Cheng Shih was purchased from a "flower boat" (a brothel), tied up and hauled onto ship. The captain released her to get a better look - and she laid into him like a wildcat. Apparently, he thought that this feisty woman was pretty epic, fell in love and they got married!
She demanded her own fleet, and to keep her own captured treasure - and soon became his greatest rival on the seas, landing more booty than he! Sadly, he was killed in a storm - and lo, the fleets came in to port and bickered over who would be the new pirate lord.
Cheng walked in, threatened off all the competition and took control. In less than three years under her Red Flag, she took the fleets to over 1000 ships strong, and became the most formidable force on the oceans - outmanning most other countries entire navies.
She also shrewdly diversified from just pillage to protection, blackmail, spying and extortion; even developing good working relationships with farmers to provide her men with good food.
At the end of her reign, she was even offered a universal pirate amnesty in exchange for peace. Of the 80,000 men in her fleet, less than 400 were punished. They ALL got to keep their booty, and most of them were given good military jobs!
Cheng went on to open a gambling house with her husband, and passed away as a 69 year old grandmother. A truly remarkable pirate.