O'Donnell, ‘Red’ Hugh (Ó Domhnaill, Aodh Ruadh) (c.1572–1602), Gaelic lord, was the eldest son of Sir Hugh O'Donnell (qv) and Fiona MacDonnell (qv), nicknamed ‘Iníon Dubh’. His father had been the ruling lord of Tyrconnell since 1566, and his mother, O'Donnell's second wife, because of close Scottish connections, had good access to the mercenary forces known as ‘Redshanks’. On account of this connection, English commentators often pejoratively referred to Red Hugh as ‘Scottish’. He was fostered among the MacSweeneys and O'Cahans and among other branches of the O'Donnell family. He saw his first military action along with his father's chief adviser, Sir Eoin O'Gallagher, against the O'Rourkes in 1584. By this stage he was widely regarded as his father's most likely successor and as a result had been betrothed to Rose, the daughter of Hugh O'Neill (qv), earl of Tyrone.
Captivity and escape To stop a powerful O'Neill–O'Donnell alliance emerging in Ulster, Lord Deputy John Perrot (qv) hatched a plan to kidnap Red Hugh. In September 1587 Sir Hugh O'Donnell was called to a conference with the lord deputy while the Matthew of Dublin, captained by Nicholas Barnes, was dispatched to Rathmullen. There Red Hugh, along with the sons of MacSweeny Fanad, MacSweeny na d'Tuath, and O'Gallagher, were invited on board to drink wine and taken captive. After the prisoners were turned over to the gaoler of Dublin castle, Barnes was rewarded with £100 sterling for ‘his industry and policy’ (Anal. Hib., no. 1 (1930), 97).
Because of the premature senility of his father, the detention of Red Hugh proved a disaster for his family and supporters. English captains sent into Tyrconnell pillaged and ransomed at pleasure in the country, and competitors from other septs of the family set out their stall for the O'Donnellship. The earl of Tyrone, describing his son-in-law's imprisonment as ‘the most prejudice which could happen unto me’ (PRO Sp 63/132, no. 31), lobbied fruitlessly in Dublin and London for his release. O'Donnell and his wife offered large bribes for his son's release. When O'Neill's men took thirty Spanish officers captive from the shipwrecked armada vessel in Inishowen, the aging chieftain brought the prisoners to the Pale in the vain hope of exchanging them for his son.
In January 1591 Red Hugh made his first escape attempt. Having successfully broken gaol, he was, however, turned over again to the Dublin authorities by Feilim O'Toole (qv) (d. 1605). As a result of this he was more heavily shackled than before. At Christmas the same year, he and Henry O'Neill and Art mac Shane O'Neill (qv), after being unshackled to eat, escaped through the privies of Dublin castle using a silk rope supplied by Richard Weston, a servant of Hugh O'Neill. This was also achieved through corruption nurtured by bribes proffered by O'Neill – indeed, a servant of one of the gaolers acted as their guide. In Dublin Henry mac Shane parted company with the younger men, who headed southwards in search of assistance from Fiach MacHugh O'Byrne (qv). However, they were poorly dressed for the cold conditions; Art got injured and had to be carried. Eventually the guide left them behind in a cave. By the time a search party sent out by O'Byrne discovered them, Art had died of exposure. Red Hugh recuperated in O'Byrne's fastness in Glenmalure and swore oaths of mutual assistance if attacked by the English. Soon afterwards O'Donnell was escorted back to Ulster by Turlough Boye O'Hagan, one of Hugh O'Neill's household officers, staying the night in secret with Garret Moore (qv) at Mellifont and at Dungannon castle. Later surgeons in Tyrconnell had to amputate his big toes because of the frostbite he had suffered in the Dublin mountains. Not surprisingly, Hugh's imprisonment left him with a hatred of the English. Furthermore, in prison he learned the language of patriotism from fellow internees, Old English veterans of the Desmond war. When O'Donnell later complained about his captivity – no doubt speaking English also learned during his time in Dublin castle – government commissioners reminded him and O'Neill that they themselves kept hostages for policy reasons.
