Mary, seeing an opportunity, joined Calico Jack’s crew and remained hidden as a man. She and Anne became friends, and together, they became the ship’s fiercest fighters.
Anne had developed a bloody reputation on deck, where she is said to have stabbed a sailor to death after he insulted her (and being the captain’s madame, this apparently went unpunished, even if Calico Jack’s articles forbade it). Mary was known for her constant swearing and tough-as-nails attitude. Both women led at least one raid and captured a schooner.
When their ship was outgunned and attacked by pirate hunters in October 1720, Calico Jack surrendered, but Mary and Anne kept fighting. Mary is said to go below deck, where most of the crew was cowering, and ordered them to come up on deck and “fight like men.” When that didn’t work, she fired her pistols at the crew, killing one and wounding others.
Eventually, the battle was lost, and they were captured and brought to court. They were both sentenced to death, but both also received stays of execution because they were both pregnant.
Mary died in prison less than a year after being captured. Anne’s fate is completely lost to history. The only thing we know is that she was not executed, or at least there are no records of the occurrence.
