Hugh Roe O’Donnell (Aodh Rua ÓDomhnaill), sixteenth century Irish nobleman also known as Red Hugh O’Donnell, dies at Simancas Castle in Valladolid, Spain, on September 10, 1602. Evidence suggests he might have been poisoned by an English spy.

O’Donnell is born on October 30, 1572 in Lifford (which is in present-day County Donegal) and is the son of Hugh McManus O’Donnell, the Gaelic Lord of Tyrconnell, a territory which takes in most of the present-day county of Donegal except for the Inishowen peninsula. His mother, Aodh MacManus’ second wife, is the formidable and extremely well connected Scottish lady, Fionnuala Nic Dhomhnaill, known to history as the Iníon Dubh or The Dark Daughter. A daughter of James Mac Donald she had been raised at the Scottish court.

In 1587, at the age of fifteen, O’Donnell marries Rose O’Neill, the daughter of Hugh O’Neill, Earl of Tyrone, a nephew of Turlough Luineach O’Neill who is recognised by the Irish as The O’Neill. He is, therefore, a bridge between two traditional enemies, the O’Donnell’s and the O’Neills.

The English Lord Deputy of Ireland, Sir John Perrot, recognises the importance of the young O’Donnell prince and decides to secure him as a hostage thus giving him power over the O’Donnell clan and preventing them from forming a treaty with the O’Neills. In 1587, when he is sixteen, O’Donnell and two friends, a MacSweeney and an O’Gallagher, are persuaded to board a ship at Rathmullan which has been disguised as a Spanish wine barque. Once onboard they are carried off to Dublin Castle as prisoners. The O’Donnell’s offer to pay a large ransom and the Iníon Dubh also gives up 25 Spaniards rescued from the Armada. The English agree to this but as soon as the Spaniards are handed over they are beheaded. The agreement is not kept.

Perrot has his hostage but a most reluctant one. The young man continuously seeks ways to escape. His first opportunity comes at Christmas in 1590 when a rope is smuggled in to the prince. He escapes and flees into the Wicklow Mountains. He seeks shelter with Phelim O’Toole who has him returned to the English as he fears the anger of the infamous Perrot.

A year later, at Christmas in 1591, O’Donnell makes his second attempt at escape, this time by crawling through the Dublin Castle sewers. With him are Henry and Art O’Neill, two sons of Shane O’Neill (Shane the Proud). This time the escapees make their way to the Glenmalure stronghold of Fiach McHugh O’Byrne. Unfortunately, the winter is very severe and Art O’ Neill dies from exposure just as the O’Byrne rescue party finds them. Both Red Hugh and Henry O’Neill suffer severe frostbite but are safely returned to Ulster.

While O’Donnell is held prisoner by the English, his father becomes senile. In 1592, when O’Donnell is sufficiently recovered, he is inaugurated as the O’Donnell and England, for her treachery, has an avowed and implacable enemy.

O’Donnell aids the Maguires of Fermanagh against the English and when his father-in-law, Hugh O’Neill, initiates the Nine Years’ War by leading his clan against the English at the Battle of Clontibret (1595) and Battle of the Yellow Ford (1598), O’Donnell is at his side.

In 1595 O’Donnell ambushes an English force in the Curlew Mountains, killing 500 of them including their commander. However, the tide is turning against the Irish now. England is flooding the country with armies and many of the leading Gaelic families are beginning to make deals with them.

In 1601 the Spanish land in Kinsale and the English besiege them. O’Neill and O’Donnell march south from Ulster and Ballymote Castle in Sligo in an attempt to break the siege. This turns into a debacle causing the Irish to scatter and the Spanish to surrender. O’Neill marches back north and O’Donnell is sent to Spain to ask for more troops from Phillip III. In Spain, he is treated like a royal. He petitions aid from the King who gives him a promise of another Spanish force.

As a year passes and O’Donnell does not receive any news from Philip III of Spain, he leaves again for Valladolid but he dies on September 10, 1602 while en route. He is attended on his death-bed by Archbishop of Tuam Fláithrí Ó Maolchonaire and two friars from Donegal named Father Muiris mac Donnchadh Ulltach Ó Duinnshléibhe and Father Muiris mac Seaán Ulltach Ó Duinnshléibhe. The Anglo-Irish double-agent, James “Spanish” Blake, is alleged to have poisoned O’Donnell.

It is, however, unlikely that O’Donnell is poisoned. A more probable cause of death is the tapeworm that Simancas documents of the time state to be the cause of his demise. His Last Will and Testament, written in his dying moments with his loyal retinue, is an extremely evocative and moving document. One original is preserved in Simancas and the other in the Chancellery archive in Valladolid.

O’Donnell is buried in the chapter of the Franciscan monastery in Valladolid. Though the building is demolished in 1837, the exact location of the tomb may have been discovered following a Spanish archaeological dig in May 2020.

O’Donnell is succeeded as chieftain of his clan and prince of Tyrconnell by his brother Rory.

(Pictured: Statue of Gaelic Chieftain Red Hugh O’Donnell in County Donegal)