The date is January 21st, 1810, and a small flotilla of six Portuguese frigates finds itself surrounded by 300 Chinese pirate ships. Commanding the largest pirate fleet in history is Ching Shih- a former prostitute turned Pirate Queen- and she has brought the full might of her infamous Red Flag Fleet to bear on the Portuguese. But the Portuguese have been victimized by Ching Shih for too long, and they have dispatched their most powerful warships to confront her.

Though just six in number, the Portuguese frigates are large, built with thick wooden hulls that prove difficult to penetrate, and armed with explosive shells that rip through the smaller Chinese ships with ease. By the end of nine hours of fighting, Ching Shih and her fleet are forced to flee, and within weeks she will surrender to the Chinese government- but instead of being punished she will be allowed to peacefully retire with all her stolen wealth. Today, we’ll explore exactly how that came to be, in this episode of The Infographics Show, Ching Shih- the prostitute who terrorized the South China Sea.

Born a poor peasant, Ching Shih was, like many peasant girls of the time, forced into prostitution at an early age. Not much is known about her early life, but she soon developed a penchant for politics and an expertise in exfiltrating secrets from the powerful elite with simple pillow talk which she then used for her personal gain.

By the time she was 26, she caught the attention of the dread pirate Zheng Yi- accounts vary on what happened next, with some saying that upon seeing her incredible beauty, Zheng was instantly smitten, but others say that their mutual attraction was a calculated business move. Zheng Yi came from a long line of pirates, and he was no stranger to political intrigue, as his family had been instrumental in different political ploys across various Chinese dynasties. Either way, the two were soon married and Ching Shih left her life of prostitution behind.

The couple soon formally adopted a young man by the name of Cheung Po as their official ‘son’. Cheung was a favorite of Zheng Yi and had been abducted at the age of 15 and pressed into service in the pirate fleet. Uneducated but with a natural ability and charisma, Cheung Po quickly rose through the ranks earning the respect of other fleet captains.

This would prove instrumental for Ching Shih, as just years after her marriage to Zheng, he would die unexpectedly on a trip to Vietnam. Left without a leader, the pirate fleet threatened to pull apart at the seams; but shrewd as ever and with an insatiable ambition, Ching Shih saw a chance to seize control for herself. She had, after all, for years been Zheng Yi’s right-hand, fully engaging in the day-to-day operations of his pirate fleet.

The wily Ching Shih approached Cheung Po, and whether through guile or intimacy- it is rumored both- she secured his complete allegiance, and by placing him as figurehead ‘Captain’ of the fleet, earned the loyalty of the feuding pirates. Only a man was allowed to lead the pirate fleet, but all knew that Ching Shih was the true power and Cheung Po her mouthpiece. To further secure Cheung’s loyalty, the two sought out the governor of Guangdong and asked him to dissolve their adopted-mother-and-son relationship- and because you don’t say no to a fleet of 20,000 pirates at your doorstep, the governor agreed and the two were quickly married.

With her grip over the fleet secure, Ching Shih began a campaign of piracy across the southern Chinese coast that would fatten the pirate fleet’s coffers. Wily as usual, Ching Shih curbed the pirate’s natural aggression and instead spared villages in exchange for financial and material support. At the height of her reign, Ching Shih would have dozens of coastal villages actually paying monthly taxes to the fleet, and in exchange the villages would be protected both from her own and rival pirate raids.

In 1808, with political pressure mounting to finally do something about Ching Shih’s Red Flag Fleet, the Chinese government hunted down Ching and engaged her in a series of fierce battles. The government fleet however was no match for the brilliant Ching, who at the end of the disastrous campaign against her would end up seizing a large number of the government’s ships, forcing the Chinese navy to resort to converting fishing vessels for combat.

Suffering humiliating defeat after humiliating defeat, the Qin government sought the aid of rival pirate captain O-po-tae. A former ally to Ching, O-po-tae was very familiar with her capabilities and strategies both, and in alliance with the Chinese navy- or what remained of it- he managed to successfully drive Ching Shih’s fleet off, though not defeat it.

Licking her wounds but swearing revenge, Ching Shih turned the attention of the Red Flag Fleet to waters further south where they could rebuild their strength. Though she had pirated the Chinese coast for years, she had always avoided European ships. Far more advanced both in design and firepower, and crewed by professional sailors, Ching knew that her ships were no match for European frigates, and was wary of raising the ire of any of the European powers. After her defeat by O-po-tae though, and forced to abandon her former hunting grounds, Ching resorted to raiding European shipping and was initially quite successful, even to the point of seizing and ransoming British officers from the East India Company.

