Together Calico Jack, Anne Bonney and Mary Read were a force to be reckoned with in the early part of the 18th century. Each brought something different to the table; Jack – the dandily dressed, slightly cowardly, pirate captain, Anne – his fearsome lover, who could fight courageously and competently against any man – and Mary, the cross-dressing pirate who wore her heart on her sleeve. It is no wonder that this band of misfit ruffians continue to fascinate us to this day.
One of the most flamboyant pirates to ply his trade in the Spanish Main was Calico Jack, so called because of the brightly coloured printed cotton clothes he liked to wear. He was not a particularly successful pirate, mostly limiting his operations to attacking small ships, but he has remained legendary, not only because of his striking appearance but because he employed two female pirates in his crew: Anne Bonney and Mary Read.
Calico Jack is also credited with being one of the first pirates to fly the Jolly Roger, featuring a skull and crossed cutlasses. This popular design later mutated into the skull and crossbones, and has become forever associated with piracy.
Calico Jack’s real name was John Rackham. He was born in England on 21 December 1682. There is no further mention of him in the records of the period until 1718, when he found employment as quartermaster for the pirate Charles Vane (see page 46). Vane mostly preyed on weaker vessels, but in one instance he attacked a ship that turned out to be a French man of war, and had to retreat, much to the humiliation of his crew. The crew turned on Vane, called him a coward, and voted that Rackham should take his place as captain. So it was that Calico Jack came to command his first ship.
As a pirate, Rackham’s career was somewhat undistinguished. He patrolled the coastline close to the shore, and often chose to attack small fishing boats, terrifying ordinary men and women as they went about their work. He was not known for his bravery in battle, either: one story goes that he gave up his stolen ship without a fight when its Jamaican owner reclaimed it, and retired to New Providence Island in the Bahamas. At the time, the island was known as a meeting point for pirates from all over the world. Once there, he received a pardon from the Governor of the Bahamas, Woodes Rogers.
But Rackham’s retirement did not last long. He frequented the taverns in the island’s main town, Nassau, meeting the pirates who gathered there to hatch plots and launch operations. In the course of his socializing, he met a notorious firebrand, a local woman named Anne Bonney, and began a passionate affair with her. Anne was married, and at first the affair was conducted in secret. However, it was not long before the lovers became careless, and Anne’s husband found out what was going on. After a major scandal, Jack and Anne eloped together and ran away to sea, thus escaping Anne’s belligerent husband and the long arm of the law.
Once at sea, Jack reverted to his old ways as a pirate, and Anne began, literally, to learn the ropes. For the next year or so, Jack, Anne, and their pirate band plied their trade around the islands of the Caribbean, attacking small ships and amassing a sizeable fortune for themselves. In the course of their adventures, they encountered a privateer ship, attacked it, and came upon Mary Read, a female pirate who dressed as a man. Bored with life on the legal side of sea robbery, Mary decided to switch allegiance, and joined Calico Jack’s pirate crew. Once the new recruit was on board, Anne, who by all accounts had a healthy sexual appetite, was immediately attracted to the young sailor. Jack became jealous, but when Mary revealed her secret – that she was, in fact, a woman – Jack was happy to allow her to stay on board, work among the men, and keep his wife company. Mary and Anne subsequently went on to become firm friends.
However, this cosy set-up was not to last. Unbeknown to Calico Jack, time was running out for his pirate band. The Governor, Woodes Rogers, had come under public pressure to do something about the escalating levels of piracy in the Caribbean, which was adversely affecting trade in and around the islands there. He decided to begin his clean-up campaign by focusing on his old adversary, Calico Jack.
Once he learned that Jack had broken the conditions of the pardon and returned to piracy, Woodes sent a force to capture him. In October 1720, a sloop commanded by Captain Jonathan Barnet caught up with the pirates in Jamaica, attacking the ship as the crew lay drunk after a night of revelry. The ship was overtaken, the crew arrested, and the entire company taken to Spanish Town, Jamaica to await trial.
Not surprisingly, given the fact that there were two women pirates in the dock, the trial of Calico Jack and his crew caused tremendous public interest. Jack was the first to be found guilty, and was immediately sentenced to death. He was hanged on 18 November 1720. His body was then covered in tar, placed in a cage and hung on a gibbet on an island outside Port Royal, Jamaica, as a gruesome warning to other pirates. The island is now known as Rackham’s Cay. The nine men in his crew were tried the following year and were also sentenced to death. They were hanged in February 1721.
The women, however, escaped the noose. Both Anne Bonney and Mary Read announced that they were pregnant, which meant that under the law they could not be hanged until after they had given birth. But as it turned out, they never were hanged: in the event, Mary Read died of a fever related to her condition, while Anne Bonney disappeared from the records.
