It’s no secret that several of the most renowned pirates in history have been women. But while you may have heard of Anne Bonny and Grace O’Malley, I bet most people haven't met a little lady named Ching Shih. Who was she? Oh, just China's pre-eminent pirate queen. Want to learn more? Let's sail the high seas with one of history's most fascinating women.
1. She Wasn't Here To Make Friends
We don't know Ching Shih’s exact birthday, but we do know that she entered the world in 1775 in Guangzhou, China. However, fair warning here: Ching Shih lived a long time ago and one of the most important sources on her life comes from quite a biased dude: A man she held captive for three months. So maybe take the more salacious stories about her with a silo of salt. As we'll see, this lady had a lotta enemies.
2. She Started At The Bottom
Ching Shih didn't begin her working life as a pirate queen. She rose to the top, beginning her career as a street worker. This meant that for young Ching Shih, life was hard. As a street worker in 1700s China, she would have been seen as low class and judged for her profession. Begging the question, how'd this girl go from a house of ill repute to the helm of a pirate fleet? Well, Ching had a little help from her friends—or maybe I should say her friend with benefits.
3. A Powerful Man Courted Her
While hustling, Ching Shih met a strapping suitor named King Cheng I, the famous bad boy pirate. He immediately fell for our girl and according to some sources, went to disturbing lengths to get her for himself. In one story, he was so obsessed with Ching that he forced her to leave her day job by burning down the house where she worked.
Extreme, but hey, it worked? Soon enough, the couple were sailing the high seas.
4. She Had A Dicey Past
Even before Ching Shih met her beau, she just had to be at sea. Interestingly, the house where Ching Shih worked was actually a floating pleasure palace. In Chinese culture, people euphemistically called these "flower boats". They would sail along the coast to pick up customers. Or, in the case of King Cheng, fellow ships would drop off their men, their men would catch feelings, then they'd burn the ship down. 1700s China problems, amirite?
5. She Was A Regulation Hottie
Why did Cheng go so gaga for Ching Shih? Some say that the answer is exactly what you'd expect: Ching Shih was such a hottie that Cheng just had to marry her. Other sources, however, insist that Cheng had less superficial reasons. He rightly recognized Ching Shih's incredible cunning and just knew she'd be an amazing business partner.
No matter the reason, Ching Shih and Cheng I got hitched in 1801.
6. Her Husband Was A Legend
After marrying Cheng I, our girl's pirate lifestyle was basically guaranteed. Her new hubby came from a family of famous pirates and over the years, he built up such an intense reputation for his oceanic conquests that the dude just gave himself a royal moniker. He basically called himself King Cheng, The Best Pirate Ever and people just let him because he was such a big deal.
7. She Wasn't A Meek Wife
Ching Shih had no intention of being eye candy on her pirate hubby’s arm. When Ching first got married to her husband, who by the way had a pretty kick-butt nickname of "The Golden Dragon of the Imperial Staff," she had some strict conditions her man would have to meet. Ching demanded an equal marriage, getting 50% control of her hubby's stuff and becoming an active partner in Cheng I’s piracy. Go girl.
8. She Sailed The High Seas
Over the span of just a few years, Ching Shih and Cheng I assembled an enormous fleet of various pirate ships. They cleverly turned old rivals into teammates, uniting disparate pirate gangs (including a bunch of Cheng I's far flung relatives) into one juggernaut of a fleet. By 1804, the Red Flag Fleet, as it was called, was the biggest pirate fleet ever seen in China.
9. She Started A Family
Ching Shih and Cheng I had two sons together. We don't know much about them, but we can only assume that they entered the family business. Oh, but we do know one thing: Ching Shih's time in a happy nuclear family wouldn't last long. She didn't know it at the time, but a tragedy was right around the corner—and it would change her life forever.