Re-entry into Tyrconnell politics Hugh's mother was the key to his re-entry into Tyrconnell politics. Iníon Dubh, with her Scots mercenaries, had already disposed of his rivals. Hugh ‘son of the Dean’ O'Gallagher, who had been affiliated into the Lifford branch of the O'Donnell family, foolishly went to Iníon Dubh's house at Mongavlin on the Foyle, where she incited her Scots bodyguards to kill him. In 1590 she rallied the redshanks and the gallowglasses against the rising power of Donnell O'Donnell, Red Hugh's half-brother from his father's first marriage and newly appointed sheriff of Donegal, defeating and killing him at Doire Leathan. When Hugh returned from Dublin, it was his mother who organised the retirement of his aged father and stage-managed her son's inauguration at the O'Donnell inaugural site at Kilmacrenan in April 1592. Soon after, he attacked Turlough Luineach O'Neill (qv). By this, Red Hugh not only aided his father-in-law Hugh O'Neill to complete the acquisition of power in Tyrone but also halted the assistance which old O'Neill, based at Strabane, had formerly provided to O'Donnell's opponents in Tyrconnell. O'Doherty was captured at a parley and imprisoned; Niall Garvach O'Donnell (qv) fled to the Pale; and early in 1593 Hugh Dubh O'Donnell was finally reduced after his last stronghold was taken and sixteen of his followers beheaded ‘by train of a feigned treaty of friendship, mediated by Maguire’ (CSPI 1592–6, 86). Hugh O'Donnell even felt strong enough to renew O'Donnell interest in north Connacht, much to the chagrin of the lord president, Sir Richard Bingham (qv). In July 1592 he gained government recognition when, escorted by Hugh O'Neill, he travelled to Dundalk and submitted to Lord Deputy William Fitzwilliam (qv). Having greased Fitzwilliam's palm with £500, he promised to treat his rivals fairly, to banish catholic priests and prelates, and not to support the MacWilliam Bourkes in Connacht. Only the latter article seems to have been kept, and that for only a short time. The rapid rise of Red Hugh at this time was echoed in the popular belief that he was the fulfillment of the prophecy of St Columba (qv) foretelling a lord destined to liberate Ireland.
Resisting government intrusion, 1592–6 In September 1592 Archbishop Edmund Magauran (qv) returned from Spain, and in December a conference of northern bishops met in Tyrconnell. At the beginning of 1593 O'Donnell wrote to Philip II of Spain, urging an invasion of Ireland in the midst of an Irish revolt which he would promote. But it was after the crown had sent a sheriff into Fermanagh that James O'Hely, archbishop of Tuam (1591–5), carried this and other letters to Spain. There he informed the Spanish government that the Ulster lords had united to oppose further English aggression and that Hugh O'Neill was a secret member of their confederacy. O'Donnell sent soldiers to aid Maguire's resistance to crown intrusion but he feigned neutrality, and at the battle of Beleek in October 1593, according to the historian Lughaidh Ó Cléirigh (qv), ‘he withdrew himself by command of O'Neill, for there were messages between them secretly without the knowledge of the English’ (Walsh (ed.), Life of Aodh Ruadh, i, 67). Early the following year the crown demanded that O'Neill take further action in bringing O'Donnell to book, but he refused to do so. When soon after they together met government commissioners near Dundalk, the latter concluded that a strong combination existed between them and the other Ulster lords in opposition to government intrusion. In the summer of 1594 O'Donnell showed himself in open action against the state at the siege of Enniskillen, yet he continued to negotiate through the offices of O'Neill. He presented his grievances stretching over many years in a long document entitled ‘A note of such oppressions and indirect courses as hath been held in Tirconnell and other places'; on the other hand he began to demand the return of Connacht lords exiled in Tyrconnell and increasingly the restoration of former O'Donnell lands and levies in Connacht. In 1595 Red Hugh began an expansionary drive, launching big raids into Roscommon and Longford. Then in June, in a stroke of luck, the castle of Sligo – the key to the province of Connacht – was betrayed to him. Thereafter Bingham's government, and the composition of Connacht which sustained it, collapsed. Making the reestablishment of tanist law his rallying-call, O'Donnell asserted suzerainty over north Connacht in a Christmas progress which culminated in a stage-managed election of one of the exiles, Tibbot Fitzwalter Kittagh, as the Lower MacWilliam Bourke.
