O'Donnell, Hugh McHugh Dubh (Aodh Ó Domhnaill) (c.1537–1618), nobleman and bardic poet, was born in Co. Donegal, the youngest son of Aodh Dubh O'Donnell (qv), lord of Tír Conaill (d. 1537). His mother may have been Mary (d. 1548), the daughter of the head of the bardic McNamee family. He is first mentioned in the annals in 1564, when the Four Masters record that he held the new tower at Donegal town against the son of the ruling lord of Tír Conaill, Conn O'Donnell. In 1566 he signed an indenture with his nephew An Calbhach O'Donnell (qv), the lord of Tír Conaill, in which he was guaranteed possession of his castle at Rathmelton, called Cathir Annske, and the territory of Clanelly, which was traditionally the tánaiste's portion of Tír Conaill. He may indeed have become the tánaiste of the Tír Conaill lordship.
In 1567 Hugh O'Donnell commanded a detachment of Tír Conaill cavalry at the battle of Farsetmore for the new lord of Tír Conaill, his other nephew, Aodh McManus O'Donnell (qv) and in 1577 the Annals of Loch Cé record one of his exploits when he killed an enemy ‘with one cast of a spear’ (ALC, ii, 416–17). Sometime in the 1570s he fostered the eldest son of Aodh McManus, the famous Red Hugh O'Donnell (qv), who was his grandnephew, although the fosterage arrangement did not last. When the latter became lord of Tír Conaill in May 1592, Hugh O'Donnell did not attend his inauguration. In March 1593 Red Hugh retaliated by capturing O'Donnell's garrison at Belleek Castle in southern Tír Conaill and executing the sixteen principal gentlemen it contained. Hugh then implicated Red Hugh in a plot with Hugh Maguire (qv) and Hugh O'Neill (qv) against Queen Elizabeth, but eventually he made peace with Red Hugh and became one of his most important supporters.
In 1599 Hugh O'Donnell accompanied Red Hugh on his invasion of Thomond and, after the English landed at Lough Foyle in May 1600, in a skirmish with Sir Henry Docwra (qv) he hit the English commander in the forehead with ‘a forked javelin’, wounding him severely. Docwra was out of action for three weeks. When the war in Tír Conaill began to go against the Irish, Hugh O'Donnell and his family fled to Lower Connacht, where they based themselves in the fortress of Dun Aille (Donally) in Carbury. He remained loyal to Red Hugh until his lord died in Spain in September 1602. His eldest son, Caffar, then made peace with the English in Sligo.
Once peace was established with the English, Hugh refused to become involved in any further Irish intrigues. He did not join the revolt of Cahir O'Doherty (qv) in 1608, although his son Seán did take part. As a result, in 1610 in the plantation of Ulster, Hugh O'Donnell was granted his castle at Rathmelton and 1,000 acres ‘to hold during life’, to be then awarded to Sir Richard Hansard (d. 1619). His son Caffar received 128 acres in the barony of Kilmacrennan.
Besides being a great warrior, Hugh O'Donnell was an accomplished bardic poet, perhaps through the influence of his mother's family, the McNamees. After 1616 he became involved in the poetic contest known as the contention of the bards, writing one poem, beginning ‘Measa do thagrais a Thaidhg’ (‘Worse have you argued, O Tadhg’), which has survived. However, he must have composed more poetry which has not survived, as Lughaidh Ó Cléirigh (qv), the author of the Beatha Aodha Ruaidh, states that he was a skilled poet.
O'Donnell died in 1618 at a great age; he was at least eighty-one years old. An unpublished set of Tír Conaill annals states that he was ‘the very best horseman of his time in Ireland, and he who killed most enemies’ (NLI, G488, 256). According to an O'Donnell genealogical tract, Hugh McHugh Dubh married twice. By his first wife, whose name is not recorded, he had four sons, the eldest of whom was Caffar (d. 1641), and by his second wife, a daughter of O'Connor Sligo, he had two more sons. His descendants were prominent in the rebellion of 1641.