Hugh Roe O'Donnell

O'Donnell, Hugh Roe, Lord of Tirconnell, son of Hugh Duv, younger son of Manus O'Donnell, was born in 1571. His mother was a MacDonnell. As his family were rising rapidly into importance, and their influence was dreaded by the Anglo-Irish Government, young Hugh was one of those marked for capture by Sir John Perrot, in carrying out his policy of holding hostages for the good behaviour of the Irish chiefs

In the summer of 1587, an armed vessel laden with Spanish wine was sent round from Dublin to Lough Swilly, and anchored off Rathmullen, near which it was known O'Donnell was sojourning with MacSweeny, his foster-father. O'Donnell and a party of his friends were inveigled on board and plied with wine: the hatches were fastened down, and the vessel sailed, regardless of the imprecations of the crowds that lined the beach, and MacSweeny's offers of ransom. We are told by the Four Masters, who give graphic details of most of the incidents in O'Donnell's life, that "the Lord-Justice and the Council were rejoiced at the arrival of Hugh; though, indeed, not for love of him. .. They ordered him to be put into a strong stone castle [the Birmingham Tower] which was in the city, where a great number of Milesian nobles were in chains and captivity, and also some of the old English. The only amusement and conversation by which these beguiled the time by day and night was lamenting to each other their sufferings and troubles, and listening to the cruel sentences passed on the high-born nobles of Ireland in general."

In the winter of 1590, after an incarceration of more than three years, he and some of his companions managed to escape by means of a rope from the window of their prison, and made their way out of the city and into a wood on the side of Slieve Roe (the Dublin mountains). There Hugh, overcome with fatigue, was obliged to conceal himself, while his companions scattered in different directions, and his servant went to seek help from Felim O'Toole, residing at Powerscourt, whom Hugh believed to be his friend, as he had visited him when in prison. But O'Toole, on the plea that escape was impossible, and that he would be compromised by O'Donnell's presence in his territory, returned him to captivity. A year afterwards, in December 1591, he made a more successful effort, in company with Henry and Art O'Neill, sons of Shane. They managed to strike off each others' fetters, and let themselves down through the jakes.

Once clear of the Castle, they were met by Turlough Roe O'Hagan, a confidential emissary of Hugh O'Neill, and again reached the mountains. They had to throw off their outer clothes in their descent, the weather was bitterly cold, and their limbs were cramped through having long borne fetters. They lost Henry O'Neill in passing through the city, and on the side of Slieve Roe, Hugh and Art, completely exhausted, lay down under a rock, while O'Hagan hurried on to Glenmalure. Feagh O'Byrne proved a sincere friend, and sent servants with assistance. The youths were found covered with snow. Art O'Neill was dead, and O'Donnell was with difficulty restored to consciousness.

They buried Art beside the rock which had sheltered them. Hugh was carefully tended in Glenmalure for some days, and then escorted across the Liffey by a band of horsemen, amongst whom, strange to say, was his former betrayer, Felim O'Toole. Proceeding northwards, under the guidance of O'Hagan, Hugh crossed the Boyne by a ferry kept "by a poor little fisherman," whilst his attendant led their horses through Drogheda. At Mellifont they rested one night in the house of a friendly Englishman, pushed boldly through Dundalk, crossed the Fews, and on the third day reached Armagh.

Next day they were safe with Hugh O'Neill at Dungannon, where it is presumed the two chiefs entered into an alliance, and talked over their plans of resistance to the Anglo-Irish power. O'Donnell was received with great rejoicings by his relatives, the Maguires; was conveyed across Lough Erne; and soon found himself once more among his own people at Ballyshannon. There he remained under the care of physicians until April, having to suffer amputation of his great toes, which had been frostbitten on Slieve Roe. On 3rd of May (1592) his father resigned the lordship and he was solemnly inaugurated The O'Donnell. The first use he made of his power was to march into Tyrone and pillage the country of Sir Turlough Luineach O'Neill, then in alliance with the Anglo- Irish. He besieged him in his castle of Strabane, and burned the town up to the walls of the fortress. His friend, Hugh O'Neill, fearing that his exploits would bring against them both the full power of the Pale, brought about a meeting between him and the Lord-Deputy at Dundalk.

A free pardon was accorded him, his title of O'Donnell was acknowledged, and for a short time he settled down in the undisputed government of his ancestral domain. Two years afterwards, in 1594, when the Lord-Deputy placed a garrison in Enniskillen, he threw off all semblance of allegiance, proceeded to the aid of his friend Maguire, besieged the castle of Enniskillen, and wasted the lands of those who lived under English jurisdiction. A force for the relief of the town, under Bingham, Sir Edward Herbert, and Sir Henry Duke was defeated with heavy loss by Maguire at Bel-Atha-na-mBriosgaidh (Drumane bridge, on the river Arney), whereupon the garrison capitulated, and was permitted to depart unharmed. It is unnecessary to enumerate the minor operations of the war between the northern confederacy and the Government, in which he acted such an important part. In 1595, when Hugh O'Neill went openly into rebellion, O'Donnell threw himself heartily into the struggle.

In March and April he skirmished in Connaught, moving with such rapidity as to escape any serious collision with the forces of the Lord-Deputy. His successes raised the confidence of the Irish, and Sligo was given up to him by Ulick Burke. With the aid of 600 Scots under MacLeod of Ara, he overran the country as far as Tuam and Dunmore, raised the siege of Sligo, and demolished the castle, that it might not be re-occupied by the English. In the autumn he again marched out and destroyed thirteen castles. In 1596 three Spanish pinnaces arrived off the coast of Donegal, bringing a supply of military stores and encouraging letters, addressed specially to O'Donnell, who entertained Philip III.'s messenger with great state at Lifford.

