Maguire, Hugh (d. 1600), lord of Fermanagh , was the eldest son of Cúconnacht Maguire (qv) and Nuala, daughter of Manus O'Donnell (qv). On the death of his father (1589) he succeeded to the lordship and its associated lands, a considerable part of which was almost impregnably located on the islands of Lough Erne. As lord, he was at once confronted by the threat of systematic government encroachment on the independence of the Ulster lordships. The chief of the neighbouring MacMahons had also died in 1589 and within two years his heir had been hanged, Monaghan had been partitioned, and a ‘native plantation’ had been established. As a young man, Maguire had been repeatedly in trouble with the Dublin government. Although he paid 500 beeves for a pardon in 1586, he had not become more circumspect: in 1588 he attracted official attention by joining Brian O'Rourke (qv) and the Burkes in assisting survivors of the Spanish armada. After his succession, he remained defiant, most conspicuously in January 1592, when he provided a refuge for Hugh Roe O'Donnell (qv) after his escape from Dublin castle.
The threat to Maguire's lordship became pressing when the lord deputy, Sir William Fitzwilliam (qv), indicated his intention of appointing a sheriff for Fermanagh. Maguire protested and menacingly asked to be informed of the sheriff's eric (the price of compensation for his death). The appointment was made nonetheless, and Capt. Humphrey Willis, who had recently been driven out of Donegal by Hugh O'Donnell (qv), entered Maguire's country to take up his post in April 1593. Maguire was by now deeply involved in a conspiracy promoted by Archbishop Edmund Magauran (qv) (who had arrived in Ireland in December 1592 with a promise of support from Philip II of Spain for an Irish rebellion in the following summer), and had signed a joint letter to the king confirming that the Irish were ready to receive an invasion force.
It is likely that this larger design strengthened his determination to resist government intrusion into his lordship. He took the offensive, and with help from O'Donnell and the earl of Tyrone (qv), who was his father-in-law, besieged Willis and his party in a church. They were rescued after a week by Tyrone, who chose at this point to remain outwardly loyal to the queen and arranged a safe-conduct for them out of the lordship. But the forces gathered in Fermanagh did not disperse, and in May Maguire invaded Sligo and attacked Ballymote (base of George Bingham (qv), brother of Sir Richard (qv)), burning the town and district. In June he campaigned in Roscommon, where Magauran, who rode with him throughout the expedition, was killed in a skirmish. Later Maguire told Fitzwilliam that he had taken action because his complaints about the attacks of the Binghams on west Ulster had been ignored. The Irish council dismissed Maguire's allegations as ‘frivolous’, but Fitzwilliam subsequently prevented Sir Richard from taking retaliatory action in the area.
In July 1593 the government requested Maguire to disperse his forces, and he agreed to do so by 15 September. In early September, however, he invaded Monaghan, and was proclaimed a traitor. On 10 October he was defeated at the battle of the Erne ford by a force led by Sir Henry Bagenal (qv) and Tyrone. The government's position in Fermanagh was consolidated in the following February when Capt. Dowdall took the island stronghold of Enniskillen after a nine-day siege. Bagenal proposed that Fermanagh should be dealt with in the same way as Monaghan, but the suggestion proved premature: on 7 August 1594 a government column sent to relieve Enniskillen castle was driven back by Maguire and his confederates at Drumane ford on the Arney river, which became known as ‘the Ford of the Biscuits’. Enniskillen was soon after relieved by the lord deputy, Sir William Russell (qv), and remained the sole government outpost in the lordship.
In January 1595 Maguire and others were invited to submit their grievances; a conciliatory reply from the queen protested that she had not known of their maltreatment by officials and assured them that, if their complaints were found to be true, recompense would be made. In April Maguire and other northern lords made personal submissions before government commissioners in the market place at Dundalk. A peaceful settlement seemed imminent; in reality, Tyrone had decided on war, with the immediate aim of holding Ulster till the arrival of Spanish aid. In May, with the assistance of Tyrone's brother Cormac, Maguire regained Enniskillen.
Maguire's chief task thereafter was to keep his lordship free of government intervention, and he did so. He also played some part in the more general struggle, most notably in the series of time-wasting negotiations at which settlement terms were fruitlessly discussed: he was present at the meeting with commissioners outside Dundalk in January 1596 and again in April, when he was one of those who went through the motions of making submission. He had campaigned with O'Donnell in Connacht in December 1595, and did so again in August 1597 when he assisted O'Donnell in repelling Sir Conyers Clifford (qv) from Ballyshannon, which was (with Enniskillen and the Erne) a key point in the control of movement between Connacht and Ulster. He held a command under Tyrone when the English army was defeated in battle at the Yellow Ford on 14 August 1598. Returning to Connacht some months later, he joined O'Donnell in a raid for plunder in Clare. On 7 September 1599 he was one of the six witnesses who accompanied Tyrone when he parleyed with the earl of Essex (qv) at Aclint, and at the end of 1599 he moved south with Tyrone to Munster. On 4 March 1600, while reconnoitring (or perhaps raiding) near Cork, he encountered Warham St Leger (qv). In the ensuing skirmish, St Leger shot Maguire through the body, and Maguire drove his lance into St Leger's skull. Both died of their injuries.
The annals recorded that Maguire's death caused ‘a giddiness of spirits and depression of mind in O'Neill and the Irish chiefs in general’ (AFM, iv, 2165), and it does seem likely to have been the reason why Tyrone abruptly decided to return to the north. Hugh Maguire, who was said to have married a daughter of Hugh O'Neill, was succeeded as lord of Fermanagh by his younger brother Cú Chonnacht Óg Mág Uidhir (qv) (Cuconnaught Maguire).