Ching Shih, Captain Ching Shih, was possibly the most feared and successful pirate of all time. During her nine year reign of terror she amassed over 80,000 pirates under her command and had empires bowing to her will. So who was this woman? Details on her early life have been swallowed up by the times, but they probably weren’t very pleasant since she first shows up in the historical record as a prostitute marrying pirate Captain Cheng I in 1801. Now, Cheng was already one hell of a pirate, and he and his crew were largely successful. However, business took off as soon as he married the young Ching Shih, and it soon became pretty obvious that he valued and respected her intellect and cunning when it came to how a pirate fleet should be run.

Too crafty to be poisoned and too badass to be skewered by another pirate, Cheng died in 1807 in a tsunami. Ching Shih promptly married his first mate and took over Cheng’s fleet. It’s unknown if Ching Shih was in love with this first mate, or if their marriage was more of a business contract to help her secure her role as captain. What is certain, however, is that Ching Shih turned that pirate fleet into the most feared and successful on the seven seas. She ruled with an iron fist, and passed out the death penalty like candy. Caught pillaging a town that had made friendly with Ching Shih’s fleet? You were beheaded. Caught raping a captured female or fellow female pirate? Instand death. If you were caught having consensual sex on duty, surely the penalty would be less severe, right? Nope. You both got to sleep with the fish.
Ching Shih spent that first year in command traveling the Chinese coast, attacking seaside towns and even sneaking up rivers to pounce on unsuspecting inland villages. She became a real pain in everyone’s collective ass. In 1808 the Chinese government decided it was time for an ass-kicking and the Imperial fleet was sent in search of her. I’m not sure what the Imperial fleet was expecting. Having to track her down? Almost definitely. A fight? Probably. For her to turn around and meet them head on for battle? I doubt it. The Chinese government had decided it was time for an ass-kicking and Ching Shih wholeheartedly agreed. She captured sixty-three of their ships, and offered the captured crew with two options: join her or die. Upon hearing this, the Admiral Kwo Lang of the Chinese Navy killed himself rather than face death at her hands.
With the hope and determination of a child who thinks that maybe if he stands up to the bully just one more time, the Chinese Government enlisted the help of the Dutch and British Navy. Ching Shih ripped through them like tissue paper. Finally, the Chinese government admitted defeat and gave her an unprecedented offer of amnesty. She accepted on the condition that her eight-thousand pirates be able to keep their money and retire as well. The deal was struck and Ching Shih invested some of her money into a brothel/casino, dying a millionaire at the impressive age of sixty-seven.
Jack Sparrow has nothing on her. In fact, she managed to rib the famous fictional pirate from beyond the grave. A cameo of her can be seen in Pirates of the Caribbean: At World’s End.