Ching Shih

Jun 09, 2025 6:52 PM
Jun 30, 2025 3:19 PM

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Ching Shih* is a pertinent example of how tight systems of rules helped pirates succeed. Born in China in 1775, Ching Shih may have been the most successful pirate to ever live. She began her career as a sex worker in Canton, where she met the pirate Zheng Yi. He proposed to her, and she agreed—provided she had an equal share of his wealth and power aboard his Red Flag fleet. When her husband died, she took full control, becoming one of few female pirates.19 At one point, she oversaw 70,000 to 80,000 pirates and up to 2,000 ships, a fleet of unusual size.20 To give context, the most famous pirate of all, Blackbeard, probably never led more than 700 individuals, with his crew typically numbering a few hundred.21 Ching Shih was essentially leading a floating city that needed to be able to control itself without the help of the standard legal system. After all, a pirate who discovered that a crewmate had stolen his already-stolen plunder couldn’t report them to the police.

Ching Shih laid out a strict set of rules for all of her pirates that was designed to ensure both her power and their success. When they attacked other ships, she ordered her crew only to harm anyone if they failed to surrender. They could not step onto land without permission—the penalty for doing so twice was death. After the looting of a ship, they had to report all goods and not keep more than a fifth. Deserters were mutilated. It was the death penalty for anyone who gave unsanctioned orders, harmed land people without provocation, or raped a female captive.

Ching Shih’s might was so great that, unlike most pirates, she was able to peacefully retire in great wealth, having negotiated terms with the Chinese government.22