Hugh Roe O'Donnell

For the earlier ruler of Tyrconnell, see Hugh Roe O'Donnell (died 1505).

Hugh Roe O'Donnell II
1934 depiction of O'Donnell by Richard King
Lord of Tyrconnell
Reign	23 April 1592 – 30 August 1602
Inauguration	23 April 1592
Predecessor	Hugh MacManus O'Donnell
Successor	Rory O'Donnell
Born	c. 20 October 1572 Tyrconnell, Ireland
Died	30 August 1602(1602-08-30) (aged 29) Simancas Castle, Crown of Castile
Burial	30 August 1602 Convent of St. Francis, Valladolid
Spouse	Rose O'Neill ​ ​ (m. 1592; div. 1597)​
Issue	None
House	O'Donnell dynasty
Father	Hugh MacManus O'Donnell
Mother	Iníon Dubh
Signature

Hugh Roe O'Donnell II (Irish: Aodh Ruadh Ó Domhnaill; c. 20 October 1572 – 30 August 1602), also known as Red Hugh O'Donnell, was an Irish clan chief and senior leader of the Irish confederacy during the Nine Years' War. He was Lord of Tyrconnell from 1592 until his death in 1602.

He was born into the powerful O'Donnell clan of Tyrconnell (present-day County Donegal). By the age of fourteen, he was recognised as his clan's tanist and engaged to the daughter of the prominent Earl of Tyrone. The English-ruled Irish government feared that an alliance between Tyrone and the O'Donnell clan would threaten the Crown's control over Ulster, so in 1587 Lord Deputy John Perrot arranged for Hugh Roe's kidnapping. The government subsequently backed regime change in Tyrconnell. After four years' imprisonment in Dublin Castle, Hugh Roe escaped circa January 1592 with the help of Tyrone's bribery. At nineteen years old, he was inaugurated as clan chief at Kilmacrennan on 23 April [N.S. 3 May] 1592.

Along with his father-in-law Tyrone, Hugh Roe O'Donnell led a confederacy of Irish clans in the Nine Years' War, motivated to prevent English incursions into their territory and to end Catholic persecution under Elizabeth I. Throughout the war, O'Donnell expanded his territory into Connacht by launching raids against successive Lord Presidents Richard Bingham and Conyers Clifford. O'Donnell led the confederacy to victory at the Battle of Curlew Pass. In 1600, he suffered various military and personal losses. His cousin Niall Garve defected to the English, which greatly emboldened commander Henry Docwra's troops and forced O'Donnell out of Tyrconnell.

After a crushing defeat at the Siege of Kinsale, O'Donnell travelled to Habsburg Spain to acquire reinforcements from King Philip III. The promised reinforcements failed to materialise, and whilst preparing for a follow-up meeting with the king, O'Donnell died of a sudden illness at the Castle of Simancas, aged 29. His body was buried inside the Chapel of Wonders at the Convent of St. Francis in Valladolid. O'Donnell's premature death disheartened an already withering Irish resistance; Tyrone ended the Nine Years' War in 1603 with the Treaty of Mellifont.

Fiercely patriotic and militarily aggressive, O'Donnell is considered a folk hero and a symbol of Irish nationalism. He has drawn comparisons to El Cid and William Wallace. In 2020, an unsuccessful archaeological dig for his remains drew international media attention. Since 2022, the city has annually reenacted his 1602 funeral procession in period costumes.

Early life

Family background

Hugh Roe O'Donnell was born c. 20 October [N.S. c. 30 October] 1572, the eldest son of Irish lord Hugh MacManus O'Donnell and his second wife, Scottish aristocrat Fiona "Iníon Dubh" MacDonald. He was born into the ruling branch of the O'Donnell clan, a Gaelic Irish noble dynasty based in Tyrconnell, a kingdom geographically associated with present-day County Donegal. He had three younger brothers, Rory, Manus and Cathbarr (ordered oldest to youngest), and several sisters, Nuala, Margaret and Mary. He also had older half-siblings from his father's previous relationships, including Donal and Siobhán.