By this stage O'Donnell and O'Neill had tendered their submissions to the state and they entered into face-to-face negotiations with crown commissioners in January 1596. O'Donnell demanded his ancestral claims and rents in Sligo and his right to seek pardon on behalf of O'Rourke, Bourke, and the other Connacht men who had taken part with him. Like O'Neill he demanded liberty of conscience. When a compromise was cobbled together, he refused to make a personal submission or give hostages. This settlement was aborted by the arrival of Spanish agents in Tyrconnell in May 1596. Alonso Cobos met O'Donnell at Lifford but he refused to agree anything ‘because there was one above him naming O'Neill, which if he would consent unto it he would do the same’ (PRO SP 63/189, no. 40). When O'Neill arrived talks took place in secret in a small house beside the castle where he, his brother Cormac MacBaron and O'Donnell met Cobos with Hugh Boye MacDavitt of Inishowen, a veteran of the Spanish wars in the Low Countries, acting as interpreter. As a result they agreed to renege on the compromise peace and await Spanish help, with O'Neill and O'Donnell writing jointly to Philip II, asking for a Spanish expeditionary force and a Habsburg prince to rule over them.
Partners in rebellion, 1596–1601 In the meantime they set out to frustrate the peace. O'Neill sent his secretary Henry Hovenden ostensibly to assist O'Donnell in the pacification of Connacht, but the state intercepted a letter boasting that ‘all the delays that could possibly be used for prolonging the causes here have not been omitted’ (Cal. Carew MSS, 1589–1600, 178–9). Soon after O'Donnell met the other confederate lords at Strabane and together issued a circular letter to the men of Munster demanding their adherence for ‘Christ's catholic religion’. In 1597 the English went on the offensive again but O'Donnell and his allies prevented the advance of Lord President Conyers Clifford (qv) over the River Erne. In autumn of 1597 negotiations were renewed but in the spring of 1598 the government commissioners abandoned the process believing that O'Neill and O'Donnell were simply playing cat and mouse with them. In the talks process O'Neill would play ‘soft cop’ and O'Donnell ‘hard cop’. On many occasions O'Neill claimed that he could not come to agreement because O'Donnell was not present. On one occasion he brandished a letter from O'Donnell, which he alleged prevented him agreeing. At first the crown negotiators considered O'Donnell to be the extremist, but when they eventually negotiated with both of them, they concluded that O'Neill and O'Donnell were partners in rebellion. In the negotiations the two confederate leaders deliberately upped their demands to extend their oath-bound confederacy nationwide and used all manner of delaying tactics to buy time for a Spanish landing in Ireland.
However, only the occasional Spanish ship was arriving to buoy them up with official promises. In April 1600 O'Donnell sent the sons of O'Doherty and O'Gallagher as hostages, but after another mission arrived late in 1600, it was reported: ‘O'Donnell was like a madman when he saw no kind of news, neither of men nor money to come’ (CSPI, 1600–01, 152–3). While awaiting the promised Spanish armada, O'Donnell had extended his power southwards. The large devastating raids he led are vividly described by Ó Cléirigh. In 1597 and 1598 O'Donnell burned Co. Galway with the support of competitors to the Clanrickard title. In late 1599 and 1601 he raided Thomond but found no O'Briens to support because the earl had locked up his competitors. In the meantime another English offensive in Connacht had been thwarted. O'Rourke and MacDermott attacked Lord President Clifford at the Curlew pass in August 1599 and delivered his head to O'Donnell, who carried it around as a trophy. As a result O'Donnell was able to imprison O'Connor Sligo, whose power Clifford had been shoring up as a counterweight against him.
