Possibly the most successful pirate of all time was Ching Shih (https://www.infinite-women.com/women/ching-shih/)
In 1801, the woman who would be known as Ching Shih was a young prostitute who married a pirate lord, Ching I. It’s said that she demanded an equal share and command before she would marry him, which he agreed to. Six years later when her husband died, Ching Shih took command of the Guangdong Pirate Confederation, putting her in charge of about 400 junk ships and 40,000 to 600,000 pirates in her early 30s. Years earlier, she had helped her husband form the confederation, in which different pirate leaders each sacrificed some autonomy for collective benefit. Her political savvy and knowledge of players, relationships and dynamics helped her not only gain power but keep the confederation together after Ching I’s death.
She then wrecked havoc on the South China Sea for years - under her command, the confederation was far more active. Ching Shih took on everybody who was anybody, including the East India Company, the Portuguese Empire, and the Qing Chinese navy. One captive estimated that Ching Shih had 80,000 pirates, 1,000 large junks and 800 smaller junks and rowboats under her command in 1809.
She also ruled with an iron fist - any pirate caught giving his own orders or disobeying those of a superior was to be beheaded on the spot. It was also a capital offence to steal from the common treasury or from villagers who supplied the pirates. Additionally, if a pirate raped a female captive, he would be put to death, but if the sex was consensual, both would be put to death, though a captive was allowed to marry a pirate if they wanted to.
Perhaps the most impressive part of her piratical career was its ending. Ching Shih was such a powerful enemy that she was able to arrange a peaceful surrender in 1810. At the time she was in command of 17,318 pirates, 226 ships, 1,315 cannons, and 2,798 assorted weapons; her personal command encompassed 24 ships and 1,433 pirates. The terms of surrender included pardons, pork, wine and money for her crews and her lover Zhang Bao was awarded the rank of lieutenant and allowed to keep a private fleet of 20 to 30 ships. She married him, retired to run a gambling house in Macau, had more children and lived to be almost 70.
En liten tjänst av I'm With Friends. Finns även på engelska.