Paternally Hugh Roe claimed descent, via the lineage of Conall Gulban of the Cenél Conaill, from the semi-legendary High King Niall of the Nine Hostages. Through his mother, Hugh Roe was a descendant of the first six Scottish Chiefs of Clan MacDonald of Dunnyveg and from Somerled, the first Lord of the Isles. He was also descended from King of Scots Robert the Bruce and his grandson Robert II, the first Stuart king of Scotland.

Hugh Roe's father, Hugh MacManus, had ruled as clan chief and Lord of Tyrconnell since 1566. He was a wary politician who alternated between alliances with the O'Neill clan, his long-established rivals in Ulster, and the English government, which controlled the area around Dublin (the Pale). In 1569 Hugh MacManus married Iníon Dubh of Clan MacDonald of Dunnyveg, as part of a marriage alliance, which gave the O'Donnell clan access to the formidable Scottish mercenary forces known as Redshanks. Iníon Dubh pushed the O'Donnell clan further into opposition with the English, and in 1574 the clan established an alliance with ascendant O'Neill clansman Hugh O'Neill (future Earl of Tyrone) via his marriage to Siobhán.

Education and fosterage

Family tree

Hugh Roe O'Donnell and selected relatives Hugh Dubh O'Donnell d. 1537 Manus O'Donnell 1490–1563 Hugh McHugh Dubh O'Donnell c. 1537–1618 Calvagh O'Donnell c. 1515–1566 Hugh MacManus O'Donnell c. 1520–1600 Fiona "Iníon Dubh" MacDonald Hugh MacEdegany d. 1588 illegitimate Conn O'Donnell d. 1583 Donal O'Donnell d. 1590 Hugh Roe O'Donnell 1572–1602 Nuala O'Donnell c. 1575–c. 1630 Niall Garve O'Donnell c. 1569–1626 Legend XXX Subject of the article XXX Lord of Tyrconnell XXX Succession Challenger XXX Foster-father of Hugh Roe

The Franciscan friars at Donegal Abbey were the spiritual counselors of the ruling O'Donnells, and were also the educators of the dynasty's children. In medieval Ireland, the sons of Irish clan chiefs were typically trained from the age of seven in horse-riding and weaponry.

Children of the Gaelic Irish nobility were traditionally fostered to fellow clans, presumably in the hopes of developing political alliances. As such, Hugh Roe was fostered by four families of differing political alignments: Clans Sweeney na dTuath and O'Cahan, as well as two rival O'Donnell branches led by Hugh McHugh Dubh O'Donnell and Conn O'Donnell. Conn had a strong claim to the lordship as his father Calvagh was a prior ruler of Tyrconnell. In 1581 Conn turned hostile towards the ruling O'Donnells and Hugh Roe was removed from his care. Conn died in 1583 and Hugh Roe's succession seemed assured. Nevertheless, Conn's sons, particularly Niall Garve, looked to the English government as a means of restoring their branch of the family to power. By 1587, Hugh Roe was in the care of Owen Óg MacSweeney na dTuath, his final foster-father. According to historian Darren McGettigan, MacSweeney na dTuath "appears to have given [Hugh Roe] much freedom".

Ultimately Hugh Roe's fosterage did not engender much loyalty in his foster-families. Hugh McHugh Dubh antagonised the ruling O'Donnells into the 1590s, and the sons of MacSweeney na dTuath and Conn eventually opposed Hugh Roe by defecting to the English.

Rise to prominence

Hugh Roe saw his first military action in 1584, with his father's chief advisor Sir Eoin O'Gallagher, against Clan O'Rourke of West Breifne. Even before reaching the age of fifteen, Hugh Roe had become well known across Ireland. Biographer Lughaidh Ó Cléirigh praised the young noble: "He continued to grow and increase in comeliness and urbanity, tact and eloquence, wisdom and knowledge, goodly size and noble deeds". Hugh Roe began to be associated with Aodh Eangach, a prophesied high king. It was foretold that if two men named Hugh succeeded each other as O'Donnell chief, the last Hugh shall "be a monarch in Ireland and quite banish thence all foreign nations and conquerors".

