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Ahoy, Matey! That Pirate Has Breasts!

Author: Deanna J. Jones

Anne Bonny, whether you believe her to have been a woman full of grit and gumption or a conscienceless criminal, is a fascinating historical figure. Amazingly, her appeal is due to what is not known about her as much as it is due to what facts are available. Historical documents support the notion that Anne Bonny was a headstrong, independent woman, and speculation points to a legendary and fearsomely courageous temperament. In any event, it is quite evident that Anne was a woman ahead of her time, for she broke convention during a period in history when women were expected to behave in a sedate, subservient manner. Subservient was a word that simply wasn’t in her vocabulary.

The exact date of Anne Bonny’s birth is not known, but it is believed that she was born illegitimately in County Cork, Ireland between 1697 and 1700 to the maid, Mary Brennen, who was in her father’s employ. Her father, William Cormac, had a legal practice in Kinsale that was ruined when his current wife made his adulterous affair public, and he was forced to leave Ireland in shame. Deciding to make a new start in a new world, William Cormac, along with the maid, Mary Brennan, and his baby daughter, Anne, traveled together to America. The little family settled around Charleston, South Carolina, which had a large shipping community at the time, and William, after presenting Mary Brennan to polite society as his wife and Anne as his legitimate daughter, started his legal practice again there. Apparently, William Cormac’s practice was quite successful, for soon he had enough to purchase his own plantation in Charleston, and the family was accepted by the upper crust of the community.

Anne grew to have a reputation among her peers as having a fierce and courageous temper, and a fiery disposition. She certainly had reason to be so. Her mother passed away during Anne’s teen years, and Anne took over the enormous responsibility of running her father’s large household. She did this with aplomb. However, one story claims she had an odd method of dealing with recalcitrant servants. Supposedly, she killed a serving maid in her father’s household for crossing her, but there are no concrete facts to support this story, and considering her mother’s background, this tale is unlikely. It is known that she did thrash a young man for trying to sexually assault her, and injured him badly enough that he had to take to his bed for several weeks. Anne was around fourteen years old at the time.

When Anne was sixteen years old she fell in love with a sea captain who had been courting her, unbeknownst to her father. The man’s name was James Bonny, and history proclaims him to have been either a penniless soldier or a small-time pirate at the time. William Cormac, upon discovering their romance, was not a happy man. He had long wished for Anne to become a respectable lady, marry a Charleston man of his choosing, and take her place in society as a plantation owner’s wife, as she was an heiress of some renown. Anne, however, had other ideas for her future. Anne was a headstrong girl who had long made her father despair over her tomboy antics. Anne longed for adventure and excitement, and was drawn to the unsavory sort of man that could be found at the wharves and ports of Charleston. It was here that Anne met James Bonny.

Anne and James Bonny were wed against her father’s will, for which he disowned her, costing them her dowry. Not wanting to stay in Charleston, the two moved to what was then called New Providence, now Nassau. New Providence was described as “a den of iniquity” and “a pirate’s paradise” and the descriptions were not far off the mark. At the time most of the community was made up of pirates and pirate’s paramours. This suited Anne just fine, and she made friends easily and quickly, one of whom was Pierre, a celebrated homosexual who ran a popular ladies establishment on the island and had the confidence of several important personages.

Marriage to James Bonny disagreed with Anne Bonny before long. At first she simply tired of being a dutiful wife and waiting for him to return from the sea, but even after he gave up pirating and began a career as an informer to Governor Woodes Rogers, turning in his pirate friends for a reward, Anne was still discontented. Most of her friends on the islands were pirates or earned their livelihoods from piracy, so Anne probably viewed her husband as a turncoat. Anne began seeing a wealthy man by the name of Chidley Bayard, and enjoyed traveling with him and spending his money, but she had trouble getting along with the type of people he kept as friends. At one ball that he took her to he introduced her to the sister-in-law of Governor Lawes of Jamaica and left them to entertain each other. The woman waited until Bayard had walked away and then made catty insinuations about Anne’s relationship with the man, then proclaimed that she didn’t consider Anne worth knowing and told her to stay away from her. Anne cheerfully told her she’d make sure there was quite a bit of distance between them and then proceeded to punch the woman in the mouth, knocking out two of her teeth in the process. This was the end of her friendship with Bayard, and she was once again bored. Anne began to cast her eye around for another means of escape, and the means presented itself to her in the person of Captain Jack Rackham, also known as Calico Jack. It is said that Jack was a flamboyantly handsome and debonair man that the ladies made much over, and after he offered Anne a chance to get away from her husband, along with the added benefit of high adventure, it didn’t take much more convincing for Anne to consent to run away with him. After disguising herself in men’s clothing they snuck aboard his ship and headed to sea.

