1. Cheng I Sao
One of history’s most influential raiders began her career in a Chinese brothel. Cheng I Sao, or the “wife of Cheng,” was a Cantonese former prostitute who married a powerful corsair named Cheng I in 1801. The husband and wife team soon raised one of China’s most formidable pirate armies. Their outfit boasted hundreds of ships and some 50,000 men, and it preyed on the fishing vessels, supply junks and coastal villages of Southern China with impunity.
Upon her husband’s death in 1807, Mrs. Cheng elbowed her way into power and partnered with a trusted lieutenant and lover named Chang Pao. Over the next few years, she plundered her way across Southeast Asia and assembled a fleet that rivaled many countries’ navies. She also penned a rigorous code of conduct for her pirates. Rape of female prisoners was punishable by beheading, and deserters had their ears lopped off. Mrs. Cheng’s bloody reign made her public enemy number one of the Chinese government, and in 1810, the British and Portuguese navies were enlisted to bring her to justice. Rather than duking it out at sea, she shrewdly agreed to surrender her fleet and lay down her cutlass in exchange for the right to keep her ill-gotten riches. Mrs. Cheng retired as one of history’s most successful pirates and went on to run a gambling house until her death in 1844 at the age of 69.
2. Anne Bonny
The notorious pirate Anne Bonny began her life as the illegitimate daughter of a wealthy Irish lawyer. In an effort to hide her dubious parentage, her father had her dress a boy and pose as his law clerk for part of her youth. She later moved to America, where she married a sailor in 1718 and journeyed to the pirate-infested island of New Providence in the Bahamas. There, she abandoned her husband and fell under the spell of “Calico” Jack Rackam, a flamboyant buccaneer who plied his trade in the Caribbean.
Bonny had always been known for her “fierce and courageous temper”—according to one legend, she nearly beat a man to death when he tried to force himself on her—and she quickly showed she could guzzle rum, curse and wield a pistol and cutlass with the best of Calico Jack’s crew. She later forged a friendship with fellow female pirate Mary Read, and the pair played a leading role in a spree of raids against small fishing boats and trading sloops in the summer and fall of 1720. Bonny’s stint on the high seas was cut short that October when Calico Jack’s ship was captured by a band of pirate hunters. Calico Jack and several other men were executed, but Bonny and Read dodged the noose after they were both found to be pregnant.
3. Mary Read
Born in England in the late 17th century, Mary Read spent most of her youth disguised as her deceased half-brother so that her penniless mother could scam the boy’s grandmother. Hoping to quench her thirst for adventure, she later adopted the name Mark Read and took on a succession of traditionally male jobs, first as a soldier and later as a merchant sailor. Read turned pirate in the late-1710s, after buccaneers attacked the ship she was working on and impressed her into their ranks. She later found her way aboard Calico Jack Rackam’s boat, where she met and befriended Anne Bonny and revealed herself to be a woman.
Read only sailed with Calico Jack for a few months, but during that time she won a fearsome reputation. One of her most famous exploits came in October 1720, when she and Bonny fought like banshees during an attack by pirate hunters. “If there’s a man among ye,” she supposedly screamed at the male buccaneers cowering below decks, “ye’ll come up and fight like the man ye are to be!” Despite Read’s heroics, she and the rest of Calico Jack’s crew were captured and charged with piracy. Read avoided execution by admitting she was “quick with child,” but she later came down with a fever and died in prison.
4. Grace O’Malley
During a time when most women were denied an education and kept restrained to their homes, pirate Grace O’Malley led a 20-ship fleet that stood up to the might of the British monarchy. Also known as “Granuaille,” or “bald,” for her habit of cutting her hair short, O’Malley was born into a powerful clan that lorded over the coastlines of western Ireland. After taking the reins in the 1560s, she continued a family tradition of piracy by plundering English and Spanish shipping vessels and attacking rival chieftains. Her escapades were legendary—one tale claims she did battle at sea only a day after giving birth—but they also drew the ire of the authorities. She was forced to repel a siege against her stronghold at Rockfleet Castle in 1574 and later did 18 months behind bars after she was captured during one of her raids.
O’Malley resumed her marauding after her release, but more trouble arrived in the early 1590s when British authorities impounded her fleet. With nowhere else to turn, the 63-year-old buccaneer appealed directly to Queen Elizabeth I for assistance. During a famous royal audience in London, O’Malley portrayed herself as a tired and broken old woman and begged the Queen to return her ships, release one of her captured sons and allow her to retire in peace. The gambit worked, but it seems that “Granuaille” didn’t keep up her end of the bargain—records show that she and her sons continued pirating until her death in 1603.
5. Rachel Wall
Rachel Wall’s biography is peppered with myths and legends, but if certain tales about her are true, she was one of the first and only American women to try her hand at piracy. As the story goes, Wall was a Pennsylvania native who ran away from home as a teen and married a fisherman named George Wall. The couple settled in Boston and tried to scrape out a living, but constant money problems eventually led them to turn to a life of crime. In 1781, the Walls procured a small boat, teamed with a few low-life mariners and began preying on ships off the coast of New England. Their strategy was as ingenious as it was brutal. Whenever a storm passed through the region, the buccaneers would dress their boat up to look like it had been ravaged by rough seas. The comely Rachel would then stand on the deck and plead for aid from passing ships. When the unsuspecting rescuers came near, they were promptly boarded, robbed and murdered.
Wall’s siren song may have lured as many as a dozen ships to their doom, but her luck ran out in 1782 when a real storm destroyed her boat and killed George. She continued her thieving on land and was later arrested in 1789 for attacking and robbing a Boston woman. While in prison, she penned a confession admitting to “Sabbath-breaking, stealing, lying, disobedience to parents, and almost every other sin a person could commit, except murder.” Unfortunately for Wall, the mea culpa was not enough to sway the authorities. On October 8, she became the last woman ever executed in Massachusetts when she was hanged to death in Boston.