By 1587, Hugh Roe was betrothed to the Earl of Tyrone's daughter Rose. In addition to Tyrone's marriage to Siobhán, this betrothal would further cement a growing alliance between two clans who had traditionally been mortal enemies for centuries. Hugh Roe had become a focus of authority within Tyrconnell, and Tyrone described him as "the stay that his father had for the quieting of his inhabitance". As tanist of the O'Donnell clan, Hugh Roe was widely considered to be his father's most likely successor.

Imprisonment and escape

Capture at Rathmullan

The English government feared that the emergence of a powerful O'Neill-O'Donnell alliance, which would be cemented by Hugh Roe's marriage to Rose, would threaten English control over Ulster. Though Tyrone professed loyalty to the Crown, he was attracting suspicion from the government due to his growing power. Hugh Roe's familial links to various Scottish Highland clans were also a cause for concern; English officials often pejoratively referred to him as "Scottish". Additionally Hugh Roe's father had failed to pay annual rents promised to the government, and at the time the English government kept hostages for policy reasons. Ultimately the government decided that Hugh Roe must not be allowed to succeed as O'Donnell clan chief, and so the Lord Deputy of Ireland, Welsh statesman John Perrot, hatched a plan to kidnap the young noble. In May 1587, Perrot proposed to Lord Burghley that he could capture "[Hugh MacManus], his wife (who is a great bringer in of Scots), and perhaps his son [Hugh Roe], by sending thither a boat with wines".

Lord Deputy John Perrot authorised Hugh Roe's kidnapping.

Hugh MacManus was summoned to a conference with Perrot. Meanwhile the ship Matthew, captained by Dublin merchant Nicholas Barnes (alias Nicholas Skipper) was dispatched to Rathmullan on Lough Swilly, where fourteen-year-old Hugh Roe was sojourning with his foster-father MacSweeney na dTuath. The ship was anchored and the crew went on shore under the guise of ordinary merchants selling wine. Hugh Roe heard of the merchant ship and arrived with several young companions. Barnes claimed that he had no wine left unsold except for what was left on the ship, and invited Hugh Roe aboard. Chief Donnell MacSweeney Fanad (Hugh Roe's host) was ashamed that the young noble had missed out on the wine and unwittingly encouraged him to take a small boat to the Matthew.

Chief MacSweeney Fanad, Chief MacSweeney na dTuath and Eoin O'Gallagher accompanied Hugh Roe onto the Matthew. Once on board, Hugh Roe and his compatriots were conducted into a secured cabin and plied with food and wine. Whilst they were enjoying themselves, the hatches were fastened and their weapons were removed. MacSweeney Fanad was released in exchange for his eldest son Donnell Gorm MacSweeney Fanad. O'Gallagher likewise gave his nephew Hugh O'Gallagher. MacSweeney na dTuath was also released upon giving "his eldest son" (actually a young peasant dressed in his son's clothes) as a hostage. Hostages were offered in Hugh Roe's stead to no avail, and the ship set sail for Dublin.

Imprisonment

Hugh Roe arrived in Dublin on 25 September; Queen Elizabeth I was informed the next day. Perrot ascertained that the peasant was not MacSweeney na dTuath's son and dismissed him. Hugh Roe and his fellow hostages were imprisoned in Dublin Castle, most likely one of the gate towers.

"It was anguish and sickness of mind and great pain to [Hugh Roe] to be as he was, and it was not on his own account but because of the great helplessness in which his friends and kinsmen, his chieftains and leaders, his clerics and holy ecclesiastics, his poets and learned men, his subjects and whole people were, owing to their expulsion and banishment to other territories throughout Erin. He was always meditating and searching how to find a way of escape."

