O'Neill, Owen Roe (Ó Néill, Eoghan Rua) (c.1580–1649), soldier, was the son of Art O'Neill, brother of Hugh O'Neill (qv), 2nd earl of Tyrone. Art's father, Matthew (qv), baron of Dungannon, had been killed by the supporters of Shane O'Neill (qv); his grandfather was Conn Bacach O'Neill (qv), 1st earl of Tyrone. The identity of Owen Roe's mother is unknown but she was possibly Art's third wife, a daughter of Hugh Conallach O'Reilly of Breifne. Owen Roe had at least eight brothers and four sisters, connected through marriage to many of the leading native Irish families of Ulster. His nephews included Daniel O'Neill (qv) and Hugh Dubh O'Neill (qv), important figures in 1640s Ireland, as well as Conor, Lord Maguire (qv), one of the original plotters of the 1641 rebellion, and his brother Rory (qv), who commanded a regiment in the Ulster army during the 1640s. Another major northern landowner, Miles O'Reilly, married one of Owen Roe's sisters, and was also related to the powerful Magennis family, Viscounts Iveagh. Owen Roe, still a relatively young man, did not play a significant role in the Nine Years War (1593–1603), although his family lost a number of members during the conflict. The persecution continued even after the treaty of Mellifont (1603), when in 1607 the lord deputy, Sir Arthur Chichester (qv), executed his eldest brother, Brian MacArt. The plantation policies of the Stuart administration forced Owen Roe's father to relinquish the family lands of Oneilan in Co. Armagh and accept instead 2,000 inferior acres in the barony of Orior. This estate eventually reverted to the crown after Art's death in 1618.
In Spanish service, 1605–41 Owen Roe did not remain in Ireland to witness these events, but decided instead to pursue a military career abroad. Accompanied by three brothers (Phelim, Art Óg, and Cormac), he travelled to Spanish Flanders in 1605, and within a few months had secured a position as captain in the regiment of Henry O'Neill, son of the earl of Tyrone. Another new arrival from Ireland, Thomas Preston (qv), son of Christopher, Viscount Gormanston, received a similar commission at this time. A lifelong antagonism developed between the two men, partly as a result of the traditional animosity between the Old English of the Pale and the Ulster Irish, but principally personal in nature. According to the earl of Clarendon, the two young ambitious officers were in ‘perpetual jealousy of each other’ (quoted in G.E.C., Peerage, xii, 639). O'Neill served with distinction at the siege of Rheinburg in 1608, but his company was among those disbanded when the Spanish Netherlands and the United Provinces signed a truce the following year. He accompanied Henry O'Neill to Spain (August 1609), seeking an improvement in the conditions of Irish troops in Flanders, and fresh employment for himself. The death of Henry in 1610 raised the issue of who should succeed him as colonel of the Irish regiment. Owen Roe, the most experienced candidate and a sincere catholic, was favoured by Florence Conry (qv), the influential Franciscan archbishop of Tuam. Hugh O'Neill insisted, however, that the command remain within his immediate family, resulting in the appointment of his 12-year-old son, John, as the new colonel. In May 1611 Owen Roe received the commission as sergeant-major, responsible for training and supplying the regiment, but acting in effect as commander during John's minority. The logistical and martial skills he acquired over the next three decades of Spanish service would eventually be put to good use during the confederate wars in Ireland. Thomas Preston had strenuously opposed Owen Roe's appointment, further embittering relations between the two men.
