Hugh Roe O'Donnell (Irish: Aodh Ruadh mac Néill Gairbh Ó Domhnaill) was a leading figure in Gaelic Ireland, ruling as King of Tyrconnell in Ulster from 1461 to 1505. He was then head of the O'Donnell dynasty.
A son of Niall Garv O'Donnell, Hugh visited Dublin in 1464 to submit to the royal authorities. He remained a strong supporter of the Yorkist cause, and supported the claims of the pretender Perkin Warbeck against the Tudors. By 1496 he was eager to repent his actions, along with other Gaelic leaders who had supported Warbeck.
He died in 1505 and was succeeded in Tyrconnell by his son Hugh Duff O'Donnell, who was also considered a strong ruler who increased O'Donnell power into northern Connaught and enjoyed the support of the Crown authorities in Dublin. Together their reigns are sometimes considered a "golden age" of the O'Donnell's, when compared to the violent succession disputes that followed in the later sixteenth century.
He should not to be confused with the later Hugh Roe O'Donnell, who was his great, great-grandson.
Tír Connell, which between the 1460s and 1550s was the most powerful lordship north of the escir Riada. At its height, Uí Domhnaill kings exercised an imperium over what are now nine modern Irish counties, from Antrim to Mayo, with influence stretching to scotland, england, and the continent. Aodh Ruadh Ó Domnaill (r. 1461-1505) was the earl of Kildare's major ally at Knockdoe in 1504, and de facto King of The North. (Martyn, 2016, p. 122)
[Tír Connell] was not a depressed economic region in late medieval times. [It was] famous for its vast herds of cattle and flocks of sheep, as well as large unenclosed areas sown with oats. The uplands and the rugged western coastlands were then largely uninhabited, providing its lowland inhabitants with booley pastures, turf banks, large woodlands and extensive reserves of all types of wild game. Rivers and sheltered inlets were also a very valuable natural resource, giving salmon, eel, oyster and seal fisheries. Many sheltered bays attracted large numbers of foreign merchants and fishermen exploiting an immensely valuable salmon and herring fishery, which developed during the course of the early sixteenth century into one of the biggest of its kind in europe. [It] had long and well-established trading links with ports such as Bristol … st Malo and Morlaix in Brittany … Galway and Drogheda. (Mac Eiteagáin, 1995, pp. 203-28)