The most successful pirate of all time was a Chinese prostitute called Ching Shih. Also known as Cheng I Sao ("Wife of Zheng Yi"). She was a prominent pirate in middle Qing China, who terrorized the China Sea in the early 19th century.
She personally commanded over 300 junks manned by 20,000 to 40,000 pirates - men,
women, and even children. The rest of her fleet, commanded by her
subordinates, had more than 1,500 vessels with a crew upwards of 180,000.
She entered into conflict with the existing empires of the time, such as
the British, the Portuguese and the Qing dynasty. She was one of the
few pirate captains to retire from piracy.
She commanded over 1,800 ships and up to 200,000 pirates. She was one of the few pirates to actually retire.
source: wikipedia
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