The ultimate "tomboy" has to have been Mary Read, born in England circa 1685. Mary Read's mother had been abandoned by her second "husband" (there is little evidence about Mary's mother, but a great deal about her, as you'll soon understand), after she had become pregnant with her second child. That child, a boy, died in infancy. Mary's mother then decided upon a ruse to support herself and her daughter. She went to London to the home of her absent husband's mother, and, having dressed Mary as a boy, presented "him" as her son, and begged an income from the woman. She got a crown (five shillings) a week, an extremely generous settlement in that day and age. Mary continued to live life as a boy, no doubt because of the close proximity of her "grandmother." At about age 13 or 14, her "grandmother" either tired of supporting the pair, or was running low on funds, and cut the subsidy to a half-crown. So Mary's mother decided Mary needed to make her way in the world (i suspect she was on the booze, because they could have lived on a half-crown a week as it was), and put out as a footman's boy to a French noblewoman living in London. Mary didn't care at all for her new situation, and ran away, joining the Royal Navy, where she served for about three years as a ship's boy (liable for any "sh*t work" needed) and powder monkey--carrying gunpowder to the guns in battle.
One characteristic that is notable about Mary Read is that she seemed very ambitious to make her way in life. She soon learned that having no patron and no influential friends, she would have no opportunity to become a midshipman and someday become an officer, so she jumped ship in Flanders. She joined the army of the Duke of Marlborough and Prince Eugene, fighting the armies of Louis XIV in Flanders, and became a cornet (a sort of officer candidate) in a regiment of foot. Here she served with great distinction, and was noted in reports for her cool demeanor and courage under fire. But she learned that once again, her humble background and lack of funds would prevent her from becoming an officer. So she transferred to a regiment of horse, with a very high recommendation from her former regimental commander, and again showed the same courage and aplomb under fire, in fact being recommended to favorable attention of the Duke himself as "a courageous and intelligent boy." (Her lack of a beard lead others to constantly consider her an adolescent.) The commander of that cavalry regiment was so impressed that he purchased a commission for Mary, and she finally achieved her goal of becoming an officer.
However, emotion now intervened. She had fallen in love with another cornet, and revealing her true gender to him by the simple expedient of showing her breasts to him, she professed her love. To her delighted surprise, the young man was not put off, and agreed to her suit. They both sold their commissions, but as the lowest rank of officer, the two combined sums would not have provided them much support, but another officer took up their cause. Although it was now commonly known in the army that Mary was in fact a woman, this helped rather than harmed her cause, and a collection was taken up in her old infantry regiment and in the cavalry regiment in which she had recently served, and a trousseau was purchase for her, and combined with the proceeds she and her new husband had gotten from selling their commissions, and inn was purchased for them at Breda.
While the war of the Spanish Succession lasted, they had a good life, as officers and gentlemen with the army made a point of patronizing their inn when they were in Holland. But then peace broke out, and in the same year, Mary's husband died. Either the inn no longer provided sufficient income, or Mary grew restless, because she again donned men's clothing, purchased a commission with the proceeds from the sale of the inn, and joined a Dutch regiment serving on the frontier.
There, her old problem cropped up, she learned that she would likely not qualify for promotion, both because she lacked the funds to purchase a higher rank and no war meant no advancement for merit. So she took ship in a Dutch merchant sailing for the Carribean, as always, in the guise of a man. The ship was taken by pirates in the Leeward Islands, and the standard signing offer was made--sign on or swim. Mary signed on, and when the crew grew restless at what they considered the timidity of their captain, he was deposed, and Mary elected in his place because of courage and fighting abilities.
At that time, another woman had become a pirate in the Carribean. Anne Bonny had been a "bruiser" all her life, at one point while living in South Carolina, she had beaten senseless a boy who attempted to take liberties with her person. Her father, who from the accounts seems to have loved her dearly, moved to the island of New Provindence, in the Bahamas, where Nassau is now located. Anne took fencing lessons there for a short while, until she disarmed her fencing master using the technique he had taught her, and her father decided it was a waste of money to pay the man any longer. He had wanted her to marry, and she did marry Mr. Bonny, but was dissatisfied. She took up with another man, but he was ambitious for a place in the exclusive little world of New Providence "society" which did not appeal to her. After some nasty remark made to her by the daughter of the Governor or Jamaica at a ball at the Govenor's mansion on New Providence, she punched the woman out, knocking out her two front teeth. She then drifted into the society of the smugglers and pirates at New Providence, because she had always been better treated by them than by "society." Her she met John Rackham. Rackham had been quartermaster on a privateer, and when Captain Vane had not seemed ambitious enough for them, there was a mutiny and Rackham was made captain. In 1709, a general pardon had been issued, which Rackham and his crew apparently took advantage of. Rackham dabbled in smuggling, but when the Governor on New Providence announced that letters of marque (a "piracy license") would be issued for war against the Spanish, Rackham assembled a crew and taking Anne Bonny with him, set out to practice his old trade. Fond of brightly colored cotton shirts, he became known as "Calico Jack" Rackham, although style rather than piratical success seems to have been the origin of his fame. By the time Mary Read arrived in the Caribbean, Anne Bonny had been left pregnant in Cuba by Rackham, and her infant son dying, had been taken back aboard by Rackham, and increasingly ran the operation, being much more aggressive than Calico Jack.
Although accounts vary, it seems the Mary Read's ship was taken by Rackham as they sailed for New Providence to get a letter of marque. Given the option to sign on, Mary stepped forward, and is reputed to have said that "and any man with me who is not a dog
will sign on as well."
From that time forward, the trio skyrocketed to the top of the piracy business, but not because of Rackham. Anne took an interst in the aggressive "boy," and apparently did not lose her interest on learning that Mary Read was a woman. They were finally taken off the coast of Jamaica in 1720 by an English brig. Mary and Anne were the only ones who put up a real fight, with Mary stepping back to the hatch to swear at the cowards below, and fire her pistol down into the cowering mass of drunken pirates. At their trial, Anne and Mary were said to have been the first on to the deck of any ship taken, and to have been the most ferocious fighters. Jack Rackham was condemned to be hanged, but Anne and Mary "plead their bellies," meaning their sentences were commuted to imprisonment because they were pregnant. Mary Read died of childbed fever in Jamaica, at about age 36 or 37. Anne Bonny was pardoned after the birth of her son, and lived quietly in Port Royale for a few years, under supervision of the government, but one day she and her son disappeard, and were lost to history.
Now that's a real tomboy.