If pirating separated the men from the boys, how come one of the best pirates was a woman? Here’s the story of Anne Bonny. Story first published in Uncle John’s Plunges into History. 

Pirate Benjamin

If ever there was an old boys’ club it was under the Jolly Roger. Pirating was a man’s world, and most buccaneers wouldn’t let women on board unless they were captives. But some ladies managed to become pirates and beat the men at the plundering game. The woman pirate most famous for her fierceness and temper was Anne Bonny. Born Anne O’Malley, she was the heiress to a fortune. She could have lived a spoiled, genteel life as the belle of a Southern plantation, but she threw it all away for a cutlass and a pair of breeches (that’s pants, to you). 

Who She Was

She was born in Ireland, the illegitimate daughter of a lawyer and his serving maid. Her father pretended that she was a child of one of his relatives. Eventually he left his wife for Anne’s mother and took the new family to South Carolina. Daddy got rich in America, and Anne found herself living a life of luxury.
Everything changed when her father made the mistake of objecting to her choice of husband. James Bonny was a seafaring man who was later described as “not worth a groat,” old-fashioned talk for saying he was pretty much worthless. Rather than submit to her father’s wishes, Anne eloped with James to the Bahamas.

From Lady to Pirate

Most stories depict James Bonny as spinelessly unworthy of Anne. Whatever the reason, Anne soon rebelled and left home again, this time with a handsome, freespending man, a pirate named Calico Jack Rackham. Anne and Calico Jack became part of the early eighteenth-century Caribbean piracy boom. Anne’s temper and courage were legendary. A man had once attacked her, and she “beat him so, that he lay ill of it a considerable time.”

Pirate Fashions

Anne “wore men’s cloaths” into battle, but most other times she wore “women’s cloaths.” Her battle outfit was a man’s jacket, long “trouzers,” a handkerchief tied around her head, a pistol in one hand and a machete in the other.

Anne Shows Her Stuff

In 1720 the British, determined to put an end to piracy in their Caribbean colonies, chased down Calico Jack. When the British boarded the ship, only three pirates stayed on deck and fought. One of them was Anne. The rest of the pirates, including Calico Jack, holed up belowdecks. The British captured Calico Jack and his crew and took them to prison. Just before he was to be hanged, Calico Jack was granted leave to visit Anne in prison. If he hoped for any last-minute tenderness, he was disappointed. Anne told him bluntly that she was sorry, “but if he had fought like a man he need not have been hang’d like a dog.” Anne had proved her mettle in her last days at sea.

Her Last Days

Anne would have swung beside her lover, but she “pleaded her belly,” old-fashioned talk for “I’m pregnant.” She didn’t hang, and there’s no record of what did happen to her. Some say her wealthy father secretly arranged her release. Others are sure that clever, feisty Anne saved herself somehow.