He took part in the conference between O'Neill and the Queen's Commissioners at Dundalk early in the same year. On 24th July 1597, Sir Conyers Clifford assembled a large force at Boyle, marched into O'Donnell's territory, and laid siege to Ballyshannon Castle, which was defended by Crawford, a Scotchman, and a garrison of eighty men, of whom some were Spaniards. The arrival of O'Donnell obliged Clifford to retreat to Sligo, abandoning three pieces of ordnance and a quantity of stores, and losing several men in fording the Erne at Assaroe. O'Donnell commanded the cavalry in O'Neill's defeat of Marshal Bagnall, at the Yellow Ford, on 14th August 1598. In the autumn he purchased the castle of Ballymote, and made it his principal residence.

The following spring he invaded Thomond in force, and swept the country of its cattle. The Four Masters' tell us that when he saw "the surrounding hills covered and darkened with the herds and numerous cattle of the territories through which his troops had passed, he proceeded on his way homewards, over the chain of rugged-topped mountains of Burren." On 15th August 1599, O'Donnell defeated an English force under Sir Conyers Clifford at Ballaghboy, on the side of the Curlew Mountains in Sligo. According to Fynes Moryson, the English lost only 120 men; whilst O'Sullivan Beare says their loss numbered 1,400. Sir Conyers Clifford was amongst the slain. The Irish annalists mourn his tragic end:— "He had never told them a falsehood." He was buried on Trinity Island, in Lough Key.

The most important military operations of 1600 were in Munster. In the north, Niall Garv O'Donnell, Hugh's brother-in-law, with his brothers, went over to the English side. Hugh made several incursions into Thomond to harass the Queen's allies, and in May attempted to dislodge Sir Henry Docwra, who had landed 4,000 foot and 200 horse on the shores of Lough Foyle, and entrenched himself at Culmore. O'Donnell spent Christmas of 1600 at Dunneill (Castlequarter), in the County of Sligo; and a few days afterwards proceeded with O'Neill to Killybegs, to divide the money and munitions of war landed from a Spanish vessel.

The war dragged on through the summer of 1601, and in September, Hugh attacked Niall Garv O'Donnell, who with some 500 English troops occupied the old monastery of Donegal. The building was quickly set on fire; but Niall held out with indomitable bravery, and managed to make good his retreat in the night, leaving nothing but the charred walls of the building. Soon afterwards, when news reached O'Neill and O'Donnell of the arrival of the Spanish fleet, under Don Juan d'Aguila, at Kinsale, they hastened south to join him, O'Donnell, with his habitual ardour, being first on the way. With a force of about 2,500 hardy men, he set out about the end of October, and reached Ikerrin, in Tipperary, where he purposed to await O'Neill.

Finding his passage south barred by Sir George Carew and Lord St. Lawrence, he took advantage of a hard frost to pass by a circuitous route across Slieve Felim, and by the Abbey of Owney to Croom, which he reached on the 23rd November, after a march of forty miles in one day. On 21st December he and O'Neill appeared before Kinsale with some 6,000 native foot and 400 horse, besides 300 Spaniards from Castlehaven. Their effort on the morning of the 24th to raise the siege by an attack on Mountjoy's lines, was a failure, and the Spaniards were obliged to capitulate on the 2nd January.

We are told that "O'Donnell was seized with great fury, rage, and anxiety of mind, so that he did not sleep or rest soundly for the space of three days and three nights afterwards." Desiring to seek further assistance from Philip III., he sailed with a few attendants, from Castlehaven on the 6th January 1602, and landed at Corunna on the 16th. He was graciously received by Philip III. at Zamora, in Castile, was promised assistance in men and money, and desired to wait at Corunna.

The summer passed away without the royal promises being fulfilled, and heart-sick for his cause and country, he again resolved to visit the King. He set out for Valladolid, but fell sick at Simancas, and died on the 10th September 1602, aged about 30. He was buried with royal honours in the monastery of St. Francis in Valladolid — a building long since demolished. O'Donnell, who had been the sword as O'Neill had been the brain of the Ulster confederacy, is said to have married a daughter of the Earl of Tyrone.

He left no children, and his branch of the family is now believed to be extinct. Mr. Wills pays the following tribute to his character: "O'Donnell, of all the Irishmen of his day, seems to have been actuated by a purpose independent of self-interest; and though much of this is to be traced to a sense of injury and the thirst of a vindictive spirit, strongly impressed at an early age, and cherished for many years of suffering, so as to amount to an education; yet, in the mingled motives of the human breast, it may be allowed that his hatred to the English was tempered and dignified with the desire to vindicate the honour and freedom of his country. And if we look to the fickleness, venality, suppleness, and want of truth which permanently characterizes the best of his allies in the strife — their readiness to submit and to rebel — O'Donnell's steady and unbending zeal, patience, caution, firmness, tenacity of purpose, steady consistency, and indefatigable energy, may bear an honourable comparison with the virtues of any other illustrious leader whose name adorns the history of his time."


196. Irishmen, Lives of Illustrious and Distinguished, Rev. James Wills, D.D. 6 vols. or 12 parts. Dublin, 1840-'7.

52. Burke, Sir Bernard: Dormant, Abeyant, Forfeited, and Extinct Peerages. London, 1866.

134. Four Masters, Annals of Ireland by the: Translated and Edited by John O'Donovan. 7 vols. Dublin, 1856.

170a. Ireland, History of: Martin Haverty. Dublin, 1860.