10. Everything Fell Apart
In 1807, Ching Shih’s husband, Cheng I, died while he was in Vietnam. While Ching Shih may have wanted to grieve her loss, being a single woman on the high seas was a precarious position. Ching Shih stifled her feelings and got to work shmoozing with her in-laws. She managed to win over her husband's nephew and cousins. It was a clear sign to Ching Shih's enemies: even though she'd lost her hubby, she was far from alone.
11. Dark Rumors Spread
Despite the mess that King Cheng's demise threw Ching Shih into, some people actually believe that she had a hand in his passing. This isn't too surprising—Ching Shih was known to be ambitious and clever, so the accusations that she was also an Evil Woman seem guaranteed. For the record, other versions of King Cheng's passing see him perishing in a typhoon or accidentally falling overboard.
12. She Took Charge
Some sources say that Ching Shih didn't just cozy up to her in-laws following her husband's passing. Perhaps knowing that rival fleets would take her newfound single status as a sign of weakness, Ching Shih also immediately shacked up with a new man. Her new beau's name was Cheung Po and boy oh boy, their romance was completely scandalous.
13. She Became A Pirate Queen
Welp, no matter how she solidified her power, we can all agree that Ching Shih proved herself to be an incredible pirate. With the Red Fleet under her control, Ching Shih immediately became a legendary leader. She launched her ships against coastal towns all across China, crushed any resistance, held people for ransom, demanded tributes, and defeated the Chinese government countless times.
14. She Fought Back
Ching Shih really stuck it to the Chinese authorities. Over the years, they became desperate to get this girl out of their way, even specifically hiring an entire fleet to take her down. In this kind of situation, most captains might lie low—and hey, no judgment, that makes sense. The Chinese government were a powerful force. Ching Shih, however, wasn't most people. She struck back at her enemies in a jaw-dropping way.
15. She Was Brutal
Instead of hiding from the authorities, Ching Shih sailed right up and met them. Not only did she valiantly forge ahead, despite the dangerous situation, she actually beat her country's government. And that wasn't all. During her siege, she managed to take over 60 ships from her nemesis's fleet. She also, natch, kidnapped multiple sailors—and when they trudged onto her ship, Ching presented them with a devastating choice.
16. She Could Be Terrifying
On the one hand, it's important to admire Ching Shih's resolution and ambition. On the other hand, we have to recognize that she had quite a dark side. When she brought over captives from the government's ships, Ching Shih gave them a "choice". Option A) They could join her team and help Ching swashbuckle her way through the seas. Option B) They could get executed. Like, right now.
And this would not be a merciful end. Ching would tie her captives to the ship's floor and mercilessly club them until they perished.
17. She Ran A Tight Ship
One of Ching Shih’s major actions as pirate queen was the code of rules that she imposed on the pirates under her command. Among other things, pirates couldn’t disobey orders, they couldn’t steal from their own allies, they couldn’t assault captives, and if they took captives as their wives, they couldn’t mistreat them or cheat on their new wives. If they dared to defy Ching Shih's orders, they'd earn themselves a brutal punishment.
18. You Didn't Want To Mess With Her
Ching Shih was serious about treating women well. If her men dared to harm their new wives or injure the ship's captives, Ching would treat them to a taste of their own medicine. She would punish her misbehaving pirates with floggings, corporal punishment, and in extreme cases, she'd even execute her own men. For her own sailors, her preferred method wasn't walking the plank or beating them to oblivion. She'd just straight-up behead them. Yikes.
19. She Was Involved In Some Shady Deals
Oh, but her own men weren't the only ones in danger of Ching Shih's wrath. Ching made her money in some pretty sleazy ways. Sure, while captured women were on her ship, they were safe enough—but once Ching Shih delivered them to their next destination, nothing could be further from the truth. After all, Ching only captured women because she knew she could make a pretty penny by selling them to traffickers. In this way, she's less a historical heroine and more of an evil villain.
But there was one way to escape this brutal fate...
