7 Real Life Female Pirates Who Ran Their Ships Like Businesses

When most people hear the word “pirate,” they picture Pirates of the Caribbean or Black Sails. But real-world piracy stretches back centuries and included women who wielded authority on their ships long before they had the right to vote.

Many pirates operated under written contracts known as “articles.” These outlined wage shares, compensation for injury, limits on alcohol, and strict codes of conduct, including punishments for theft and sexual violence. In some ways, pirate ships were regulated workplaces with clear hierarchies and profit-sharing systems. The women below didn’t just fight; they helped enforce discipline, manage crews, and protect the bottom line.

1. Anne Bonny
2. Mary Read
3. Grace O’Malley
4. Jacquotte Delahaye 
5. Neel Cuyper
6. Sayyida al-Hurra
7. Ching Shih

Anne Bonny

When the British Royal Navy attacked John “Calico Jack” Rackham’s ship off the coast of Jamaica, witnesses reported two fierce fighters on deck armed with pistols and cutlasses. The shock came later when the crew learned they were women: Anne Bonny and Mary Read.

Though women were typically barred from pirate ships, Bonny operated as a full member of the crew. She fought alongside the men, intimidated prisoners, and helped maintain order during raids. Rackham’s crew followed a profit-sharing model common to Caribbean pirates, and Bonny was part of that system, risking her life for a share of captured goods.

Accounts suggest she was fearless in battle and quick to challenge cowardice among her crewmates. When much of the crew hid below deck during the Navy’s attack, Bonny reportedly stayed above, fighting. In a world where authority depended on strength and reputation, she proved she could command both.

Mary Read

Mary Read’s life was shaped by reinvention and strategy. Raised as a boy to secure financial support for her family, she later served as a soldier in the Dutch military. After marrying and briefly living openly as a woman, she returned to male dress following her husband’s death and eventually sailed to the West Indies.

On Rackham’s ship, Read was a working pirate likely entitled to a share of plunder under the crew’s articles. She fought fiercely alongside Bonny and earned the respect of hardened sailors. Like any effective officer in a high-risk enterprise, she protected both morale and profits.

When the crew was captured in 1720, both Read and Bonny avoided immediate execution by “pleading the belly” and declaring pregnancy, which delayed hanging under British law. Even in defeat, Read understood how to use the system to her advantage. Historical records indicate she died of a fever in prison following her capture by the British Royal Navy.

Grace O’Malley

Long before the so-called Golden Age of Caribbean piracy, Ireland had its own maritime powerhouse: Grace O’Malley, often called the “Pirate Queen.” Born into a seafaring clan in County Mayo, she grew up immersed in trade, taxation, and naval strategy.

After her father’s death, O’Malley took control of his fleet and expanded operations along Ireland’s western coast. She levied fees on ships passing through her territory and effectively ran a protection-based maritime enterprise. 

Her influence was so significant that she negotiated directly with Queen Elizabeth I in 1593 to secure the release of family members and protect her lands. Over decades, she survived sieges, shifting allegiances, and English expansion. By the time of her death around 1603, she had commanded fleets, fortified castles, and managed a coastal network that blended trade, taxation, and armed enforcement. 

She was buried on the island of Clare off the coast of County Mayo, having outlived two husbands and one son, and having outwitted many of the men who opposed her and her family on land and sea.

Jacquotte Delahaye 

There is no substantial historical evidence that Jacquotte Delahaye existed, but according to Caribbean lore, she ran her ship like she meant it.

Very little documentation about her survives, which has pushed her into semi-legendary territory. Still, stories describe her as a pirate captain who didn’t rely on a husband or partner to justify her place at sea. According to tradition, she turned to sex to work and then was later forced into piracy to support her brother, but then quickly built a reputation for being strictly controlling.

On her ship, she was said to be ruthless, quick to punish disobedience, and unwilling to tolerate disorder, which earned her the nickname “The Lash.” In the 17th-century Caribbean, pirate crews operated under written agreements that divided profits and outlined rules. A captain who couldn’t enforce those rules lost money and authority. If Delahaye commanded a crew, she would have had to manage both.

Her story is often tied to the island of Tortuga in the 1600s, a time when many buccaneers sailed under letters of marque, a government-approved form of piracy. They attacked enemy ships, traded goods like tobacco and ginger, and operated in a gray zone between outlaw and contractor. 

