Charlotte de Berry

Charlotte de Berry, born in England in 1636, followed her husband into the navy by dressing as a man. When she was forced aboard an Africa-bound vessel, she led a mutiny against the captain who had assaulted her, cutting off his head with a dagger. She then turned the crew to piracy and became captain, her ship cruising the African coast capturing gold ships.

Charlotte's pirate career demonstrates not only her own abilities, but also the thin line (or morally, no line) between then-legal imperialism and piracy. After all, the gold she stole had originally been stolen from Africans, who were themselves being violently kidnapped by the slave trade - rapine of the worse possible kind. Similarly, the pirates of the Spanish Main were taking what the conquistadores had stolen from the Aztecs, Incas, and other Mesoamerican peoples. Charlotte's crew had been law-abiding sailors when serving under a sadistic rapist, but outlaws when she led them. This, of course, in no way excuses the crimes she and these other pirates committed, it just speaks of the violence of their time, and that at least these criminals were straightforward about what they were doing.