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 was to change 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.
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.
1546
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:
1564
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.
1565
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'.
1566
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.
1593
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. She is mentioned in the English State Papers and in other documents of the kind, as well.
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, rarely as Grace O'Malley.
In popular culture, she is often referred to as "The Pirate Queen".
1603
Gráinne O'Malley (Gráinne Ní Mháille, ; – c. 1603), also known as Grace 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.
