Who was the Most Successful Pirate?

When you think of the folks who have ever imitated a pirate and let out a deep ; "Haarrr me maties !", you probaby immediately thought of some crusty, bearded, peg legged man. Maybe you thought of that movie with Johnny Depp, and his face flickered across your mind for a second. But the most successful pirate is probably not a bit like our sterotyped visions we have stored up in our thoughts.

In fact, the most successful pirate may not even be male, but female. Yes, I said female, and she was good looking to boot ! In the 1800's, the China seas had a fiery pirate princess, not with "guidelines" , but with rules that could get your head chopped off if you disobeyed. Her name was Cheng I Sao, wife of a pirate named Cheng.

She started on the wrong side of the law. Cheng I Sao was a prostitute when Chen married her. She married him on agreement that she would have half of the powers of Cheng. Cheng agreed, and so started a legacy. Under the astute rule of Cheng I Sao, business boomed. Piracy became a profit. While Cheng was taking care of the enemies, fighting as any other pirate would do, Cheng I Sao took care of the business of piracy.

She planned and organized lucrative deals, organized cartels, and did so with a good measure of success. So much so, that the number of pirates reportedly were as much as 50,000 and maybe more under her command. Every day business ranged from ransoming captives to that ever popular making a "deal you could not refuse" to those who happened to be on the shore ( also called extortion ) .

The rules were stern indeed, no pun intended. A disobedience was a swift beheading, stealing from the booty was also a beheading. If you wanted out, you lost your ears. But of course, the stooping to violence came at a cost to regular people.

Under her command, regular sailors on ships that dared to fight her pirate ships were nailed to the floor, and beaten until they vomited blood. Later they were butchered on shore. After all, she was a pirate ! All total she and her husband had about 1500 confederate ships, called "the Red Flag Fleet". Now that is a successful pirate.

Cheng, husband of Cheng I Sao died before she did. She was a smart woman and had his right hand man made into the captain over the fleet, while she took the position of admiral, or "admiraless" depending on how you like it. The official Chinese fleet tried to contain the Red Flag Fleet unsuccessfully. Battles were drawn up and fought with literally hundreds of ships from the rebel fleet.

After failing to submerge the pirate fleet, the Chinese sought help from the navies of Portugal and Britian. The title of "Portugese Man of War" had little effect on the Red Flag fleet and Cheng I Sao was remained undefeated. She went on to marry the new captain.

China subdued her by making a deal with her. In 1810 she negotiated a striking deal with the Chinese government, saving most of her men from death. They had to surrender their arms, but they were allowed to keep their plunder.

As colorful as her history is, Cheng I Sao died peacefully. She settled down, had a son, and started a house of gambling and ill repute. In 1844, when she was a grandmother, she passed away, not by sword, or gun, or sweeping winds and waves, but of old age. She was perhaps the most successful pirate.