A ne'er-do-well pirate/sailor named James Bonny married Anne in an attempt to steal the plantation but Anne's father instead disowned her. Bonny then took Anne to the Bahamas where he turned informer to Governor Woodes Rogers, turning in any sailor he didn't like as a pirate for a handsome reward.
Anne quickly grew to dislike her spineless husband and quickly caught the eye of one Calico Jack Rackham, a pirate of some renown. Governor Rogers had recently passed an amnesty for pirates which left Bonny out of work. The admiration between Anne and Calico was mutual. Calico Jack was a handsome man who knew how to spend money as well as steal it. Anne was a well endowed lass with a fiery spirit and a temper that matched that of any man.
In any event, Calico offered to buy Anne from Bonny but Bonny instead took the matter up with Governor Rogers, who said that Anne was to be flogged and returned to her true husband. That night Calico and Anne slipped out in the harbor, stole a sloop and began a life of piracy together.
Anne fought in men's clothing, was an expert with pistol and cutlass and considered as dangerous as any male pirate. She was fearless in battle and often was a member of any boarding party.In October of 1720, retribution was close at hand. The governor of Jamaica, hearing of Calico's presence sent an armed sloop to intervene and capture the Captain and crew. Calico's ship "Revenge", was caught by surprise and much to Anne dismay, the pirates fought like cowards and were taken far too easily.
Anne and Mary Read, were also captured but, upon capture, confessed their "sex" and pleaded to be tried separately after they gave birth. (Both women were pregnant at the time). Both received separate trials from the men but were still sentenced to hang. Mary Read escaped the hangman by dying from fever while in jail. Anne however, received several stays of execution before mysteriously vanishing from official records. It is believed that her father, who had contacts in the island, forgave his daughter for her acts and ransomed her back to the Carolinas where she assumed a new name and a new life.