HUGH ROE O'DONNELL (1572-1602), eldest son of Hugh Mac Manus O'Donnell, and grandson of Manus O'Donnell by his second marriage with Judith O'Neill, was the most celebrated member of his clan. His mother was Ineen Dubh, daughter of James MacDonnell of Kintyre; his sister, the second wife of Hugh O'Neill, 2nd earl of Tyrone. These family connections with the Hebridean Scots and with the O'Neills made the lord deputy, Sir John Perrot, afraid of a powerful combination against the English Government, and induced him to establish garrisons in Tyrconnel and to demand hostages from Hugh MacManus O'Don nell, which the latter ref ased to hand over. In 1587 Perrot con ceived a plan for kidnapping Hugh Roe (Hugh the Red), now a youth of 15, who had already given proof of exceptional ability. A merchant vessel laden with Spanish wines was sent to Lough Swilly, and Hugh Roe with some youthful companions was en ticed on board, when the ship immediately set sail and conveyed the party to Dublin. The boys were kept in prison for more than three years. In 1591 young O'Donnell escaped; and after en during terrible privations he made his way to Tyrconnel, where in the following year his father handed the chieftainship over to him.
Red Hugh then led an expedition against Turlough Luineach O'Neill, who was at war with his kinsman Hugh, earl of Tyrone, with whom O'Donnell was in alliance, at the same time assuring the lord deputy of his loyalty. Determined to vindicate the tra ditional claims of his family in north Connaught, he aided Hugh Maguire against the English, though on the advice of Tyrone he abstained for a time from committing himself too far. When, however, in 1594 Enniskillen castle was taken and the women and children flung into the river from its walls by order of Sir Rich ard Bingham, the English governor of Connaught, O'Donnell sent urgent messages to Tyrone for help; and while he himself hurried to Derry to withstand an invasion of Scots from the isles, Ma guire defeated the English with heavy loss at Bellanabriska (The Ford of the Biscuits). In 1595 Red Hugh again invaded Con
naught, putting to the sword all above 15 years of age unable to speak Irish; he captured Longford and Sligo, which placed north Connaught at his mercy. In 1596 he agreed in conjunction with Tyrone to a cessation of hostilities with the English, and met the Government commissioners near Dundalk.
The terms he demanded were, however, refused. He hoped for help from Philip II. of Spain, with whom he and Tyrone had been in correspondence. In the beginning of 1597 he raided Con naught, where O'Conor Sligo had been set up by the English as a counterpoise to O'Donnell. He devastated the country and re turned to Tyrconnel with rich spoils; in 1598 he helped to defeat the English at the Yellow Ford on the Blackwater; and in 1599 he defeated an attempt by the English under Sir Conyers Clifford, governor of Connaught, to succour O'Conor Sligo in Collooney castle, which O'Donnell captured, forcing Sligo to sub mission. The Government now sent Sir Henry Docwra to Derry, and O'Donnell entrusted to his cousin Niall Garve the task of opposing him. Niall Garve, however, went over to the English. making himself master of O'Donnell's fortresses of Lifford and Donegal. While Hugh Roe was besieging Donegal in 1601, he heard that a Spanish force had landed in Munster. He marched rapidly to the south, and was joined by Tyrone at Bandon, but a night-attack on the English besieging the Spaniards in Kinsale having utterly failed, O'Donnell, who attributed the disaster to the incapacity of the Spanish commander, took ship to Spain on Jan. 6, 1602, to lay his complaint before Philip III. He was favourably received by the Spanish king, but he died at Simancas on Sept. Io in the same year.