Anne Bonny

"Toothless Annie"

Anne Bonny, history's most famous woman pirate, was a plunderer, cutthroat, sailor, ransomer, raider, and general menace to maritime commerce in the Caribbean. In short, most pirates probably would have considered her an asset to their trade. 

Anne Bonny was born in Ireland in the late 1690's. She was the daughter of a penniless maid and her employer. The two ran off to America and established themselves as respected plantation owners in South Carolina. For young Anne, however, the rural comforts of plantation life were far less alluring than the stories floating around the nearby port of Charleston, a well-known pirate haunt. There, she met and married a small-time pirate named James Bonny, and the two moved to Nassau, and island in the Caribbean Sea.

Pirates virtually ruled the city at that time. There Anne wassurrounded by legendary figures like Calico Jack Rackham (the man who allegedly invented the skull and crossbones symbol).

Anne soon left James Bonny for Calico Jack, joining him on his ship. Because the pirate code explicitly forbade female crew members, she disguised herself as a man and fought alongside the rest of the crew. It was only a matter of time before she was discovered, however, and according to one legend, the first fellow shipmate to express anger at having a woman aboard paid for his opinion with his life. She stabbed him through the heart. 

However incredible a woman's presence on board may have seemed to Rackham's crew, amazingly, Bonny was not the only female on board. Also disguised as a man was a woman named Mary Read, and the two became fast friends. They shared the secret with Rackham, and the trio happily wreaked havoc throughout the Caribbean for nearly a year. 

In 1720, Rackham's ship was captured by pirate-hunters. During the fight, Rackham hid in the hold along with most of the crew, while the two women stayed on deck and attempted to fight off the attackers. After their capture, Rackham and the other men were hanged.

Somehow, Bonny was granted a reprieve, and what happened to her afterwards is entirely unknown. Some say she went back to her father and some say she resumed the pirate's life. Whatever she did, her most memorable words are those she said to Calico Jack on the eve of his execution: "I'm sorry to see you here, Jack, but if you'd have fought like a man you needn't hang like a dog."