In early 1614 O'Neill married Rosa O'Doherty, sister of Sir Cahir O'Doherty (qv), leader of an ill-fated rebellion in 1608, and widow of Caffar O'Donnell, brother of the earl of Tyrconnell. Hugh, her son by this first marriage, was the oldest surviving O'Donnell male and prospective heir to the O'Doherty estates. For the next thirty-five years Rosa provided Owen Roe with love and companionship, enduring great hardship at times, but always supporting his military and political endeavours. Their eldest son, Henry, also embarked on a military career, accompanying his father to Ireland in 1642 to join the army of Ulster. For the duration of the Spanish–Dutch truce Owen Roe served as military governor of the strategic town of Rheinburg on the German frontier, before returning to active service when the war began again (1621). He served with distinction in a number of military engagements, during which the Irish regiment suffered heavy casualties, including his stepson Hugh O'Donnell, killed at the siege of Breda (1625). The renewal of hostilities between Spain and England revived plans for using Irish troops in Flanders to lead an invasion of Ireland. Tensions between the earls of Tyrone and Tyrconnell over precedence threatened to undermine the project, so Owen Roe proposed a radical alternative. In November 1627 he travelled to the Spanish court with John O'Neill, earl of Tyrone, seeking approval for plans to establish a republic in Ireland, the first known use of the term in this context. The campaign would be conducted in ‘the name of the liberty of the fatherland, and of oppressed religion’ (Casway, Owen Roe O'Neill, 33), with the people of Ireland, regardless of ethnic background, establishing a provisional governing council. They would urge the papacy to excommunicate anybody who opposed the republic, and appeal to the catholic princes of Europe for recognition and assistance. These remarkable proposals, mirroring in many ways subsequent confederate actions, never saw fruition, as improving relations with England led Spain to cancel any invasion plans. Fear of intervention from Flanders, however, prompted Charles I to promise a number of concessions to Irish catholics in 1628. The failure to enact these ‘graces’ proved a source of major grievance throughout the 1630s and contributed to the decision of many catholics to join the Ulster revolt in October 1641.
Thwarted for the moment in his Irish ambitions, Owen Roe returned to his command in Flanders, but the creation (1632) of a second Irish regiment, under the command of the earl of Tyrconnell, infuriated him. O'Neill threatened to resign from the army unless he received a similar commission. The Spanish authorities, anxious to retain the services of such a respected soldier, granted his request the following year. By September 1634 he had recruited thirteen companies, principally in Ireland, despite the opposition of the lord deputy, Thomas Wentworth (qv). The Dublin administration, wary of any O'Neill involvement in Irish affairs, favoured Owen Roe's great rival, Thomas Preston, who became colonel of his own regiment in 1635. As the war with France intensified, Owen Roe was appointed military governor of the strategic town of Arras in June 1640. He soon found himself besieged by a large invading French army, which the Spanish in turn attempted to encircle, in order to relieve the beleaguered Irish regiment. After a skilled defence against overwhelming odds, Owen Roe finally surrendered (9 August), marching from the town with full colours flying, his military reputation greatly enhanced. After a spell at the military hospital in Douai, he returned to active service in 1641 at the border town of Aire, but took leave of absence the following year and returned to Brussels.
Rebellion in Ireland, 1641–3 From as early as 1640 he had been in contact with his kinsman Sir Phelim O'Neill (qv), MP for Dungannon and one of the ‘deserving Irish’ of the plantation process. The conspirators, increasingly concerned by the anti-catholic rhetoric of the Scottish covenanters and Westminster parliament, hoped to take advantage of Charles I's domestic difficulties to exact concessions in Ireland. Owen Roe, de facto leader of the O'Neill interest on the Continent after the death of the earl of Tyrone near Barcelona (January 1641), promised to provide military assistance in the event of an uprising. He continually exhorted the conspirators to act, using a number of trusted agents, including the cleric Heber MacMahon (qv) who subsequently became bishop of Clogher and a leading figure in confederate political circles. Weary of exile, Owen Roe believed that in the absence of Spanish military assistance the Irish had to proceed alone. When news of the Ulster rebellion reached the Continent, he began to make preparations to return home. These developments greatly concerned the English authorities, who closely monitored his activities and demanded that the Spanish prevent the departure of Irish troops from Flanders. None the less, Owen Roe managed to slip away from Ostend with a couple of hundred men and officers, landing at Doe Castle in northern Donegal on 8 July 1642.
