# Dictionary of National Biography, 1885-1900/O'Donnell, Hugh Roe

​O'DONNELL, HUGH ROE (1571?–1602), lord of Tyrconnel, grandson of Manus O'Donnell [q. v.], and eldest son of Sir Hugh MacManus O'Donnell and Ineenduv MacDonnell, daughter of James MacDonnell, lord of the Isles, was born about 1571. Rory O'Donnell [q. v.] was his brother. His father, Sir Hugh, had succeeded to the lordship of Tyrconnel on the death of his half-brother, Calvagh O'Donnell [q. v.], in 1566, but his right was disputed by Calvagh's illegitimate son Hugh, called by some MacDeaganach, or the son of the Deacon O'Gallagher. For a long time past there had existed two parties in Tyrconnel—the one inclining to an alliance with the English, the other siding with the O'Neills. The accession of Sir Hugh was more or less a triumph for the anti-English party; but Sir Hugh was a wary politician, and tried to avoid giving offence to either side. By doing so he forfeited the confidence of his own party without entirely satisfying the government. Under the influence of his wife, Ineenduv, Sir Hugh, while stoutly protesting his loyalty, drifted more and more into opposition. Sir John Perrot [q. v.], who disbelieved his assertions and was jealous of his alliance with the Hebridean Scots, fearing complications like those which had occurred in Antrim, placed the country under military control, though subsequently, in 1586, he consented to withdraw the garrison on Sir Hugh agreeing to pay a composition of seven hundred beeves. Meanwhile Hugh Roe O'Donnell was rising to manhood under the supervision of his foster-parent, MacSuibhne na dTuath, and his party were filled with joy at the prospect of ​the realisation of an ancient prophecy, which declared that, when one Hugh should succeed another Hugh immediately and lawfully as O'Donnell, the land should be freed from the yoke of the foreigner.
Sir Hugh having neglected to redeem his promise or surrender hostages for his loyalty, Perrot in September 1587 sent a vessel laden with wine round to Lough Swilly, and the master having inveigled Hugh Roe and his companions, Daniel MacSwiney and Hugh O'Gallagher, on board, under pretence of hospitality, shut the hatches on them and sailed back to Dublin. They were immediately incarcerated in Dublin Castle. Their capture caused an immense sensation, and Hugh Roe's father-in-law, the Earl of Tyrone, offered 1,000l. for his release. After lingering in prison for more than three years, Hugh Roe and his companions managed to escape early in 1591. They succeeded in reaching the Wicklow mountains; but Hugh Roe, after seeking shelter with Phelim O'Toole at Castlekevin, was recaptured and carried back to Dublin. This time extra precautions were taken for his safe custody; but, though heavily ironed, he was able, with the help of a file and a long silken rope secretly conveyed to him, to effect his escape and that of his fellow-prisoners, Henry and Art O'Neill, the sons of Shane O'Neill [q. v.], on Christmas-eve 1591. After two days' wandering among the mountains and exposure to intense cold, they were discovered by friends almost within sight of Ballinacor. Art O'Neill died from the effects of his privations, but Hugh revived sufficiently to be removed to a solitary house in the woods of Glenmalure, where he was affectionately nursed.
The news of his escape was soon noised abroad, and, a messenger from the Earl of Tyrone arriving to escort him home, he passed the Liffey near Dublin, avoiding Drogheda, and, taking the high road through Dundalk, reached Dungannon in safety. After resting there for a few days he was escorted by Hugh Maguire [q. v.] to Ballyshannon on the confines of his own country. His old rival, Hugh MacDeaganach, was no longer alive, having been murdered at the instigation of Ineenduv; but the country was torn with dissensions and entirely at the mercy of Turlough Luineach O'Neill [q. v.] and an English garrison at Donegal under Captain Willis, who kept Sir Hugh ‘as a thrall or vassal to be, as it were, a guide for him in the country.’ With the help of a few faithful followers, Hugh Roe at once marched to Donegal and expelled Willis and his soldiers. But the pain in his feet, which had been badly frost-bitten during his escape, increasing, he returned to Ballyshannon, and, by the advice of his physicians, submitted to have his great toes amputated. The operation afforded him relief, but it was many months before he was completely cured. As soon as he was able to leave his bed he summoned a meeting of the clan to Kilmacrenan at the beginning of May, and, his father having voluntarily surrendered the chieftaincy in his favour, he was inaugurated O'Donnell with the customary ceremonies, though not without signs of dissatisfaction on the part of his cousin, Niall Garv O'Donnell [q. v.]
