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Five Female Pirates from the Golden Age of Piracy

Updated on September 6, 2017
S R Gibby-Brown profile image

Sckylar is a graduate from Arizona State University where she studied English literature, creative writing, film, and history.

Pirates are as old as the invention of the first canoe. But the image of the pirate that we all know and love- the black eye patches, the feathered hats, and the jolly Roger flags- comes from the Golden Age of Piracy. This was a time when pirates flourished from the early 16th century to the end of the 19th century.

Despite the sailor’s superstition that women were bad luck aboard a ship, many women ruled the seas during the Golden Age of Piracy. Pirate women from all corners of the world defied the conventions of their countries and found freedom and adventure as swashbuckling pirates on the high seas.

Cheng I Sao was a brutal, feared, and successful pirate who led an entire armada of ships.
Cheng I Sao was a brutal, feared, and successful pirate who led an entire armada of ships.

Cheng I Sao

Many pirate scholars believe Cheng I Sao to be the most successful female pirate to ever rule a fleet of ships. Madame Cheng, also known as Ching Shih, was born as Shi Xiang Gu in China. She left her original career as a prostitute when she was captured by pirates around the turn of the 19th century. In 1801 Cheng married the pirate Zheng Yi (aka, Cheng I). Together, the husband and wife team terrorized China during the beginning of the 19th century. Their armada, the Red Flag Fleet, comprised of hundreds of ships and 50,000 men. The fleet ravaged China, preying on fishing vessels, supply ships, and Southern China’s coastal villages.

On November 16, 1807 Cheng Yi “accidentally” drowned when he fell overboard his ship. Left as his widow, Madame Cheng took over his fleet. Already feared and respected by her late husband’s company, Cheng became a successful leader. Cheng’s fleet plundered across Southeast Asia and grew to 80,000 crew members. To control so many pirates, Cheng created her own government, laws, and taxes. Among her laws, rape was punishable by beheading and deserters had their ears cut off.

When the Chinese navy was sent to stop Cheng, she defeated them. The government offered her amnesty, but Cheng refused to accept it without conditions. She secured pensions for her crew and was allowed to retire from piracy with all of her pirate-earned riches. Cheng lived out the rest of her days in China and ran a gambling house until she died in her sleep in 1844 at the age of 69.

Anne Bonny and her pirate pal Mary Read. While Anne dressed for her femininity, Mary was known to dress as a man, with few knowing her secret that she was actually female.
Anne Bonny and her pirate pal Mary Read. While Anne dressed for her femininity, Mary was known to dress as a man, with few knowing her secret that she was actually female.

Anne Bonny

Born Anne Cormac in 1702 in Cork, Ireland, Anne was the daughter of a servant woman named Mary Brennan and affluent lawyer named William Cormac. In an effort to hide his affair, Cormac would have Anne dress as a boy and pose as his law clerk. When his affair was discovered, Cormac left his wife and moved to London with Anne and her mother where Cormac became a merchant.

Anne’s mother died when Anne was twelve. Around that same time, Anne’s temper began to grow as red as her hair. At age thirteen Anne stabbed a servant girl with a table knife. Soon later she married a small-time pirate names James Bonny. Cormac disowned his daughter for this and in retaliation Anne burnt down Cormac’s plantation. Anne and Bonny moved to New Providence Island in the Bahamas, which was known as a sanctuary for pirates. Here, Anne met John “Calico Jack” Rackham, the captain of the pirate ship Revenge. Anne fell in love with the successful pirate and abandoned Bonny to become Rackham’s mistress.

On board Revenge, Anne found that she was a natural pirate. Quick with a pistol, a shot of rum, and with her temper, Anne gained a reputation for herself and became Rackham’s first mate. In October of 1720, Anne’s ship was attacked by a King’s ship. Most of the crew was too drunk to fight, only Anne and fellow female pirate Mary Read attempted to fight off the King’s navy. Despite their efforts, the ship was captured. Anne blamed Rackham for the capture. Her last words to him were recorded in prison, “Sorry to see you there, but if you’d fought like a man, you would not have been hang’d like a dog.”

Rackham and his company were hung as pirates, however, Anne and Read were given a stay of execution when it was found they were both pregnant. The end of Anne’s life is left a mystery. There is no record of her execution, nor of a pardon. It is rumored that Anne’s father paid for her ransom, that she returned to her husband Bonny, or perhaps she escaped and returned to piracy under a new identity.

