Anne Bonny’s life was by far not as adventurous as Mary’s, but it had been a hard life. She was a bastard daughter of an attorney of Cork in Ireland, whose wife had left him because of his loose way of life. Her mother was a maid in his father’s household. In the beginning she was dressed as a boy, pretending to be the son of her father’s friends, who had been apprenticed to him to learn the legal business. Her father later put aside all pretensions and decided to live openly with his former maid. Needless to say this was at the time deleterious to his legal carrier, and he was forced to search for work elsewhere.

Her father, her mother, and she sailed for Carolina, where he was successful as a lawyer and merchant, and was thus able to buy a plantation. When her mother died, she took over the duties of her father’s housekeeper.

She grew up to be a hardy girl with a "fierce and courageous temper". She had a very fiery disposition, and was said to have killed a serving girl with a knife during one of her fits of rage, granted this was never proven. But it was common knowledge that she had thrashed a young man, who attempted to make uncalled-for advances. He was so badly injured that he was confined to his bed for several weeks.

Anne married James Bonny, a young soldier, for which she was turned out of her father’s home, for whom the young man was "not worth a Groat". Her husband’s ambitions of inheriting a fortune were lost, and he took his wife to the West Indies looking for employment.

She met Jack Rackham on New Providence, who swept her away from her husband, and the two made their way to the sea, with Anne disguised in men’s clothing. After several months she became pregnant, and Rackham took her to friends in Cuba, who saw her through the pregnancy until term. Immediately after the child was born, she rejoined her lover at sea, there is no record of what became of her baby.

Despite their sex, Mary and Anne both made fierce pirates, and as many of their ship mates claimed, were "resolute and ready to board or undertake anything that was hazardous" in the time of action. A witness at their trial stated that the both of them cursed and swore with the best of males, and never cringed at murder. Their sex became known to the rest of their fellow crew, and the two would dress in women’s attire during moments of peace, and dressed in men’s jackets, trousers, with handkerchiefs tied around their heads, when the possibility of action arose. This costume after all was more suitable for fighting.

The two were captured on the ship of John Rackham, by a Captain Burnet, and tried under St. Jago de la Vega. When asked if there should be any reason why sentence of death should not be passed on them, the two (still dressed in male clothing) plead pregnancy as a reason for temporarily escaping the noose. Pregnancy saved Mary Read from the gallows, but she died soon afterwards with a violent fever, and died in prison. Anne Bonny also found to be an expectant mother, was given a reprieve. She remained in prison until the baby was delivered, after which she was reprieved from time to time until she disappeared, thus never hanged.