On March 8, 1700 an unwed mother, Peg Brennan, had a baby girl, Anne. Anne was lucky because her lawyer father, William Cormac, not only wanted her around, but went to great pains to have her involved in his life. Unfortunately, he was married and didn't want his wife to know about Anne. That problem was solved, for a short time, by him having Anne dress like a boy and coming into his home with the excuse that Anne was being taught how to be a lawyer’s clerk. Of course, such a lie like that couldn’t be kept up for long and when the truth came out, William Cormac’s wife cut him off he was made into such a spectacle that he took Anne and Peg Brennan to America where he bought a plantation in South Carolina. It was on that plantation that Anne grew up and there that she showed signs of not being the most polished of young ladies.

In John Reeve Carpenter’s Pirates Scourge of the Seas, he writes about two accounts of Anne’s youth as told by Captain Charles Johnson. One of the stories from Captain Johnson that Carpenter mentioned was that Anne had killed a servant in the household with a knife and the other that when someone “…would have lain with her, against her will, she beat him so that he lay ill of it a considerable time” (143).

Anne didn’t become any more gentile as she grew.

Married at sixteen-years-old to a young sailor, Anne’s father disinherited her and she went to live with her husband in the Bahamas. There, she had an affair with one man and, reputedly, fought a duel with the man’s other lover. Another story holds that, due to an insult, Anne once punched the governor’s sister-in-law in the mouth so hard that two of the woman's teeth were knocked out. Anne’s next lover was John Rackham, otherwise known as “Calico” Jack Rackham. With Calico Jack at her side, Anne began her life as a pirate.

Together, Anne and Calico Jack stole the ship, William, and, with it, attacked a Dutch ship where they forced their captives to sign articles (a contract detailing rules of the ship) and join their crew.

While Anne and Calico Jack may have forced the decision for their prisoners, it is interesting to note that pirates frequently gave their captives the choice of whether or not to join up. It is even more interesting that the invitation to join the pirate crews was frequently accepted. A seafaring life was immensely hard, not only physically, but also in the sometimes brutal treatment endured by the crew of a law-abiding vessel. Seamen were also not paid well. Considering that aboard many pirate ships all hands were considered equal and free and that they had a promised share of the plunder, the chance to become a pirate must have been very tempting. Another path that some seamen followed to piracy was, oddly enough, peace. During wartime, many seamen made their living as privateers. Privateers, who worked attacking the ships of an enemy nation, had no use during times of peace. The former privateers who couldn't find work still needed a way to support themselves and piracy would have been one way to do that.

One of the recruited men who’d been made to join Calico Jack and Anne’s crew managed to catch Anne’s eye, but when Anne made advances, the young crewman turned out to be another woman wearing men’s clothes who went by the name of Mary Read.

Once Calico Jack had been let in on the secret, Mary seems to have taken to the life of a pirate as well as Anne had. They were said to have fought as viciously as any and were apparently at ease using their weapons.

In 1720, when Anne was only twenty-years-old, Calico Jack’s ship was captured by Captain Jonathan Barnet and the crew was brought in for trial. Anne and Mary, once they were found out to be women, were given a separate trial from the men and though they were found as guilty as the rest of the crew had been and were sentenced to hang, Anne and Mary escaped execution by declaring that they were pregnant. Both women were given an examination and their pregnancies were confirmed. The courts wouldn’t kill an unborn child and so both women were spared the fate of dancing on the end of a rope. It was a short lived reprieve for Mary Read as she died of a fever shortly after the trial, but no one seems to know what became of Anne Bonny.