20. She Had A Devastating Loophole
Allegedly, Ching Shih was all about delivering a quality product. If you hired her to capture some women for you, Ching would present a bevy of beautiful ladies. This meant that any, ahem, less than conventionally attractive lasses would actually get a far better deal than their more glamorous peers. Ching actually had an absolutely devastating rule: if a woman was too ugly to be sold, she'd just let them go. Ouch, but also thanks?
21. She Broke Records
We don't know just how many pirates took orders from Ching Shih at the height of her power, but it was up to 70,0000 people. No wonder they call her a pirate queen!
22. She Had An Insane Romantic Life
Here's the thing about Ching Shih. She wasn't just a bad girl in her professional life. Her personal life was absolutely wild too. After King Cheng passed, Ching Shih took a new lover—and to say he was an inappropriate suitor would be an extreme understatement. Remember how we mentioned Ching's new boo, Cheung Po? Well, get this, he wasn't a stranger.
He had been her second-in-command for years, but their employer/employee power difference was far from the diciest part of their romance.
23. She Met Her New Man In The Worst Way
Okay, get ready for this back-story because honestly, it's a lot. There are two versions of Ching Shih and Cheung Po's meet-creepy and they're both...something else. In one version, Ching's husband and Cheung Po actually got together first. After they became lovers, King Cheng adopted his boyfriend (!) so that he would be legally recognized in case Cheng passed.
So yes, this means Ching Shih shacked up with her husband's ex-boyfriend/adopted son. But if you think that's wacky, just wait for the other story of how Ching met her new boyfriend...
24. Her Family Was Freaky
In the other version of this "romance", Ching Shih and her husband King Cheng I stole (!) Cheung Po when he was a child. After they abducted him, they raised him as their own son. Now, this is definitely better than being mean to the poor kid, but on the other hand, it obviously makes Ching Shih’s later relationship with Cheung Po highly questionable—and that's putting it lightly.
25. Her Past Came Back To Haunt Her
Whether Cheung Po Tsai was originally Ching Shih’s adopted son or her first husband’s ex (god, what a sentence), their ending is the same. After years of working together as pirate lovers, they wanted to make their relationship official. They planned to tie the knot, only to learn that they couldn't. Surprise surprise, their dicey history had come back to haunt them.
26. There Was Just One Problem
You see, Ching Shih was still recognized as Cheung Po Tsai’s mother in the eyes of Chinese law. When she took the offer of amnesty, Ching Shih requested that this mother-son status be removed so that she could legally marry Cheung Po Tsai. The provincial governor effectively said, "Oh...that's weird. But sure, let's undo that so that you crazy kids can get hitched".
With that settled, the marriage went forward.
27. She Made It Official
Despite their, ahem, rocky romantic start, Ching Shih and Cheung Po Tsai seemed to be a very happy couple? They were married for more than ten years and even welcomed two children, a son and a daughter. Their working relationship also continued to succeed. Cheung Po regularly took over as captain when Ching needed some me-time and always supported his wife's ambition.
But some sources say the marriage was less "star-crossed lovers" and more "business arrangement"...
28. Her New Relationship Had A Dark Side
Related, uh, some people think that Ching Shih got busy with Cheung Po for a dark reason. She knew she had the upper hand in the relationship. Cheung Po had grown up thinking of Ching as his superior, so he'd be easy to control. Plus, he was illiterate and allegedly simple-minded. So was it a marriage of the minds, or a savvy business arrangement?
I leave that up to my reader—but I will say that there's a very important moment when Cheung Po's, ahem, deficient intelligence pops up and royally screws up Ching Shih's plans....
29. She Was Clever
Ching Shih was a brilliant tactician and leader—so she knew that she had to preempt judgments based on her gender. She had a clever way of making people follow her orders: She used her younger boyfriend, Cheung Po, as her spokesperson. Ching would giver her lover orders, then make him repeat them to pirates who didn't like obeying a woman.
