O'Toole, Feilim (c.1525–1603), was the third son of Toirdhealbhach O'Toole (qv) (d. 1542), lord of the O'Tooles, and Sadhbh MacMurrough, daughter of Muircheartach MacMurrough Kavanagh (qv) (d. 1547). On 15 May 1543 Lord Deputy Sir Anthony St Leger (qv) and the Dublin council wrote to Henry VIII, informing him of the death of Feilim's eldest brother, Toirdhealbhach O'Toole (qv). They asked that the lands of Toirdhealbhach Óg be granted to the next in line, Brian O'Toole (qv) (Brian an Chogaidh). The latter realised that Feilim commanded strong support among the O'Tooles, so he was shrewd enough to accommodate his younger brother. This he achieved by sharing Powerscourt and some of the lands of Fercullen (now Co. Wicklow) with Feilim, greatly stabilising his own power as the leading lord of the O'Tooles. Indeed, this situation proved satisfactory for both brothers, but the sudden death of Brian on 23 March 1549 changed everything.
Brian left two sons, Arthur Severus O'Toole (qv) and his brother Donnchadh O'Toole. Feilim proved less than generous, dispossessing the sons of Brian An Chogaidh of their lands, leaving him the unchallenged lord of Powerscourt and Fercullen. As the 1550s wore on, Feilim, like so many of his fellow nobles in Leinster, became increasingly concerned about the government's intentions. Much of this concern centred on the government's curtailing of the traditional power of the Irish nobility. In May 1556 he with his cousin Fiach O'Toole (qv) of Castlekevin (d. 1578) and the O'Tooles of Imaal joined Diarmait Kavanagh (d. p.1570) and Brian MacMurrough Kavanagh (qv) (d. 1578) to attack the Pale. Their raid proved unsuccessful and they retreated to Feilim's castle at Powerscourt, but surrendered after the English threatened to bombard them. All the prisoners were taken to Dublin. In 1591 Arthur Severus said that eighty prisoners were taken from Powerscourt to Dublin, to be executed publicly on the green there. The leaders, including Fiach of Castlekevin, the O'Tooles of Imaal and the Kavanaghs, were pardoned on 8 June, but strangely Feilim was not included in this pardon.
In spite of this Feilim returned to Fercullen and ruthlessly consolidated his hold on his lands. Later in local folklore Feilim was remembered as a strict enforcer of his rights over his tenants. In particular he directed his attention upon the freeholders in the uplands of Glencap in north Wicklow, persecuting them mercilessly until they gave him his traditional rents. This led him into conflict with Fiach of Castlekevin, who also had a claim to the rents there. Soon a local war broke out between the O'Tooles, leading the freeholders of Glencap in July 1557 to bring a case before Lord Deputy Thomas Radcliffe (qv), 3rd earl of Sussex. As Glencap fell under the jurisdiction of the sheriff of Co. Dublin, Sussex ordered the O'Tooles to cease their dispute and desist from levying their traditional dues. It is likely that Feilim simply ignored this decision and continued as usual, earning a pardon on 22 November 1559 for his involvement in the killing of a Hugh MacCostello.
In spite of this Feilim – like Fiach of Castlekevin – moved closer to the marcher families of Dublin, taking Mary Talbot of Belgard as his first wife. He also appears to have caused some trouble in the Pale during the summer and autumn of 1566, earning another pardon on 4 February 1567. Feilim though was appalled by the grant of 17 December 1568 of Idrone to Sir Peter Carew (qv), which dispossessed Sir Edmund Butler (qv) of Cloghgrenan (d. 1602) and many of the Kavanaghs. His sympathy for their cause went beyond mere sentiment: he and some of the O'Byrnes of Newrath were implicated in the Butler rebellion after it broke out in June 1569. Feilim's actions went unpunished, and he was again pardoned on 12 March 1571. It appears, though, that the government tried to reconcile Feilim between 1571 and 1577, appointing him sheriff of Co. Dublin.
About 1578 Feilim began to turn against the government, and obtained another pardon with Apollenaris Talbot that year. Increasingly he was to turn to Fiach O'Byrne (qv) of Crioch Raghnuill. Over the previous decade, O'Byrne had emerged from the shadows of his charismatic father – Aodh O'Byrne (qv) – to become the most powerful Irish warlord in Leinster. Feilim was probably attracted into O'Byrne's camp by his fervent championing of the catholic cause. Clearly O'Byrne's views got an eager audience from Feilim, a devout catholic. Later he was said to have proved his zeal by hanging unfortunate protestants near his castle of Powerscourt. The new alliance was sealed in 1579–80 by Feilim's marriage to O'Byrne's sister Elizabeth O'Byrne (d. p.1609), the widow of Brian MacMurrough Kavanagh.
Another reason behind Feilim's alliance with O'Byrne was probably the threat posed by the claims of his nephew Arthur Severus, who apparently returned to Ireland from England during the early 1570s, and began a long campaign to obtain entry into the lands of his father, Brian an Chogaidh. Feilim, however, held that he was the legitimate lord of Powerscourt and Fercullen. Arthur Severus – possessed of his father's letters patent to the lordship – then pressed his claims under common law before the English privy council. In March 1578 the privy council, agreeing with Arthur's case, decided to seek a resolution to his dispute with Feilim. A letter was dispatched to the Dublin government, ordering it ‘to make some reasonable composicion between them to the relief of them both’. For the time being, the privy council also decreed that Arthur Severus be accorded a horseman's wages and granted him licence to repair to England for resolution of his case. Unfortunately for him, the growing instability in Leinster from 1578 onwards meant that his case was shelved for years.
