The most infamous female pirate in history was a teenage girl who disguised as a man to escape her brutal estranged husband, after she slew a fellow prostitute in a duel while trying to woo a powerful politician in the Caribbean. Not shying in battle, Anne proved herself a heartless pirate. She emboldened Calico Jack, her latest lover, to take over a ship and compete with Blackbeard and his crew for booty along the Carolina coast and the Caribbean.