other claimants to the O'Donnell Chiefdom including Hugh Roe's great uncle Hugh Dubh O'Donnell. In 1587, at the age of fifteen, he was either married or betrothed to Rose O'Neill, the daughter of Hugh O'Neill, 2nd Earl of Tyrone. This cemented a growing alliance between the two clans. The same year he was kidnapped by Sir John Perrot, then the English Lord Deputy of Ireland, in an attempt to prevent an alliance between the O'Donnell and O'Neill clans. At Rathmullan, O'Donnell was invited aboard a ship from Dublin to drink wine but was then carried away as part of a pre-planned operation. Meanwhile, Donnell O'Donnell's position as Chief of the Name was strengthened by the arrival of Royal Irish Army troops dispatched from Dublin Castle under the command of John Connill. Fiona MacDonald counteracted this by hiring large numbers of Redshank mercenaries from her native Scotland. She then defeated and killed her stepson at the Battle of Doire Leathan in 1590, while Red Hugh was a prisoner in Dublin. Subsequently imprisoned in Dublin Castle, O'Donnell escaped briefly on Christmas Day 1591 but was recaptured within days. Hugh O'Donnell made his successful escape only in January 1592, assisted by his High O'Neill's cousins Art and Henry O'Neill, who arranged for his flight from Dublin into the Wicklow Mountains in the depths of winter. It is likely that corruption played a part in his escape, and he was assisted by the Lord Deputy William FitzWilliam. O'Donnell successfully reached the stronghold of Fiach McHugh O'Byrne (another of O'Neill's allies) at Glenmalure, where he found refuge, but he had lost both big toes to frostbite and his companion and fellow escapee Art O'Neill had died of hypothermia on the slopes of Conavalla. Hugh O'Donnell and his two companions, the brothers Art and Henry (Hugh) O'Neill, were the only prisoners ever to successfully escape from Dublin Castle. The Nine Years War Upon his return to Ulster, he gained the leadership of the O'Donnell Clan. At the "Rock of Doon", near Termon, he was acclaimed as, "The O'Donnell", Chief of the Name and Lord of Tyrconnell, after his father abdicated in his favour later that year. He successfully led two expeditions against Turlough Luineach O'Neill in 1593, to force Turlough O'Neill to abdicate his chieftainship in favour of Hugh O'Neill. At this point, O'Neill did not join O'Donnell in open war but secretly backed him to