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The Most Feared Pirate of the South China Sea

Wed, 21 May 2025

Description

It began in the crowded harbors of Guangdong, where intelligent woman, Zheng Yi Sao, worked aboard a floating brothel. Through strategy, negotiation and an unshakable understanding of power, she went on to become the leader of 70,000 pirates, command hundreds of ships and take control over trade in the South China Sea—making her one of the most feared pirates ever recorded in history.   Sources: ⁠History of the Pirates Who Infested the China Sea From 1807 to 1810⁠ ⁠Royal Museums Greenwich⁠ ⁠Great Explorers: Zheng Yi Sao⁠ ⁠Cheng Yi Sao, Female pirate extraordinaire ⁠ ⁠Zheng Yi Sao: The most successful pirate you’ve never heard of⁠ ⁠Chinese piracy in the late 18th and 19th centuries  Learn more about your ad choices. Visit podcastchoices.com/adchoices

Audio
Transcription

Chapter 1: Who is the most feared pirate of the South China Sea?

454.217 - 462.98 Cassie

Education for girls was rare unless they came from wealthy families, and a woman's value was often measured by her ability to bear a son to carry on the family name.

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463.877 - 483.274 Danielle

Foot binding was a painful practice where a girl's toes were broken and their feet were tightly bound into a smaller shape, and it was still common among the upper-class Han women, seen as a symbol of beauty and status. However, obviously, it severely limited mobility and meant that wealthy women were not expected to work.

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483.914 - 497.176 Danielle

For women from poorer backgrounds, survival often meant doing whatever jobs were available, which was often sex work. This is where the story of Cheng Yi Cao, who still went by the name Shi Young, at the time began.

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497.937 - 511.179 Danielle

She worked as a sex worker on a floating brothel, commonly referred as a flower boat, where it is believed that she had a reputation as a savvy businesswoman, often involving herself in conversations with the wealthy men who visited.

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512.426 - 516.468 Cassie

Very smart. Keeping ears open, eyes open at all times.

517.348 - 521.61 Danielle

She's like, I might be in this role, but I'm still a businesswoman at heart.

522.47 - 543.515 Cassie

And just like that's where lips are loose. It's like people feel relaxed and comfortable and share things that maybe is important information that she could benefit from. She's surrounded by men in power. Right. During this time, she met Cheng Yi, the leader of a large pirate confederation.

Chapter 2: What strategies did Cheng Yi Sao use to rise to power?

544.115 - 560.818 Cassie

It's unclear whether Cheng Yi asked for her hand in marriage or if it was a negotiation on Shi Yang's part, but the two tied the knot and grew both a personal and professional relationship. This is where she became known as Cheng Yi Cao, which translates to Cheng Yi's wife.

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561.879 - 563.799 Danielle

I like to think that it was a negotiation.

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564.451 - 566.092 Cassie

Let's go with that. It feels better.

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566.112 - 580.143 Danielle

Yeah. If she's a savvy businesswoman, she meets this guy who's a leader of a large pirate ship. And, you know, she sees the opportunity here to get out of her work. I imagine it was some type of negotiation.

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581.462 - 603.594 Cassie

Yeah, I think she was smart and she realized that this is a power move and it would set her up for success in life. So I don't see that being far-fetched at all for it to be a negotiation. But I know you kind of made a comment with your eyes about the three obedience rules, laws type of thing. Yeah.

604.574 - 621.724 Cassie

it's, that's like a tall order to just always like, no matter who it is, you're always taking orders from the men in your life. Even if it's, it doesn't matter who, you know, it's like your, your father, your husband, and then your sons. Like it's never, it's never you.

621.944 - 648.009 Danielle

It's never you. Yeah. And your, your worth is surrounded by the importance of men and you are only important if you can give birth to a son if you give birth to a girl that's that's not the same you know it's just i think it's sad and i know it's a it was a cultural thing and but it just i don't i don't like it

648.757 - 666.372 Cassie

Yeah. Well, it reminds me a little bit of – and it's not particularly in this context, but do you remember in Disney's Mulan, which is one of my favorite Disney movies of all time, and Mushu, her – and I'm talking about the OG Mulan, not the remake –

667.413 - 681.543 Danielle

I watched the remake actually kind of recently. Really? Did you like it? Yeah, I did. I haven't seen the original Mulan since I was a kid, though. But I thought that they did a really good job of portraying the story.

Chapter 3: How did the Qing Dynasty influence piracy in China?

846.553 - 863.116 Danielle

Although the number of pirates grew, they lacked the structure and order that would have been needed to make a big impact. This came into play after the outbreak of the Taishan Rebellion in Vietnam, which was a civil war between rival Vietnamese factions vying for control of the region.

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863.596 - 881.525 Danielle

Pirates and mercenaries, which are soldiers who are hired from foreign nations, were recruited from southern China by all sides, gaining weapons, combat experience, and powerful networks in the process. When the war ended, these hardened pirate crews returned to the South China Sea with organized power and ambition.

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882.372 - 900.823 Cassie

To eliminate competition, Cheng Yi, who had built his reputation during the Taishan Rebellion, persuaded fleet leaders to join a confederation, agreeing to support each other in conflicts. By 1807, it is estimated that together, Cheng Yi and Cheng Yi Cao grew the force to around 40,000 to 60,000 pirates, operating 400 ships known as junks.

