O'Donnell, Hugh Balldearg (Balderick, Balderock) (d. c.1704), soldier and sometime Jacobite, was son of John O'Donnell of Co. Donegal, soldier in the Spanish army, and Catherine O'Rourke. His early life remains obscure; he may have been born in Spain, and at some point he entered the Spanish military. Seemingly a descendant of Calvagh (An Calbhach) O'Donnell (qv), he possessed both property in Spain and the letters patent to the earldom of Tyrconnell issued by James I, being recognised by the Spanish as conde de Tyrconnell. He offered his services to the exiled Stuart court in the 1650s, but was rebuffed, and rose instead to the rank of brigadier in the Spanish army.
The restoration of Charles II in 1660 saw the return of many Irish soldiers previously employed overseas, and by the 1680s O'Donnell commanded one of only two remaining Irish regiments in the Spanish army, seeing service mainly against the French. O'Donnell's position in 1689 was problematic; at this juncture William III (qv) was aligned with Spain, and at war with France. The new Jacobite alignment with France saw O'Donnell denied permission to travel to Ireland on news of William's landing there. He absconded to Lisbon, contacted the French, and arrived in Cork in July 1690, four days after the battle of the Boyne; he waited upon James II (qv) in Cork harbour prior to the latter's departure to France. Recommended to Richard Talbot (qv), earl of Tyrconnell, he was commissioned to raise 5,000 men, though Tyrconnell suggested that 15,000 would be more useful. O'Donnell had an advantage here; the sobriquet Balldearg (‘red spot’), referred to a red mark on his head, possibly a birthmark. There was a prophecy that an O'Donnell with a red mark would return from overseas to become the vengeful saviour of the Irish. For many, Hugh Balldearg seemed to fulfil the first part of the prediction, and so ‘they applied their ridiculous belief impertinently to this man’ (Gilbert, Jacobite narrative, 151). In this context his presence served as a morale booster, and he recruited between 7,000 and 10,000 men in Ulster over six weeks, claiming the ability to raise 30,000 should weapons be available.
O'Donnell was aware of his lineage as a Gaelic noble, and his strongest sympathies lay with the Gaelic Irish as the most oppressed group in Ireland, though he avoided attempts to foster division between the Irish and the Old English. However, he was unhappy at the exclusion of the native Irish from power by James II, and his relations with Tyrconnell were tense, especially as the latter now possessed O'Donnell's ancestral title. His troops lacked weapons and supplies, but were given licence to procure them wherever they saw fit until French supplies landed; their subsequent depredations devastated parts of the countryside, thereby denying supplies to Williamite forces. While he officially commanded in Ulster, O'Donnell was instructed to hold the line of the Shannon. Tyrconnell refused him a commission after the first siege of Limerick, and it was suggested that he disband his forces, though he later received commissions for nine regiments from James Fitzjames (qv), duke of Berwick, in Tyrconnell's absence. However, O'Donnell was wary of the ethnic division in the Jacobite ranks, and in late 1690 contacted the French to determine whether aid would still be forthcoming for the Gaelic Irish to continue resistance if the Old English came to terms. Tyrconnell returned from France in January 1691 and appointed O'Donnell a brigadier; but as James had promised to make him a major-general the tension between the two was intensified, being further exacerbated by Tyrconnell's refusal to provide arms or equipment for O'Donnell's men. He obtained some from Charles Chalmont, marquis de St Ruth (qv), but nowhere near enough for a force estimated at 9,100. Despite this, his own followers’ enthusiasm was unabated. Prior to the battle of Aughrim (12 July 1691) O'Donnell had offered reinforcements for Galway, but these were refused. He then attacked and burned Tuam, and after the battle dispersed his troops throughout Connacht, retaining 1,000 men, with whom he captured Cong, Co. Mayo. When the defenders of Galway requested assistance, O'Donnell's men were blocked north of the city by the forces of Godard van Reede, Baron de Ginkel (qv), and retreated towards Sligo. O'Donnell was later blamed for the fall of Galway, which added to his disgruntlement.
By now O'Donnell viewed the Jacobite cause as lost, and in August 1691 he defected to the Williamites, coming to terms with Ginkel near Sligo; though it was later disputed, O'Donnell would appear to have made the initial approach. However, after the defenders of Sligo requested assistance, O'Donnell, in a show of strength, moved his forces into the vicinity of the town, thereby bolstering his negotiating position. However, his arrival prompted a Williamite force under Sir John Michelburne (qv) to withdraw, and encouraged the defenders of Sligo under Sir Tegue O'Regan to go back on their own agreement with Ginkel to surrender. Ginkel was wary lest O'Donnell do likewise, though he appreciated the strategic value of O'Donnell's force and the prestige he had in Ulster; indeed, their potential value had been noted in late 1690. O'Donnell demanded recognition as earl of Tyrconnell, or at least a recommendation to that effect, payment of his expenses, and assurances about the safety and future of his men. These initial terms were unacceptable, but Ginkel remained favourably disposed. However, the negotiations were publicised, and provoked a mutiny from O'Donnell's supporters; out of 3,000–4,000 perhaps only 1,000 followed him when he came to terms and ‘thereby revolting from his natural prince, he unhappily joined with the enemies of his country’ (O'Kelly, Macariae excidium, 143). He took part in Williamite forays around Sligo and the final assault on Sligo town (September), at one point narrowly avoiding capture and probable execution by Jacobite forces.
After the treaty of Limerick (3 October 1691), O'Donnell was apparently eager to fight against the French somewhere. Having deserted from the Spanish service, he had lost everything. Equally, he was in no position to go to France, and given his past record, employment in Ireland was bound to provoke protestant hostility; he had fewer options than most. There were also concerns over his forces, who would inevitably become ‘highwaymen and rapparees’ (HMC, Finch MSS, iii, 304), and O'Donnell was retained to command the remnants of them; c.1,400 remained but were later disbanded. O'Donnell arrived in London in December 1691, being recommended by Ginkel for the earldom of Tyrconnell, and in January 1692 received £1,500 and a pension of £500 per year from the Irish establishment; compensation for the losses incurred in leaving Spain. While c.500–700 of his former troops were eventually recruited for overseas service, their regiment was commanded by Bryan Magennis, Lord Iveagh, with O'Donnell as his deputy. Despite his subsequent efforts, O'Donnell could not procure Iveagh's dismissal, and thereby his own promotion.
When the troops went into the imperial service, fighting in Hungary, O'Donnell returned to Flanders and rejoined the Spanish army as a volunteer. In May 1694 he arrived in Madrid, and in September travelled to Turin, where he assembled a force of c.400 Irish deserters from the French army, leading them into Catalonia in operations against the French. In February 1695 he suggested the possibility of an invasion of France by the forces of the league of Augsburg to William Blathwayt, the English secretary of war, and was present when Barcelona fell to the forces of the league in August 1697. By October 1698 he had been promoted to major-general and was sent once more to the Spanish Netherlands, and in January 1700 it was rumoured that he might command a possible ‘Franco-Spanish’ invasion of Ireland (CSPD 1699–1700, 369). O'Donnell's Irish pension was paid until at least 1703; it had been voted down as unnecessary by the Irish parliament, but was maintained by the viceroy, James Butler (qv), 2nd duke of Ormond. O'Donnell died in Spain c.1704. His place of death remains obscure. However, his reputation as a prospective messianic deliverer remained vibrant in poetry and folklore throughout the eighteenth century.