Grace O'Malley amassed more than nine tons of treasure, had deep scars on her face from where an eagle had attacked her and gave birth to one of her children while being attacked by Barbary pirates. She was a legend in her own time. Born around 1530 she didn't know the meaning of the word "no". She began her pirate career as a teenager, likely begging her father "Black Oak" O'Malley to go on a trading trip to Spain. When he told her that her hair would get caught in the ropes, she cut it off and everyone began calling her "Grace the Bald". She was soon an expert sailor.
The O'Malley's motto was "Powerful by land and by sea." They ate a lot of fish and had better furniture and beer than their neighbors because they stole it from ships that cruised by. Their three-story castle on the out of the way island of Clare was cold and damp but provided a site from which to hit ships that were on their way to Galway. They would hide out in secret inlets and raid ships then let it go. The family would also gamble with dice, have fun with traveling musicians, and gobble down on meats and vegetables and mead while fighting with their neighbors.
There were at least sixty independent Irish tribes ruled by chieftains like Black Oak who were constantly fighting with each other and England who tried to impose its rule. Black Oak was one of the few who never gave into English rule and he taught his spirited daughter the same.
At sixteen she got married to "Donal of the Battles". While he was out battling the neighbors she raised their three children. While she was supposed to be taking care of the home and kids instead she was out raiding ships. Donal died when she was in her thirties, his enemies attacking Cock's Castle. Grace sent the enemy running so fast that the castle soon became known as "Hen's Castle". When the English came to take the castle she would run out of ammunition and she would melt down the roof and pour it on top of the Englishmen's heads.
When Black Oak died, Grace took control of her father's fleet of ships. Three and twenty ships at a time raided all the way from Scotland to Spain and she had around two hundred loyal men under her command bringing in salt, wine, silk, and steel. It's pretty amazing that all those men would follow a woman but perhaps its because she was so successful or because she was the daughter of Big Oak and the wife of Donal.
Grace would marry again for property to a man who wore a coat of mail and was called Iron Richard. He had a castle called Rockfleet Castle that offered her even more wealth and a haven for her work. This marriage was what is known as handfasting. After the year and a day she called it off but kept his castle calling out from it "I dismiss you!" She may have dismissed him that day, but she wouldn't from her life as the two would keep in touch and have a child, Toby of the Ships together.
Grace considered herself doing the job of "maintenance by land and sea" rather than that of a pirate. She was caught once and arrested as "director of thieves and murders at sea." Those arreseted with her were killed but she spent a horrid year and a half in prison before being set free. Her biggest enemy was provincial governor Rochard Bingham who hated her and felt that she was a "woman who overstepped the part of womanhood." He killed her son Owen, took lots of her cattle and horses, put her son Toby in prison for a year, and just generally made her life hell, even creating a gallows for her.
After one of her sons sided with Bingham and she killed four of his men she was now sixty-four and had had enough. She set out for London to meet with the most powerful woman in the world, Queen Elizabeth I. Queen Elizabeth I sent her a list of eighteen questions about her family and Ireland proved to be interesting enough for the Queen to agree to meet with her. So the Queen of England and the Queen of the Pirates met and whatever was said must have been interesting enough for the Queen because she decreed that Bingham was to "have pity on the poor aged woman" and allow her "maintenance" to continue. She also said that Grace "hath at times lived out of order." Grace returned to a life at sea and outlived many of her enemies. She died at age seventy-three.
*Those at Howth Castle, north of Dublin still set out an extra chair and place setting at meals, because one day Grace was traveling by needing respite. The lord of Howth turned her away. She, in turn, kidnapped his grandson and held him until the Lord promised to always hold a place at his table for travelers.
**Thanks to Kathleen Krull who wrote Lives of the Pirates: Swashbucklers, Scoundrels (Neighbors Beware!)
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