Today, Calico Jack is remembered as the gaudily dressed pirate who sailed the high seas with two females in his crew, flying the Jolly Roger in a gesture of defiance to the law of the land.
The story of Anne Bonney is one of passion, violence and adventure. Of Irish-American extraction, she was one of very few women to go down in history as a female pirate. (Another was her friend, Mary Read, whose story you can read below.) She was renowned for her volatile temper, her courage and her prowess as a fighter. She survived many skirmishes at sea, but was eventually imprisoned. However, in the end she managed to escape the hangman’s noose, whether through luck or cunning we do not know.
There are few official records concerning Anne Bonney’s early years. Most of what we know about her comes from Captain Charles Johnson’s A General History of the Pyrates, published in 1724 and thought by some to be the work of Daniel Defoe. Johnson writes that Bonney was born near Cork, Ireland, the illegitimate daughter of a well-to-do lawyer named William Cormac and his maidservant, whose surname was Brennan. After the baby was born, the couple moved to Charleston, Carolina, to avoid scandal, Miss Brennan posing as his wife. There, Cormac amassed a fortune and went on to buy a plantation.
When Anne’s mother died, Anne kept house for her father, and by all accounts grew to be a violently bad-tempered young person. Aged only 13, she was reputed to have stabbed a servant girl with a kitchen knife. It was also rumoured that on one occasion she rebuffed an unfortunate young man’s advances by giving him a thorough beating for his pains.
By the time she reached adulthood, Anne had developed a taste for excitement and adventure. Against her father’s wishes, she married a disreputable sailor, James Bonney, and moved to Nassau, New Providence. There, her new husband immediately made himself unpopular by becoming a paid informer to the governor of the Bahamas, Woodes Rogers.
The Bonneys’ marriage was not a success. When Anne realized that her husband was an informer, and had only married her to get his hands on her father’s estate, she took to going out by herself, frequenting the local inns and mixing with the pirates there. When she began an affair with the notorious Calico Jack, her husband was outraged, and brought her before Governor Rogers, demanding that the Governor order a public flogging for her. Rogers suggested that, instead, James might like to make some kind of divorce settlement, which would involve him ‘selling’ his wife to her new lover, in a practice that was common at the time. Avaricious as ever, Anne’s husband jumped at the chance. Anne, however, put up a spirited resistance to the idea, refusing to take part in the deal, and protesting that she would not be ‘bought and sold like cattle’. Rogers duly ordered the flogging, but before it could take place, Jack and Anne had fled the island.
Johnson recounts how, once at sea, Anne took to wearing men’s clothes to disguise herself. However, this is disputed by some historians, who point to a circular printed in the Boston Newsletter at the time, which specifically names her as a ‘wanted pirate’. This suggests that she was well known to be female, and did not try to hide the fact. Nevertheless, she did gain a reputation as a woman who was as tough, or tougher, than any man: on board ship, she proved both a competent sailor and a courageous fighter.
Before long, however, Anne became pregnant, and it looked for a time as though she would have to retire from life as a sea robber to take up the responsibilities of motherhood on shore. But instead, Rackham merely dropped her off with friends in Cuba, waited until she had had the baby, and then picked her up again, leaving the child to be brought up by the ever-obliging friends. Lacking a maternal streak, Anne seemed happy with the arrangement, returning to pirate life with gusto.
Despite her notoriety, Bonney never commanded her own ship. That duty was always left to her lover, Calico Jack. But it might have been better if she had, since when Governor Rogers finally sent a naval posse to capture them, it was Bonney, along with her friend Read, who fought manfully to evade capture while Jack and his men lay drunk and incapable below deck. When the crew were finally taken prisoner, Anne was apparently furious at Jack’s behaviour. The story goes that when she visited her lover in jail, instead of commiserating with him, she told him, ‘I am sorry to see you here, Jack, but if you had fought like a man, you would not be hanged like a dog’.
While Anne was in jail, it transpired that she was again pregnant, which this time proved extremely fortunate for her. She was able to obtain a stay of execution from the judge, who ordered that she could not be hanged until after her baby was born. (English law maintained that a condemned woman, if pregnant, should not be put to death until after childbirth, so that the baby would survive.)
Strangely, however, at this point Anne Bonney completely disappeared from the historical record. There is no documentation of her execution, and many believe that it never happened. It is argued that, had she been executed, the matter would have been noted down, whether in prison records or in the press, since she was a female pirate of such notoriety. So what could have happened to her? To this day, nobody really knows.
