StMU Research Scholars

From Teahouses to Trading Ports: The Scallywag Empress Ching Shih

Winner of the Spring 2019 StMU History Media Award for

The Article with the Best Introduction

The boiling clouds roll back, the tumultuous sky reduced to a slow simmer. A terrible maelstrom has just passed, wreaking havoc on this small fleet of ships. Shouting commands and curses, men in patchwork clothes run back and forth on the deck of a Chinese junk, hoisting its massive red sails to check for tears. Amidst the chaos, a crew member leans over the side, his eyes growing wide with shock and his words quivering at his lips. Crying out, he finally shouts the reason for his devastation.

Chuánzhǎng sǐle! The captain is dead!1

At this exclamation, the deck falls silent. The sails flap listlessly in the wind, accompanied only by the constant rainfall and the water that rocks the ship. Nobody says a word, the only break in the tableau being a crew member or two removing their hat in respect. Finally, from the cabin below the helm, a woman emerges into the gloom with a young man at her side. She has heard the news. Slowly, she makes her way across the ship to peer down into the sea below. Sure enough, she immediately spies her husband’s body floating like a piece of driftwood among the waves. However, instead of retreating to the cabin to mourn him, as was expected of a woman at that time, she turns to face the rest of the crew. A few high-ranking members have already convened to nominate a successor, but the woman waves her hand dismissively. There is no need for schemes, she says, for she will step up to fulfill the role. The young man beside her eagerly nods his head, immediately vouching for her. In stunned silence and with a perplexed curiosity, all eyes are on her. Who is this woman to assume command over an entire fleet of hardened pirates?2

Her official name was Cheng I Sao. Before that, however, she was Ching Shih.3


Ching Shih was born in 1775 to a poor family in Guangzhou, China, where she would grow up to work as a prostitute in a seedy brothel before her capture in 1801 by the infamous pirate captain Cheng I. He intended to exploit her in the same manner that he found her, but fell in love with her almost immediately upon bringing her back to his ship. From the moment she entered the scene, Shih exuded an aura of utmost poise and shrewd confidence. Only a few days after Shih nearly maimed the captain in a retaliatory assault, they were wed. Before the nuptials, though, Shih insisted she would only avow herself to him on one condition—that she would rule over his six fleets beside him. He agreed, and some time after, Shih bore him two sons. The couple later kidnapped and adopted an additional son named Chang Po Tsai during one of their many raids on small villages.4 For years, the family terrorized the southern coast of China—especially the area around the Pearl River Delta—until one fateful day in 1807. A typhoon unlike any other ravaged “the Red Flags,” their principal fleet. During the storm, Cheng I was swept overboard and later perished in the sea, leaving the crew without a captain. It was at this time that Shih stepped up to the plate and volunteered herself as leader, and, with her adopted son and lover vouching for her, it was generally agreed upon that he would become the commander of the Red Flags. Within a few years, Shih gathered around twelve hundred war junks and tens of thousands of buccaneers under her authority.5

Guangzhou in the Pearl River Delta (2007) | Courtesy of Wikimedia Commons

During this period, the Emperor of China heard many reports from emissaries about the issue of piracy in the Middle Kingdom, including those of the dreaded Cheng I and his wife, the “Dragon Lady”; but, with so much on his agenda, he could barely spare any attention to these ragtag rapscallions aside from sending ships to investigate and engage in small skirmishes in harbors and up the river. Despite the Emperor’s lackadaisical attitude towards the situation, underestimating the Dragon Lady would soon prove a fatal mistake.6

Now a captain, Ching Shih proved herself an able leader through her management of finances and her establishment of a code of ethics. Aside from the standard fare of punishment for setting ashore without leave, it contained such unusual stipulations as forbidding the rape of female captives on pain of death, as well as requiring villagers to be paid compensation for certain suppliesPerhaps owing to her time spent in poverty as a prostitute, it seemed she held a tender spot in her heart for the most vulnerable among the populationNevertheless, she refused to return to a life of destitution and was reported to have had no qualms about raiding as many villages as her fleets could manage, as well as ambushing imperial junks and charging protection for merchant ships hauling salt and opium. All passed relatively unnoticed, but when an important government official was killed in an attack, the Emperor finally took notice. He ordered the navy to track the “Dragon Lady” down to Macau, where a vicious standoff left the imperial forces defeated and the entire Pearl River up to Guangzhou available for the taking. Unfortunately, all this pillaging left her Red Flag fleet in desperate need of repairs and her funds in need of replenishing, so she retreated to the island of Lantau near Hong Kong to recuperate—the island where a great battle awaited her.7


Lantau Island | Courtesy of Wikimedia Commons

It’s all quiet on the coastal front, a little too quiet. A northerly wind pushes onto the shore, the leaves in the trees rustling gently on the island of Lantau. Ching Shih sits at her desk, a portrait of sheer consternation, the wrinkles in her forehead having deepened over the course of the last few days. Reviewing her finances for what seems like the thousandth time, she sets the ink down and heads topside. It is only when she arrives on deck that she sees them. Imperial junks and Portuguese man o’ wars emerge from the morning mist like ghosts, all armed to the teeth and speedy to boot. Of course, she has been expecting a showdown like this for quite a while. She just wishes it had been a little later, as most of her flagship fleet is beached and out of use. Still, she shrugs and mutters a prayer to her deceased husband for protection and guidance. Now that she thinks about it, a shift in the breeze would do nicely at this point.8

