Hugh Roe O’Donnell, better known as Red Hugh O’Donnell, was the leading claimant to the title of Lord of Tyrconnell in Donegal. In the turbulent years at the end of the 16th century, the English captured Red Hugh and imprisoned him in Dublin Castle to prevent him from forging an alliance with the Earl of Tyrone, as the English feared that such an alliance would threaten their hold over Ireland.
No-one had managed to escape the dark depths of Dublin Castle, but this did not stop Red Hugh from trying, firstly in 1591. It is said that during this escape, he crossed over Two Rock Mountain to seek refuge with Felim O’ Toole who had his stronghold at what is now Powerscourt. O’ Donnell was recaptured not long after, but made a second successful attempt in January 1592. This time he succeeded in reaching Fiach McHugh O’Byrne in Glenmalure, although his fellow escapee, Art O’Neill, perished from exposure in the freezing mountains. O’Donnell’s escape is still regarded as a key event in Irish history. He returned to Donegal to become leader of the O’ Donnell clan and forged an alliance with Hugh O’ Neill in the Nine Year’s War which came so close to overthrowing England’s hold over Ireland.
Ultimately all their efforts ended in failure after the Battle of Kinsale in 1602. Like many other Irish leaders, Red Hugh left Ireland in the Flight of the Earls, and went to Spain in the hopes of returning to Ireland with a large Spanish army. His dream was never to be realised and he died in 1602. An English spy, James Blake, claimed to have poisoned him, though that is the subject of debate. He was buried in Valladolid’s Chapel of Wonders – the same church where Christopher Columbus was interred almost a century earlier. Archaeologists are currently seeking his final resting place, and his time spent in the Dublin and Wicklow Mountains may just be the thing that allows them to identify his remains. According to accounts, he lost the big toe of each foot to frostbite in the freezing mountains.