Some believe her wealthy father ransomed her; others that she returned home to her husband; still others that she went on to pursue a life of piracy under another name. There is also a theory, put forward by her descendents, that she married a Charleston man, Joseph Burleigh, and went on to raise a family of nine children, including her second child by Calico Jack. According to this claim, Anne lived to a ripe old age – with more than a few wild stories of her youth to tell her grandchildren, no doubt – until her death on 25 April 1782 at the age of 82 .
The image of the cross-dressing female pirate is one that has always intrigued and delighted the public. Yet it appears that, of the small band of female pirates that existed in the 18th century, very few actually dressed as men. Mary Read was an exception: she really did cross-dress, and has gone down in history as the swashbuckling pirate with a secret to hide: that she was, in fact, a woman.
Read was born in London to a sea captain and his wife, who decided to bring their daughter up as a boy. Accounts vary as to why. Some suggest that the couple’s first child had indeed been a boy, but that he had died while an infant, and that the mother had then had an affair while the sea captain was away, resulting in Mary’s birth. When the captain did not return, the wife dressed the child in boy’s clothes and went to visit her wealthy mother-in-law, claiming that he was the son, and so managed to get an allowance for them. Others claim that Mary’s mother simply dressed her daughter as a boy because she thought that it would be good for her to have all the privileges of a man when she became an adult.
In her teenage years, Mary found employment as a footboy to a wealthy French family living in London. However, she hated being a servant, so she decided to run away to sea. She joined a warship, but soon realized that she had made a mistake. For several years she endured the miserable conditions on board ship, before joining the army. She became a foot soldier at the lowest rank, but showed such bravery at the Battle of Flanders that she was promoted to the cavalry. During this time, she met a soldier and fell in love with him. When she revealed that she was a woman, he offered to marry her, and the pair left the army to become civilians.
Mary and her new husband went on to run an inn, The Three Horseshoes. The inn prospered, and for a while, she lived contentedly in her new role as pub landlady, dressing as a woman for the first time in her life. However, her happiness was not to last. When her husband died, she donned her man’s clothes once more, left the inn, and went back to the army. She then joined the crew of a privateer vessel sailing to the Spanish Main. When the ship was attacked by pirates, she was held prisoner.
Her captors turned out to be Calico Jack and his mistress Anne Bonney. Anne immediately took a fancy to Mary, thinking her to be a man. Whether they had a sexual relationship or not remains unclear – some reports suggest that Calico Jack found the two of them in his bed together – but whatever happened, Mary’s secret came out.
Read then joined the pirate crew, making friends with Anne, and fighting side by side with the men as they robbed and plundered cargo ships in the Caribbean. Of a passionate nature, she fell madly in love with a young sailor, and when he was in danger, offered to lay down her life for him. The sailor had been challenged to a duel by an older and much stronger seaman, so Mary decided to take the young man’s place. She and the seaman fought fiercely, with pistols and swords, until at one point he made a lunge at her. So as to confuse him, she ripped open her shirt, revealing her breasts, and as he reeled back in surprise, she stabbed him to death.
Mary and the young sailor celebrated this triumph by getting married, but once again domestic bliss was to elude her. Shortly after the nuptials, Calico Jack and his crew were captured, imprisoned, and sentenced to death. Mary was found to be pregnant, and thus escaped execution, only to die of a fever soon afterwards. Her unborn child perished with her.
Today, she is remembered as one of the most intriguing pirates of the 18th century. Despite her reputation as a tough soldier, a bloodthirsty pirate and a brave fighter, she also had a reputation as a tender-hearted woman in her personal life. She was prone to falling in love, and to forming intense friendships, and when she did, treated the objects of her affection with great loyalty and devotion. She was also admired for her courage; she was not intimidated by the punishment for piracy, which was the death sentence, and once remarked, ‘As to hanging, it is no great hardship. For were it not for that, every cowardly fellow would turn pirate and so unfit the sea, that men of courage must starve.’
Like many other pirates of the day, Mary Read appears to have lived by her own moral code, which valued honour and bravery in battle, and personal loyalty to those she loved. She was part of a renegade band of outcasts: some were from poverty-stricken backgrounds who had been hounded by the law for various misdemeanours, while others came from wealthier stock but had flouted the rules of social convention in one way or another. Despite, or perhaps because of, their rejection from polite society, these individuals nevertheless formed strong alliances with each other, and were a great deal more tolerant of deviation from the norm, whether physical, moral or social, than the general public of the period. Thus, although the pirates were feared, they were also, to some extent, admired and envied.
Women like Mary Read, who were not afraid to live a life of passion, independence and self-determination, just as men did, were especially few and far between. These were the rebels, who refused to slot into the roles prescribed for them, as dutiful daughters, wives and mothers. Such women were as unusual then as they are now; and for this reason, to this day, they continue to fascinate us.