One of the most dramatic legends about her claims Delahaye faked her own death during a battle, adopted a male alias, and later returned to Tortuga. With her striking red hair, she became known as “Back From the Dead Red.”

Whether she was real or embellished over time, she remains known as a captain who understood that fear, discipline, and control were as important to a pirate operation as cannons and cutlasses.

Neel Cuyper

Pirate codes were strict about one thing: no women on board. According to the articles attributed to Bartholomew Roberts—better known as Black Bart—any man who smuggled a woman onto a ship could face death. So when Neel Cuyper’s gender was discovered aboard Captain Ned Low’s vessel, she was tossed ashore near Tortuga.

Tortuga’s port town of Basse-Terre was a pirate marketplace and an entertainment district. Buccaneers came there to sell plunder, restock supplies, gamble, and plan their next capture. 

According to Arne Zuidhoek’s Lady Pirates, Cuyper turned her spoils into capital. Instead of returning to sea, she entered the money trade. She exchanged currencies—trading crowns, pieces-of-eight, doubloons, ducats—and lent money at interest.

As her profits increased, Cuyper (sometimes spelled Cowper) built an elegant villa overlooking the sea and even funded a chapel. While others chased prizes, she managed risk from shore, operating more like a financier than a raider.

But port cities built on plunder were never stable. In 1695, during the Nine Years’ War, Spanish and British forces attacked Tortuga. The invasion devastated the settlement, killing settlers and pirates alike. Cuyper’s inn and her life were lost in the assault.

If accurate, Cuyper’s story is proof that in the business of piracy, controlling the money could be just as powerful as firing the cannons.

Sayyida al-Hurra

In the Strait of Gibraltar, ships moving between the Mediterranean and the Atlantic often looked like harmless trading vessels. Some carried hidden cannons. One of them was commanded by Sayyida al-Hurra.

Long before Caribbean piracy peaked, Barbary corsairs were raiding European ships and coastal towns. Cargo was seized, crews were captured, and prisoners were either ransomed or sold in slave markets across North Africa and the Ottoman world. 

Sayyida al-Hurra was born into a noble family that fled Granada after the fall of Muslim Spain. She rose through elite Moroccan circles and eventually governed Tétouan, a key northern port. From there, she oversaw corsair activity against Spanish and Portuguese targets, possibly as a form of personal revenge. 

Her raids brought in captives, but ransom was the real leverage. European nobles were bargaining assets, and negotiations were formal, as shown in Spanish records from the 1540s that describe talks with al-Hurra after successful attacks near Gibraltar. Over the years, she developed a reputation as a prudent negotiator and became a central figure in discussions over European captives held along the Barbary Coast by other pirates. She ruled for decades before being removed in a palace coup in 1542.

In one of the most contested waterways in the world, al-Hurra treated piracy as a form of strategy and governance. 

Ching Shih

While the Caribbean had its famous pirates and the Mediterranean its corsairs, the South China Sea had Ching Shih.

Born in 1775 near Canton, she grew up among the Tanka people, a marginalized community who lived and worked on boats and refused foot-binding. She began working in the floating brothels of Canton’s “flower boats,” but her life changed when the pirate leader Zheng Yi married her. 

Zheng Yi had been building alliances among rival Cantonese pirate fleets. With family ties, reputation, and force, he united hundreds of ships into what became known as the Red Flag Fleet. When he died, Ching Shih moved quickly. She secured the backing of key captains, strengthened her alliance with her stepson Cheung Po Tsai—whom she later married—and consolidated control of the confederation.

At its height, the pirate alliance counted hundreds of ships and tens of thousands of sailors, outnumbering the Imperial Chinese Navy. By 1810, Ching Shih personally commanded dozens of ships and more than a thousand pirates. The fleet itself was divided into color-coded squadrons, with the Red Flag Fleet at its head.

Ching Shih enforced a strict code of conduct. Unauthorized orders or disobedience meant execution. All plunder had to be registered before distribution. The pirate who seized goods received a fixed percentage; the rest went into a common fund used to supply the fleet. Theft from that fund brought violent consequences. Gold and silver were centralized and redistributed to sustain weaker ships. She also imposed rules regarding captives. Rape was punishable by death. Pirates who took wives from among captives were required to remain faithful and treat them properly. 

Unlike most pirates, Ching Shih did not die in battle or on the gallows. She built a maritime confederation, enforced one of the strictest pirate codes in history, negotiated her own surrender, retired on her own terms, built a gambling house, and lived until the age of 69.