O'Malley, Gráinne (Grace) (‘Granuaile’) (c.1530–1603?), noblewoman and sea captain, was the daughter of Eoghan O'Malley (usually known as Dubhdarra O'Malley), lord of Umhall (now the barony of Murrisk, Co. Mayo), and Margaret, daughter of Conchobhar O'Malley. Gráinne (or Grace) had only one other sibling – a natural brother known as Domhnall an Piopa O'Malley; that she was the only issue of her parents’ marriage is confirmed by the fact that she was the sole heir to her mother's lands in the Owles. She was a spirited and wilful child. An anecdote tells how, when Eoghan refused to take her on a voyage to Spain, believing that a ship was no place for a girl, she cropped her hair so that she looked like a boy, which earned her the nickname ‘Grainne Mhaol’ (Grace the Bald). In her youth she developed a liking for cards and gambling; her skill at playing her hand led to another nickname, ‘Grainne na gCearbhach’ (Grace of the Gamblers).
Grainne was first married, about 1546, to the well-born Domhnall An Chogaidh O'Flaherty; as his sobriquet (‘of the War’) suggests, he was an adventurous and ambitious man. They had two sons – Eoghan (d. 1586) and Murchadh (d. in or after 1599) – and a daughter, Margaret (d. in or after 1588). In 1564 the ambitions of Domhnall An Chogaidh, now tánaiste of his dynasty, to become lord of the Flathertys were thwarted when Elizabeth appointed to that position his cousin and rival Murchadh na dTuadh O'Flaherty (Murchadh of the Battleaxes; d. in or after 1593). Soon after this Domhnall An Chogaidh entered into a violent struggle with the Joyces for control of Hen's castle on Lough Corrib, Co. Galway; he was ambushed and killed about 1565 while hunting in the hills above the lough. His enemies now moved to take the castle, thinking that Gráinne would surrender to them, but she defended it successfully and forced them to retreat. After the murder of her husband, Gráinne returned to her own lands, establishing her principal residence on Clare Island. About this time she is said to have taken a lover, a sailor whose ship was wrecked off the island; but the affair was brief as her MacMahon enemies of Ballyvoy caught and killed her lover to spite her. She took revenge by ambushing and killing the murderers on Cahir Island, and then seized the MacMahon castle of Doona in Blacksod Bay, earning herself the sinister epithet ‘Dark Lady of Doona’.
She was married again about 1566 – to Richard An Iarainn Burke (qv) (d. 1583), with whom she had a son, Theobald Bourke (qv) (Tibbot na Long’ – ‘Tibbot of the Ships’; (1567–1629)). With her husband alongside, she became the most feared sea captain on the western seaboard of Ireland, where she used her galleys to harass the shipping that ploughed those seas. She was clearly the dominant partner in this marriage, as Lord Deputy Sir Henry Sidney (qv) observed in his memoirs: ‘she was as well by sea as by land more than a master's mate for him’. Her activities attracted the attention of the government, which led to an unsuccessful siege of her castle of Rockfleet in March 1574. Her meeting with Sir Henry Sidney, and his son Sir Philip Sidney, with whom she engaged in much conversation, took place at Galway in March 1576; when the lord deputy and his entourage wanted a maritime tour around Galway Bay, she took them in her ship but charged them for the experience. It is also said that about this time she sailed to Dublin, putting in at Howth and kidnapping the son of the lord of Howth, whom she held to ransom.
Some time in 1576 Gráinne was captured off Thomond by Gerald fitz James Fitzgerald (qv) (d. 1583), 15th earl of Desmond. He imprisoned her for about eighteen months in Limerick, before, in November 1577, transferring her into the custody of Sir William Drury (qv), president of Munster, as a sign of his loyalty. Gráinne was sent to Dublin, but was released on condition that she mend her ways. In her absence Richard An Iarainn had become involved with the Fitzgeralds of Desmond in plotting a catholic rebellion. Gráinne refused to participate, having no liking for the Fitzgerald architects of the plot, and in 1580 when her husband wished to withdraw she helped him to rehabilitate himself in the eyes of the government. In 1580–81 they gained government recognition of Richard An Iarainn's right to the title of MacWilliam Burke through a policy of diplomacy and force. In October 1582, at the height of their powers, the couple shone at a gathering of the Connacht nobility at the residence of the provincial governor, Sir Nicholas Malby (qv); one observer, noting her confidence among the men, commented: ‘Grany O'Maly thinketh herself to be no small lady’.