—Lughaidh Ó Cléirigh, on Hugh Roe's imprisonment

Within three months, Tyrone was lobbying the queen for Hugh Roe's release. In 1588, he offered a bribe of £1000 to William FitzWilliam (Perrot's successor as Lord Deputy) plus £300 to newly-appointed officials. Tyrone was later accused of offering a further £1000 to Dublin Castle's constable. In spring 1588, Iníon Dubh offered Perrot a bribe of £2000, plus sureties and hostages, for her son's release. After the Spanish Armada's September 1588 shipwreck in Inishowen, Hugh MacManus offered the government thirty captured Spanish officers in exchange for his son. FitzWilliam refused due to "the dangers that might grow unto this miserable realm by letting loose the reins unto so harebrain and ungracious an imp". In 1590 he indicated a willingness to release Hugh Roe, but this came to naught.

The English attempted to convert Hugh Roe and his fellow Catholic hostages to Protestantism by bringing them to a Protestant service, but the boys shouted over the hymns and music so the service could not be heard. They did not desist even when carried out of the church and sent back to their cell, and were never again summoned.

During his time in Dublin Castle, Hugh Roe had little interaction with the outside world beyond conversations with fellow political prisoners (particularly the Anglo-Irish Munster lords imprisoned from the Desmond Rebellions). In witnessing first-hand the brutality inflicted by the Dublin government on Irish rebels, he became embittered and resentful of English authority. Ó Cléirigh stated that "[O'Donnell] had been listening to [stories about the English] during the four years and three months he was in the prison in Dublin, and that was the tale which he remembered best from the captives cast into prison with him... he said that the promises of the English were always vain and deceitful, and that it was by false promises they had stolen their patrimony from the Irish of the province of Leinster and of the province of [Munster]... The English tell you lies now, and they will attack you when they find you unprepared". Ironically, Hugh Roe learnt to speak English during his imprisonment. This period in Dublin is seen as the defining event of his short life.

Chaos in Tyrconnell

Hugh MacManus became prematurely senile, and Hugh Roe's imprisonment exacerbated a long-running succession dispute which had consumed Tyrconnell since October 1580. The dispute was bloody; three of Conn's sons were violently killed in the conflict. Iníon Dubh effectively took over Tyrconnell and ruled in her husband's name. She pushed successfully for Hugh Roe to become her husband's successor by spreading the Aodh Eangach prophecy and by directing her Redshanks to kill any challengers. Hugh MacEdegany, an illegitimate son of Calvagh O'Donnell, was the first major challenger. He was assassinated on Iníon Dubh's orders during a visit to her residence, Mongavlin Castle, in May 1588, leaving Niall Garve as head of the "MacCalvagh" branch.

Map of Ulster's Gaelic kingdoms in the 16th century

Further disruptions developed as the government appointed various administrators in Tyrconnell who ransacked and pillaged the kingdom. Perrot appointed William Mostian as Sheriff of Tyrconnell—he quickly carried out eight cattle raids, ransacking Donegal Abbey and murdering its guardian. Later the same year, FitzWilliam gave Captain John Connill charge of Tyrconnell after being bribed with two Spanish gold chains. Connill assisted the opponents of the ruling O'Donnells. He was later joined by Captain Humphrey Willis and two hundred soldiers. At one point Connill befriended then captured Hugh MacManus, but he was freed by Niall Garve. Another brutal administrator was Captain Bowen, a notorious torturer who fried the soles of his victims' feet. This chaos created mass resentment towards the English government.

Hugh Roe's elder half-brother Donal became the Crown's favored candidate for the chiefdom, and shortly after the Armada's shipwreck, FitzWilliam knighted and appointed Donal as Sheriff. FitzWilliam also imprisoned important Tyrconnell nobles Sean O'Doherty (Lord of Inishowen) and Eoin O'Gallagher, believing them to possess Spanish treasure from the Armada. O'Gallagher's imprisonment also had political motivations as he was a major adherent of Hugh Roe during the succession dispute. Donal made an effort to depose his father, backed by Connill's troops. Iníon Dubh, backed by her Redshanks and the clans of the Cenél Conaill who remained loyal to her husband, crushed Donal at the Battle of Doire Leathan on 3 September [N.S. 14 September] 1590.