While modern artists depict Grace with long, red hair, Grace actually wore her hair cut short. When she was 12 her father refused to let her sail because her long hair would be caught in the mast. So, Grace cut her hair short and kept it that way.
While modern artists depict Grace with long, red hair, Grace actually wore her hair cut short. When she was 12 her father refused to let her sail because her long hair would be caught in the mast. So, Grace cut her hair short and kept it that way.

Grace O'Malley

Born into nobility around 1530, Grace’s family lorded over the coastlines of Western Ireland. Grace’s father owned a shipping company involved with international trade. As a child, Grace was educated on her father’s business and she longed to join his fleet. Her father refused, however, and married her to a man named Donal O’Flaherty in 1546. O’Flaherty died in 1565 and Grace returned to her father’s estate where she took shipwrecked sailor, Hugh de Lacy, as her lover. Her affair was short lived as Lacy was soon murdered by the MacMahons of Ballyvoy. Grace sought revenge and attacked the MacMahon castle of Doona where she killed her lover’s murderers and took their castle for her own. The attack earned her the nickname of Dark Lady of Doona.

In the 1560s Grace inherited her father’s company and took command over 20 fleet ships. She raided ships of the English and Spanish and became legendary in Irish history for her captures and escapes. One legend claims that she fought battle at sea only a day after giving birth. Another claims that she kidnapped the heir to Howth Castle in Dublin when Lord Howth refused her at his dinner table. His heir was only returned once Howth swore to Grace that he would always leave his gates open to any unexpected visitors.

Grace was captured by the authorities several times, at one point doing 18 months behind bars, but she always continued her raids after her release. In the early 1590s the British authorities impounded her fleet and Grace, at that point an aged pirate in her 60s, was forced to appeal directly to Queen Elizabeth. It is said that the two conversed in Latin during a royal audience in London. Grace convinced the Queen to return her ships and her son who had been captured, promising that she would retire from her pirating ways. The Queen agreed, but Grace did not uphold her promise. She continued pirating until her death in 1603.

Rachel Wall was one of the first and only female-American pirates.
Rachel Wall was one of the first and only female-American pirates.

Rachel Wall

Rachel Schmidt was born in the Province of Pennsylvania around 1760. As a teenager, Rachel ran away from home and married a fisherman named George Wall. Despite their effort to make a living, the couple was very poor, forcing Rachel to get creative in her career choices. In 1781, Rachel obtained a small boat and teamed up with a handful of lowlife sailors. After storms, Rachel and her crew would sail around the coast of New Hampshire. Rachel would stand on the deck and scream for help, pretending that their ship had been damaged in the storm. When a passing ship would come to help, Rachel and her team would board the boat, murder the sailors, and steal their goods. In one year, the crew was successful in boarding 12 boats, stealing $6,000 in cash, and murdering 24 sailors.

But karma made for sweet revenge. In 1782, Rachel’s ship was caught in a real storm which destroyed her boat and killed her husband George. After his death, Rachel continued her career of stealing and killing on land. She was finally caught in 1789 in Boston for attacking and robbing a woman there. She was sent to prison where she wrote a confession of her sins to sway the government away from a harsh sentence. She admitted to “Sabbath-breaking, stealing, lying, disobedience to parents, and almost every other sin a person could commit, except murder.” Unfortunately for Rachel, the authorities were not convinced and she was sentenced to death by hanging. Her last words were recorded, “Into the hands of the Almighty God I commit my soul, relying on his mercy… and die an unworthy member of the Presbyterian Church, in the 29th year of my age.” She was one of the first and only American-born female pirates and the last women to ever be hung in Massachusetts.

Back from the dead Red turned to piracy in order to provide for herself and her brother.
Back from the dead Red turned to piracy in order to provide for herself and her brother.

Jacquotte Delahaye

The daughter of a French father and a Haitian mother, Jacquotte was born in Saint-Dominique, a French-Haitian colony on the Caribbean. Her mother died in childbirth and her father was murdered leaving Jacquotte an orphan and the only care giver to her mentally handicapped brother. To provide for herself and her brother, Jacquotte resorted to stealing and eventually to piracy. When government officials began to close in on her, Jacquotte faked her death and took on a male alias for many years. When she returned, she became known as “back from the dead red” because of her brilliant red hair.

Much that is known about Jacquotte is legend and dates are not exact. However, we do know that her piracy reigned the seas in the mid-17th century. She was leader to a company of hundreds of pirates and in 1665 she took over a small Caribbean island and called it a “freebooter republic.” A few years later, she died defending it.

© 2017 Sckylar Gibby-Brown

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