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Ching Shih was one of the most successful Pirates who ever lived, one who ran her operation more like the Mafia than the more smash grab and run types more common to her time.

What If? She had decided to try and make something of her resources? With the ships and men and women she led could have set herself up with her own country if she picked the right target.

So any ideas on the right target?

How much control she had over all her ships (all 1800 of them) is debatable but she almost certainly had the loyalty of a core force that rivalled the militarises of some not insignificant nations. She also recognised that their wasn't much of a future in being a Pirate and is one of the few who managed to get out with life limb and loot.

Ching Shih (also known as Shi Xainggu, Cheng I Sao, Ching Yih Saou, and Zheng Yi Sao) is today remembered as one of the most successful female pirates in the history of the world. During her active years as a pirate lord in early 19th century, she commanded over the famous Red Flag Fleet that was consisted form over 1800 ships and 80 thousands male and female pirates. Under her rule, Chinese pirates became invincible, resisting attacks from every major naval power of her time.

Ching Shih was born in 1785 in unknown location, and has spent her youth and young adulthood as a prostitute in Chinese city Canton. Her lifestyle changed dramatically in 1801 when she married Zheng Yi, famous pirate captain that came from the long and prosperous family of pirates. Before marrying her Zheng Yi managed to unite every major Chinese pirate organization into Red Flag Fleet, but after his death in 1807 Ching Shih managed to maneuver herself into place of power and took control over entire organization.

Under her rule Red Flag Fleet flourished. Their incredible strength and power enabled them to pillage and raid every town and ship between Macao to Canton. In addition to controlling the fleet, she also controlled every aspect of the organization's business. Many stories from that time describe her as ruthless - not only to her victims but even to her own crew (executions were not uncommon). Fear that she inflicted to the pirate crew was so big that she had final word in every raid decision, and all captured wealth were presented to her before dividing it to the surviving pirates.

After several years Chinese government came to conclusion that their military forces (even with combined help of England and Portuguese) will never break defenses of Shih's pirate operation, they finally issued amnesty for all pirates who were willing to return to the shore as a free citizens. She took advantage of this and negotiated pardon for herself and vast majority of her fleet (while even retaining all her wealth).


Edit: Sorry I suck. The main thrust is that Ching Shih arguably knew what she had couldn't last forever; either she'd finally get taken down by the Chinese, Portuguese or English or some up and coming Pirate would stick a knife in her back, as shown by her jumping at the chance to get out and that she had an awful lot of resources WI she had decided to carve her own way out on her own?
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