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The Flight of the Earls

On September 4, 1607, Hugh O’Neill, Earl of Tyrone, and Rory O’Donnell, 1st Earl of Tyrconnell, and about ninety followers depart from Lough Swilly for the European continent. It is known in Irish history as the “Flight of the Earls.” Their permanent exile is a watershed event in Irish history, symbolizing the end of the old Gaelic order.

After the defeat at the Siege of Kinsale in 1601, Hugh Roe O’Donnell of Tyrconnell travels to Spain to seek support from Philip III. Unsuccessful, he dies in Spain and is succeeded by his younger brother Rory O’Donnell.

The O’Neills and O’Donnells retain their lands and titles, although with much-diminished extent and authority. However, the countryside is laid bare in a campaign of destruction in 1602, which induces famine in 1603. Hugh O’Neill, Earl of Tyrone, is pardoned under the terms of the Treaty of Mellifont in March 1603 and submits to the crown.

When King James VI and I takes the English throne in 1603, he quickly proceeds to issue pardons for the Irish lords and their rebel forces. Already reigning as king of Scotland, he has a better understanding of the advantages from working with local chiefs in the Scottish Highlands. However, as in other Irish lordships, the 1603 peace involves O’Neill losing substantial areas of land to his cousins and neighbors, who would be granted freeholds under the English system, instead of the looser arrangements under the former Brehon law system. This is not a new policy but is a well-understood and longstanding practice in the Tudor conquest of Ireland.

On September 10, 1602, the Prince of Tyrconnell has already died, allegedly assassinated, in Spain, and his brother succeeds him as 25th Chieftain of the O’Donnell clan. He is later granted the Earldom of Tyrconnell by King James I on September 4, 1603, and restored to a somewhat diminished scale of territories in Tyrconnell on February 10, 1604.

In 1605, the new Lord Deputy of Ireland, Sir Arthur Chichester, begins to encroach on the former freedoms of the two Earls and The Maguire, enforcing the new freeholds, especially that granted in North Ulster to the O’Cahan chief. The O’Cahan had formerly been important subjects of the O’Neills and required protection; in turn, Chichester wants to reduce O’Neill’s authority. O’Cahan has also wanted to remove himself from O’Neill’s overlordship. An option is to charge O’Neill with treason if he does not comply with the new arrangements. The discovery of the Gunpowder Plot in the same year makes it harder for Catholics to appear loyal to both the crown and the papacy. A lengthy legal battle however finds in O’Neill’s favor.

By 1607, O’Neill’s allies the Maguires and the Earl of Tyrconnell are finding it hard to maintain their prestige on lower incomes. They plan to seek Spanish support before news of the Battle of Gibraltar arrives. When their ship drops anchor, O’Neill seems to have joined them on impulse. He had three options:

  • Flee with his friends and hope for a reinvasion by Spain
  • Go to London and stay at court until his grievances are redressed
  • Do nothing and live on a reduced income as a large landowner in Ulster

Fearing arrest, they choose to flee to Continental Europe, where they hope to recruit an army for the invasion of Ireland with Spanish help. However, earlier in 1607 the main Spanish fleet in Europe had been defeated by the Dutch in the Battle of Gibraltar. But the oft-repeated theory that they are all about to be arrested contradicts writer Tadhg Ó Cianáin, the main historical source on the Flight, who says at the start of his account that O’Neill heard news of the ship anchored at Rathmullen on Thursday September 6, and “took his leave of the Lord Justice (Chichester) the following Saturday.” They had been meeting at Slane for several days, and there is no proof that warrants for his arrest have been drawn up, nor is it a hurried departure.

Also, as the Anglo-Spanish War (1585–1604) has been ended by the Treaty of London in 1604, King Philip III of Spain wants to remain at peace with England under its new Stuart dynasty. As a part of the peace proposals, a Spanish princess is to marry James’ son, Henry, though this never happens. Spain had also gone bankrupt in 1598. Tyrone ignores all these realities, remains in Italy, and persists with his invasion plan until his death in exile in 1616.

The earls set sail from Rathmullan, a village on the shore of Lough Swilly in County Donegal, with some of the leading Gaelic families in Ulster. Several leave their wives behind, hoping either to return or retrieve them later. They travel down Lough Swilly on a French ship. Their departure is the end of the old Gaelic order, in that the earls are descended from Gaelic clan dynasties that had ruled their parts of Ulster for centuries. They finally reach the Continent on October 4, 1607.

Their destination is Spain, but they disembark in France. The party proceeds overland to Spanish Flanders, some remaining in Leuven, while the main party continues to Italy. Tadhg Ó Cianáin subsequently describes the journey in great detail. While the party is welcomed by many important officials in the Spanish Netherlands, he makes no mention of any negotiations or planning between the earls and the Spanish to start a new war to regain the earls’ properties.

James I soon plants the O’Neill and O’Donnell lands with Protestant settlers, helping to sow the seeds of the present “Troubles.” O’Donnell dies in Rome in 1608 and O’Neill dies there also in 1616.

Ó Cianáin’s diary is important as the only continuous and contemporaneous account of the Flight. Its original title, Turas na dTaoiseach nUltach as Éirinn – the departure of the Chiefs of Ulster from Ireland – has been changed since the creation of the more dramatic phrase “Flight of the Earls” to the latter’s modern literal translation, Imeacht na nIarlaí.

The Flight of the Earls is a watershed event in Irish history, as the ancient Gaelic aristocracy of Ulster goes into permanent exile. Despite their attachment to and importance in the Gaelic system, the Earls’ ancestors had accepted their Earldoms from the English-run Kingdom of Ireland in the 1540s, under the policy of surrender and regrant. Some historians argue that their flight is forced upon them by the fallout from the Tudor conquest of Ireland, while others that it is an enormous strategic mistake that clears the way for the Plantation of Ulster.

From 1616, a number of bards outside Ulster have a poetic debate in the “Contention of the bards” and one of the arguments celebrates King James’s Gaelic-Irish Milesian ancestry through Malcolm III of Scotland. So, it is debatable whether the Gaelic order has ended or is evolving.

(Pictured: A bronze sculpture commemorating the Flight in Rathmullan, County Donegal)


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Death of Red Hugh O’Donnell

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 Lynagh 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 deathbed 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)