Anne Bonny: When You Give A Redhead A Cutlass

When the authorities finally caught up with Anne Bonny in October 1720, her crew was drunk, her boyfriend was hiding below deck, and she was one of the only people on the ship still holding a weapon. This tells you almost everything you need to know about the type of woman she was.

Anne was born around 1697; red-haired and, by all accounts, furious about something from the very start — the illegitimate daughter of an Irish lawyer and his housemaid. When the scandal got too loud in County Cork, her father sailed the family to the Province of Carolina, reinvented himself as a planter, and did quite well. Anne repaid his efforts by marrying James Bonny, a sailor of no particular distinction or income, entirely against his wishes. Her father disowned her. The couple decamped to Nassau, in the Bahamas — essentially a playground to revel in debauchery and shenanigans.

Nassau was lawless, loud, and full of the most interesting criminals in the Atlantic world. It was there that Anne met John Rackham — "Calico Jack," named for the brightly patterned breeches he wore, because pirates had opinions about fashion. He was bold, charming, and captaining his own crew. Anne was immediately done with James Bonny.

Rackham tried the legal route — he offered to buy Anne's freedom outright, a practice called "divorce by sale" that was, improbably, a real thing. James refused. So on the night of 22 August 1720, Anne disguised herself as a man, helped Rackham steal the William — a sloop belonging to a man named John Ham — right out of Nassau harbour, and joined the crew. She wasn't alone in the deception: Mary Read, also sailing under a male alias, was already aboard. The two became close companions and, presumably, the only people on the ship with any shared secrets.

In October 1720, former privateer Jonathan Barnet caught up with them at night off the coast of Jamaica. Most of Rackham's crew were below decks, deep in rum, and in no condition to fight. Anne Bonny, Mary Read, and one other crew member held the deck alone. Anne reportedly screamed at the men hiding below to come up and fight. They did not. The William was taken.

At trial in Spanish Town, Calico Jack was convicted and sentenced to hang. Anne was allowed a final visit. She looked at the man she'd abandoned everything for and delivered one of the great send-offs in recorded history: "I am sorry to see you here, but if you had fought like a man, you need not have been hang'd like a dog."

Both Anne and Mary Read were condemned to death but pleaded pregnancy, stalling their executions. Mary Read died in prison the following year.

And Anne? She simply vanishes. No execution, no confirmed death. Some historians think her father bought her freedom. Others believe she quietly returned to South Carolina, remarried, and lived out an entirely ordinary life — which, after everything, would be the most surprising ending of all.

History never found her again. Somehow, that tracks perfectly.