Ching Shih

Aside from being an extremely famous pirate, Ching Shih was arguably the most successful one. Little is known of her early life except that she was a prostitute, but in 1801 she was captured by—and subsequently became the wife of—a pirate named Cheng Yi. Together they sailed the seas and amassed a pirate army known as the Red Flag Fleet. Upon Cheng Yi’s death in 1807, Ching Shih took command of the fleet, which consisted of hundreds of ships and some 50,000 pirates. She kept them in line with a strict code of conduct, with most offenses being punished by beheading. The fleet proved so unstoppable—sometimes even venturing upstream in smaller boats to hit cities and towns that weren’t on the coast—that the admiral of the Chinese navy committed suicide rather than be captured by her. In the end, she was offered amnesty by the Chinese government and retired to the countryside