Category: Archive

Hibernian Chronicle 409 years ago: Red Hugh escapes

February 16, 2011

By Staff Reporter

By Edward T. O’Donnell

Four hundred nine years ago this week, on Dec. 25, 1591, Red Hugh O’Donnell regained his freedom. He’d been kidnapped four years earlier by the British and jailed in Dublin Castle. Crown officials hoped this would prevent his family from leading a rebellion against British authority. It worked only so long as O’Donnell remained in prison. His escape in the early hours of Christmas morning 1591 caused a sensation throughout Ireland and before long the English faced an armed uprising that came to be known as the Nine Years War.

Hugh Roe O’Donnell was born on Oct. 30, 1572. He was a prince, the son of Hugh the Black O’Donnell, King of Tyrconnell, and Finola MacDonnell, known popularly as the Dark Daughter. In keeping with his high birth, Hugh received a full classical education and training in the military arts. Early on he acquired the nickname "Red" because of his flaming red hair.

At the time of his birth, many of Ireland’s leading families had begun to chafe under an increasingly heavy-handed and exploitative English policy. Two of Ireland’s most prominent families were the O’Donnells and the O’Neills. The latter had recently submitted to the Crown and received the title of Earl of Tyrone. The O’Donnell’s of Tyrconnell refused and were thus deemed a threat to English plans to control all of Ireland.

In 1587, Sir John Perrott, the top Crown official in Ireland, decided that the best way to prevent Hugh the Black from leading a rebellion was to kidnap his 14-year-old son. Young and trusting, Hugh was enticed aboard a cargo ship and quickly spirited away to Dublin Castle. So long as he held his son and heir, reasoned Perrott, of one of Ulster’s most restless chieftains wouldn’t dare challenge the power of the Crown.

Red Hugh was held for three years, chained in a cold tower, before he managed to escape with two companions. They were quickly captured and re-imprisoned. But O’Donnell had tasted freedom and was determined to regain it for good. With Henry and Art O’Neill, sons of Shane O’Neill, who had led a major rebellion in 1560-67, they plotted an escape. They decided on Christmas night on the theory that security would be light, if not lax.

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Their intuition proved correct and the three slipped into the night undetected. Unfortunately, the Christmas night escape sent them out into a fierce winter storm. With no heavy clothing or food, they endured severe hardships as they struggled to evade recapture. Art O’Neill died of exposure and O’Donnell nearly perished himself before being rescued by a friendly Irish chieftain. After a period of recuperation, though still unable to walk, he mounted a horse and rode to his father’s castle in Donegal.

The 19-year-old O’Donnell was appalled by what he saw on his journey and what he found on his arrival at Tyrconnell. Everywhere English armies terrorized local chieftains, seizing land, imprisoning leaders, and destroying monasteries. Tyrconnell was no exception. An English force under a Captain Willis controlled much of the region and was at that moment laying siege to the castle occupied by O’Donnell’s mother. Despite his badly injured feet (doctors later amputated his two big toes), Red Hugh rallied the nobles of Tyrconnell, raised an army and drove off Willis and his men. Enraged by the suffering inflicted upon him by the English and the continued threat they posed to his family and people, Red Hugh O’Donnell vowed revenge.

O’Donnell’s escape and subsequent victory over the English in Tyrconnell electrified Ireland, especially Ulster. It came on the heels of a notorious incident in which Perrott’s successor, Sir William Fitzwilliam, forcibly partitioned the kingdom of Monaghan and then executed a local chieftain. Outraged by the incident and fearing the precedent it set, Ulster’s most powerful chieftain, Hugh O’Neill, reconsidered his loyalty to the Crown and began to plot a rebellion. He raised an army and made contact with Catholic Spain to gain military support once the rebellion began. More important, he established an alliance with Red Hugh O’Donnell, who in May 1592 had succeeded his father to become King of Tyrconnell.

The long-anticipated uprising, subsequently known as the Nine Years War, began in 1593. O’Neill, O’Donnell, and other like-minded Ulster chieftains waged a spirited campaign and quickly scored victories against English troops advancing north into Ulster. The rebellion reached its high point in 1598 when O’Neill and O’Donnell routed an English army at the Battle of Yellow Ford. Resistance continued for another five years, but eventually superior English numbers and firepower prevailed. O’Neill signed a peace treaty in 1603. Four years later he and the remaining Irish earls fled to the continent and die in exile.

Red Hugh O’Donnell was not there to witness these dreary events. The year before the surrender, in a desperate attempt to acquire reinforcements, he’d journeyed to Spain. After eight frustrating months he fell ill, some say by poison. He lingered for 17 days but on Sept. 10, 1602, 11 years after his legendary escape from Dublin Castle, the last of Ireland’s great independent kings died. He was just 29 years old.

Special Note: I wish to thank reader Edward J. O’Donnell of Lakewood, Ohio for suggesting this story and providing much useful information on it.


Dec. 20, 1954: Jackie Gleason signs one of the largest entertainment contracts ever, a $6.1 million deal with the Buick Motor Company to produce 78 30-minute shows for 1955 and 1956.

Dec. 22, 1691: Defeated by King William, Patrick Sarsfield and 16,000 soldiers (known as the Wild Geese) sail for France.

Dec. 24, 1889: Home Rule leader Charles Stewart Parnell is named as "co-respondent" in divorce papers filed by Capt. William O’Shea. Revelation of Parnell’s affair with O’Shea’s wife Kitty leads to his downfall as a public figure.

Dec. 24, 1948: St. Patrick’s Cathedral in New York City provides the setting for the first midnight Mass broadcast on television.


Dec. 20, 1820: playwright Dion Boucicault born in Dublin.

Dec. 21, 1865: Revolutionary Maude Gonne born in Hamshire, England.

Dec. 21, 1876: Labor leader James Larkin born in Liverpool, England.

Dec. 23, 1862: Baseball manager Connie Mack (born Cornelius Alexander McGilicuddy) born in East Brookfield, Mass.

Dec. 25, 1829: Bandleader Patrick Sarsfield Gilmore born in Dublin.

Readers may reach Edward T. O’Donnell at odonnell@PastWise.com.

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