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Title : Bad-ass Lady Pirates
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A woman dressed as a pirate with a parrot on her shoulder at the King Mango Strut, annual satire parade.

If you thought marauding was a man’s job, think again! In the age of pirates and epic high-seas plundering and pillaging, a few tough, bad-ass women joined the ranks of these naughty nautical criminals to prove that women can do more than swab the deck…they can captain a ship, steal treasures, fight with swords and cutlasses, and in most cases, pay the ultimate price for their crimes. Here are some of history’s most bad-ass lady pirates.

This artist rendering of Anne Bonny is far from historically accurate. Bonny most often wore men's clothing and kept her gender a secret.

Anne Bonny

A fiery redhead, Anne Bonny, who was born sometime around 1700, was always known for her temper. According to legend, she was only 13 years old when she stabbed a servant girl with a knife. The beautiful daughter of a Caribbean plantation owner, Anne went behind her father’s back to marry a petty pirate, James Bonny, who was a gold-digger looking to claim his new father-in-law’s land. Anne’s father was furious and disowned her. She settled the score by burning down his plantation house. Anne and her husband went to the Bahamas and there, Anne met John Rackham, also known as Calico Jack. She and Calico Jack became lovers and she divorced her first husband and sailed away with Calico Jack aboard his pirate ship. For most of the time, she disguised herself as a man, worked aboard the ship and fought alongside the other pirates. Anne Bonny’s name was listed with other wanted pirates in a “Wanted” ad in the newspaper. When she was captured and sentenced for piracy, she asked for mercy, claiming to be pregnant. She was jailed, and her execution date was delayed until after she gave birth, but her story fades away at this point. There are no records of her execution or that she gave birth while in prison. Many people speculate that her estranged father arranged for her quiet release.

Mary Read

Mary Read, who was born in 1685, was a contemporary of Anne Bonny’s. In fact, the two women were friends who sailed with Calico Jack together. They were arrested and imprisoned together, as well. But Mary Read’s story starts several years before Anne Bonny’s. Mary spent most of her childhood pretending to be a boy. Her mother had married a sailor who fathered a son with her before dying at sea. Shortly after, Mary’s mother had an affair and became pregnant with Mary. Then the legitimate son died. Mary’s mother began dressing Mary as a boy and passed her off as her legitimate son in order to continue to receive financial support from her late husband’s family. It worked and Mary was raised as a boy well into her teens. She even took odd jobs, while pretending to be a boy. She joined the British military and proved herself to be a capable soldier. After she was married and widowed, she embarked for the West Indies. Her ship was captured by pirates and Mary decided to join them. She signed on with Calico Jack and Anne Bonny in 1720, still pretending to be a man. She only revealed her gender to Bonny, who was also disguised as a man. In all likelihood, Calico Jack was sleeping with both women, because, upon their capture, Mary Read, too, claimed to be pregnant. Unlike Bonny, there are records of Mary Read’s death. She and her unborn child died in prison due to a fever.

Cheng I Sao

Cheng I Sao was a prostitute before becoming a pirate. Unlike Anne Bonny and Mary Read, Cheng I Sao did captain her own ships and even commanded a fleet of 300 Chinese junks with a combined crew of nearly 40,000 pirates that terrorized the China Seas in the early 1800s. Her Red Flag Fleet was a formidable and well-organized pirating machine. Cheng I Sao terrorized several coastal villages. In one such village, Sanshan, Cheng I Sao and her men captured and beheaded 80 of the village’s men and abducted the women and children, who were then sold into slavery. Other villages were luckier. They were only forced to pay huge taxes to the pirates. Cheng I Sao led her fleet into battle after battle on the open seas, against the Chinese government, the East India Company and bounty hunters from England and Portugal. During one such battle, Cheng I Sao overtook all of the military’s ships and the Chinese government was forced to fight from fishing boats. In a series of fights between 1809 and 1810, Cheng I Sao’s Red Flag Fleet was on the brink of defeat, therefore she surrendered and accepted an amnesty agreement for herself and the majority of her pirates.

Rachel Well

Rachel Well has the distinction of being the first American-born female pirate and the last woman to be hanged in Massachusetts. Born in 1760 in Pennsylvania, Rachel Well hated farm life and was drawn to the sea. As a young woman, she married a sailor, George Well and moved to Boston. Rachel Well took a job as a serving girl while her husband was at sea. One day, he returned with a group of five other sailors and their lovers. George Well borrowed a schooner and suggested they all take to the seas to become pirates. The schooner would anchor off the New Hampshire coast during stormy weather and Rachel Well would stand on the deck yelling for help. When a passing boat stopped to offer assistance, the rest of the pirates would overtake their ship, kill everyone aboard, and steal their valuables. Rachel Well was not arrested on the high seas. She was arrested back in Boston when she attacked a woman to steal the bonnet she was wearing. But her pirating way had earned her a price on her head. She was hanged on October 8, 1789.

Awilda, a Viking pirate

Awilda

Awilda was a Scandinavian princess-turned-pirate in the 5th century. According to legend, Awilda’s father had arranged for her to marry the crown prince of Denmark, but Awilda was not thrilled with the match. So she gathered a group of her female friends, dressed as sailors and hijacked a ship. The women came upon a pirate ship that had just lost its captain and the pirates asked Awilda to become their new captain. Awilda and her crew of pirates and lady sailors continued on with their pirating ways. Meanwhile, the King of Denmark sent his son…the crown prince that Awilda refused to married…to stop the pirates. The prince’s naval ship overtook the pirate ship and a hand-to-hand battle ensued. The crown prince and his men were victorious and Awilda found herself impressed with the courage and strength that the crown prince had displayed. She revealed to him her true identity and the two were immediately married aboard the pirate ship. They served as the King and Queen of Denmark thereafter.

Charlotte de Berry

Born in England around 1636, Charlotte de Berry was a teenager when she married a sailor against her parents’ wishes. She disguised herself as a man and joined him aboard his ship, where she worked and fought alongside him. An officer aboard the ship discovered Charlotte’s true gender and made advances toward her. When those weren’t successful, the officer devised a plan to get Charlotte’s husband out of the picture. He accused the husband of plotting a mutiny and had him flogged to death. Charlotte still refused the officer’s proposals. When they docked and went ashore, Charlotte murdered the officer. She began dressing like a woman again and took a job at a tavern. There a merchant ship captain saw her and became fascinated by her. Again, Charlotte rejected his advanced so he kidnapped her and forced her to accompany him on his voyage to Africa. This captain was a cruel, sadistic man who repeatedly raped Charlotte. She slowly gained the trust and respect of the crew and convinced them to mutiny with her. She beheaded the evil captain and took control of the vessel herself. Charlotte and her crew turned to piracy and attacked a Dutch ship. Charlotte de Berry was wounded in battle and fell overboard. Her loyal crew blew up their own ship to avoid capture.

Grace O’Malley

An Irish pirate, Grace O’Malley was a royal who was drawn to the sea. She raided other ships for their valuables as a way to boost her own family’s wealth and influence, albeit through terror tactics. In 1576, legend says, O’Malley sailed to Howth Castle for a visit with the Lord and Lady of the manor. When she arrived, the gates to the castle were closed to visitors and the servants explained that Lord Howth was away. O’Malley was angered and insulted to be turned away at the door so she kidnapped the young grandson of Lord Howth, his heir Christopher St. Lawrence, the 10th Baron of Howth. She agreed to release the boy on the condition that Howth Castle’s doors would always be open for unexpected guests and that there would always be a place set at the table for visitors. To this day, the descendants of Lord Howth still honor this agreement.