Captain John Rackham, often called Calico Jack because he loved to wear clothes made of calico, is probably best known not for his own pirating but for two members of his crew. During the Golden Age of piracy, when the few women who were sailing the seas were doing everything within their power to hide their sex, Calico Jack had not one but two female pirates in his crew — and everyone knew it. Anne Bonny and Mary Read are two of the most notorious female pirates in history, and their stories are the stuff legends are made of.

A Bonny Lass

Anne Bonny was born in Kinsale, County Cork, Ireland, in 1698, the illegitimate daughter of lawyer William Cormac and his mistress, Mary Brennan. Mary was employed as a maid for William's wife, who discovered her husband's affair with Mary and left him. What happened next is uncertain. One account states that William, who deeply loved the maid and their daughter, actually brought Anne into his household after his wife's departure. To avoid questions of impropriety (and losing the stipend his estranged wife was still granting him), he dressed Anne as a boy and told people that he'd taken the lad in and was raising him to be his clerk. Eventually his wife discovered the true identity of the child and ceased William's financing. William then moved Mary and Anne to the colonies, the three of them settling in South Carolina. Other accounts suggest that William's wife had both William and Mary arrested for adultery and fornication, and that when Mary was sentenced to take her child and move to the colonies, William traveled with her.

The couple and their daughter settled in Charleston, South Carolina, and William became a very successful planter, raising Anne in privilege as the daughter of a plantation owner. When she was thirteen, her mother died and she took over the management of the plantation. Things went well until, at age twenty, she married a fisherman named James Bonny. William was furious, as he'd planned on betrothing Mary to someone with a higher social status, and as a result, he removed her from his will. The newlywed couple left for the Bahamas in 1718, and it was there, in the pirate haven of New Providence, that Anne would meet Calico Jack. So charmed was she by the dandy pirate that she deserted James Bonny to run off and lead a pirate's life.

The Double Life of Mark Read

Like Anne Bonny, Englishwoman Mary Read also began life as an illegitimate child. Her mother, whose husband had disappeared or died at sea shortly after the birth of their son, found herself pregnant by another man, so she moved away from her husband's family, lest they discover her scandalous pregnancy. Soon after Mary's birth, which is said to have occurred sometime around 1699, her older brother died, and after a short while Mary's mother found herself in financial trouble. In order to continue receiving payments from her mother-in-law to support her child, she moved back and dressed Mary in boy's clothing, pretending that she was her brother. This worked for awhile, but the grandmother eventually uncovered the truth and stopped giving her money. Mary, in the meantime, continued to dress as a male, and was subsequently hired out to work as a footboy in order to help support her mother.

In her early teens, Mary — still dressing as a boy and using the name Mark Read — found work on a British warship as a cabin boy. At some point she left the navy and joined the army instead, and there she met a handsome Flemish soldier and fell in love. Obviously, she was faced with a serious sexual dilemma and was forced to inform the object of her affection that she was really a woman. Apparently delighted with Mary's revelation, the man married her and they both left the army. For awhile they ran a tavern, catering to soldiers and making a good living, but then Mary's husband died, and peace brought a shortage of soldiers to their tavern. Finding herself in poverty once again, Mary returned to her cross-dressing ways, and around 1717 secured a job on a Dutch ship that was sailing for the West Indies.

Under her assumed name, Mary sailed as a pirate for about a year, then was granted and accepted a pardon from King George I while she was in the Bahamas. She subsequently delved into privateering against Spain, and was sailing on a Dutch ship when she decided to join Calico Jack and Anne Bonny's crew. The three began a journey that would eventually end in doom.

A Tale of Two Women

When Anne Bonny took up sailing with Jack, the other men in Jack's crew were apparently aware that Anne was a woman. It wasn't long after she joined the crew that she realized she was pregnant, either by Jack or by her husband. After delivering the child in Cuba, she quickly rejoined Jack on his ship. There's no record of what happened to the child, but it's assumed that Anne gave the baby away or it died. Some stories say that Mary joined their crew as Mark Read, and that it was only when Anne became enamored with “Mark” and Jack became jealous of him that Mary revealed her true sex. Regardless of how it came about, Mary and Anne became close friends. Both were comfortable dressing as women during average days on the ship, but during battles they dressed as men.

As pirates, Anne and Mary proved that they were excellent fighters who were highly skilled at handling weapons. As such, they were accepted as equals by the men of the crew, and drank, swore, and gambled with them. In battle they were utterly fearless, and as a result, tales of Calico Jack and his wild women soon spread back to the Bahamas where Governor Woodes Rogers issued a proclamation for their arrest. The mere fact that Jack had not one but two wanted women onboard was nothing short of extraordinary.

During the summer and fall of 1720, Jack's crew plundered their way through the Caribbean, boarding and raiding many ships and sharing a wealth of booty. On October 22, 1720, the crew was down in the hold of the ship, drinking and playing cards. Mary and Anne went up on the deck and noticed a governor's ship drawing alongside them. They yelled for the men to come on deck, but the majority were too drunk. Captain Jonathan Barnett asked the pirates to surrender peacefully, and at first Jack refused. A few cannon shots were then exchanged, and when Jack's ship was disabled, he surrendered and joined his men below deck. Mary and Anne did not. Instead they fought the governor's men as they boarded. Both women fired their pistols and swung their swords, but were finally overpowered and taken to jail with the rest of the crew to await their trials.

Trying Times

On November 16, 1720, the trial of Calico Jack Rackham and his men began. In the end, they were all charged with piracy, and the very next day were found guilty and sentenced to hang. Rackham himself was hung on November 18, but before he was executed he asked if he could see Anne. His request was granted, but being the wily wench that she was, she didn't have much sympathy for him. Legend has it that she looked him in the eye and curtly stated that “If he had fought like a Man, he need not have been hang'd like a Dog.”

Ten days later, the two women were tried on the same charges as Calico Jack. Both pleaded not guilty despite witness after witness taking the stand to testify how the women were willing participants in the pirate way of life and the violence of battle. Anne and Mary were subsequently found guilty and sentenced to be hanged like the rest of their fallen comrades. After their sentencing, both women immediately claimed to be with child, however, and after examinations proved they were indeed pregnant, the courts temporarily suspended their execution.

Questionable Ends

Details of what actually became of Anne Bonny and Mary Read are still in dispute. Mary Read allegedly died in prison, and some stories say that she died of fever. The date of her death, April 28, 1721, corresponds to the end of her pregnancy. This, coupled with the fact that she was given a proper burial despite being a condemned woman, makes it seem more likely that she died in childbirth. What happened to Anne and her child is less clear.

After delivering her child, it appears that Anne received several stays of execution and was eventually pardoned and allowed to return to the colonies. The most common story is that Anne's father, upon hearing of his daughter's plight, used his connections or a bribe to secure her release. Other stories allude to pirate Captain Bartholomew Roberts threatening to “release his wrath on all the Bahamas” if she wasn't released. It does appear that Anne somehow escaped to America, as her father's records showed her marrying a Virginia man in December of 1721. If that is to be believed, she apparently lived out her life in anonymity and without causing any further problems.