Cheng I Sao

The pirate queen known only as Cheng I Sao, or "wife of Cheng," started out as a prostitute in Canton. In 1801, she married the raider Cheng I, who was organizing a confederation of sea brigands to prey on fishing and cargo boats around the Southern edge of China. When Cheng died in 1807, Mrs. Cheng seized her chance and took full control of the operation. Eventually, she governed more than 50,000 pirates. She was notorious for her ruthless sentencing: Looters that disobeyed orders were summarily beheaded, and first-time deserters lost their ears. Mrs. Cheng also entered into a politic fling with a promising young lieutenant, Chang Pao, after appointing him captain of the Red Flag Fleet, her most powerful squadron. Trouble arrived when the Chinese government sought protection against the pirates from the British and Portuguese navy. To avoid an epic battle, Mrs. Cheng brought 17 women and children with her to the Governor-General's house and asked for pardon. She got it, along with permission to keep the wealth she'd acquired through plundering. Then, clearly craving respectability, she retired to open a gambling house in Canton.