Calculated as it was, Ching Shih’s boldness eventually led her to one raid too many and it was the Portuguese who in 1810 would finally put an end to her infamous Red Flag Fleet.

Early in September, 1809, Ching’s pirates seized a Portuguese trade ship and killed its entire crew. The colonial government of Macau, fearful of a pirate blockade, contacted the Portuguese government directly and received approval to dispatch three ships to hunt down and destroy the pirates. Ching Shih initially commanded her fleet to avoid direct engagement and instead targeted the smaller Portuguese resupply ship which came under attack by a squadron of Chinese junks.

Armed with superior cannons and rifles though, the Portuguese crew managed to fend off the attack and sink several of Ching’s ships. On September 15th, the three-ship flotilla finally engaged the bulk of Ching’s Red Flag Fleet- a force of over 200 ships! For over 12 hours the two fleets exchanged withering fire, but Ching’s fleet, mostly made up of converted junks and armed with stolen or inferior cannons, was no match for the superior technology and firepower of the Portuguese. With the sun setting and suffering dozens of losses, the Red Flag Fleet scattered, and the Portuguese returned to port having lost not a single ship.

Seeing an opportunity, the Chinese government contacted the Portuguese and offered to join forces to destroy the Red Flag Fleet once and for all. In mid-November the Portuguese added three more frigates to their forces and set sail for the Humen Strait to link up with Chinese government ships. Ching, aware of the plot against her, dispatched her fleet to intercept the Portuguese before they could join with the government ships. In two different engagements, Ching suffered over 30 sunken ships and dozens damaged, and was forced to retreat both times. The Portuguese suffered no lost ships and pressed on, but after reaching the agreed-upon rendezvous point found that the Chinese government fleet never showed up. With no Chinese support, the Portuguese then sailed back home to Macau.

Seeking a decisive battle against the Portuguese, Ching dispatched her fleet to Macau to force the Europeans into battle on her terms. The battle however would not go well for Ching, but knowing that her days were numbered if she did not defeat the Portuguese now before the Chinese government found its nerve, engaged the Europeans several more times throughout December, each time suffering defeat. Finally, in late January 1810, Ching ordered the full might of her Red Flag Fleet against the small Portuguese flotilla- a force of over 300 ships, 1500 guns and 22,000 men!

The battle would end in absolute disaster for Ching Shih. Though the power of numbers was overwhelmingly on her side, the pirates found it difficult to fire on the small Portuguese flotilla without hitting their own ships. The Portuguese on the other hand were able to concentrate their fire on the pirates, blasting groups of pirate junks with explosive shells. The Red Flag Fleet fought on however, until after many hours of battle the Portuguese commander, José Pinto Alcoforado, noticed a very large junk that had been transformed into a floating pagoda and ordered his ships to fire upon it. Under withering fire, Ching’s flagship sunk, and upon seeing the loss, the pirate fleet broke and ran, hiding upstream in the Hiang San river where the bigger Portuguese ships with their deeper drafts could not enter.

Unable to give chase, the Portuguese instead blockaded the river mouth and after two weeks, Ching Shih and her husband Cheung Po finally surrendered to the Portuguese. Crafty as ever, Ching Shih leveraged the remains of her fleet into a deal with the Chinese government- Ching Shih and her pirate fleet would be forgiven all crimes committed and allowed to keep their massed treasure, and in exchange Cheung Po would be made a Lieutenant in the Chinese navy and tasked with using the former Red Flag Fleet to hunt down and destroy other pirates.

Ching Shih would go on to retire peacefully in her hometown of Guangzhou, and though her reign as Pirate Queen was brief, it would shape Chinese history and folklore for centuries to come. Rising from a mere prostitute, at the height of her power Ching Shih and her pirates would defy the Chinese government itself and levy taxes on dozens of villages and ports, and it would take the combined might of the entire Chinese navy and rival pirate fleets to drive her off. Wounded, but not defeated, Ching would rise again and though she would face ultimate defeat at the hands of the Portuguese, she would as usual leverage defeat into victory and walk away from a life of high-seas crime a rich and free woman.

What would have happened though if Ching Shih’s ambition had not led her to target European ships? Shortly before her defeat it was rumored that Ching had plans to put her husband Cheung Po on the Chinese throne- could the might of the Red Flag Fleet really been enough to overthrow the entire Chinese government? Was Ching Shih truly resourceful enough to pull off such a feat? Let us know your thoughts in the comments! Also, be sure to check out our other video called  The Story of The Man Who Stole $65 Billion! Thanks for watching, and, as always, don’t forget to like, share, and subscribe. See you next time!

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