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Promoting Irish Culture and History from Little Rock, Arkansas, USA


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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 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)


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The Battle of Curlew Pass

The Battle of Curlew Pass is fought on August 15, 1599, during the campaign of the Earl of Essex in the Nine Years’ War, between an English force under Sir Conyers Clifford and a rebel Irish force led by Hugh Roe O’Donnell. The English are ambushed and routed while marching through a pass in the Curlew Mountains, near the town of Boyle, in northwestern Ireland. The English forces suffer heavy casualties. Losses by allied Irish forces are not recorded but are probably minimal.

In April 1599, Robert Devereux, 2nd Earl of Essex, lands in Ireland with over 17,000 troops and cavalry to put down the rebellion of Hugh O’Neill and Red Hugh O’Donnell, which has spread from Ulster to all Ireland. To this end, he supports an Irish enemy of O’Donnell’s, Sir Donogh O’Connor (O’Connor Sligo), encouraging him to repossess those territories of his in Sligo that O’Donnell has occupied. Sligo Town is an excellent advance base, with Ballyshannon 20 miles to the northeast commanding an important river-ford at the principal western passage into O’Donnell’s country in Ulster. English military advisers have long urged the government councils in Dublin and London to capture these strategic points. O’Connor’s brother-in-law, Tibbot ne Long Bourke, is appointed joint-commander with an English captain of a force sailing from Galway, and O’Connor is expected to receive them in Sligo. However, O’Donnell quickly besieges O’Connor at Collooney Castle with over 2,000 men in an effort to starve him out, and Essex is put on the back foot. Essex has no option but to support the besieged O’Connor, one of the few Gaelic chieftains the Crown can rely upon for support. He orders the experienced Sir Conyers Clifford, who is based in Athlone, to relieve the castle with 1,500 English infantry and 200 cavalry. It is hoped that the operation would also distract the chief rebel, O’Neill, and afford the crown an opportunity to march into his Ulster territory across its southeastern border.

O’Donnell leaves 300 men at Collooney Castle under his cousin, Niall Garbh O’Donnell, and sends another 600 to Sligo town to prevent the landing of English reinforcements under Tibbot ne Long Bourke. He then marches to Dunavaragh with 1,500 of his men, where he is joined by additional forces under local chieftains Conor MacDermott and Brian Óg na Samhthach Ó Ruairc. The Irish then carefully prepare an ambush site in the Curlew Mountains, along the English line of march. O’Donnell has trees felled and placed along the road to impede their progress. When he gets word of the English passing through Boyle, O’Donnell positions his men. Musketeers, archers and javelin men are placed in the woods alongside the road to harass the English. The main body of Irish infantry, armed with pikes and axes, are placed out of sight behind the ridge of the mountain.

In hot harvest weather, Clifford’s force marches from Athlone through Roscommon, Tulsk and Boyle. At 4:00 PM on August 15, they reach the foot of the Curlew Mountains, which have to be crossed before Sligo can be approached. The expedition is poorly supplied, and Clifford’s men are tired and hungry, and probably in no fit state to continue. But Clifford has received false intelligence that the pass is undefended, and he therefore chooses to seize the opportunity and march across, promising his troops plenty of beef in the evening. This means that his men miss out on the rest that had been planned for them in Boyle, whereas the Irish are well fed and prepared.

The English come under gunfire, arrow and javelin attack as soon as they reach the first of O’Donnell’s barricades, between Boyle and Ballinafad. The barricade is immediately abandoned by the Irish but as the English moved past and proceed up the hill they sustain further casualties. The road consists of “stones of six or seven foot broad, lying above ground, with plashes of bog between them,” and is lined with woodland on one side. The further the English advance, the more intensive the rebels’ fire becomes, and some English soldiers begin to lose their nerve and slip away. Eventually, there is a firefight, lasting about 90 minutes, at the end of which the English vanguard has run out of gunpowder. The commander of the vanguard, Alexander Radcliffe, can no longer control his troops. They wheel about in a panic and collide with the main column, which breaks and flees. The commander leads a charge with his remaining pikemen but is shot dead. With the English ranks in disarray, the main body of Irish infantry, which has concealed itself on the reverse slope of the hill, closes in and fights hand to hand. Clifford tries to regain control over his men, but appears overcome by his circumstances. He manages to rally himself and is killed by a pike-thrust as he rushes the enemy. The English are routed, but the situation is prevented from becoming a complete disaster for them when the commander of the horse, Sir Griffin Markham, charges uphill and temporarily drives the rebels back.

