Despite what you’ve read — or seen in the movies — many think the most-feared pirate was actually a Chinese woman. Her name was Ching Shih (widow of Cheng), nicknamed Madame Ching, and she lived from 1775 until 1844. Her territory was the China Sea in the early 19th century.
She began as a Cantonese prostitute, but was captured by pirates and eventually married the notorious pirate Cheng I. Through military ability and reputation, Cheng I was able to consolidate a coalition of Cantonese pirates into an alliance. By 1804, this “Red Flag Fleet” was one of the most powerful pirate fleets in China.
After Chang I’s death in Vietnam in 1807, Ching Shih began maneuvering her way into the leadership position. She issued a strict code of laws and controlled many coastal villages. At her height, some say she commanded over 300 junks and up to 40,000 pirates; others put the figure much higher — as many as 1800 junks and 80,000 pirates.
It was said her Red Flag Fleet could not be defeated, but finally , in late 1809 and early 1810, her fleet suffered a series of defeats by the Portuguese Navy, after which she accepted an amnesty from the Chinese government. She was able to keep her loot and opened a gambling house. She was one of the few pirate captains who were able to retire, and many consider her the most successful pirate in history.
She has been featured in many books and films in Asia. In the movie Pirates of the Caribbean: At World’s End, she appears as one of the nine Pirate Lords.
The main source is https://en.wikipedia.org/wiki/Ching_Shih . The picture came from that site. Also see http://www.atlasobscura.com/articles/the-chinese-female-pirate-who-commanded-80000-outlaws .