Red Hugh's escape from Dublin Castle

Aodh Ruadh Ó Domhnaill was kidnapped in 1587 at the age of fifteen by Sir John Perrot's agents at Rathmullan in Donegal — invited aboard a merchant ship under safe conduct, locked below decks, and delivered to Dublin Castle as a hostage to keep his father quiet. The taking of teenagers from the great Gaelic families as 'pupils' of Tudor justice was systematic crown policy through the 1580s. Red Hugh was one of about a dozen young men of the northern dynasties held in the castle through that decade.

He escaped first in January 1591, with two companions, lowering himself with a rope through a high window — but was recaptured at Powerscourt in the Wicklow foothills within days, betrayed by his hosts. He was returned to harsher confinement, this time in fetters in the keep.

The second escape, on Christmas night 1591, was prepared with the help of Henry O'Hagan, a kinsman in the city, and of Fiach McHugh O'Byrne of Glenmalure (see the Byrne page) who agreed to receive the escapees in his mountain stronghold. Red Hugh and two of the other northern hostages — Henry and Art O'Neill — bribed a sentry, descended into the castle's privy shaft (the literal cesspit underneath the building), made their way out through a sewer that emptied into the Poddle, and walked from Dublin city up into the Wicklow hills in a heavy December snowstorm.

It was the worst winter of the decade. Art O'Neill, weakened by years of imprisonment, sat down in the snow on the slopes of Lugnaquilla, refused to go further, and froze to death where he sat. Red Hugh's feet were frostbitten so badly that he lost both big toes; he was carried the last miles by O'Byrne's men into Glenmalure, where he was hidden through January and February 1592.

From Glenmalure he was taken north in stages — to Mellifont, to the protection of his cousin Maguire in Fermanagh, and finally home to Donegal in March. He was inaugurated as the Ó Domhnaill at the Rock of Doon in Kilmacrenan on 3 May 1592, aged twenty. He was nineteen when he was carried out of Glenmalure with the snow still on his crippled feet, and within two years was leading the western half of the longest Gaelic war ever fought against the Tudor crown.

He died in Spain a decade later, at twenty-nine, with the shoes still always slightly modified for the missing toes. The escape itself, and the death of Art O'Neill in the snow at Slievemaan above Glenmalure, are the central founding episodes of the Tír Chonaill heritage tradition. A small commemorative cross stands at Slievemaan today.