Anne stayed in the guise of a man for some time, as most seagoing men of the time believed that a woman aboard a ship was bad luck. It is said that she was so vicious and fought so well with both pistol and cutlass that no one questioned her, anyway, and the one man that did challenge her lost his life to the tip of her cutlass. It is rumored that she gutted the man, and this likely went a long way towards ensuring that the rest of the crew gave her a wide birth and fearful respect. Soon, however, her sex became known to all, as she became pregnant. Agreeing that a pirate ship was no place to give birth to a baby, Jack sailed to Cuba, where he left Anne in the care of friends until she had the child. Sadly, the infant did not live, and Anne was heartbroken, believing that her lifestyle had contributed to her misfortune. As time passed her mental condition worsened. When Jack came back to collect her and the child he was saddened by the news and concerned about his lover’s condition. He took her back to New Providence to recover, taking the King’s pardon and temporarily giving up piracy to privateer on commission.

During Anne’s convalescence she learned from her old friend, Pierre, of a plot to assassinate Governor Woodes Rogers. Having met the man during her marriage to Bonny, Anne decided to warn him and saved his life. He was extremely grateful for her interference. Unfortunately, soon he was called upon to express his gratitude in a more tangible way, for James Bonny, who still lived on the island, had discovered that Anne and Jack Rackham were staying in his vicinity again and so he sent troops to arrest them both for piracy. When they were unceremoniously dragged before the governor in the middle of the night Bonny was almost hysterical in his rage, because they had been flaunting their affair under his nose, and he refused to be merciful. He wanted Jack and his wife to hang, and was afraid that Anne would kill him if she were set free.

Governor Woodes Rogers, remembering the favor Anne had so recently done him, decided to spare their lives. He commanded that Anne be flogged and returned to her rightful husband, and that Jack Rackham be set free. He believed this to be a lenient solution, but Anne was enraged at being treated like a piece of property and refused to be dictated to. The next evening Anne and Jack escaped to their ship and gleefully returned to a life of piracy, throwing all convention and reservations to the wind.

They continued on in this vein for several years, and their notoriety grew and grew. Amazingly enough, Anne was not the only woman on board Jack’s ship. There was one other, Mary Read, who also dressed in men’s clothing and was said to have been as brave and as dangerous as any male pirate on the sea. One of their shipmates was said to have proclaimed that both were “resolute and ready to board or undertake anything that was hazardous in the time of action”, and another stated that both of the women cursed and swore with the best of males, and never cringed at murder. Anne and Mary became fast friends, and were the first in battle and the first to volunteer in any boarding parties. They became well respected by their crew for their ferociousness, and were feared as well for their unpredictability.

In October of 1720 their life of piracy and adventure came to an end. Governor Lawes of Jamaica, the man with the spiteful sister-in-law, heard of their presence and sent troops to commandeer their ship and bring them to trial. Calico Jack and his crew were unprepared for the assault. The troops did not strike until the day after Jack had captured a commercial vessal, and he and all the men aboard ship were in a drunken stupor from their celebrations, leaving only Anne Bonny and Mary Read to fend off the attackers. The two women became so disgusted with the men for not fighting that they periodically turned their guns on their own crew before they were all captured.

Both women, along with Jack and the rest of the men, were condemned to hang, but received a stay of execution because they were both with child at the time. Mary Read did not live to hang. She died in prison, along with her unborn child. Anne, however, survived, and when Jack received permission to speak to her before his hanging, she said to him “I’m sorry, Jack, but if you had fought like a man you would not now be about to die like a dog. Do straighten yourself up!” Anne never was executed, and there is much speculation as to what her fate actually was. The most common story is that her father ransomed her back through his powerful connections, another was that she escaped with an unknown lover. One much-loved legend states that pirates up and down the coast collected with their guns pointed towards the governor’s estates, with the message “Let Anne Bonny go or feel the thunder of pirate guns from Port Royal to Kingston and back again!”

According to the book Mistress of the Seas by John Carlova, Anne, whose unborn child was fathered not by Jack but by a Dr. Michael Radcliffe, a man whose life Anne had saved and who dearly loved her and vowed to save her from the hangman’s noose, was granted a pardon by Governor Lawes on the condition that she leave the West Indies and never return. Carlova went on to proclaim that James Bonny had drowned in a hurricane, and Anne, now a widow, and Radcliffe were then married. Two days later they boarded a trading sloop bound for Norfolk, Virginia. There they were known to have joined a party of pioneers heading westward…and there is where the story of Anne Bonny came to an end.

What actually happened to Anne Bonny will probably never be known, but one fact remains: Anne Bonny was a woman who embraced life head on and then molded it to her own terms. Hero or villain, she left her rather impressive mark on history, and she should not be forgotten.


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