Hugh Roe O'Donnell (Irish: Aodh Ruadh Ó Domhnaill), also known as Red Hugh O'Donnell (30 October 1572 – 10 September 1602), was a sixteenth-century leader of the Gaelic nobility of Ireland. He became Chief of the Name of Clan O'Donnell and Lord of Tyrconnell in 1593, following a lengthy succession dispute within the derbhfine of the O'Donnell dynasty, and after escaping a five-year imprisonment without trial in Dublin Castle. Along with his father-in-law Hugh O'Neill of Tyrone, he led an alliance of Irish clans in the Nine Years' War against the English government in Ireland. Hugh Roe led an Irish army to victory in the Battle of Curlew Pass. After defeat in the Siege of Kinsale, he travelled to Spain to seek support from King Philip III. Unsuccessful, he died in Spain and was succeeded by his younger brother Rory O'Donnell. He is sometimes also known as Aodh Ruadh II or Red Hugh II, especially in his native County Donegal. Biography Early life, imprisonment, and escape For the political context of O'Donnell's life see the Tudor conquest of Ireland Hugh Roe O'Donnell was born in 1572, as a son to the Chief of the Name and Lord of Tyrconnell, Sir Hugh O'Donnell, and his second wife, Fiona MacDonald, the daughter of the Chief of Clan MacDonald of Dunnyveg. He was fostered by the MacSweeneys and O'Cahans and other cadet branches of the O'Donnell dynasty's derbhfine.<ref name=Hiram>[https://www.dib.ie/biography/odonnell-red-hugh-o-domhnaill-aodh-ruadh-a6343 Morgan, Hiram. "O'Donnell, ‘Red’ Hugh (Ó Domhnaill, Aodh Ruadh)", Dictionary of Irish Biography]</ref> Hugh Roe had numerous brothers and sisters including Donnell, Rory and Cathbarr. His father, Sir Hugh, was a long-standing ally of the Crown, in an attempt to counterbalance the power of Shane O'Neill and Sir Turlough Luineach O'Neill, the Chiefs of Clan O'Neill in neighbouring Tír Eoghain. In Sir Hugh's later years, a long-running succession dispute broke out to determine who would succeed him. Although Fiona, better known as Iníon Dubh (Lit. "The Dark Lady", pronounced in Ulster Irish as 'In-neen Doo'), pushed for Red Hugh to become the Tanist of Tyrconnell, it was Red Hugh's elder half-brother Donnell O'Donnell who emerged as the leading candidate. The Crown chose to support Donnell as it regarded him as the least dangerous potential Clan leader, partly due to the fact that Donnell's mother was an Irishwoman while Red Hugh's mother was the daughter of a Scottish clan chief. There were a number of