing dynasty, which ordered a fleet constructed to destroy the pirates. Instead, Ching led the combined fleets out and easily dispatched the government forces.
Ching even captured about 63 of the Chinese ships, more than she lost of her own vessels, and pressed most of the crews into service with her own forces. She won the battle so hard, she came out of it with more forces than when she started.
Unsurprisingly, the emperor took his loss personally and ordered the Chinese navy to challenge her fleet. He enlisted the aid of the British and Portuguese navies in the effort and hired Dutch mercenaries to assist.
For the next two years, Ching's fleets fought their way through the enemy forces, still gaining power and loot despite the ships arrayed against them.
But the writing was on the wall. The dangerous business would have to end sooner or later, and Ching wanted her and her pirates well set up for it. Some articles on Ching also point to a conflict between the Red and Black Fleets for what happened next.
The emperor offered an amnesty to draw away many of the pirates working in his territory, and Ching herself took him up on it. But, like when she married Zheng, she required a few additional incentives.
First, nearly all of her workers, from the pirates who engaged in combat to the farmers who supplied them, were to get off without punishment. Second, the government had to provide money to help the pirates transition to shore life.
Third, Ching was to receive a title in the Chinese nobility.
The government caved, and Ching got her list. At the young age of 35, only nine years after escaping a brothel in Canton, Ching was made a member of the nobility and sat on a massive fortune. She opened a gambling house and brothel in China and settled into a semi-quiet retirement.