O'Toole, Rose (d. c. 1629), politically significant member of O'Toole family, was the eldest child of Fiach O'Toole (qv) (d. 1578), lord of Fartry and Ferter, and Rose Basnett, daughter of Edward Basnett (d. 1545), dean of St Patrick's cathedral. The Basnett family originated in Denbighshire and may have come to Ireland as clients of Sir Anthony St Leger (qv), lord deputy of Ireland; in the 1540s and 1550s they acquired lands in the lordships of the O'Tooles and the O'Byrne , bringing them into closer contact with local Irish nobility. Fiach O'Toole probably married Rose Basnett in the mid-1550s. As a child Rose O'Toole was fostered with Thomas Garrahall of ‘Ballelocha’. She was said to be beautiful and intelligent, and in the mythology of Glenmalure she was remembered as a strange and wicked figure who wore a long, blood-red cloak. About 1573 she became the second wife of Fiach O'Byrne (qv), son of Aodh O'Byrne (qv), lord of Crioch Raghnuill; their union was happy though they had no children, and Rose became a devout catholic like her husband, abandoning completely her loyalist protestant background.
O'Byrne's rising stock among the Leinster nobility overshadowed both his own father and Fiach O'Toole, which led to a serious rift between him and his father-in-law. On 11 February 1575 Fiach O'Toole made a statement to government officials investigating the dealings of the Leinster Irish with Gerald FitzGerald (qv) (d. 1585), earl of Kildare. He stated that O'Byrne had colluded with Kildare in a programme of extortion throughout western Wicklow and Kildare, and accused the earl of authorising O'Byrne to attack the Wesleys of Bishopscourt, Co. Kildare, and to destroy much of Castledermot. Rose probably saved her father by dissuading O'Byrne from taking revenge on him. The government cemented their links with Fiach O'Toole by appointing him sheriff of Co. Dublin, probably in 1576.
In 1578–9 a number of deaths among the Leinster nobility – Ruaidhri Óg O'More (qv), Brian MacMurrough Kavanagh (qv), Fiach O'Toole, and Aodh O'Byrne – left Fiach O'Byrne as the most powerful lord in the region. In August 1579, with Rose's help and advice, he began to plot with James Eustace (qv), 3rd Viscount Baltinglass, against the Dublin government. When war broke out in June 1580 Rose remained in the mountains, but she was captured by English forces in January 1581, and under interrogation told her captors that Kildare had promised his support when O'Byrne went to war; her motive may have been to take revenge on the earl for his failure to stand by her husband. O'Byrne made peace terms in August 1581 and Rose was released. Together they set about repairing their dynasty's position within the Wicklow region. They appeared together with their followers in pardons of 1584 and 1586. To consolidate the connection of their two families, O'Byrne's younger sons from his first marriage, Phelim O'Byrne (qv) and Reamain O'Byrne (d. in or after 1642), were married to Rose's sisters Una O'Toole (d. 1628) and Katharine O'Toole. Rose had a notoriously bad relationship with O'Byrne's eldest son and heir, Toirdhealbhach O'Byrne (d. 1595), and it is significant that he was not given in marriage to one of her sisters; instead he married Dorothy, daughter of Murchadh mac Edmund O'Byrne. Feilim and Reamain and their wives reputedly hated Toirdhealbhach, and, according to English intelligence reports, the tensions between him and his stepmother worsened in the early 1590s: Rose was intent on his destruction in order to procure Crioch Raghnuill for her younger stepsons when Fiach died.
By the early 1590s O'Byrne and Rose's family were again at odds, this time owing to the hostility of her brother Barnaby O'Toole (qv) of Castlekevin (d. 1597). These poor relations manifested themselves during the escape of Hugh O'Donnell (qv) (d. 1602) from Dublin castle in January 1591. Accounts of what happened vary but it is clear that O'Donnell fled into the Wicklow mountains with the English in pursuit and took refuge at Castlekevin; he was given up to the English either under duress by Rose and her brother Feilim O'Toole (qv) (d. in or after 1603) or voluntarily by Barnaby O'Toole. In any event O'Donnell's fate was a serious embarassment to O'Byrne.