His arrival coincided with a crisis meeting of the Ulster insurgents in Armagh. Despite some initial successes, the rebels had been forced on the defensive in March 1642, after the failure of Sir Phelim O'Neill to capture the town of Drogheda. Government forces from Dublin, led by James Butler (qv), earl of Ormond, went on the offensive, while to the north Gen. Robert Monro (qv) landed in Co. Antrim with 10,000 Scottish covenanter troops. Under threat from two directions, the rebel leadership considered fleeing the country, when the dramatic news arrived from Doe Castle. Sir Phelim dispatched troops to escort the returned exiles to the fort of Charlemont in Co. Armagh. On 29 August a provincial assembly nominated Owen Roe as ‘lord general’ of the Ulster forces, while Sir Phelim accepted the nominal title of ‘lord president of Ulster’ and the position of cavalry commander. Fears that rivalry between the two men might disrupt proceedings in the province proved unfounded, for the moment at least. Sir Phelim's decision shortly afterwards, however, to marry Louise, daughter of Thomas Preston (who had also returned to Ireland), did create the potential for future conflict. When the euphoria of his return had subsided, Owen Roe began to assess his position in more realistic terms. He described the province of Ulster as ‘like a hell’, unrecognisable from the place he had spent his childhood, while the native troops under his command behaved ‘nothing better than animals’ (quoted in Casway, Owen Roe O'Neill, 64–5). Their lack of training and discipline shocked the Flanders veteran, who immediately set about trying to create a professional force.
Owen Roe's motivation in returning to Ireland was the subject of intense scrutiny throughout the 1640s, not only among his enemies but even within confederate ranks. Described by the cleric Hugh Bourke (qv) as ‘a man of great prudence and conduct, very adroit and crafty in the handling of great matters’ (quoted in Casway, Owen Roe O'Neill, 61), he never fully revealed his hand. Without question, the interests of the dispossessed landowners of Ulster remained paramount in his thinking, but he also sought the full restoration of the catholic church in Ireland, or at least its official recognition by the state. Owen Roe believed that these aims could best be achieved through an accommodation with the Stuart monarchy, and throughout his time in Ireland he repeatedly stressed his loyalty to Charles I. The Ulster general reminded his troops that ‘they were no mercenary soldiers but natives of the kingdom’ (quoted in Ó Siochrú, 241), and should behave accordingly. None the less, his family's rebellious history convinced many confederates that Owen Roe in fact wished to see a return to the old Gaelic political order and the complete severance of all links with the crown. Although officially recognised as Ulster general by the first general assembly (November 1642), he was not admitted to the inner councils of confederate government, unlike the Leinster commander Thomas Preston. O'Neill's rival had already commandeered military equipment from the Continent intended for Ulster, and the northern army remained chronically under-supplied for the duration of the war.
O'Neill returned to Charlemont from Kilkenny in January 1643 to continue training his troops, moulding them into an effective military force. At the beginning of the campaigning season the covenanters raided deep into Armagh and Monaghan, supported by the Lagan army of Sir Robert Stewart (qv). Anxious to engage an enemy that had destroyed much of Ulster, Owen Roe's subordinate officers persuaded him, against his better judgement, to oppose Stewart in open battle. He suffered a serious defeat at Clones on 13 June 1643, losing a number of continental veterans including Hugh Dubh O'Neill, who remained a prisoner until 1646. Owen Roe then retreated into the remote areas of Longford and Leitrim with the scattered remnants of his forces and quickly reorganised. The defeat reinforced his cautious temperament, and the preservation of the Ulster army, in whose hands the hopes of the native Irish rested, became his primary concern. In August 1643 he entered Meath to counter Charles Moore (qv), 2nd Viscount Moore, who was anxious to seize as much territory as possible for the king before a proposed cessation between the royalists and confederates (signed in September). The two armies clashed at Portlester, but the royalists retreated after the death of Moore from a cannon shot while attempting to ford a river.
The Ulster campaign 1643–6 For the next three years an uneasy peace existed between royalists and confederates, with both sides regularly accusing the other of breaching the terms of the cease-fire. The principal disputes centred on the ownership of large herds of cattle,which supplied the food necessary to sustain a large army. O'Neill commented bitterly that ‘it was better for us to have absolute wars than this corrupted cessation’ (quoted in Casway, Owen Roe O'Neill, 121). The Ulster Scots, however, rejected the truce and signed the Solemn League and Covenant with the English parliamentarians, vowing to destroy Irish catholics by force. Owen Roe travelled to the general assembly in Waterford at the end of 1643, seeking assistance for his beleaguered forces. The assembly members devised a dual strategy to end the war in the north, thus facilitating a permanent peace agreement with the royalists. In the first instance, they sanctioned a plan by Randal MacDonnell (qv), 2nd earl of Antrim, to dispatch troops, led by Alasdair MacColla MacDonnell (qv), to Scotland. MacColla, in alliance with James Graham, earl of Montrose, would open a new front to relieve pressure on the king in England, while at the same time diverting the attention of the Ulster Scots away from Ireland. The second stage of the strategy involved launching a major confederate offensive in Ulster itself, with forces assembled from all four provinces. O'Neill, the natural choice to command an Ulster campaign, proved unacceptable to many confederates, and the assembly eventually selected James Tuchet (qv), earl of Castlehaven, as a compromise candidate. This public rebuff dismayed Owen Roe, although according to one contemporary source he ‘carried it fairly’ (quoted in Casway, Owen Roe O'Neill, 97).