30. She Had A Way With Words
Sometimes Ching Shih delegated tasks to her boyfriend. Other times, she more than took the reins herself. According to some sources, Ching had some iconic words for her men when she took over the fleet after her husband's passing. At the time, many of King Cheng's men figured they'd leave the Red Fleet once their leader kicked the bucket.
Ching Shih had some words for these guys. She allegedly declared, "Under the leadership of a man you have all chosen to flee. We shall see how you prove yourselves under the hand of a woman". Daaaaaamn, Ching Shih.
31. She Outsmarted Her Enemies
Because of British interest in China, they became involved in the attempt to bring down Ching Shih. Ching Shih proved her mettle against the British when she successfully captured seven British sailors and one official from the East India Company in 1809. We can only imagine how big of a smirk she had when it came time to ransom those captives.
32. She Was Unstoppable
1809 and 1810 were very busy years for Ching Shih. With all her pillaging and raiding, she'd become a huge thorn in the side of the Chinese authorities—and they were desperate to put her away. They even partnered with the British in an effort to take down Ching Shih. But guess what? The combined forces of China and Britain couldn't catch her.
But Ching Shih's time in the sun wouldn't last forever.
33. She Met Her Match
Ching Shih’s illustrious career as a pirate queen hit a snag at "The Battle of the Tiger's Mouth". These intense fights with the Portuguese Navy were incredibly brutal and bloody affairs. Even though Ching Shih had more ships and men, the Portuguese used much smaller ships that could weave around Ching's fleet. Eventually, their maneuvers overpowered her fleet—leading Ching to make a stunning decision.
34. Everything Went Wrong
On January 4, 1810, Ching Shih was in a desperate situation. She had come out swinging so many times before, but today, the Portuguese's small ships managed to sneak up to her vessels and bombard them with cannons. After one of her most important ships sank, Ching ordered her fleet to, well, sail away. Unfortunately for her, there was one very big problem with this plan.
35. She Was Trapped
Credit where credit is due, the Portuguese attack plan was genius. They'd intentionally struck at this particular spot, knowing that eventually, they'd be able to force Ching Shih's fleet into a corner. Well, that's exactly what happened. Ching's ships fell back to the Hiang San River, leading the Portuguese captain to block the river mouth and prevent Ching's fleet from leaving. The great pirate queen was officially trapped.
36. She Finally Admitted Defeat
At this point, Ching Shih knew that for the very first time in her decades at sea, she had officially lost. After getting stuck in the river for two long weeks (some sources even say three), even China's most fierce pirate simply couldn't figure out a way to escape the situation. And so, with her head held high, Ching Shih finally surrendered to the Portuguese. This ignoble end to her seafaring career made everyone's jaws drop.
But there were more surprises in store.
37. There Was An Offer She Couldn't Refuse
At this point, I would've expected the Portuguese to make Ching walk the plank. Instead, Ching Shih somehow managed to come out swinging again. The Chinese authorities entered the scene, cleverly realizing that this was the perfect time to make Ching Shih give up her underhanded ways. When Ching was at her lowest point, they made her an offer she couldn't refuse.
38. She Cut A Deal
The Qing Dynasty said that if Ching Shih's pirate fleet surrendered their weapons, the entire group (which at this point meant thousands of pirates) would receive pardons. Despite years of defying the government, it looked like Ching Shih and her crew would get off without even a slap on the wrist. Because she wasn't an idiot, Ching Shih decided that she’d enough fun over her time as pirate queen, and accepted the deal.
39. She Was A Total Boss
Even when she put the pirate life behind her, Ching Shih was still a total boss. You'd think she'd be at a disadvantage when she was, y'know, negotiating with the people who had just kicked her butt. But nope! Somehow, Ching managed to make the Chinese authorities agree to a stunning condition. She'd only call time on her tenure as a pirate queen if she got to keep all the wealth that she'd accumulated over the years. Respect to you, ma'am.