Rose was without doubt privy to all O'Byrne's plans, and played a central role as his emissary, attracting the attention both of powerful men and of the government: in 1594, for example, James fitz Piers FitzGerald accused Adam Loftus (qv), archbishop of Dublin, of entertaining her in his house. Her subtle political skills, beauty, and ruthlessness were all put to good use in pursuit of her husband's interests. After 18 March 1594 O'Byrne was effectively at war again with the government, and in an attack on Ballinacor in Glenmalure by Sir William Russell (qv), lord deputy of Ireland, Rose was present as a spectator of the fighting. O'Byrne was defeated and he and his wife were forced to flee for their lives. On 28 April Rose was captured by Sir Henry Harrington (d. 1605), seneschal of the O'Byrne and O'Toole countries, and was sent to Dublin for trial on charges of treason; on 27 May she was sentenced to be burned as a witch. Three days later O'Byrne was wounded by English soldiers, and, realising that the catholic leadership was in disarray, Russell decided to exploit their weakness, using Rose as a bargaining counter. He persuaded her that Toirdhealbhach intended to betray his father to the English; Rose warned O'Byrne, who arrested his son and opened negotiations with Harrington through an intermediary, offering to trade Toirdhealbhach and Uaithne O'More (qv) for Rose. On 1 June Harrington informed Russell that O'Byrne would surrender Toirdhealbhach and Maurice FitzGerald (d. 1595), and on the 7th O'Byrne wrote asking for a pardon for him, Rose, and his followers, in exchange for the promised hostages. Toirdhealbhach and FitzGerald were sent to Dublin on 18 June, where English officials tried to bargain with Toirdhealbhach to kill his father, which he refused to do. He was accordingly executed on 18 July and Rose was quietly released and returned to her husband.
In early 1596 O'Byrne probably used Rose to help repair his nexus of alliances, for he made an alliance at this time with her brother Barnaby. In September 1596 Barnaby and Feilim O'Toole threw their weight behind the campaign of O'Byrne and Domhnall MacMurrough Kavanagh (qv) (d. 1632), king of Leinster, threatening to besiege Castlekevin, and burning throughout much of east Wicklow and south Dublin; Russell counter-attacked around Glenmalure throughout October. Barnaby O'Toole died of cholera on 17 January 1597, and his loss prompted O'Byrne to shore up his alliance with the O'Tooles of Castlekevin by marrying his daughter Margaret O'Byrne (d. in or after 1601), the widow of Walter Riabhach FitzGerald (d. 1595), to Feilim. With Russell in the ascendant, O'Byrne is alleged to have negotiated secretly with both Harrington and Sir William Harpoole, constable of Carlow, using Rose as his envoy: Captain Thomas Lee claimed that Harrington held several secret conferences with Rose at Newcastle McKynegan during the height of Russell's offensive, and Donnchadh O'Brien (d. 1624), 4th earl of Thomond, accused Harpoole of harbouring Rose during Russell's campaign. While this evidence is not wholly trustworthy, it is not implausible, and O'Byrne may also have wanted to send his wife away from the war zone as the military situation became increasingly desperate.
In April 1597 Hugh O'Neill (qv), 2nd earl of Tyrone, threatened to send a force to Wicklow and met with Sir John Norris (qv), president of Munster, before telling O'Byrne to send Rose to attend peace talks on 17 April. While these plans were in train O'Byrne was killed by Russell's soldiers on 8 May, and Rose was again captured and brought to Dublin on 18 June, where she was again sentenced on 3 July to be burned at the stake. But again her execution was postponed: according to Captain Thomas Lee the sentence was not carried out because Rose ‘offered if she may have her liberty and pardon, she will draw such a draught upon Feagh's sons whom Lee has banished that he would have the killing of them’. While no evidence can be found to prove that Rose harmed O'Byrne's sons, it is strange that she was released on 7 January 1598 and pardoned on 1 February. The English placed bonds on her freedom again when she failed to attend an interview to which she had been summoned, but Phelim O'Byrne made her freedom a condition of his submission in June 1598. At this time she was held in such high esteem by her stepsons that poems were commissioned to commend her decision to remain single despite offers of marriage; but by 1599 a serious rift had emerged between them, for unknown reasons, and Rose left the O'Byrne lands. She was recorded as living in Dublin in May 1606 and reputedly ended her days as a prisoner in Carlow castle, dying there in the late 1620s.