Anne Bonny is probably the most famous female pirate to sail the Spanish Main. She was a ruthless plunderer, raider, and menace to the sea faring vessels in the Caribbean Sea. She is commonly referred to as "Toothless Annie."

Anne was born in Ireland during the 1690's. Her parents moved to America and became well respected plantation owners. She grew up in South Carolina and was fascinated with stories of pirates that were told at the nearby Charleston Port. At Charleston she met a pirate named James Bonny. She married him and the two of them moved to an island in the Caribbean named Nassau. This island was basically run by pirates. Here Anne was surrounded by famous pirates.

James proved a coward and a traitor, becoming a paid snitch for the governor. Anne distanced herself from him, preferring the company of the island's notorious pirates.

She soon became romantically involved with the dashing pirate "Calico Jack" Rackham (nicknamed for his loud striped pants.) When James Bonny objected to the affair, he abducted Anne, brought her naked before the governor and charged her with the felony of deserting him—Anne was considered to be stolen property. Calico Jack suggested instead putting Anne up for sale to the highest bidder, a 'kinder' legal practice for divorce at the time. Despite Jack's rather less-than-romantic proposal, as well as a court order James got forbidding Jack and Anne to see each other, Anne ran away with Calico Jack, joining his ship's crew, apparently disguised as a man.
 
At that time there was a code of piracy that stated women crew members were forbidden. This didn't stop Anne. She went aboard the ship as a man and fought just as the rest of the crew did. Eventually she was discovered and some of the crew members openly voiced their opinions. Anne returned these opinions by killing those crew members. 

Anne was not the only female pirate aboard Rackham's ship. Mary Reed was another woman disguised as a man.  She was captured from an English ship in 1717 and turned pirate.

Mary's mother who had a legitimate son became pregnant after her husband died. She fled to the country to give birth to Mary.  During this time, her son died. The mother returned and brought Mary up as the dead son to get money from her husband's parents.

Still pretending to be male, Mary joined first the navy, then the cavalry. She loved and married a fellow soldier and lived a few years as his wife. When he died, she put on male clothes again and went to the Caribbean.

Before long, Mary fell in love with a man forced to join the pirates. She let him know her secret "by carelessly showing her breasts, which were very white." The man "being made of Flesh and Blood," wanted to go further but Mary resisted. Soon after he quarreled with another pirate and was challenged to a duel. Mary deliberately picked a fight with the same man and ran him through with her cutlass.

Having thus proved her love, Mary and the forced man "plighted their troth to each other, which Mary Read said she look'd upon to be as good as a marriage, in conscience, as if it had been done by a minister in Church."

Through these pirates she met Anne Bonny.  Mary learned Anne's secret when Anne seduced her, thinking her a handsome fellow. In any event, the women became friends and she ended up as a pirate with John Rackham and Anne Bonny. She became Rackham's lover. It is not clear if her 'husband' had died, or Rackham persuaded her to leave him.

Both women were very good at pirating, never shirking from battle. According to one witness, none among the crew were "more resolute, or ready to board or undertake anything that was hazardous."

On a night in October, 1720, sloop William was attacked by a privateer commissioned to take pirates. Witnesses from the privateer stated that only two of the pirates had put up any fight. These two fought like wildcats using pistols, cutlasses and boarding axes. One of them fired a pistol into the hold where the other pirates were hiding while screaming they should come up and fight like men. When the pair were finally overpowered it turned out that they were Anne Bonny and Mary Read.

A trial followed and Rackham, Bonny, Read and many other members of the crew were sentenced to hang. When asked if they had anything to say the women replied, "Milord, we plead our bellies." Both were pregnant. The court decided it could not hang any woman who carried a child.

Mary died of a fever before she could deliver her child. It is not known what happened to Anne, but she may have been paroled because of her father's influence. No matter what happened to her, Anne is probably most famous for the words she exchange with Calico Jack when he was granted the permission to see Anne the last time on the night before his execution. She scolded him: "I'm sorry to see you here, Jack, but if you'd have fought like a man you needn't hang like a dog."

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