Red Hugh's marriage policy also was part of his expansionary strategy. In 1595, with O'Neill's consent, he had separated from Rose, who had not borne him any children, in the hope of marrying or even kidnapping Lady Margaret Burke, daughter of the earl of Clanrickard, who had refused to join in the revolt. He took Rose back but she was soon after married to Donnell Ballach O'Cahan (qv). In 1600 there was another plot, this time for him to marry the sister of the earl of Desmond (qv) (d. 1601). As was the case in the Clanrickard plot, the government placed Lady Joan under house arrest as a precaution against her being spirited away. Although these abortive marriages are reminiscent of O'Neill's own marriage to Mabel Bagenal (qv), there is no doubt that the alliance with O'Neill, which reached a high point with their victory at the Yellow Ford in August 1598, was coming under strain. Part of the argument was over the division of arms and money being sent from Spain. At Lifford O'Neill had claimed the king's dividend, but after an argument over the Barrionuevo delivery in the summer of 1599, a treaty of equality was established between them. There may have been further controversy between them over the appointment of Cú Chonnacht Óg (qv) as Maguire in 1600, when at a banquet in Dungannon O'Donnell allegedly ‘called him by the title of Maguidhir in the presence of the chief men of the province’ (Walsh (ed.), Life of Aodh Ruadh, i, 247) but this account by Ó Cléirigh is uncorroborated.
A major reason for the tension between the confederate leaders was their failure to dislodge Sir Henry Docwra (qv) from Derry where he had landed in May 1600. The object of his expedition was to destablise their war effort, wasting the country and winning over men dissatisfied with their rule. Undoubtedly Docwra had his greatest success in Tyrconnell when Niall Garvach defected from the confederacy in October. Niall Garvach, with the assistance of English troops, took Lifford and then began to wrest the north of Tyrconnell from Red Hugh's control. The latter is said to have hung other potential dissidents and to have dashed out the brains of Niall Garvach's four-year old son, his own nephew, against a post. In 1601 Niall Garvach, having returned from Dublin with a custodiam of the lordship, swept through the Barnesmore gap and took Red Hugh's headquarters at Donegal castle. A bitter siege ensued.
By the time news of the Spanish landing at Kinsale in September 1601 arrived, O'Donnell had been more or less driven out of his patrimony. Instead he assembled his forces at Ballymote in Sligo. O'Donnell, accompanied by O'Rourke and other allies, took an army of 2,000, crossed the Shannon south of Athlone, and famously evaded Carew's opposing army by marching through the frozen Slieve Felim pass into Munster. While awaiting O'Neill, O'Donnell expanded his alliance into Munster by supporting John Fitzmaurice and John O'Connor Kerry. Ó Cléirigh claimed that the subsequent battle of Kinsale was fought at the urging of O'Donnell against the better judgment of O'Neill. There is no contemporary evidence of this, or of a dispute between the leaders about precedence. At the battle itself (24 December 1601) O'Donnell's forces were late in arriving and were able to escape with little loss, but O'Donnell himself had no home to return to and decided to take ship for Spain on 27 December in the hope of gaining further assistance.
Exile and death O'Donnell met Philip III at Zamora in February 1602, who promised a bigger and better-appointed relief expedition. However, O'Donnell died 30 August 1602 at Simancas en route to a second royal audience. He died of a fever, not poison at the hands of an English-paid assassin, as is sometimes claimed. He was buried at the Franciscan church in nearby Valladolid.
When Spanish interest in Ireland was renewed again in the Anglo-Spanish war of 1625–31, Lughaidh Ó Cléirigh wrote a biography of Red Hugh in the anachronistic style, placing him in a vaunted role in the nine years war in the hope of another O'Donnell leading the recovery of Ireland. In fashioning this bellicose Irish hero, Ó Cléirigh deliberately marginalised the role of O'Neill in the war. Scrutiny of the state papers shows a different O'Donnell. One more like O'Neill – a counter-reformation Irish dynast living in the world of Machiavelli's Prince rather than the cattle-raid of Cooley.