When O'Byrne and James Eustace (qv), 3rd Viscount Baltinglass, began their war on the government during the summer of 1580, Feilim unsurprisingly was one of its most eager supporters. After their victory at Glenmalure on 25 August 1580, the war turned steadily in favour of Lord Deputy Arthur Grey de Wilton (qv). By late April 1581 Feilim found the pressure too intense, and he was granted a pardon on 13 May. However, Feilim quickly returned to the fight, but reapplied for a pardon on 17 July. On 23 August 1581 Grey authorised Sir Henry Harrington to receive O'Byrne to mercy on condition he disband his forces. Baltinglass was clearly protected by O'Byrne and still had access to his nexus in Leinster.
With O'Byrne's approval, Feilim and the O'Connor Falys joined Baltinglass in attacks upon the Pale in October 1581. That Baltinglass was preparing to flee to Spain was confirmed by the petitions of Feilim and Conchobhar O'Connor Faly (d. 1583) for pardons on 10 October. On 13 November Geoffrey Fenton (qv) (d. 1608), secretary of the council in Dublin, recommended that Feilim be admitted to protection. He, though, was playing a double game, having links also with the rebel Nugents in Westmeath. On the night of 17 December 1581, Feilim burnt much of St Patrick's Street in Dublin – a direct slight upon Archbishop Adam Loftus (qv). However, one of the raiding party was captured, and under interrogation confessed to coming from Glenmalure, thereby implicating O'Byrne in the actions of Feilim. The next day Feilim paid dearly for his daring when Captain Edward Denny (d. 1599) killed his son Garret O'Toole. Briefly, Feilim continued to fight, but the execution of another of his sons along with two sons of Ruaidhrí Óg O'More (qv) (d. 1578) convinced him of the benefits of peace. In January 1582 it was decided once more to pardon Feilim. On 22 February Feilim, in the company of Harrington, went to Dublin for his pardon. However, it was not formally issued until 18 March.
Feilim now sought to secure his tenure on his lands against Arthur Severus, petitioning the queen for letters patent on 27 May. Elizabeth, however, would not accede to his wish. For the next few years, Feilim remained at peace, but in an obscure incident he ran foul of the government during 1586 and was condemned to death. He was reprieved, though, and at this stage he appears to have turned against O'Byrne. Feilim's decision to change tack may have been influenced by the re-emergence of Arthur Severus's suit. In October 1587 Arthur Severus wrote to Elizabeth, asking her to intercede for him. News of his demands were received with trepidation in government circles at Dublin, as the memory of Feilim's attacks during the early 1580s remained.
But Lord Deputy John Perrot (qv) took Arthur Severus under his wing and promoted his claims. Perrot's patronage had a hidden agenda: he used Arthur Severus's claims as a lever to force Feilim to fight O'Byrne during 1587 and 1588. By September 1588 O'Byrne had the ridden the storm, and he took his revenge. During a venomous parley, O'Byrne clashed violently with Feilim, forcing Feilim to flee for his life. On O'Byrne's orders, his son Toirdhealbhach O'Byrne (d. 1595), with Kavanagh help, ruthlessly stamped out Feilim's rebellion, forcing his recognition of O'Byrne overlordship about Christmas 1588.
After Feilim's failure to curb O'Byrne and his reluctant return to the latter's camp, he caused trouble along the borders of Dublin, which convinced Perrot that he was mistaken in supporting Arthur Severus. The need for the security of the Pale now forced the government to ignore Arthur Severus's case. In 1590 Feilim, realising that advantage lay with him, suggested that the case should be tried before a Dublin jury. This proved unacceptable and the case dragged on. Again Arthur Severus petitioned Elizabeth for redress of his grievances in June 1591, accusing Lord Deputy Sir William Fitzwilliam (qv) and Perrot of supporting Feilim and of trying to have him killed. In desperation, he even challenged Feilim to a duel, offering to tie one hand behind his back to give the latter a chance. Feilim did not dignify him with a reply, as the government continued to appease him and his O'Byrne master. Arthur Severus, though, remained defiant and never relinquished his claims to Fercullen. He died shortly after 1597.
Feilim still longed to free himself of the dominance of O'Byrne. And when conflict broke out between O'Byrne and the government in the autumn of 1594, he supported the government. As the net closed around O'Byrne in the early months of 1597, Feilim stepped up his efforts to win government favour, killing and capturing several of O'Byrne's supporters in March. Old habits died hard with Feilim, though, and he was again in trouble with the government during 1599. Then he was pardoned along with his wife and Nicholas Walsh for unspecified offences.
Although Feilim did take care not to become implicated in the ongoing Nine Years War, government figures cast covetous eyes over his lands. On 14 May 1603 at a place near Powerscourt known as the Killing Hollow, Feilim was confronted by a party of English led by Jacques Wingfield. This was the latest episode in an ongoing feud. On this occasion Feilim used a leather bridle and reins to control his horse, not his usual metal ones. Wingfield now spotted his chance, and cut the reins of Feilim's horse, making it unmanageable. Feilim, then almost eighty, fell off, and was hacked to death before being beheaded. Thus the life of the last and most ruthless but effective Irish lord of Powerscourt and Fercullen was ended. He was succeeded by his grandson Toirdhealbhach mac Garret O'Toole (d. 1616), but the Wingfields were granted Powerscourt in September 1603.