History is full of stories of pirates, evil men who preyed on unarmed merchant and fishing vessels all along the Atlantic coast.  The politicians and businessmen of the colonial period often encouraged their despicable deeds, causing the line between honest seaman and pirate to be a fuzzy one.  But, the fuzziest line of all was drawn in the case of two pirates who sailed under the black flag of “Calico Jack” Rackham.  The question was not of what side of the law they sailed under—there was no doubt they were pirates— the question was that of their gender.  The two in question are Anne Bonny and Mary Read.

Blazing red hair and a fiery temperament to match is how history and lore remembers Anne Bonny.  Her father, an Irish lawyer who had a wandering eye, is said to have spoiled his little girl rotten.  Anne Cormac was born in County Cork, Ireland at the turn of the sixteenth century.  She was the illegitimate daughter of William Cormac and his house servant, Mary Brennan.  Their story runs like a sixteenth century soap opera.

After Cormac’s wife discovered the affair he sailed with his lover and baby to America.  They settled near Charles Town in the Carolina colony, which is now Charleston, South Carolina. He prospered there as a wealthy plantation owner. 

Anne was a young teen when her mother died of a fever.  William turned the management of the plantation over to his daughter, a position she didn’t handle well because of her short temper. Anne is said to have stabbed to death a servant who made her angry.  Nor did Mistress Cormac deal kindly with men who tried to woo her. Legend tells us she beat a man nearly to death with a chair when he made unwanted advances.

Anne was still in her teens when she met James Bonny. Fed up with the genteel life of the colonial south, she married this man who was known to dabble in pirating.  Her father was furious, and to make sure the pirate would not inherit his wealth he disowned his daughter.  Mysteriously the plantation home of William Cormac burned to the ground soon after. Coincidently the Bonnys chose this time to move to New Providence, Jamaica.

In this pirate’s hotbed, James took a job working for the government as a snitch.  Evidently Anne found his work distasteful and in rebellion she began “hanging out” with the very the pirates who her husband was helping to bring to justice.   She was especially attracted to “Calico Jack” Rackham who earned his nickname from the fancy clothes he wore; he earned his reputation by pirating up and down the Atlantic.  Anne and Jack became lovers and Jack offered to buy her divorce from Bonny. Bonny refused the offer, and took out a restraining order to keep Anne from seeing her new lover.  His attempt was futile because the rebellious lady promptly ran off to sea with Rackham.

Anne became pregnant and gave birth to Jack’s child in Cuba.  It is believed they left the baby with friends, while Anne went back to sea with the pirates.

Anne was a full-fledged member of the crew. She dressed in men’s clothing, probably at Jack’s request. After all, it was considered bad luck to have a woman aboard ship, and at the very least she would have been a distraction to the crewmen.  Drawings portray Anne as a beautiful woman with a buxom figure.

The woman pirate proved to be as vicious and courageous a fighter as any of the men aboard, maybe more.  She was handy with sword and pistol and quick to use them.

Having inherited her father’s wandering eye, Anne fell for one of Jack’s crewmen.  When the flirtation advanced to a more intimate stage Anne was in for a surprise. “Mark” Read was also a female disguised in men’s clothing.

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Mary, aka Mark, Read began life differently than Anne. Born in England, she was disguised as a boy from infancy.  Her widowed mother pretended Mary was a boy to receive a death benefit, not available to a girl child, from her late husband’s family. The plan worked and the grandparents paid for their supposed grandson’s support.  Eventually the grandparents died and the support died with them when Mary was thirteen.

Mrs. Read, still concealing her daughter’s true sex, hired Mary out as a footboy.  It wasn’t long before Mary tired of that job and ran away. She took on a position with a British man-of-war, and later joined the army as a soldier.

Mary, still believed to be a man by all, fell in love with a fellow soldier.  She managed to let her beloved learn her true sex when they were bunked together in a tent.  After the war they became publicly married.  They set up a tavern near Breda Castle. Mary and her husband lived a normal and happy life for a while.

Things took a turn for the worse when Mary’s husband died.  She failed with the tavern business and returned to the life she knew best. She put on men’s clothing and joined an army in Holland. When that conflict was over she withdrew from service in the army and took a position on board a ship sailing for the West Indies.

This decision led Mary onto a path of lawlessness that she is said to have despised in the beginning. Pirates, led by Jack Rackham , attacked the merchant ship and Mary was taken prisoner. Perhaps it was her survival instinct that took over, but from that time on Mary was a pirate.  She managed to keep her gender secret until Anne Bonny entered her life.

Mary had worked her way up to being a lieutenant for the infamous Calico Jack.  Until this point, we do not have any stories of Mary having another romantic affair since her husband’s death, but a new young sailor was making advances toward her. She must have wondered about that, or maybe in the culture of pirates homosexuality wasn’t that unusual.  Captain Charles Johnson’s (aka Daniel Defoe) A General History of Pyrates, says of Mary, “thus much is certain, that she did not want Bravery, nor indeed was she less remarkable for her Modesty, according to the Notions of Virtue: Her sex was not so much as suspected by any Person on board till Anne Bonny, who was not altogether so reserved in Point of Chastity, took a particular liking to her.”

It wasn’t long before Mary and Anne became aware that they were each women. They vowed to keep their secret together, and became close friends. Some speculate their relationship was more.  In any case they spent enough time together that Calico Jack became jealous of “Mark” and threatened to slit his throat.  Anne had to let him in on her and Mary’s secret.  Anne and Mary, having proven themselves in a man’s world, gave up the secret that they were women.  They only dressed in men’s clothing when they were “working” at pirating.

Mary, according to legend, met another young man on the ship and fell in love and they became common law husband and wife. Mary became pregnant. Meanwhile, Rackham’s ship was captured and the pirates were put on trial.  The men were all sentenced to hang – Jack was scheduled to die the next day. He asked to see his beloved Anne before his execution. If he’d hoped for sympathy he got none.  Anne said, “I am sorry to see you in this predicament, but had you fought like a man you would not have to die like a dog.”

Several witnesses testified against the pirates at the trial. Dorothy Thomas, who was one of Rackham’s prisoners, assured the officials the women were indeed part of the pirate crew.  She testified that the women wore “men’s jackets and long trousers, and handkerchiefs tied about their heads: and that each of them had a machete and pistol in their hands and cursed and swore at the men, to murder (Thomas); and they should kill her to prevent her coming against them; and (Thomas) further said, that the reason of her knowing and believing them to be women then was by the largeness of their breasts.”

Mary and Anne told their stories and “plead their bellies.” They were tried and their sentences delayed until after the birth of the babies. A pregnant woman could not receive the death penalty because it was unlawful to kill an unborn child.  Unfortunately Mary died while in prison from a fever before the birth of her child.  From there we lose track of Anne until the twentieth century.

In recent years a rumor has surfaced that Anne’s name was found in a family Bible, along with a birth certificate and some letters. The birth certificate had three signatures: Anne’s father, the midwife and midwife’s husband. The boy child was named John Cormac Bonny; the father was named as John Rackham.

The letters describe Anne’s trial and the birth of her and Rackham’s son. They also reveal that Anne was engaged to a man in Virginia who was kind to her and her son.

This rumor supports the theory that Anne’s father bought her pardon and sent her back to the Carolinas.  Some report Anne Bonny lived a ripe old age and is buried in Virginia. Others say she went west with her new husband. So far Anne’s later years remain a mystery.