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Wiki Deep Dives: You've Never Heard Of The Most Successful Pirate In History

Dive #2: Massacre at Katyn Forrest 

TLDR: A prostitute became the head of of a giant pirate confederation

A year before our country was born, Zheng Yi Sao was born in south China. She was likely part of the Tanka people, which is an ethnic group that were nomadic boat people in that region. She was supposedly a hooker/madame, but her life changed when she married a famous pirate by the name of Zheng Yi

Zheng Yi was contracted by the Vietnamese Tay Son dynasty to fight against the Chinese Qing forces and the future Emperor of Vietnam, Gia Long. Zheng Yi's cousin was killed by Long's forces, so Yi took over his fleet and took it back to China. Before this, he "adopted" a son that he had abducted at the age of 15 named Zhang Bao. Think of this as a Yondo/Peter Quill relationship. 

More on Bao soon. Zheng Yi's fleet of pirates in south China was in disarray. They were on the brink of civil conflict, but Yi convinced them to come together for the common cause of cold hard cash. He organized them into 6 distinct fleets coordinated by the colors red, black, blue, white, yellow and purple. The Red Flag Fleet was the largest one, and was commanded by Yi himself. 

This is where things get dicey. Yi "falls overboard" during a storm and drowns in 1807. Zheng Yi Sao, our heroine, takes over this massive fleet with the support of her dead husbands adopted son, Zhang Bao, who was the de-facto leader of that Red Flag Fleet. Not long after this, Zheng Yi Sao and Zhang Bao enter a public relationship, with speculation that they had been having an affair prior to her husbands seemingly random death. 

Giphy Images.

Doesn't take a genius to put that together, folks. Zheng Yi Sao starts leading this fleet, which is growing larger by the day, out pillaging in South China. In 1808, she manages to destroy over half the Chinese provincial fleet in 2 engagements around the areas circled below, just north of Hong Kong and Macau. This freed up her pirate fleet to raid up the Zhujiang river, which was a very rich area. They also set up their own pirate code, which had 3 rules.

1. If you go to shore privately, you get your ears cut off before getting dragged around the fleet and executed.

2. All plunder is registered, none is taken privately. For every 10 parts plundered, the pirate gets 2 with the rest going to the fleet's general fund. Anyone caught stealing gets executed.

3. Anyone who harms women captives in any way is executed. 

A year later, she joins a giant naval battle between a Chinese provincial fleet that is 100+ ships strong and some of her pirate friends just south of the same area. She has her fleets break apart to flank the Chinese, while personally leading the charge right into the heart of their forces. She routes them, sending them back north with their tail tucked between their legs. 

She then decides to organize a massive raid of the now unprotected river cities. She organizes them into three groups. The Red Flag fleet under her boy toy Zheng Bao to Dongguan, the Black Flag fleet to Shunde, and she personally lead her own fleet to Xinhui. The Black Flag fleet alone killed over 10,000 people during their raiding during this year (1809).

At this point, the Chinese are desperate. Their provincial fleet was defeated again while trying to stop Zheng Yi Sao, and they were forced to look for outside help. The Portuguese were the rulers Macau at that point, and they decided to lend a hand since the pirates were bad for trade and had recently commandeered one of their brigs. They cornered Yi Sao at Tung Chung bay, and she called for Zhang Bao and his Red Flag Fleet for backup. the Portuguese were gone by the time he got there, so they decided to dock and prep the ships. The Portuguese suddenly returned with a frigate and 5 brigs to do battle vs the pirate junks. The Chinese provincial fleet of 100 ships arrived not long after to reinforce them. 

They were essentially in a stalemate. The Pirates didn't have the wind, so they couldn't escape. The Portuguese and Chinese didn't have the numbers or the space to operate in the bay, so they couldn't destroy the fleet. The Chinese decided to convert almost half their fleet into fireships to burn the Pirates out. They sent them adrift towards the Pirate fleet, but the pirates diverted most of them to shore and chopped them up for firewood while others blew back on the Chinese fleet, burning down their own ships. After a few weeks, the pirates got the wind and Zheng Yi Sao and Zhang Bao escaped the blockade without losing a single ship.

This is where things start to go south for our pirate queen. The leader of the Black Flag Fleet, Guo Podai, betrayed her and fought against her fleet. He later surrendered to the dynasty and became part of their navy.  Around this time, the British and Portuguese went in league with the Chinese, sending warships to patrol the area around Guangzhou. With 2 of the biggest colonial empires protecting their prey and their pirate confederation breaking down, Zheng Yi Sao decided to negotiate a surrender. 

She officially surrendered her fleet of 17,300 pirates, and 226 ships in 1810. To put the sheer size of these numbers in perspective, lets look at a naval battle you might be familiar with from the time period. in 1805, the battle of Trafalgar changed the course of the Napoleonic wars. The British navy under Admiral Nelson consisted of 33 ships (much larger actual ships, mind you), and roughly 20,000 men. And to put even more perspective into this, remember that the size of Zheng Yi Sao's fleet had been severely reduced by the time of this surrender. At it's peak, Zheng Yi Sao's fleet was estimated to be around 60,000 pirates strong with over 400 ships. This means she commanded more sailors than both sides at Trafalgar combined! 

This might sound crazy, but this negotiated surrender is part of what makes her the most successful pirate in my opinion. She walked away alive with her lover Zhang Bao, who she later married, and he was given the rank of Lieutenant in the navy and walked away from the bargaining table with a private fleet of 40 ships. He died a colonel in 1822, and Zheng Yi Sao died in 1844. In her post-pirate years, she ran one of the biggest gambling houses in south China. 

So, again, look at her piracy career from a grand perspective using other pirates that you probably have heard of before. 

Blackbeard: Edward Teach's pirate career lasted all of 2 years, and in that time he had no more than 4 ships and 400 pirates. He was killed by the British. 

Black Bart Roberts: His pirate career lasted 3 years, he also had a fleet of no more than 4 ships and was killed by the British. 

Calico Jack: His pirate career lasted 2 years, he never commanded a real pirate fleet and was killed by the British. 

William Kidd: His pirate career lasted 2 years, he never commanded a real pirate fleet and was killed by the British 

Meanwhile, our queen of the pirates commanded 60,000 men, 400 ships, had a 5 year run making a shit ton of money, escaped justice with a nice buyout and died a fat and happy gambler at age 69. Nice. If only we could all go out that lucky.

Giphy Images.