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While Henry VIII was on the throne of England divorcing his wives the O'Malley (Ó Máille) clan ruled the north west coast of Ireland. Unlike most Irish of the time they were seafarers, taxing anyone who fished off their coast which included ships from as far away as England. The leader of the clan bore the title "The O'Malley."

The O'Malley had a daughter, Grace. Legend says that when she was a young teenage girl she asked her father to take her along on a trading expedition to Spain that he was leading. He came up with what was, admittedly, a lame excuse: he would like to but her long hair might get caught in the ships ropes. Showing the spirit that would eventually put her in front of the most powerful ruler in Europe she cut off most of her hair and presented herself to her father, ready to sail, daring him to come up with another excuse. Whether the legend is true or not, her nickname reflects it: in Gaelic it was Gráinne Mhaol, meaning bald or cropped hair...

Grace went on to become The O'Malley herself, demonstrating remarkable leadership skills, vision and daring. She was a warrior woman in an age when that was against all odds.

And she was a pirate... at least in the eyes of the English who branded her that. That is no small irony, given that the definition of the word "pirate" was the subject of much international debate, diplomacy and dispute in those days: this was the season of Francis Drake after all. Grace O'Malley claimed the northwest coast of Ireland for her clan and raided ships that dared visit there without paying tribute or tax.

At 16 the O'Malley married his daughter to the son of the O'Flaherty, thus uniting the two clans. For a number of years Grace fulfilled that role, bearing three sons to the chief of the Flaherty clan. But when he was killed in battle she returned to O'Malley territory, bringing many loyal O'Flaherty followers with her, thus strengthening her clan.

She then shrewdly married another warlike clan leader, Richard-an-Iarainn Burke, called "Iron Richard," because he always war an ancestral coat of chain mail. Here the story gets unclear. Legend has that she married Burke to gain control of Rockfleet Castle (below), an ideal base for her sea-raiding, and that after one year -- under Irish law at the time -- she divorced him and got to keep the castle. Other accounts say that they stayed married, at least legally, and she bore him a a son before he died or was killed. In any case, Rockfleet Castle became the headquarters for the O'Malley pirate operations from that point onward.

In English documents of the period -- in which she was seen as a dangerous enemy, so their objectivity is questionable -- Grace was accused of promiscuity and other wildness. Whether or not she was promiscuous she was dangerous:

Around the time of her first husband's death came the initial complaints to the English Council in Dublin from Galway's city leaders that O'Flaherty and Ní Mháille ships were behaving like pirates. Because Galway imposed taxes on the ships that traded their goods there, the O'Flahertys, led by Ní Mháille, decided to extract a similar tax from ships traveling in waters off their lands. Ní Mháille's ships would stop and board the traders and demand either cash or a portion of the cargo in exchange for safe passage the rest of the way to Galway. Resistance was met with violence and even murder. Once they obtained their toll, the O'Flaherty ships would disappear into one of the many bays in the area.

By the early 1560s, Ní Mháille had left O'Flaherty territory and returned to her father's holdings on Clare Island. She recruited fighting men from both Ireland and Scotland, transporting the gallowglass mercenaries between their Scottish homes and Irish employers and plundering Scotland's outlying islands on her return trips. In an apparent effort to curry favor with the English, which were engaged in a re-conquest of Ireland at the time, Ní Mháille went to the Lord Deputy of Ireland and offered two hundred fighting men to serve English interests in Ireland and Scotland.

Ní Mháille's attacked other ships at least as far away as Waterford on the south central coast of Ireland, as well as closer to her home port in northwestern Ireland. She did not limit her attacks to other ships. She attacked fortresses on the shoreline, including Curradh Castle at Renvyle and the O'Loughlin castle in the Burren. She also attacked the O'Boyle and MacSweeney clans in their holdings in Burtonport, Killybegs and Lough Swilly.

Eventually Grace became one of the wealthiest and most powerful people in Ireland, increasing her holdings on land as well as her revenue from sea-raids.

She became so powerful and influential that the English began to seriously push back. In 1593 the English governor of Connaught took two of her sons captive. Grace petitioned to Queen Elizabeth I (yes, that Elizabeth: the queen of Shakespeare and Drake and the Spanish Armada), who sent Grace a list of questions about her life, holdings and operations. Apparently the answers were sufficient or impressive enough that Elizabeth granted an audience to Grace, who sailed to England for the meeting.

She met with Elizabeth at Greenwich Palace, wearing a fine gown, the two of them surrounded by guards and the members of Elizabeth's royal Court. Ní Mháille refused to bow before Elizabeth because she did not recognize her as the Queen of Ireland, and wished to show Elizabeth this. It is also rumored that Ní Mháille had a dagger concealed about her person, which guards found upon searching her. Elizabeth's courtiers were said to be very upset and worried, but Ní Mháille informed the queen that she carried it for her own safety--Elizabeth accepted this and, though the dagger was removed from Ní Mháille's possession, did not seem to worry. Some also reported that Ní Mháille sneezed and was given a lace-edged handkerchief from a noblewoman. She apparently blew her nose into the handkerchief and then threw the piece of cloth into a nearby fireplace, much to the shock of the court. Ní Mháille amusedly informed Elizabeth and her court that, in Ireland, a used handkerchief was considered dirty and was destroyed.

They agreed to a list of compromises, but after a short time Grace realized that the English had no intention of making any real changes in their policy, so she reverted to her former policies...
although in her later years she nominally targeted her raids only on the "enemies" of England, which was a slippery definition at best.

Grace O'Malley was a larger than life figure in an age of such figures. During a time of pirates, privateers and explorers she was as wild and adventurous as any of them.