Taking advantage of the occasion, he immediately invaded the territory of Turlough Luineach O'Neill; but fearing lest his conduct might provoke the lord deputy, Sir William Fitzwilliam [q. v.], to retaliatory measures, he despatched letters to the state explaining his election as O'Donnell and his reasons for invading Turlough Luineach, offering, if the deputy would lend him 800l. or 900l., to repair to him in person. Fitzwilliam, who recognised the necessity of conciliating him, reprimanded him for his arrogant demeanour, but promised, if he would meet him at Dundalk by 6 July, to pardon his escape and lend him 200l. It is not likely that O'Donnell's offers were meant seriously, but, by the advice of the Earl of Tyrone, who was anxious to improve his position with the government, he yielded a reluctant consent, and on 1 Aug. arrived at Dundalk. ‘And the next day, in the afternoon, in the church there, before a great assembly, delivered his humble submission, making great show of sorrow for his misdemeanours committed, protesting hereafter to hold a more dutiful course of life, and very willingly yielded himself to be sworn to perform the several parts of his submission and certain other articles.’ His submission greatly strengthened his position in Tyrconnel, and he at once took advantage of it to crush his opponents, particularly Sir John O'Dogherty, father of Cahir [q. v.], whom he placed in confinement. But there can be no question that his submission was merely a ruse to gain time in which to perfect measures of hostility to the government. In January 1593 information reached Fitzwilliam that emissaries from the pope and king of Spain, chief among whom was Edmund Magauran [q. v.], titular primate of all Ireland, were hospitably entertained by him, and from letters preserved at Simancas (O'Clery, p. 1) it is beyond dispute that application was at this time made by him and Tyrone to Spain for assistance. In March he wrested Belleek from Hugh Duve O'Donnell, and shortly afterwards secured Bundroes, thus opening for himself a pas​sage into Lower Connaught, over which he was determined, when strong enough, to exercise the ancient rights of his clan. Hugh Maguire was drawn into the alliance, and, at O'Donnell's instigation, he in June attacked and defeated Sir Richard Bingham at Tulsk, co. Roscommon. When preparations were made to punish Maguire, O'Donnell, instead of closing the fords of the Erne against him, allowed his cattle to find refuge in Tyrconnel; and, as Bingham was credibly informed, spent four days in his company, arranging a plan of defence. ‘As for O'Donnell,’ remarks his biographer, ‘it was a great affliction of mind and soul to him that the English should go back as they had done. But yet, as they did not attack him, he did not attack them, on account of the unprepared state in which he was, and he left a large body of his people at the aforesaid ford, which he gave for Maguire's protection, though he withdrew himself by command of O'Neill, for there were messages between them secretly, without the knowledge of the English.’ But after the capture of Enniskillen early in 1594 he refused to be bound any longer by Tyrone's Fabian tactics, and in June sat down before the castle, vowing not to leave the siege before he had eaten the last cow in his country. News of the arrival of a body of Scottish mercenaries under Donald Gorme MacDonnell and m'Leod of Arran compelled him to go to Derry, but he left the main body of his army under Maguire. During his absence Sir Henry Duke and the garrison of Philipstown made an attempt to relieve Enniskillen, but they were defeated by Maguire with great loss at the battle of ‘the ford of the biscuits.’ The castle was subsequently relieved by Sir William Russell [q. v.], but in May 1595 was recaptured by Maguire.
On his return to Tyrconnel, O'Donnell, in order to throw dust in the deputy's eyes, offered to submit; but the following year, 1595, opened with a marauding expedition into Connaught, in which, it is said by his biographer, O'Donnell ‘spared no one over fifteen years of age who could not speak Irish.’ In April he invaded the Annaly, in conjunction with Maguire and Tyrone's brother, Cormac MacBaron O'Neill, and captured the castle of Longford, the constable, Christopher Brown, who was held to ransom at 120l., his wife, and two thousand head of cattle. The governor of Sligo, George Bingham the younger, retaliated by destroying the Carmelite monastery at Rathmullen, and plundering Tory Island. But on his return he was murdered by Ulick Burke, a cousin of the Earl of Clanricarde, who handed the castle over to O'Donnell. The possession of Sligo was a great acquisition, and laid Connaught at his feet. In August m'Leod of Arran returned with a contingent of Scottish mercenaries, and O'Donnell again invaded Connaught. He successfully withstood a determined attempt on the part of Sir Richard Bingham to recover Sligo Castle, and, in order that it should not fall into Bingham's hands, he destroyed it, together with thirteen other fortresses. He was now practically master of Connaught, and, having interfered to prevent the Burkes submitting to Sir William Russell, he set up a MacWilliam, a MacDermot, and an O'Conor Sligo of his own. Having some time previously repudiated his wife, the daughter of the Earl of Tyrone, he was anxious, probably for political reasons, to contract an alliance with the Lady Margaret Burke, daughter of the Earl of Clanricarde, and, in order to avoid her forcible abduction, the young lady was placed under the protection of a merchant of Galway.