The prospects for the northern campaign appeared good at first, as MacColla and Montrose recorded a succession of victories in Scotland, forcing covenanter regiments to return home from Ulster. Castlehaven, however, had no experience in commanding a large army, knew little of the Ulster terrain, and wasted the opening months of the campaigning season dealing with malcontents in north Connacht. Mutual suspicion marked his relationship with O'Neill, who proved reluctant to commit his forces to the offensive. The campaign itself achieved little, resulting in a military stalemate, with the confederates and Ulster Scots digging into defensive positions around the fort of Charlemont in Armagh, before retiring to winter quarters. Owen Roe publicly criticised Castlehaven for adopting negative tactics, but in return the earl accused him of reneging on promises of men and supplies. Both men presented their cases at the end of 1644 before the supreme council in Kilkenny, which decided not to pursue the matter. The following year witnessed no campaign of significance in the north, as O'Neill lacked the supplies for a sustained offensive, while MacColla's activities in Scotland continued to distract the covenanters. In October 1645 Owen Roe travelled to Kilkenny to welcome the papal nuncio, GianBattista Rinuccini (qv). Rinuccini arrived with money and equipment, two-thirds of which he gave to the already well supplied Leinster army of Thomas Preston. O'Neill received the remaining third, and in early June 1646, with his forces relatively well supplied and paid, he was at last ready to confront the covenanters on the battlefield. From their winter quarters in Cavan, the Ulster troops marched northwards through Monaghan into Tyrone, while Gen. Monro advanced to meet them, having coordinated his movements with another covenanter force from Coleraine, hoping to catch O'Neill in a giant pincer movement.
Instead of seeking the safety of Charlemont fort, as Castlehaven had done in 1644, or retreating into the midlands, Owen Roe prepared for battle. He dispatched a unit of cavalry northwards to prevent reinforcements arriving from Coleraine, while he dealt with the main covenanter army. Monro, anxious to confront an elusive enemy, forced his troops forward, and as the day drew to a close committed them to battle on unfavourable terms, attacking uphill into the setting sun. O'Neill took full advantage of the situation, and in a masterful display of generalship won a stunning victory at Benburb in east Tyrone (5 June 1646), the greatest ever achieved by an Irish commander on native soil. The Ulster troops, making effective use of their shortened pikes, inflicted over 3,000 loses on the covenanters, and forced Monro to flee back to Antrim with the remnants of his army. The northern province appeared to be at O'Neill's mercy, with Monro confined to Carrickfergus, Belfast, and a few isolated strongholds. Nonetheless, Owen Roe failed to press home his advantage, launching only a few minor raids into Antrim and Down. By August Monro had returned to the field ‘with a good number of men’ (quoted in Ó Siochrú, 119), seemingly negating many of the confederate gains. Military realities, however, had limited O'Neill's options in the aftermath of his victory at Benburb. The covenanters, although depleted, still controlled significant forces, while the Lagan army in Derry remained intact. O'Neill also lacked the necessary siege equipment to undertake a determined assault on the Ulster Scots heartland in east Ulster, while many of his troops had dispersed to return home with the spoils of battle.
Confederate dissensions, 1646–9 Faced with these difficulties, O'Neill adopted a cautious strategy awaiting developments elsewhere in the kingdom before deciding on his next move. The summer of 1646 marked the high point of confederate military power, as Donough MacCarthy (qv), Viscount Muskerry, seized the vital fortress of Bunratty at the mouth of the Shannon, while Preston made significant gains in Connacht, capturing the town of Boyle, Co. Roscommon. Political developments however, soon overshadowed any success on the battlefield. The ruling peace faction in Kilkenny, led by Muskerry, had privately agreed a peace settlement with the king's lord lieutenant, Ormond, in March 1646. The clergy opposed the deal because of the absence of any religious guarantees, and throughout the summer the two main confederate factions engaged in increasingly bitter recriminations. An internal power struggle erupted when at the end of July Ormond publicly proclaimed the treaty in Dublin. The confederate supreme council followed suit shortly afterwards, a move condemned by the clergy gathered at an ecclesiastical congregation in Waterford.
