Gráinne O'Malley (, ; – ) was the head of the Ó Máille dynasty in the west of Ireland, and the daughter of Eóghan Dubhdara Ó Máille.

Upon her father's death, she took over active leadership of the lordship by land and sea, despite having a brother, Dónal an Phíopa Ó Máille. Marriage to Dónal an Chogaidh (Donal "of the war") Ó Flaithbheartaigh brought her greater wealth and influence, reportedly owning as much as 1,000 head of cattle and horses. In 1593, when her sons Tibbot Bourke and Murchadh Ó Flaithbheartaigh (Murrough O'Flaherty) and her half-brother Dónal an Phíopa ("Donal of the Pipes") were taken captive by the English governor of Connacht, Sir Richard Bingham, O'Malley sailed to England to petition for their release. She formally presented her request to Queen Elizabeth I at her court in Greenwich Palace.

O'Malley is not mentioned in the Irish annals, so documentary evidence for her life comes mostly from English sources, especially the eighteen "Articles of Interrogatory", questions put to her in writing on behalf of Elizabeth I.See the supplement to Chambers, 2003. She is mentioned in the English State Papers and in other documents of the kind.Lambeth Palace Library, ms. no 601, p. 10, cited in Chambers 2003, p. 85

In Irish folklore she is commonly known as Gráinne Mhaol (anglicised as Granuaile) and is a well-known historical figure in sixteenth-century Irish history. Her name was also rendered in contemporaneous English documents in various ways, including Gráinne O'Maly, Graney O'Mally, Granny ni Maille, Grany O'Mally, Grayn Ny Mayle, Grane ne Male, Grainy O'Maly, and Granee O'Maillie,> never known as Grace O'Malley. In popular culture, she is often referred to as "The Pirate Queen".

Early life O'Malley was born in Ireland around 1530, when Henry VIII was King of England and held the title Lord of Ireland. Under the policies of the English government at the time, the semi-autonomous Irish clans were left mostly to their own devices. However, this changed over the course of O'Malley's life as the Tudor conquest of Ireland gathered pace.

Eoghan Dubhdara Ó Máille, her father, and his family were based in Clew Bay, County Mayo. He was Chief of the Name of Clan Ó Máille and Lord of Umhaill, and claimed descent from Maille mac Conall. The Uí Mháille were one of the seafaring clans of Connacht, and they had built a row of castles facing the sea to protect their territory. They controlled most of what is now the barony of Murrisk in south-west County Mayo and recognised as their nominal overlords the Mac William Íochtar branch of the Bourkes, who controlled much of what is now County Mayo. The Bourke family (Irish: de Búrca) were originally Anglo-Norman (de Burgh) but by O'Malley's lifetime had become completely Gaelicised. Her mother, Margaret or Maeve, was also an O'Malley. Although she was the only child of Dubhdara and his wife, O'Malley had a paternal half-brother called Dónal na Píopa. Although under Brehon Law only male members of the derbhfine could inherit the mantle of Chief of the Name through tanistry, O'Malley "was considered to be the legal retainer of the family land and seafaring activities".

With shore castles like Carrickkildavnet, the Clan Uí Mháille demanded and received black rent from those who fished off their coasts, which included fishermen from as far away as England. The head of the family was known simply by his surname as Ó Máille (anglicised as The O'Malley). The local oral tradition has it that O'Malley, as a young girl, wished to go on a trading expedition to Spain with her father. Upon being told she could not because her long hair would catch in the ship's ropes, she cut off most of her hair to shame her father into taking her. This earned her the nickname "Gráinne Mhaol" (; from maol, meaning 'bald' or 'having cropped hair'), usually anglicised as Granuaile ( ).As used to name the ships ILV Granuaile of the Commissioners of Irish Lights. The nickname may also come from Gráinne Umhaill ("Gráinne of Umhall", Umhall being a historical district of west Connacht dominated by the Uí Mháille).

As a child she most likely lived at her family's residence of Belclare and Clare Island, but she may have been fostered by another family, as fosterage was traditional among the Gaelic nobility of Ireland.

Marriage to Ó Flaithbheartaigh

O'Malley was married in 1546 to Dónal an Chogaidh Ó Flaithbheartaigh, tánaiste or heir to the Chief of the Name of Clan Ó Flaithbheartaigh, which would have been a good political match for the daughter of the Chief of Clan Ó Máille. As Ó Flaithbheartaigh tánaiste, Dónal an Chogaidh had expectations of one day ruling as Lord of Iar Connacht, which was roughly equivalent to modern Connemara.

She bore three children during her marriage to Dónal an Chogaidh: Eóghan (Owen): The eldest child, known to be kind and forgiving. Sir Richard Bingham tricked him; Owen was murdered as a result, and Bingham and his troops took over his castle. Méadhbh (Maeve): Said to be much like her mother, she married Richard "the Devils Hook" Bourke, 22nd Mac William Íochtar (d.1601) with whom she had several children. O'Malley and Bourke were supposedly very close, more than once he saved her from death. Murchadh (Murrough): Murrough was said to take after his father, for he enjoyed warfare. He often beat his sister Maeve, and refused to listen to his mother because of her sex. Many sources report that he betrayed his family and joined forces with Sir Richard Bingham after the murder of Owen. When O'Malley heard of this she swore she would never speak to Murrough again for the rest of her life, though she would often insult him. After Dónal an Chogaidh's death, O'Malley left Iar Connacht and returned to Umhaill, taking with her many Clan Ó Flaithbheartaigh warriors.