Towards the close of the year O'Donnell and Tyrone consented to an armistice, and in the beginning of 1596 commissioners Wallop and Gardiner were sent to Dundalk to treat for peace. But O'Donnell, though he agreed to go to the Narrow Acre, flatly refused to enter Dundalk, and the commissioners were fain to treat in the open fields a mile outside the town. Liberty of conscience, pardon for himself and his followers, recognition of his claims in Lower Connaught and Inishowen, and exemption from the jurisdiction of a sheriff, were the only terms on which he would treat, and these not being granted he returned home, strongly urging Tyrone to put an end to the cessation. He was confirmed in his determination by the arrival shortly afterwards of a messenger from Spain, bearing a letter to Tyrone. There can be no question as to the nature of the reply sent by O'Donnell, Tyrone, O'Rourke, and the other chiefs, for their letters are extant (O'Clery, p. lxxviii), but at the time they were successful in deluding the government with their professions of loyalty. Assured of the favour of Philip II, O'Donnell's great object was to postpone an open rupture till the autumn, when assistance from Spain was expected, and to establish his authority in Connaught on a firm basis. With this object, he and Tyrone proffered their assistance to Sir John Norris [q. v.] for the purpose of restoring order in Connaught, and in June O'Donnell actually went thither for the avowed purpose of inducing O'Rourke (Brian Oge) and MacWilliam (Theobald Burke) to submit. Nothing, of course, came of his intervention, and Norris, whose belief in ​Tyrone's loyalty reached infatuation, persisted in hoping against hope, attributing his failure to Russell's bad faith in detaining Philip's letter to Tyrone. At the end of August two ‘barks of adviso’ were announced to have arrived at Killybegs, and O'Donnell, Tyrone, and O'Rourke at once posted thither. Letters signed by them addressed to the king of Spain, the Infante, and Don Juan d'Aquila, were betrayed to the government by Tyrone's secretary, Nott, after which further dissimulation was impossible.
Towards the end of the year Donough O'Conor Sligo was restored; and O'Donnell, after vainly trying to win him over by bribes and threats, again invaded Connaught in January 1597. Accompanied by MacWilliam (Theobald Burke), he plundered O'Conor Sligo's adherents, fired Athenry, and harried the country to the very gates of Galway, returning to Tyrconnel laden with an immense quantity of booty. With the exception of Thomond the whole province lay at his mercy, when Sir Conyers Clifford [q. v.] arrived in February to vindicate the authority of the crown. Owing to the smallness of the force at his disposal, Clifford was for some time compelled to act mainly on the defensive; but, with his assistance, O'Conor Sligo succeeded in March in establishing himself in Sligo, and in forcing O'Donnell to retreat across the Erne. In May Theobald Burke was expelled from Mayo; and, stimulated by his success, Clifford in July made an attempt to capture Ballyshannon. He succeeded in crossing the Erne, but was repulsed with heavy loss by O'Donnell in the neighbourhood of Ballyshannon. Relieved from all apprehension on the side of Connaught, O'Donnell marched to assist Tyrone in an attack on the new fort on the Blackwater, but subsequently consented to a cessation of hostilities. On the renewal of the war in the following summer he again went to Tyrone's assistance, and took part in the memorable defeat of Sir Henry Bagnal at the Yellow Ford on 14 Aug. But hearing that Clifford had designs on Ballymote, he marched thither, and, having forced MacDonough to surrender it, he fixed his residence there and plundered Connaught and Thomond at his pleasure. But his main object was to reduce O'Conor Sligo, and accordingly, in the summer of 1599, he besieged him in Collooney Castle. Essex sent Clifford to O'Conor's assistance; but O'Donnell, who was fully informed of his movements, despatched a strong force under O'Rourke against him. While crossing the Curlews Clifford was attacked by O'Rourke and utterly defeated. O'Conor Sligo thereupon submitted, and his example was followed by Theobald-na-Long (son of Richard-of-the-Iron Burke) [see Malby, Sir Nicholas].
