Hugh Roe O'Donnell, also known as Red Hugh O'Donnell, was a sixteenth-century Irish clan chief, Lord of Tyrconnell, and senior leader during the rising of the Irish clans against English rule in Ireland known as the Nine Years War (1593-1602). While Hiram Morgan has contemptuously dubbed Hugh Roe O'Donnell, "a counter-reformation Irish dynast living in the world of Machiavelli's Prince rather than The Cattle-Raid of Cooley", Morgan also concedes that primary sources other than the Elizabethan era English officials who wrote the Calendar of State Papers depict Hugh Roe as a man who genuinely believed in and lived by the traditional code of conduct demanded of an Irish clan chief. For this reason, Hugh Roe remains an iconic figure in the history of Irish nationalism and has recently drawn comparisons in the Spanish news media to both El Cid and William Wallace.

The Tudor conquest of Ireland took place during the 16th century under the Tudor dynasty, which ruled the Kingdom of England. The Anglo-Normans had conquered swathes of Ireland in the late 12th century, bringing it under English rule. In the 14th century, the effective area of English rule shrank markedly, and from then most of Ireland was held by native Gaelic chiefdoms. Following a failed rebellion by the Earl of Kildare in the 1530s, the English Crown set about restoring its authority. Henry VIII of England was made "King of Ireland" by the Crown of Ireland Act 1542. The conquest involved assimilating the Gaelic nobility by way of "surrender and regrant"; the confiscation and colonization ('plantation') of lands with settlers from Britain; imposing English law and language; banning Catholicism, dissolving the monasteries and making Anglican Protestantism the state religion.