Willis (who replaced Donal as Sheriff) and Connill exploited the ensuing chaos. They took control of western Tyrconnell and began raiding into the east, accompanied by a Captain Fuller. Their forces also ransacked southern Tyrconnell and forced many of the population to flee to the mountains.

Iníon Dubh bought off Niall Garve with a political marriage to her daughter Nuala, in an attempt to temper his hostility. By 1592, Niall Garve was in a strong position to claim Tyrconnell's lordship. Despite the continual presence of freebooting government troops, Tyrconnell's nobility remained obsessed with their succession conflict.

First escape attempt

Hugh Roe was imprisoned in Dublin Castle's Bermingham Tower.

After three years and three months in captivity, Hugh Roe made his first escape attempt in January 1591, in the company of fellow Ulster hostages Donnell Gorm MacSweeney Fanad and Hugh O'Gallagher. It is possible that the escape was incentivised by news of Donal's death. Before Hugh Roe and his companions were put in their cells one night, they escaped through a nearby window and climbed down a rope onto the drawbridge. They jammed a block of timber into the door, preventing the guards from pursuing them. By the time the guards noticed Hugh Roe's absence and gave chase, the fugitives had already escaped past the open city gates.

Hugh Roe's shoes fell apart and he was left behind by his companions in the thick woods beyond Three Rock Mountain. He sent word to Castlekevin in County Wicklow, the territory of Chief Felim O'Toole, who had visited him in Dublin Castle. O'Toole wanted to assist Hugh Roe but faced pressure from his clan, who feared the consequences of aiding a high profile fugitive. O'Toole's sister Rose quickly planned for her husband Fiach McHugh O'Byrne, of Clan O'Byrne, to take Hugh Roe to his house in Glenmalure. According to O'Sullivan Beare, O'Byrne and his clansmen immediately set out to rescue Hugh Roe, but their inability to cross a flooded river prevented them from reaching Castlekevin in time. English officer George Carew was dispatched to Castlekevin on 15 January [N.S. 25 January] and Hugh Roe was surrendered and returned to Dublin Castle in chains. Ó Cléirigh states the Privy Council were pleased with Hugh Roe's recapture: "they made little or no account of all the hostages and pledges who escaped from them, and they were thankful for the visit which restored him to them again". Hugh Roe was lodged in Dublin Castle's record tower (the Bermingham Tower), shackled more heavily than before, and checked by the chief gaoler twice a day.

Second escape attempt

Further information: Art O'Neill Challenge

Around January 1592, Hugh Roe made a successful escape attempt with his fellow prisoners Henry MacShane O'Neill and Art MacShane O'Neill. After years of lobbying and bribery, Tyrone had finally succeeded in bribing officials to help facilitate Hugh Roe's escape. FitzWilliam, considered one of Tudor Ireland's most corrupt Lord Deputies, was most likely the recipient of this bribe, though this has never been conclusively proven. A 17th-century account by Donegal priests alleged that Tyrone successfully bribed FitzWilliam with £1,000 (equivalent to £287,000 in March 2024). In summer 1590, Conn MacShane O'Neill alleged that Tyrone "did lay down a plot and practised the escape of Hugh Roe" from prison—the plot apparently involved a silk rope and prepared horses. This is obviously a reference to some previous attempt, but is an accurate forecast of Hugh Roe's eventually successful escape.

Hugh Roe O'Donnell's father-in-law, Hugh O'Neill, Earl of Tyrone, bribed officials to ensure the successful prison escape.