Gráinne was a consummate politician and diplomat when need arose. In January 1583, when the soldiers of Theobald Dillon (qv), the government tax collector, appeared on her lands demanding arrears of 600 l., she entertained him and his men with wine and gave them 300 cows to pacify them while she persuaded Malby to cancel her debts. Her fortunes changed in 1584, when, on 3 March, Malby died, to be succeeded as governor of Connacht by Sir Richard Bingham (qv); in September of the same year her husband also died. Gráinne and the new governor were at odds from the start, and in February 1586 they clashed in earnest when Gráinne aided members of the Burke family to escape after they had beaten off Bingham's attack upon their castle on Lough Mask. About June she was arrested by Captain John Bingham, the governor's brother, for alleged involvement in the Connacht rebellion. He treated her harshly, binding her with a rope, and brought her to his brother who threatened to hang her. However, her step-son Richard Burke gained her liberty by pledging his son in her place. In July of that year she suffered another tragedy when her son Murchadh O'Flaherty was murdered by Bingham's soldiers; Burke's subsequent revolt against the English terrified her so much that she fled in her galleys to Ulster, and took refuge with the O'Neills and the O'Donnells until peace was restored. As part of the treaty she was forced to give her son Theobald as a hostage to John Bingham, while she travelled to Dublin and obtained her pardon on 4 May 1588.
The peace was short-lived. On 7 February 1589 Burke killed John Browne, sheriff of Mayo, leading to a rebellion of the catholic nobility of Mayo and north Galway. Gráinne supported Burke, using her ships to supply him with Scots troops as reinforcements. By February 1590 the rebellion had run its course and much of Mayo was devastated. While Burke gained favourable terms for himself, Gráinne fought on until April, plundering the Aran islands, but finally made peace under Burke's surety. In June 1591 she was engaged in fighting Scottish marauders, but Bingham's ships now began to undermine her dominance of the sea, threatening her livelihood. In July 1593 Gráinne petitioned Queen Elizabeth for redress against Bingham, who had lately arrested her son Theobald, on charges of treason, and her brother Domhnall an Piopa O'Malley of Westport. As Bingham was clearly intent on executing her son, Gráinne went with Sir Murchadh na dTuadh O'Flaherty to London to gain an audience with Elizabeth. In early September she was summoned to Greenwich castle, where she made her case to the queen in such terms that on 6 September Elizabeth instigated immediate inquiries into Bingham's behaviour as governor of Connacht. By 19 September Grainne was back in Ireland; under threat that she would make another application to the queen, Bingham finally released his prisoners in late November or early December.
Her feud with Bingham continued, and in 1594 the governor quartered his troops on her lands. She enlisted the help of Elizabeth's cousin Thomas Butler (qv) (d. 1614), 10th earl of Ormond, who championed her cause in a letter to the privy council on 19 April 1595. As her fortunes waned, Gráinne attempted to obtain her widow's share of her late husband's estates, but she was thwarted by her son Murchadh O'Flaherty who had no intention of losing a third of his lands to her. She continued to try to make an income from the sea, in 1596 raiding Thomond and the Scottish lands of MacNeill of Barna. During the Nine Years War, by now an old woman, Grainne sided with the government, and persuaded her sons Theobald and Murchadh to do likewise. In August 1597 the three of them earned a fee of £200 for their service to the crown, but a year later they were punished when the forces of Hugh O'Neill (qv) and Red Hugh O'Donnell (qv) (d. 1602) invaded Connacht and devastated their lands. Gráinne was still alive in July 1601, but it is held that she died about 1603 and was interred on her home island of Clare off the Mayo coast. A statue of her was unveiled in Westport on 18 June 2003 by her descendant Lord Altamont and Dr K. T. Whitaker.