January 6th 1592 - Red Hugh O’Donnell escapes Dublin Castle

Imprisoned at the age of 15, the heir to the O’Donnell leadership staged a daring breakout.

On 6 January 1592, Red Hugh O'Donnell escaped from Dublin Castle, where he had been imprisoned for five years. The son of Sir Hugh O'Donnell, the ruler of Tyrconnell, Red Hugh (known also as Hugh Roe) was kidnapped at the age of 15 on the orders of John Perrot, the Lord Deputy of Ireland (and rumoured illegitimate son of Henry VIII). Red Hugh was lured onto a boat in Rathmullan, Co Donegal to drink wine, after which he was promptly abducted by Nicholas Barnes, a Dublin merchant, who was paid £100. The year Red Hugh was taken – 1587 – he was engaged to be married to Rose O'Neill, daughter of Hugh O'Neill, Earl of Tyrone. Perrot feared an alliance between the O'Donnells and the O'Neills, and thus sought to prevent it by having Red Hugh locked up.

The 1592 escape was not Red Hugh's first attempt. In 1591, he had broken out of the Gate Tower, using rope which had been smuggled into Dublin Castle. He made it as far as Wicklow, territory of Felim O'Toole, but O'Toole feared for his own safety, and thus had Red Hugh returned to Dublin, where he faced even stricter conditions. Now kept in the Record Tower, he and brothers Art and Henry O'Neill managed to overpower their captors in January 1592, and exited the castle by sliding down “privy-chutes” (in other words, sewage pipes). They had abandoned their cloaks, and their light clothing was ill-suited to the harsh January weather. Nevertheless, with the help of a guide, who provided them with food, they arrived at the foothills of the Dublin Mountains, where Red Hugh and Art parted company with Henry.

Their destination was the fortress of Fiach McHugh O'Byrne in Glenmalure, in the valley of the Wicklow Mountains, but the journey was far from easy. Art O'Neill had grown weak and heavy from his time in Dublin Castle, and had to be carried by Red Hugh and the guide. The three took shelter at the base of a cliff in Glenreemore (the 'glen of the big king'), before the guide was sent on to seek help from O'Byrne. When O'Byrne's men made their way to Glenreemore, they found Art and Red Hugh unconscious in the freezing cold. Art died from exposure not long afterwards, and Red Hugh was suffering from frostbite.

After recovering for a time in Glenmalure, Red Hugh returned to Ballyshannon in Donegal. Two of his frostbitten toes had to be amputated. He eventually succeeded his father as leader of the O'Donnells. Following the Battle of Kinsale 1601, he left Ireland for Spain, seeking help from King Philip III, where he died.

Sources

Hopkins, Frank, ‘Recalling the great escape’, Evening Herald (Dublin), 14 June 2003, p. 20.

Morgan, Hiram, Tyrone's Rebellion: The Outbreak of the Nine Years War in Tudor Ireland (London: Royal Historical Society, 1993).