This escape plan was far more prepared than Hugh Roe's prior attempt. The constable of Dublin Castle John Maplesden was on his deathbed which distracted the chief gaoler from his duties, making it the perfect time to mount an escape. A gaoler's servant named Edward Eustace promised four horses which would be saddled in a nearby stable for three days prior. Fiach McHugh O'Byrne promised shelter for the fugitives at Glenmalure. Richard Weston, a servant of Tyrone, managed to supply Hugh Roe with a silk rope, and winter clothes were acquired for the long journey.

When the three prisoners were unshackled to eat, they took advantage of the gaolers. The prisoners made their way to the privy house. They tied one end of the rope there, and fed the other end down the privy hole which led outside the castle. Henry became separated from the others. According to Ó Cléirigh, "the darkness of the night and the hurry of the flight separated [Henry] who was the oldest of the party... [The others] were not pleased at the separation". According to O'Sullivan Beare, Henry made his way down the rope first, and without waiting for the others, escaped safely back to Ulster. Hugh Roe followed, but Art MacShane was badly injured by a falling stone whilst sliding down the rope. Although Eustace had promised horses, on that day they had been removed without his knowledge. Once outside the castle, Hugh Roe and Art MacShane met with Eustace who guided them through Dublin. The trio proceeded through the dark streets, mixing with the crowds, and safely escaped the city.

The escape plan went awry. The fugitives had left their winter clothes in prison and Hugh Roe's shoes became worn out, exposing him to the elements. Art MacShane had to be carried by the others, either because he had grown fat and unfit in prison, or because of his injury from the falling stone. The trio made it into the Wicklow Mountains at which point they sought shelter in a cave, traditionally said to be along the slopes of Conavalla. Hugh Roe and Art MacShane were too weak to reach Glenmalure, so Eustace left them in the cave and went on ahead to get help. According to O'Sullivan Beare, Hugh Roe managed to survive by eating leaves and bark, but despite his pleas, Art MacShane could not eat. After three nights, when O'Byrne's men arrived to rescue them, Hugh Roe and Art MacShane were found covered in snow. Art MacShane died of hypothermia. O'Sullivan Beare claimed that Hugh Roe refused to eat due to his grief over Art MacShane's death, but was compelled to do so by O'Byrne's men. He was taken to Glenmalure where he was revived with difficulty, tended to and recovered. Art MacShane's family were rivals to Tyrone, so it was speculated that Tyrone had O'Byrne's party kill him, though it is more likely he died of exposure. He was buried on the mountainside.

A cross marks the spot where Art MacShane O'Neill is said to have died.

Unusually, the state papers do not reference Hugh Roe's escape until his return to Ulster. This could point to corruption or embarrassment on the part of government officials. In a letter to Lord Burghley, FitzWilliam attempted to vindicate himself by declaring he had sacked Maplesden (who died mere days after the escape) and imprisoned the chief gaoler. An outraged Queen Elizabeth I wrote to statesman Thomas Burgh in May 1592 and decreed that "O'Donnell escaped by the practice of money bestowed on somebody. Call to you the Chancellor, Chief Justice Gardiner, and the Treasurer, and inquire who they are that have been touched by it".

Accession as clan chief

Return to Ulster

For a few days after his rescue, Hugh Roe was tended to in a hidden cabin in Glenmalure. Hugh Roe and O'Byrne swore oaths to mutually assist each other if they came under English attack, and Hugh Roe promised to make Tyrone and Chief Hugh Maguire of Fermanagh swear similar oaths. Turlough Boye O'Hagan, a trusted emissary of Tyrone, arrived to escort Hugh Roe back to Ulster; they set out immediately. Hugh Roe's feet were frostbitten so he had to be lifted up and off of his horse. He was escorted across the Liffey by a band of horsemen (which included Felim O'Toole). He proceeded northwards under O'Hagan's guidance and crossed the Boyne on a small ferry kept by a "poor little fisherman", whilst his attendant led their horses through Drogheda. At Mellifont, he rested one night at the house of English ally Garret Moore, travelled through Dundalk and the Fews, and on the third day reached Armagh. The next day Hugh Roe arrived at Dungannon, Tyrone's residence, where the two men presumably discussed their plans to retake Tyrconnell's lordship. It is also here that they may have planned their future attack on Turlough Luineach O'Neill, Tyrone's rival in Tír Eoghain. Hugh Roe remained at Tyrone's residence for four days, hidden in a secret chamber to avoid corrupting Tyrone's loyalist public image. Afterwards, Hugh Roe was received by Maguire in Fermanagh. Maguire conveyed Hugh Roe across Lough Erne and brought him to the border of Tyrconnell where a party of supporters welcomed him. Hugh Roe then arrived at his father's castle in Ballyshannon.

