In 1587, the English inside the Pale (a fortified district around Dublin) were concerned about the Irish whom they had not yet brought under their control – especially in Ulster. The Ulster clans were an independent lot, and something had to be done to insure their non-interference with Crown activities. One of the more powerful clans was the O'Donnell of Tír Connail, the present day Donegal. One day, a trading ship sailed across Lough Swilly offering Spanish wines and fine fabrics for the Donegal Chieftains and their ladies. Hugh Roe (Red Hugh) O'Donnell, the 15-year old heir to the Tír Connail Chieftainship, was lured aboard to see the merchandise and, once on board, his guards were overpowered and the young prince was taken prisoner. The kidnapping infuriated the Irish, but Lord Deputy Perrot told them that Red Hugh would remain alive, as long as the O'Donnells remained passive, and the young hostage was taken to Dublin Castle.
Many Christmases passed without Red Hugh at the hearth of his father, The O’Donnell – Chieftain of Tír Connaill – as he remained a prisoner of Lord Deputy Perrot. Perrot was later recalled and charged with treason and sent to the Tower of London where he was poisoned. Sir William Fitzwilliam replaced Perrot and it is doubtful that he even knew the story of a 15-year old red-haired boy who had been remanded to a cell in the Bermingham tower of Dublin Castle, but the O'Donnell's had not forgotten their prince. Over the previous years as Christmas snow blanketed the hills of Donegal, those hills echoed with prayers for the safety of their young prince.
Then, on a cold winter night after Christmas 1590, while the sentries sheltered themselves from a pitiless sleet, Red Hugh, Art Kavanaugh and several others let themselves down from a tower window by a rope to the drawbridge, crossed the moat, fled through the town and into the woods. O'Donnell, emaciated from three years in captivity was unable to keep up with his companions and rather than delay their escape, sought refuge at the house of Felim O'Toole, the beautiful site of which is now called Powerscourt. Fearing the British, O’Toole turned O’Donnell in and Red Hugh was returned to Castle captivity. Having learned a lesson, Red Hugh strengthened himself with exercise for another try; next time, he would not falter. Meanwhile, Henry and Art O’Neill, sons of Chieftain Shane O’Neill, were imprisoned. With these sons of another Ulster Chieftain from Tír Eoghain (Tyrone), Red Hugh hatched another plan of escape when the celebrating guardsmen were at their least attentive.
On Christmas Eve 1591, they let themselves down through the privy into the sewer beneath the castle and out to the moat and, leaving their soiled outer garments behind, they were met by young Turlough O'Hagan, who had been sent by Hugh O’Neill, Earl of Tyrone, to be their guide. While fleeing the city, they lost Henry who later made it to Tyrone on his own. O’Donnell, O’Neill and O’Hagan made it to the Slieve Rua (Red Mountain). Art O'Neill has been injured descending from the castle and could go no further. Red Hugh took him to shelter beneath a huge rock and sent O’Hagan to Glenmalure, to Feagh Mac Hugh O'Byrne, a chieftain famed for his heroism against the Crown. Days later, close to death, covered with snow, and embracing the lifeless body of his comrade in a vain attempt to keep him from freezing, Red Hugh was found by Fiach McHugh O'Byrne. Red Hugh's escape sent a thrill through all of Ireland: the heir of Tir-Connaill was safe. After many close encounters, O'Donnell made his way to Hugh O’Neill at Dungannon, who escorted him to Hugh Maguire, War Chief of Fermanagh. The Maguire brought him home to Tir-Connaill, where in May, 1593, the young O'Donnell stood on the Rock of Doone, the ancient crowning stone of Clan O'Donnell, and received a title higher than any foreigner could give – that of The O'Donnell, Prince of Tir-Connaill. Clan O’Donnell, formerly peaceful, was now eager for revenge and there were now two War Chiefs in Ulster. Hugh O'Neill decided to make it three and he renounced the title, Earl of Tyrone, taking instead the ancient Gaelic title of The O'Neill.
Thus the English, worried by the possibility of losing control of the northern Chieftains, had created the strongest Irish alliance in history. The three Hughs – O’Donnell, Maguire and O’Neill – in command of close to 1,000 horse-soldiers and 7,000 foot, at a time when the entire English force in Ireland was less than 2,000, united to take Ireland back from the Crown. And they did! That precipitated the Nine Years War in which Elizabeth regained control after the Battle of Kinsale which took place on another Christmas Eve in 1601 – but that’s another story!