Anne Bonny, born in the 1690s in Ireland is probably the most famous female pirate to have sailed the Spanish Main. Her reputation was of a ruthless plunderer, a real scourge of the Caribbean seas.

Nicknamed ‘Toothless Annie’, her family moved from Ireland to America when she was a young child. There they became a respectable family, owners of a plantation. Growing up in South Carolina, Anne was fascinated by stories of pirates and buccaneers that she heard in the nearby port of Charleston.

At Charleston she met and later married James Bonny and the two of them moved to Nassau, an island in the Caribbean. Nassau had a reputation for being a pirate’s den. In fact it wasn’t long before Anne met the legendary Calico Jack Rackham. She left her husband for Calico Jack and joined his crew.

At that time seafairers in general were a superstitious group and they did not allow female crew members. Therefore, Anne dressed as a man and engaged in all the activities that the men did, including fighting. After some time her true identity was discovered and several members of the crew expressed their concerns. Anne’s reply was to kill them all.

Anne wasn’t the only female hidden aboard Calico Jack’s ship. Another woman by the name of Mary Reed was on board too. Together with Calico Jack the three of them wreaked havoc throughout the Caribbean for almost a year.

Eventually, in 1720, their ship was captured. Jack and most of the men hid below decks in the hold whilst the women fought to defend the ship. After the battle the crew were tried and sentenced. Somehow, Anne was reprieved from the death sentence. Jack, however, was not so fortunate.

Before Jack’s execution Anne went to see him and famously said “I’m sorry to see you here, Jack, but if you’d have fought like a man you needn’t hang like a dog”.

There are no records of what happened to Anne Bonny after this time. Some say she went back to a simple life and lived in relative peace. Others claim she continued as a pirate of the Caribbean.

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