40. Her Boyfriend Messed Up Big Time
Justice for Ching Shih: There's a little detail about the fight with the Portuguese that far too many people ignore. You see, during this decisive battle, Ching Shih had actually trusted her command to her trusty co-captain, her lover/adopted son, Cheung Po. Remember when I mentioned that he might have been a bit of a dummy? Welp, this failure doesn't exactly prove me wrong.
The loss had to make their already awkward relationship even dicier. But just wait—this odd couple had a far bigger complication in their near future.
41. She Suffered A Tremendous Loss
Despite Cheung Po's enormous failure, Ching Shih stood by him. The couple remained married until 1822—when tragedy struck. That year, Cheung Po tragically perished at sea. At the time of his demise, he was just 39 years old. This meant that Ching Shih was now a widow two times over, and that she'd have to navigate the harsh world all on her own.
42. She Defied Expectations
After all this drama, you'd expect Ching Shih's wild life to basically be over. But as always, our girl lived to defy expectations. Ching realized that being a widow and lying on a pile of money gets boring after a while. Soon enough, she returned to her illicit ways. In her "retirement," Ching Shih opened up a gambling house. Oh, and she also traded opium on the down low.
43. Her "Retirement" Was Scandalous
Ching Shih relocated her family and opened another gambling house in Macau. Gambling wasn’t Ching Shih’s only venture into the world of dicey businesses. She got herself involved in Macau’s salt trade. And in a case of a story coming full circle, Ching Shih also opened up a house of ill repute in Macau. This time, she wasn't a worker bee, but the head honcho.
44. She Had A Strange Last Hurrah
Even in retirement, Ching Shih couldn’t stay away from the action and the good fights. In 1839, the Chinese government was so fed up with the rampant use of opium that they tried to have the drug banned. The British, who were making a bundle off getting China hooked on opium, actually started a war to improve "diplomatic relations" with China. Yeah...this didn't go great—and once again, Ching was right in the middle of the action.
45. There Was A Late Game Twist
Despite her less-than-straight-arrow reputation, Ching Shih entered the fray as a military advisor to the leader Lin Zexu. Ironically, given her old job as an opium dealer, she was now an official advisor to the Chinese government during the Opium Wars. Sadly, the British ultimately won, presumably leading Ching Shih to sigh and say, "I’m too old for this".
46. She Had A Surprising End
After years of taking on the Chinese government, the East India Company, and the Portuguese Navy, it might have baffled some people to think that Ching Shih passed peacefully. But that’s exactly what she did. In 1844, when Ching was an impressive 69 years old, she breathed her last. Despite her raucous life, her passing was very calm. Her family surrounded her when she perished.
47. A Huge Franchise Honored Her Legacy
Those of you familiar with the Pirates of the Caribbean franchise might vaguely recall a minor Chinese woman who was one of the great pirate lords present in Pirates of the Caribbean: At World’s End. Identified as "Mistress Cheng," this character was a reference to Ching Shih herself. We’d argue that she got short-changed by Hollywood, but given the quality drop in the Pirates movies after the first one, maybe she was the lucky one!
48. A TV Show About Her Is In The Works
In 2015, a Hong Kong drama series titled Captain of Destiny portrayed a character who was very obviously based on Ching Shih, though the details of her life were liberally adapted. It wasn’t the first time that Shih's life was planned to grace the silver screen. The previous year, Maggie Q had been set to star as Ching Shih for the limited series Red Flag.
49. She Had A Chilling Nickname
Based on the huge numbers of pirates that Ching Shih commanded in her heyday and the fact that she managed to retire and live peacefully after her pirate career, it’s been accepted by many historians that Ching Shih was the most successful pirate in human history. For others, though, Ching Shih had a darker reputation. After all, people called her "The Terror of South China" for a reason.
50. She's A Mystery
While Ching Shih is the most famous Asian woman pirate, much of her life is still murky. In fact, we don't even know Ching Shih's name. Ching Shih simply means that she was the widow of King Cheng I, her first husband.