After marrying a poor sailor who accepted clemency to give up piracy, Anne began a legendary affair with Calico Jack Rackam and became pregnant with his child, but that did not stop them from plundering the high seas aboard his pirate ship Revenge, at least until they were captured by British authorities. Like Anne, Mary Read was an illegitimate child who spent some of her childhood dressed up as and disguised as a little boy through incredibly strange circumstances. But unlike her future shipmate, Mary ultimately took a liking to it, and she continued to disguise her gender to take on roles reserved for men, including in the British army.
In , Mary's ship was captured by Calico Jack, who already had his lover Anne Bonny as part of his crew and now unwittingly added a second female when Mary opted to join.
Together the three played a legendary role as shipmates and possible lovers while continuing their piracy around the Bahamas, only to eventually be captured by authorities in October This spared her the noose, but Mary died of illness before giving birth anyway. History's Famous Women Pirates chronicles the lives and legacies of the three famous women.
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Anne avoided execution by "pleading her belly", getting a temporary stay of execution due to her pregnancy. Among all the pirates of the "Golden Age of Piracy", none were as unique as Mary Read, who was one of just two known women to be tried as a pirate during the Golden Age, alongside her own crewmate and possible lover Anne Bonny.