The death of Hugh Maguire early in 1600, and the question of the appointment of his successor, led to a serious difference of opinion between O'Donnell and Tyrone, the former supporting the claims of Maguire's brother Cuconnacht, the latter those of his son Conor. In the end O'Donnell carried the day, but not without giving great offence to Tyrone. In May Sir Henry Docwra [q. v.] arrived in Lough Foyle, and succeeded in entrenching himself at Derry. O'Donnell, who was then at Ballymote, sent his cousin Niall Garv to dislodge him, while he himself went on a marauding expedition into Thomond. The summer passed away, and Docwra continuing to defy Niall Garv, O'Donnell marched against him in September; but failing to draw him from his entrenchments, he returned to Ballymote, and was already preparing for a fresh campaign into Thomond when he was hastily recalled by the news that Niall Garv had gone over to Docwra and that Lifford had fallen into his hands. After several determined but unsuccessful attempts to recover the place, O'Donnell retired across the Finn into winter quarters. His spirits were somewhat revived by the arrival shortly afterwards from Spain of Matthew de Oviedo with a considerable supply of money and arms, which he shared equally with Tyrone. But his policy of aggression was beginning to bear its natural fruit, and old Ulick Burke, earl of Clanricarde, having died in May 1601, his successor, Richard, prepared to attack O'Donnell in his own country. Ever prone to strike the first blow, O'Donnell moved towards Ballymote. His absence afforded Niall Garv an opportunity, which he did not neglect, to capture Donegal and to fortify the abbey. Recalled by this fresh disaster, O'Donnell was still engaged in besieging the place when the news of the arrival of the Spaniards in Kinsale Harbour reached him.
Immediately raising the siege and collecting all his followers together at Ballymote, he moved rapidly southwards, plundering his enemies by the way and successfully evading Sir George Carew, who had been sent to intercept him. Fixing his camp at Bandon, he was joined there at the end of November by Tyrone, when the two chiefs moved to Belgoly, intercepting all communications between the English investing Kinsale and the surrounding country. Both seem to have been agreed as to the policy of starving out the English; but the impatience, or perhaps the privations, of the Spanish commander urging ​them to take the offensive, it was agreed to make a night attack on the besiegers. The attack proved an utter fiasco. O'Donnell's guide lost his way in the dark, and his contingent never came into action at all. Retreating in disorder to Inishannon, the question of renewing the attack was debated; but O'Donnell, who was indignant at their failure, and particularly with the behaviour of the Spanish commander, Don Juan d'Aquila, so that ‘he did not sleep or rest for three days and three nights after,’ refused to listen to the proposal, and having transferred his authority to his brother, Rory O'Donnell, first earl of Tyrconnel [q. v.], he sailed from Castlehaven to Spain on 6 Jan. 1602. Arriving on the 14th at Coruña, where he was hospitably entertained by the Conde de Caraçena, he proceeded to Zamora, where he obtained an audience with Philip III. He was graciously received, but his complaints were listened to coldly, and he was ordered to return to Coruña. The summer passed away and nothing was done. Sick at heart with hope deferred, and vexed with himself for having gone on such a fruitless errand, he complained bitterly to Philip of his treatment. The disgrace of D'Aquila revived his credit, and in August he was summoned to court. But he was taken seriously ill at Simancas, and, after lingering sixteen days, he died on 10 Sept. It was rumoured that he met his death by foul play; and there can be little doubt that he was poisoned by one James Blake of Galway, with the cognisance, if not at the instigation, of Sir George Carew (cf. Cal. Carew MSS. iv. 241, 350). His body was removed to Valladolid, and ‘buried in the chapter of the monastery of St. Francis with great honour and respect, in the most solemn manner any Gael ever before had been interred.’
[O'Clery's Life of Hugh Roe O'Donnell, translated by Edward O'Reilly and edited by the Rev. Denis Murphy, Dublin, 1893, from a manuscript in the Royal Irish Academy, is the principal and best authority. Another copy of the translation is in the British Museum, Egerton MS. 123. Additional sources of information are: Cal. State Papers, Ireland, Eliz.; Cal. Carew MSS.; Stafford's Pacata Hibernia; Rawlinson's Life of Perrot; Fynes Moryson's Itinerary; O'Sullivan-Beare's Historiæ Catholicæ Hiberniæ Compendium; Annals of the Four Masters, chiefly extracts from O'Clery's Life; Docwra's Narration, ed. O'Donovan; O'Rorke's Hist. of Sligo; Irish Genealogies in Harl. MS. 1425.]
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