O'Neill carefully monitored these events, refusing to commit himself despite sympathising with the nuncio and the clerical faction. Rinuccini urged the Ulster general to march on Dublin, but instead he moved southwards towards the confederate capital in Kilkenny, forcing Ormond to abandon a proposed procession throughout Munster and south Leinster. In the ensuing chaos, the clerical faction assumed control of confederate government, creating a new supreme council, headed by Rinuccini, which included O'Neill and Thomas Preston. Preston had only rejected the treaty after the threat of clerical sanctions, and he maintained contact with the royalist leadership, principally through Ulick Burke (qv), marquis of Clanricarde. The ruling junta ordered an immediate assault on Dublin, led by both O'Neill and Preston, in the hope that the joint command would prevent any disputes over precedence. The decision proved disastrous, as the long-standing animosity between the two generals created an atmosphere of distrust which undermined the confederate campaign. None the less, in early November a large confederate army reached the outskirts of Dublin, which would almost certainly have fallen in the face of a determined attack. Instead, the arrival of parliamentary ships in Dublin Bay, combined with bad weather and Preston's treachery, convinced O'Neill to withdraw into the midlands. The nuncio abandoned the siege, allowing a moderate faction in Kilkenny, headed by Nicholas Plunkett (qv), speaker of the general assembly, and Nicholas French (qv), bishop of Ferns, to assume control. They summoned a general assembly in January 1647, which rejected the Ormond peace treaty but exonerated its authors from any blame. In July the lord lieutenant rebuffed an attempt by the moderates to negotiate a new peace settlement, surrendered the city of Dublin to parliamentary control, and sailed for England.
The confederate leadership ordered a new offensive against Dublin, but this time commanded by Preston alone. O'Neill's troops and their accompanying creaghts had spent the winter scattered throughout Leinster, where their presence aroused the resentment of the local population, already heavily burdened after years of conflict. Complaints flooded into Kilkenny, provoking a sympathetic response from all factions, including the clergy. Rinuccini, angry over O'Neill's refusal to hand over the vital fortress of Athlone to Thomas Dillon (qv), Lord Costello, a recent convert to catholicism, condemned the conduct of the Ulster soldiers. Anxious to avoid conflict, in May 1647 the supreme council ordered O'Neill into Connacht to attack the town of Sligo, which Preston had failed to capture the previous year. This diversion not only relieved the pressure on confederate resources, but also left the field clear for Preston to regain control in Leinster. The three councillors, Francis Bermingham (qv), Sir Lucas Dillon (qv), and Father Oliver Burke (qv), appointed to supply provisions and equipment during the campaign, neglected their duties, eventually forcing the Ulster army to withdraw from north Connacht. At the same time (early August) the parliamentary commander Michael Jones (qv) inflicted a crushing defeat on Thomas Preston at Dungans Hill, near Trim, Co. Meath. In desperation, the supreme council ordered O'Neill back into Leinster, to prevent any further gains by Jones. Owen Roe's compliance with this command sparked a near-mutiny in the Ulster army, angry over arrears of pay and their shabby treatment at the hands of the council. Although temporarily resolved, the dispute reflected the growing tensions within the ranks of the Ulster leadership, principally between those who held land prior to the 1641 revolt, and returned exiles like Owen Roe who sought to overturn the entire plantation process.
