Anne eventually married the unsuccessful James Bonny. The marriage faired poorly as James, taking his wife to the pirate haven of New Providence, had a hard time supporting his wife. He eventually turned informer for the new governor, Woodes Rogers, further alienating his headstrong wife. Disillusioned with her husband, Anne transferred her affections to the peacock like figure of Calico Jack Rackam. Rackam returned Anne's affections by lavishing her with gifts. When James Bonny refused Rackam's offer to buy Anne, the couple snuck aboard a merchant sloop with a handful of Rackam's old pirate buddies and took over the ship. Thus began Anne's pirate carreer.
While Calico Jack looked the part of the dashing pirate, his career was somewhat lackluster, at least after taking up with Anne. The prizes taken seem to have been mostly coastal traders and fishing boats. Mary Read seems to have joined the pirates when a Dutch trader she was serving on was taken by the pirates. At some point during Anne's time with Calico Jack she is said to have gotten pregnant and have been set ashore in Cuba to deliver the baby. She was later picked up and carried on with Rackam as before.
In late October, 1720, off the coast of Jamaica, a British Navy sloop, commanded by a Captain Barnet, came across Rackam's anchored ship. With most of the crew drunk the only resistance the pirates put up was offered by Anne and Mary. Realizing that the fight was lost the women turned on their less than courageous crewmates, killing one and wounding others, screaming at them to 'fight like men'. Anne and the others of the pirate crew were captured and put on trial for piracy. All were sentenced to death, but Anne and Mary escaped the noose by pleading their bellies (no English court would kill an unborn child).
Anne seems to have disappeared from the world's stage at this point, there is some conjecture that her wealthy father bought her release after the birth of the child. This is one version of her life after the trial. Anne's child, born five months after the trial, on April 21, 1721, was named John Cormac Bonny. John Rackham seems to have been listed as the illegitimate child's father. After the child's birth the mother and child return to Virginia via South Carolina. There are some records that imply that she married a Joseph Burleigh at this time, 1721. It is guessed that this marriage was arranged by Anne's father to get her started upon a clean slate when she returned (one can only imagine the dowry required to get a man to marry a woman reputed to be such a wildcat). The Anne thus recorded gave birth to eight more children with her husband, three of whom died young. This Anne is said to have died on April 25, 1782 (which would have put her age at somewhere around 70-80) and was buried in a place called Sweethaven (possibly in York County, Virginia)