Captain Ching Shih stares death in the face, as she has done many times in her life. This time, though, she does it with a smile. This time, she will win.9


Many days passed through fire and cannon shot in November of 1809, and the air turned black with smoke as volleys passed between the Chinese and foreign navies and Ching Shih’s meager forces. Only a few of her junks were in any sort of fighting shape, and they possessed next to nothing in capability compared to the juggernaut before them. To add salt to the wound, her most intimidating fighting power, the Black Flag fleet, had deserted Shih, even attacking the Red Flag fleet at some points. On top of that, the Red Flag fleet had been damaged in previous battles with the Chinese navy. In order to have at least a sliver of hope of victory, the remaining pirates cast flaming rafts in the water towards the enemy lines, aiming to gain the upper hand by burning their way to triumph, but the wind merely pushed them back towards Shih and her men. At last, when all hope seemed lost, a fortuitous change in the wind caused a flaming raft to smash straight into the midst of the blockade, sending a ship up in smoke. Gaining the upper hand, Shih and the pirates still loyal to her were finally able to get the most seaworthy junks on the waves to wage a great last stand, demolishing many of the enemy’s ships and pushing their way back into the Pearl River.10

A famous painting in the Hong Kong Maritime Museum depicting the battle between Knaves and the Imperial Navy | Courtesy of Wikimedia Commons

The Emperor’s emissaries pressured her to surrender, but she continued to send her fleet to attack and raid around the Pearl River. However, after having balancing more conflicts with the Chinese government and the Black Flag fleet, Ching Shih realized that she must accept the offers of pardon. Although she agreed to surrender, being a woman of an immensely strategic disposition, she insisted that all terms be in her favor. Should the Emperor’s emissaries have balked and refused, she would simply resume her pillaging. After much negotiation and more than a fair amount of threats, legitimate and bluffed on both sides, the Chinese government was out of options and unable to refuse the famed Dragon Lady. They agreed to allow her and her crew to surrender with amnesty from the original executions they were sentenced to, in addition to all the wealth that Shih amassed since the day she married Cheng I in 1801.​ Retiring at the age of thirty-five, Shih inevitably returned to the brothel she wished she’d never see again—this time, however, as a very rich and successful manager, never to live in poverty again until she passed away at the age of sixty-nine.11


Resting by the water, an aging Ching Shih is reminded of the dauntless years of her youth. In small ripples on the surfaceshe sees distorted reflections of her beloved husband, the battles she fought, and the conquest of the waves which will forever be attributed to her name. No longer wielding a cutlass or beheading unruly subordinates, Shih has found peace at long last.12

  1. Pirates Through the Ages Reference Library, 2011, s.v.Pirate Surrender Document.
  2. Pirates Through the Ages Reference Library, 2011, s.v. “Pirate Surrender Document.”
  3. Pirates Through the Ages Reference Library, 2011, s.v. “Sao, Cheng I.”
  4. Pirates Through the Ages Reference Library, 2011, s.v. “Sao, Cheng I.”
  5. Pirates Through the Ages Reference Library, 2011, s.v. “Pirate Surrender Document.”
  6. Alfred S. Bradford, Flying the Black Flag (Westport: Praeger Publishers, 2007), 144-148.
  7. Cheng I Sao – Pirate Queen, video file, 10:50, YouTube, posted 2013,
  8. Cheng I Sao – Pirate Queen, video file, 10:50, YouTube, posted 2013,
  9. Cheng I Sao – Pirate Queen, video file, 10:50, YouTube, posted 2013,
  10. Cheng I Sao – Pirate Queen, video file, 10:50, YouTube, posted 2013,
  11. Ann Shen, Bad Girls Throughout History: 100 Remarkable Women Who Changed the World (San Francisco: Chronicle Books, 2016), 45.
  12. Ann Shen, Bad Girls Throughout History: 100 Remarkable Women Who Changed the World (San Francisco: Chronicle Books, 2016), 45.

67 Responses

  1. The intelligence and ingenuity of Ching Shih, especially how she was able to operate up and down the Pearl River Delta and successfully ensure her and her crew a favorable pardon after the tides began to turn against her. Being able to foresee a crushing defeat while you still have the power to stop it takes a high level of intelligence and wit to make sure things ended up favorably for them.

  2. The award for best introduction was well deserved. The entire article was well written and had a smooth flow to it. I am curious how the author came to find out about Chen Shih because so often stories of incredible, resilient and multifaceted women are lost in history. In China especially, being a woman can harbor stigma and prejudice. Chen Shih had a remarkable and unique life and it was fascinating to learn about a female pirate.

  3. This was overall a very impressive article. Not only was the story very detailed, but it was also very unique and very refreshing to read. What is truly fascinating is to see when these events took place, because, given the time period and setting, you would not expect this type of story to happen. The fact that Chen Shih was able to do all that she did is truly interesting.

  4. Learning about Captain Ching Shih was really interesting! I had no idea who she was, which is really disappointing considering who she was as an individual. She went from a prostitute to a captain of pirates, which probably doesn’t even cover how strong she was, especially since she was a woman and it’s not particularly an easy time to be a woman. It was an amazing article!

  5. A very well written article and an incredible read. I find it interesting that given Chinese culture and society at the time, Chen Shih was able to seize command of a large pirate fleet. What is even more impressive is that she wasn’t executed or killed in action but died in peace, a fate few pirates managed to achieve. A very interesting look at an Asian pirate.

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