On October 30, 1810, Ching Shih — known in Chinese as Zhèng Yī Sǎo, "wife of Zheng Yi" — commanded a confederation of approximately 1,800 vessels and between 50,000 and 80,000 sailors in the South China Sea. She had been in command for three years, having inherited the Cantonese pirate confederation from her husband Zheng Yi, who died in 1807. She had expanded it substantially.

Ching Shih was born around 1775, believed to be in Canton. She was working in a floating brothel when Zheng Yi, a powerful pirate commander, proposed marriage. She accepted on the condition that she receive co-command of his fleet. He agreed. When he died in 1807, she secured her position through a combination of political maneuvering — aligning herself with Zheng Yi's adopted son and second-in-command Zhang Bao, whom she later married — and direct authority.

She imposed a military code on the confederation that made her fleet uniquely disciplined for the era: strict rules governing the treatment of captured women, distribution of plunder, and behavior toward friendly villages. Violations were punished by execution. The code made her sailors predictable in ways that worked to their tactical advantage.

The Qing dynasty attempted to suppress the confederation with its imperial navy and failed. The Portuguese navy attempted the same and failed. The British East India Company declined to engage. The Qing government eventually negotiated her retirement in 1810, offering terms so favorable they amounted to a surrender: she kept the ships, the money, and most of her sailors, who were integrated into the imperial military.

She opened a gambling house and lived to around 1844.