Attack on English occupation

Tyrconnell had suffered much repression and turmoil in Hugh Roe's absence. Not long before his return, Willis and Connill's forces raided Donegal in the dead of night and occupied Donegal Abbey as a garrison. Ballyshannon Castle and Donegal Castle were the two major strongholds in Tyrconnell not yet deprived by the Crown. Even nobles in Tyrconnell who previously favoured the Crown had become resentful by this time. Hugh Roe made expelling the English forces his first order of business, and he rallied his family's followers to Ballyshannon.

Donegal Castle and Ballyshannon Castle were Hugh Roe O'Donnell's two major strongholds. The former (pictured) was restored in the 1990s; the latter was demolished in 1720.

As soon as Chief Donough MacSweeney Banagh heard of Hugh Roe's safe return, he attacked Willis, forcing him and his soldiers into their garrison in Donegal Abbey. Hugh Roe's forces killed a number of English troops, forcing them to abandon plunder. Hugh Roe travelled to Donegal to face Willis and forced the English troops to depart Tyrconnell. Sources conflict on the exact circumstances. According to Ó Cléirigh, Hugh Roe informed Willis that if he and his men left, they would not be harmed. According to a 17th-century account written by the clergy of Donegal Abbey, Willis threatened to set the church on fire, but Hugh Roe was "anxious to preserve the sacred edifice" and allowed Willis to depart unharmed. According to Captain Thomas Lee, O'Donnell intended to slaughter Willis's men but was held back by Tyrone. According to O'Sullivan Beare, Willis surrendered to Hugh Roe, who dismissed the English forces in safety with an injunction that Tyrconnell would neither give tribute or allegiance to the Crown. Afterwards the clergy returned to the abbey.

Inauguration

1885 illustration of O'Donnell's inauguration by John Dooley Reigh

After expelling Willis's forces in February, Hugh Roe returned to Ballyshannon where his big toes were amputated due to frostbite. He remained ill and in recovery for a year.

On 23 April [N.S. 3 May] 1592 at Kilmacrennan Friary, 19-year-old Hugh Roe O'Donnell was inaugurated as O'Donnell clan chief before an audience of his family and their supporters. The inauguration ceremony was part-religious and part-secular, and involved the O'Donnell clan's ornamental inauguration stone. Hugh MacManus's apparently voluntary abdication was "stage-managed" by Iníon Dubh, who remained the "head of advice and counsel" in Tyrconnell. Following his abdication, Hugh MacManus spent his final years living in retirement among the Franciscans at Donegal Abbey and doing penance for his sins. Hugh Roe's younger brother Rory was appointed as tanist.

Hugh Roe O'Donnell was inaugurated at Kilmacrennan Friary.

The major surviving opponents to Hugh Roe's succession—including Niall Garve, Hugh McHugh Dubh and Sean O'Doherty—did not attend the inauguration out of protest. At the time, Niall Garve was in Dublin unsuccessfully seeking support from authorities. Tomás G. Ó Canann noted that, as Hugh Roe O'Donnell failed to secure the attendance of such a significant chunk of the Cenél Conaill, his inauguration was arguably illegitimate. With the exception of Niall Garve in 1603, Hugh Roe was the last O'Donnell clansman to be traditionally inaugurated as clan chief.