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905.666 - 922.577 Cassie

It was divided into six fleets, each flying a different flag color and commanded by their own leader. Together, they ran the Red Flag Fleet, the largest in the confederation. While Cheng Yi led with authority and force, Cheng Yi Cao was the strategic mind behind their success.

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923.337 - 930.242 Cassie

The Qing government struggled to challenge their powerful confederation, which operated more like a floating empire than a criminal gang.

930.953 - 936.477 Danielle

I don't know about you, but I was so shocked to learn the 40,000 to 60,000 pirates.

937.098 - 945.604 Cassie

Yeah, that's a ton of people. That's a huge number, but it's also such a large number to control so well.

945.965 - 961.376 Danielle

Right. It's not like you just said. It's not just this criminal gang. It's more of this empire that's being built. And now you have the actual government that's like, hey, wait a second. Hey, can you not do that? That's... It's like, excuse me, we put a ban on this.

962.798 - 982.714 Cassie

But yeah, part-time pirates don't give a crap. And also that's so funny, like part-time piracy. I just have always in my mind been like, okay, if you're a pirate, you're throwing your life away. And you're headed out to the high seas for the rest of your life, you know? And it's just like, no, actually, I do that at night. That's my nighttime job.

Chapter 4: What was the significance of the Taishan Rebellion for pirates?

989.736 - 1015.842 Danielle

I fly into the night under a flag and get my gold and loot. It is really, it's an interesting time. I think that this whole era is very interesting. So in 1807, tragedy struck when Cheng Yi died under unknown circumstances. Some accounts suggest he may have fallen overboard, been caught in a typhoon, or struck by cannon fire.

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1016.783 - 1032.975 Danielle

Though it's unclear how involved Cheng Yi Tsao was, it is clear that she was involved by how she quickly stepped up to assume leadership. She began by securing her authority, gaining the backing of her late husband's most influential commanders to prevent any rivals from challenging her.

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1033.536 - 1041.421 Danielle

She next worked to reinforce her importance within the pirate alliance that she and Cheng Yi had built, ensuring that the fleets remained loyal to her.

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1042.958 - 1062.536 Cassie

In China's patriarchal society, a woman in a position of power was extremely uncommon, especially for Cheng Yi Cao, who was suspected to have grown up lower class. Historians believe she was part of the Tonka people, an ethnic group who traditionally lived on boats, and therefore would have been exposed to piracy throughout her life.

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1063.397 - 1086.659 Cassie

She knew that being a woman in command of tens of thousands of pirates would make her vulnerable. So she solidified her authority by appointing Zheng Bao, Cheng Yi's adopted son, whom she later married, as commander of the Red Flag Fleet, while she oversaw the entire confederation from above. Again, playing chess. Or playing go. Playing chess. Whatever we want to say. Whichever, yeah.

1089.124 - 1115.601 Danielle

Well, she married her stepson? Yeah, essentially. Okay, queen. They're not blood related, so... So anyway, she marries her adopted son, and then she becomes the leader of this massive pirate organization. And under her leadership, the Pirate Confederation became even more organized as she implemented a rigid but effective code of laws.

1116.161 - 1135.073 Danielle

According to surviving records, some of these include, and I have them quoted because I think that these are really important to mention, quote, If any man goes privately on shore, he shall be taken and his ears be perforated in the presence of the whole fleet. Repeating the same act, he shall suffer death.

1135.673 - 1146.298 Cassie

That's a jump. Perforated ears to death. And perforated ears, like to be clear, like that's just like puncturing holes in your ear, right? Sounds like it.

1147.304 - 1147.864 Danielle

I think so.

Chapter 5: How did Cheng Yi Sao maintain control over her pirate confederation?

1198.573 - 1206.957 Danielle

I mean, this is a time people are living in poverty too. So 20% and not death sounds pretty good to me. I would take it.

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1206.977 - 1207.798 Cassie

20% and not dying. Yes.

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1209.014 - 1234.373 Danielle

And then this last one was my favorite of her loss. No person shall debauch at his pleasure captive women taken in the villages and open spaces and brought on board a ship. He must first request the ship's pursuer for permission and then go aside in the ship's hold to use violence against any woman or to wed her without permission shall be punished with death.

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1235.468 - 1238.866 Cassie

All right. Straight to the point. Love it. Don't mess with women.

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1239.898 - 1250.282 Danielle

Yeah, she's a woman leader and she says, nope, no violence towards women. Absolutely not. Or death. No violence under any circumstance unless it's against men.

1250.643 - 1252.783 Cassie

Unless I'm doing it to you also. Yeah.

1255.625 - 1265.869 Danielle

And their methods of punishment were severe, including flogging, dismemberment, shackling limbs in heavy irons before throwing them overboard and decapitation.

1266.589 - 1278.615 Cassie

Walk the plank, if you will. It was a real thing. Give me decapitation. I'd rather have decapitation than the shackling of limbs and being thrown overboard. That is terrifying. Just get to the point. Cut my head off.

1279.035 - 1304.872 Danielle

Yeah, I agree. I already don't love water that much. And unless I'm some kind of Houdini, I'm good with the shackles and the water. However, with all of this stuff, all of these rules and laws that she had in place, this system was well-respected. It maintained order, and because of the fair incentives allowing them to keep a portion of the loot, it created a sense of unity and loyalty.

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