Though the actions of the English cavalry allows many of their foot soldiers to escape, Clifford’s men are pursued as far as the town of Boyle, where they find shelter in Boyle Abbey. About 500 English are killed in the battle. Irish losses are not recorded, but are probably small, having been firing from prepared positions and then routing a disorganised and demoralised enemy.

Clifford’s head is cut off and delivered to O’Donnell, who has remained nearby but without taking part in the fight. While the head is brought to Collooney Castle to intimidate its defenders, the trunk is carried by MacDermott to the monastery of Lough Key, where he hopes to use it to ransom his own prisoners. At last, the trunk is given a decent burial in the monastery.

O’Connor Sligo surrenders the castle shortly afterwards and reluctantly joins with the rebels. After the victory, there is a noticeable increase in the rate of desertion by Irish troops from the ranks of Essex’s army, and the earl orders that the surviving troops be divided up as fit only to hold walls.

The battle is a classic Gaelic Irish ambush, similar to the Battle of Glenmalure in 1580 or the Battle of the Yellow Ford in 1598. According to the Annals of the Four Masters, the victory is put down to the intercession of the Blessed Mary, rather than to arms. But Clifford had been overconfident, a trait in him that Essex once warned against, and it is clear that English military commanders are choosing to learn the hard way about the increased effectiveness of Irish rebel forces. Queen Elizabeth I‘s principal secretary, Sir Robert Cecil, rates this defeat (and the simultaneous defeat of Sir Henry Harrington in the Battle of Deputy’s Pass in County Wicklow) as the two heaviest blows ever suffered by the English in Ireland, and seeks to lay the blame indirectly on Essex. It leaves O’Donnell and O’Neill free from any threat from the Connacht side, and renders a land-based attack through Armagh highly improbable, a factor that weighs with Essex as he marches northward later in the year and enters a truce with O’Neill.

In August 1602, the Curlew Pass is the scene of the last victory won by the rebels during the war, when a panicking English force is again routed and suffers significant losses. This time the rebels are led by Rory O’Donnell who commands 400 musketeers.

Today the battlefield at Curlew Pass is overlooked by an impressionistic sculpture by Maurice Harron called “The Gaelic Chieftain”, unveiled in 1999.


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Death of Hugh O’Neill, Earl of Tyrone

hugh-o-neillHugh O’Neill (Irish: Aodh Mór Ó Néill), the 3rd Baron Dungannon and 2nd Earl of Tyrone, dies in Rome on July 20, 1616. His career is played out against the background of the Tudor conquest of Ireland and he is best known for leading the resistance during the Nine Years’ War, the strongest threat to Tudor authority in Ireland since the revolt of Silken Thomas. The defeat of O’Neill and the conquest of his province of Ulster is the final step in the subjugation of Ireland by the English.

Although born into the powerful O’Neill dynasty of Ulster, O’Neill is fostered as a ward of the Crown in County Dublin after the assassination of his father, Matthew, in 1558. His wardship ends in 1567 and, after a visit to the court in London, he returns to Ireland in 1568 and assumes his grandfather’s title of Earl of Tyrone. By initially cooperating with the government of Queen Elizabeth I, he establishes his base of power, and in 1593 he replaces Turlough Luineach O’Neill as chieftain of the O’Neills. But his dominance in Ulster leads to a deterioration in his relations with the Crown, and skirmishes between his forces and the English in 1595 are followed by three years of fruitless negotiations between the two sides.

In 1598 O’Neill reopens hostilities. His victory over the English on August 14 in the Battle of the Yellow Ford on the River Blackwater, Ulster, the most serious defeat sustained by the English in the Irish wars, sparks a general revolt throughout the country. Pope Clement VIII lends moral support to his cause and, in September 1601, four thousand Spanish troops arrive at Kinsale, Munster, to assist the insurrection. But those reinforcements are quickly surrounded at Kinsale, and O’Neill suffers a staggering defeat in December 1601 while attempting to break the siege. He continues to resist until forced to surrender on March 30, 1603, six days after the death of Queen Elizabeth.

Elizabeth’s successor, King James I, allows O’Neill to keep most of his lands, but the chieftain soon finds that he cannot bear the loss of his former independence and prestige. In September 1607 he, with Rory O’Donnell, 1st Earl of Tyrconnell, and their followers, secretly embark on a ship bound for Spain. The vessel is blown off course and lands in Normandy. From there the refugees make their way via the Spanish Netherlands to Rome, where they are acclaimed by Pope Paul V. This “Flight of the Earls” signals the end of Gaelic Ulster and thereafter the province is rapidly Anglicized. Outlawed by the English, O’Neill lives in Rome the rest of his life. He dies there at the age of 66 on July 20, 1616. He is interred in the Spanish church of San Pietro in Montorio.