The Ulster army advanced towards Dublin, adopting a scorched-earth policy to starve the city's parliamentary garrison into submission, before withdrawing to the midlands with the onset of winter. A general assembly in November 1647 further exposed internal confederate divisions, with a resurgent peace faction threatening to imprison Owen Roe's trusted lieutenant, Bishop MacMahon, over his refusal to accept an order of the assembly. The presence of Ulster troops in the vicinity of Kilkenny prevented the dispute escalating, but the prospect of a civil war loomed ever closer. In February 1648 O'Neill reassembled his forces, successfully preventing a linkup between Michael Jones and Murrough O'Brien (qv), Lord Inchiquin, the parliamentary commander in Cork. Inchiquin had defeated the confederate army of Munster under Theobald, Lord Taaffe (qv), at Knocknanuss, Co. Cork, in November 1647, and controlled much of the southern province as a result. Desperate to relieve the military pressure, the supreme council contemplated a truce with the virulently anti-catholic Inchiquin, despite the opposition of the papal nuncio. Rinuccini feared that the proposed cease-fire was part of a wider plot, involving the return of Ormond and a new settlement with the royalists. His suspicions appeared to be confirmed when Inchiquin declared for the king in April 1648, and agreed a truce with the confederate leadership the following month. Rinuccini and Bishop MacMahon fled to Owen Roe's camp in Maryborough, inexorably linking the Ulster general with the clerical faction.
The nuncio's excommunication of supporters of the truce sparked a civil war, with Preston and Taaffe joining with the royalist commanders Inchiquin and Clanricarde in attacking the Ulster forces. The 1641 Ulster landowners (Sir Phelim O'Neill, Miles O'Reilly, and Alexander MacDonnell (qv), among others) sided with the supreme council, anxious for a new settlement with Ormond (who returned to Ireland in September 1648) to preserve their estates. Owen Roe skilfully avoided battle with those he considered his fellow Irishmen, but he desperately needed to find an alternative source of supplies. Outlawed by a meeting of the general assembly (October), he initiated a series of negotiations with parliamentary commanders, equally threatened by the royalist revival. He agreed an effective cease-fire with Michael Jones towards the end of the year, exchanging cattle for military equipment. In January 1649 the confederate assembly signed a peace treaty with Ormond, creating a powerful new alliance, excluding O'Neill. Rinuccini left for Rome shortly afterwards, while Ormond sent Nicholas Plunkett and Nicholas French to seek a rapprochement with O'Neill. The talks faltered in early April, and O'Neill turned his attention once more to the parliamentarians, hoping to reach an agreement that would safeguard the catholic religion and allow the Ulster Irish to regain their former properties. While Castlehaven moved against his garrisons in the midlands, O'Neill arranged a cease-fire with Colonel George Monck (qv), parliamentarian commander of Dundalk. In July he relieved Charles Coote (qv) in the city of Derry, under siege from royalist forces. Shortly afterwards, Jones defeated Ormond at Rathmines, allowing Oliver Cromwell (qv) to land unchallenged with a large army at Ringsend on 12 August 1649. In a matter of weeks the balance of power in the kingdom had shifted dramatically, with the parliamentarians now clearly posing the greatest threat to Irish catholic interests. Ormond and O'Neill finally agreed terms in late October, but the latter, who had suffered from increasingly bad health due to the rigours of military campaigning, was only weeks from death. His army moved slowly southwards to assist the royalists, but the general could go no further than Cloughoughter, Miles O'Reilly's castle in Co. Cavan. He died there on 6 November 1649 shortly before his wife Rosa arrived from Galway.
Assessment and aftermath One of Ireland's greatest military commanders, O'Neill found his career during the 1640s blighted by ill-health, inadequate resources, political machinations, and blatant hostility from within confederate ranks. With greater support from the administration in Kilkenny he would almost certainly have altered the course of the confederate wars. In March 1650 the Ulster assembly elected Bishop MacMahon to command the army maintained with such great care and skill by O'Neill. An able politician, the bishop proved inexperienced on the battlefield: he led his troops to a disastrous defeat at Scarrifhollis, Co. Donegal, in June 1650, and was executed shortly afterwards. Many of O'Neill's subordinates, however, served with distinction against Cromwell over the next three years, providing the most effective opposition to the parliamentary forces. Hugh Dubh, for example, inflicted heavy losses on Cromwell's army at Clonmel in May 1650, while Philip MacHugh O'Reilly (qv) was the last commander to surrender formally (April 1653). Owen Roe's only son, Henry O'Neill, continued to serve in the Ulster army, but was executed by Charles Coote after the defeat of Scarrifhollis. His son Hugh (b. 1647) later assumed the title of 6th earl of Tyrone, but died without issue in 1673.