In 1564, Dónal's ambitions were dashed when his kinsman Murrough na dTuadh Ó Flaithbheartaigh was appointed by Queen Elizabeth as Chief of the Name instead of him. In 1565, Dónal was killed in an ambush while hunting in the hills surrounding Lough Corrib. His assassination was, undoubtedly, part of Dónal's wider struggle against Clan Joyce for control of Hen's Castle upon the lough. When the Joyces moved to take the Castle, thinking that Gráinne would not resist, she fought back successfully and forced Clan Joyce to retreat. O'Malley then returned to her own lands and established her principal residence upon Clare Island (now called Granuaile's Castle). She allegedly took a shipwrecked sailor as her lover. The affair lasted only briefly as he was killed by Clan MacMahon of Ballyvoy. Seeking vengeance, O'Malley attacked Clan MacMahon's stronghold of Doona Castle in Blacksod Bay and slew her lover's murderers upon Caher Island. Her veangence against Clan MacMahon earned Gráinne the nickname the 'Dark Lady of Doona'.

Marriage to Bourke

By 1566, O'Malley had married a second time, this time to Risdeárd an Iarainn ("Iron Richard") Bourke, 18th Mac William Íochtar (d.1583), his nickname deriving from his ironworks at Burrishoole, the place of his principal castle and residence. Tibbot, 1st Viscount Mayo, was a child of this marriage.

Still not satisfied with her revenge, O'Malley then sailed for Ballycroy and attacked the garrison at Doona Castle, overpowering the defenders and taking the castle for herself. Her attack against the MacMahons was not the first time she interrupted someone at their prayers. Legend tells of another lord who stole property from her and fled to a church for sanctuary. She was determined to wait out the thief, maintaining that he could starve or surrender. The thief dug a tunnel and escaped, however, and the hermit who took care of the church broke his vow of silence to scold her for attempting to harm someone who had sought sanctuary. Her reply is not recorded.

More than twenty years after her death, an English Lord Deputy of Ireland recalled her ability as a leader of fighting men, noting the fame she still had among the Irish people.Calendar of State Papers Relating to Ireland (James I) 1623, no. 997. (London 1860–1912)

Autonomous status In 1576, O'Malley engaged in the surrender and regrant process with the Lord Deputy Sir Henry Sidney in respect of her lands. Because Rockfleet was over a week's march from Dublin, and as she was so often at sea, control by the Crown was very weak.

In 1593, in his letter to protest O'Malley's claims against him, Sir Richard Bingham claimed that she was "nurse to all rebellions in the province for this forty years".Lambeth Palace Library MS 601, p. 111 Bingham was Lord President of Connacht, tasked with controlling local lords who had, until then, been mostly autonomous.

O'Malley had every reason, and used every opportunity, to limit the power of the Kingdom of Ireland over her part of the country. An expedition from Galway led by Sheriff William Óge Martyn attacked her castle at Clare Island in March 1579. However, they were put to flight and barely escaped.

Meeting with Elizabeth

In the late 16th century, English power steadily grew in Ireland and O'Malley's power was steadily encroached upon. In June 1593, O'Malley sent a petition to the Queen. She asked her "to grant her some reasonable maintenance for the little tyme she hath to live". In return she offered "a surrender at her hands" of the lands of her two sons and those of her two surviving Bourke nephews. She asked for "free libertye during her lyve to envade with sword and fire all your highness enemyes wheresoever they are or shall be ... without any interruption of any person or persons whatsoever".Grace O'Malley: the biography of Ireland's Pirate Queen (40th anniversary ed.), 2018 In May 1593, Hugh Maguire (Lord of Fermanagh) rebelled and burned Ballymote, then under the control of Sir George Bingham. One of Maguire's men was captured and implicated Grace's son Tibbott-ne-Long in a wider Tyrone- inspired conspiracy against the English. Tibbott was promptly captured by Sir Richard Bingham, sent to Athlone prison and charged with treason. Grace's half-brother Dónal na Píopa was also arrested by Sir Richard Bingham and charged with the murder of some English soldiers. Grace sailed to England to petition Queen Elizabeth I for their release. She was accompanied by Sir-Murrough-ne-Doe O'Flaherty. Sir Richard Bingham implied that Grace sailed her own ship to England as he stated she brought over the son of Ulick Bourke of Erris and her grandnephew, the son of Tibbott Reagh Bourke who "attended uppon Grany O'Maille in her late beyinge at court". The Earl of Ormond, cousin and favourite of the Queen, gave Grace an introduction to Lord Burghley, chief advisor to the Queen. Burghley sent O'Malley a list of questions, "eighteen articles of interrogatory" which were answered and returned.

At around the same time, Sir Richard Bingham wrote to Burghley: "There be 2 notable traitors gon over Sir Morrow ne doe and Grainy O’Maly both rebelle from their childhoode and continually in accion ... for notwithstanding that they have many pardons there ys matter ynough of late found out against them to hang them by justice".

Tradition but not the written sources states that O'Malley met with the Queen at Greenwich Palace, wearing a fine gown; the two of them were surrounded by guards and the members of Elizabeth's royal court.