You're Dead to Me: Zheng Yi Sao
Host: Greg Jenner
Guests: Comedians and script performers (Malian Reese, Richard David Kane)
Episode Air Date: December 22, 2025
Episode Overview
This episode dives into the swashbuckling life and legacy of Zheng Yi Sao (also known as Ching Shih), the formidable pirate queen who dominated the South China Sea in the early 19th century. Host Greg Jenner, with his signature blend of humor and historical insight, explores how Zheng Yi Sao rose from humble origins to command a massive pirate confederation, outwitting the Qing Empire and foreign navies alike—all with impressive management skills, ruthless discipline, and a flair for innovative piracy.
Key Discussion Points & Insights
Zheng Yi Sao’s Origins (01:11–02:11)
- Born Shi Yang around 1775 in Guangdong, China. She grew up poor, in a turbulent region where fishing folk often moonlighted as part-time pirates.
- She worked on a floating brothel, where she supplemented her income by selling gossip and secrets from influential clients.
Quote:
"She was quite poor and lived in a part of China called Guangdong, right by the sea... Fishermen and boatmen in her neighbourhood often had to make up the extra money by getting second jobs as part time pirates."
— Greg Jenner (01:31)
Marriage & Rise to Power (02:20–03:37)
- Married notorious pirate Zheng Yi, hence the name Zheng Yi Sao (“wife of Zheng Yi”). Despite Qing laws barring women from official roles, she quickly asserted herself as a leader, primarily due to her “incredible admin skills.”
Memorable Bit:
- The hosts joke about the most fearsome pirate weapon being not a cutlass or rifle, but “a spreadsheet.” (03:29–03:34)
Building a Pirate Empire (03:37–05:06)
- United disparate pirate groups and smugglers into a single confederation of around 70,000 pirates.
- Organized the fleet into six color-coded squadrons for efficiency, in a tongue-in-cheek nod to Power Rangers.
Quote:
"At one point, they had a workforce of 70,000 pirates. Imagine the queue in the canteen at lunchtime!"
— Greg Jenner (03:37)
Tragedy Sets the Stage for Leadership (05:06–06:34)
- Zheng Yi dies in 1807 (explosively, as per pirate tradition).
- Zheng Yi Sao consolidates her power, appoints her adopted son-turned-husband Cheung Pao as squadron head, and cements her hold over the pirate fleet.
Funny Exchange:
E: "Mrs. Boss, the bad news is your husband is dead."
C: "The love of my life, my pookie. Boo. This is the worst day ever."
E: "Yeah, I know. The good news is it looked really cool and piratey." (05:23–05:39)
Pirate Management & Discipline (06:34–07:40)
- Strict code: death for disobedience or stealing, loss of ears for truancy—offset by perks like health care and pensions.
Memorable Parody:
- "I'm Zheng Yi Sao, CEO of Pirates. For the small fee of your absolute loyalty, I offer competitive pay, health care, and a pension fund. Your ears and head could be at risk if you do not keep up loyalty to your boss."
— C (07:14–07:29)
Controlling the Salt Trade (07:40–08:45)
- Targeted the valuable government-run salt trade, commandeering almost all of it and leaving the Qing government with just four ships.
- Expanded piracy to merchant vessels and innovated by selling “protection certificates” that allowed merchants safe passage for a fee.
Quote:
"Why go to the trouble of me stealing from you when you can simply give me the money? It's just good business."
— C (09:34–09:39)
Military Superiority (09:52–10:59)
- By 1805, her fleet was three times the size of the Qing navy, equipped with powerful eight-foot Jingao cannons.
- Fearsome tactics included polearms and intimidation, causing cities like Canton to panic at the mere announcement of her intentions.
Comedic Moment:
E (as Cheung Pao): “Dear people of Canton, just a little note to say that we would simply love to invade you with our massive guns, so you might want to think about surrendering. No worries. If not, love and kisses.” (10:59–11:11)
Government Response & Pirate Retirement (11:16–12:54)
- Qing government, overwhelmed, enlists help of Portuguese and British navies.
- Some Qing sailors sabotaged their own ships rather than fight Zheng Yi Sao.
- Eventually, government offers her a deal: retire in luxury (“Please, pack it in, we'll give you loads of money”). She accepts and becomes extraordinarily wealthy.
Memorable Line:
"Pirate's Haven Retirement. Because if you do it on a big enough scale, crime does pay."
— C (12:54)
Aftermath & Legacy (13:03–13:40)
- Little is known about her post-piracy years; she may have run a gambling house.
- Dies in 1844, one of history’s richest, most successful pirates.
Notable Quotes & Memorable Moments
-
“The one thing you need to be a really good pirate isn’t singing shanties or keeping a parrot. It’s actually management skills and paperwork.”
— Greg Jenner (03:11) -
"For the small fee of your absolute loyalty, I offer competitive pay, health care, and a pension fund. Your ears and head could be at risk if you do not keep up loyalty to your boss."
— C (07:14) -
“Why go to the trouble of me stealing from you when you can simply give me the money? It's just good business.”
— C (09:39) -
"Because if you do it on a big enough scale, crime does pay."
— C (12:54)
Important Segment Timestamps
- 01:11–02:11 Zheng Yi Sao’s early life and entry into piracy
- 03:37–05:06 Establishing the pirate confederacy
- 05:06–06:34 After Zheng Yi’s death—Zheng Yi Sao’s consolidation of power
- 06:34–07:40 Her management methods (violent and effective)
- 07:40–08:45 Cornering the salt trade and white-collar piracy
- 09:52–10:59 Military might and infamous weaponry
- 11:16–12:54 Retirement offer from Qing government—crime pays
- 13:03–13:40 Legacy and closing thoughts
Quiz Recap (14:06–14:27)
-
Q1: How were Zheng Yi Sao’s pirate squadrons organized?
A: By color -
Q2: How could merchants avoid pirate attacks?
A: Pay for a protection certificate -
Q3: Name of the eight-foot gun?
A: Jingao
Episode Tone and Language
Lively and comedic; Greg Jenner’s narration is peppered with historical insight and irreverent banter from the cast. Roleplay skits and breaking of the fourth wall are used throughout, making the historical narrative accessible and entertaining.
Summary Assessment
This episode of You’re Dead to Me transforms the fearsome story of Zheng Yi Sao into a relatable saga of workplace skills, ambition, and age-old piracy—with a wink and a nudge toward the modern office. It balances historical detail with irreverent comedy, painting the “Pirate Queen of Admin” as both ruthless and remarkably business-savvy—a template for unlikely, but highly effective, female leadership in a time and place that rarely allowed it.
Interested in more detail? Greg recommends the expert episode featuring Dr. Ron Poe for adult listeners.