Making a name for himself as Quartermaster on Captain Vane's ship until Vane was ousted and Calico Jack was elected captain. Rackam then plied the pirate trade around Jamaica with some small success. He made his way to the Bahamas and met Anne Bonney, they courted in earnest and when she became pregnant he sent her to friends in Cuba to care for her. Their money eventually ran low and Calico Jack convinced Anne to join him on the high seas, disguised as a man. They plundered small merchant vessels sailing from island to island in the West Indies. After her ship was captured Mary Read, disguised as a man, joined the crew. The two women bonded closely because among other things they clearly had in common, they were both pregnant.
While they mostly pirated small-time vessels when they stole the sloop, William, from Nassau Harbor, they drew the Governor's undivided attention. They were captured and taken to Jamaica for trial. Calico Jack was hanged, but Anne and Mary both escaped the noose because of their pregnancies, the innocent child being protected from execution by English Common Law.
Anne's response to her husband's death is recorded in Defoe's General History of the Pyrates,
that she was sorry to see him there, but if he had fought like a man, he need not have been hanged like a dog.Mary Read died in prison, either from a fever or from childbirth. Anne Bonney, however, did not stay in prison forever, there is evidence that her father ransomed her and she returned home to South Carolina.
Evidence provided by the descendants of Anne Bonny suggests that her father managed to secure her release from gaol and bring her back to Charles Town, South Carolina, where she gave birth to Rackam's second child. On 21 December 1721 she married a local man, Joseph Burleigh, and they had eight children. She died in South Carolina, a respectable woman, at the age of eighty-four and was buried on 25 April 1782.