Rise in power

Immediately after his inauguration, Hugh Roe O'Donnell and Tyrone mounted raids against Turlough Luineach, who had provided assistance to O'Donnell's rivals such as Niall Garve. O'Donnell desired revenge and sought to assist his new ally Tyrone, whose alliance with O'Donnell was founded on using the latter's military power to take control of Tír Eoghain.

In June 1592, O'Donnell renewed his clan's interest in north Connacht by supporting a revolt among the lower MacWilliam Bourkes, to the chagrin of Lord President Richard Bingham. O'Donnell imposed his control over Tyrconnell. He dispelled bandits from Barnesmore Gap, established an execution site at Mullaghnashee beside Ballyshannon Castle, and took pledges from all nobles wealthy enough to maintain four horsemen.

Turlough Luineach O'Neill supported O'Donnell's opponents.

O'Donnell dispatched letters to the state informing of his inauguration and justifying his attack on Turlough Luineach. He offered to submit to FitzWilliam in person if he was lent £800. FitzWilliam, who recognised the necessity of conciliating with O'Donnell, reprimanded him for his arrogance but promised to pardon him and lend him £200 if they met at Dundalk by July. Tyrone was anxious to improve his own standing with the government, and at FitzWilliam's request, he travelled to Donegal to confer with O'Donnell. After some convincing, O'Donnell accompanied Tyrone to Dundalk to submit to FitzWilliam. Bribery was probably involved in the meeting, which took place in a church on 2 August 1592. According to Thomas Lee, O'Donnell bribed FitzWilliam with £500 to ensure favourable negotiations. O'Donnell made various agreements with FitzWilliam: he pledged his loyalty to Elizabeth I, agreed to receive a Sheriff in Tyrconnell, promised to pay his father's covenanted rents, to treat his rivals (O'Doherty, Niall Garve and Hugh McHugh Dubh) fairly, to banish Catholic clergy from Tyrconnell, and to avoid supporting the MacWilliam Bourkes in Connacht. O'Donnell successfully negotiated to retain about 100 redshanks in Tyrconnell for use as his mother's bodyguards, ostensibly because he was concerned for her safety. After the meeting, the two Hughs feasted at Dungannon where they further discussed their developing alliance.

Tyrone's daughter Rose was escorted to Tyrconnell in expectation of her marriage to O'Donnell. The couple were formally married during Christmas-time 1592 at O'Donnell's house. According to McGettigan, the marriage started out as a success with Rose having some measure of influence over O'Donnell.

Despite his promises to FitzWilliam, O'Donnell subjugated his rivals. Sean O'Doherty was captured at a parley and imprisoned; only then did he acknowledge O'Donnell's lordship. In early 1593, O'Donnell obtained Hugh McHugh Dubh's submission by taking his last stronghold at Belleek and beheading sixteen of his followers "by train of a feigned treaty of friendship, mediated by Maguire". This sufficiently intimidated Niall Garve that he submitted to his younger cousin through fear. He was forced to turn over control of Lifford's castle, though he did not give up his ambitions to seize the lordship. With the Tyrone-O'Donnell alliance against him, Turlough Luineach surrendered his lordship in May 1593. Tyrone took control of Tír Eoghain, making both O'Donnell and his father-in-law the rulers of the two major kingdoms of Gaelic Ulster.

Initial rebellion

Conference of bishops

O'Donnell sought military aid from King Philip II of Spain.

By late 1592 the Crown's continual advances into Ireland, as well as the recent executions of chieftains Hugh Roe MacMahon (1590) and Brian O'Rourke (1591) had created a fierce resentment in the Gaelic nobility and Irish Catholic clergy. Catholic priests were suffering harassment and imprisonment from English authorities, and Spain had been a refuge to the Irish Catholic clergy since the 1570s. Archbishop Edmund MacGauran returned from Spain having met with King Philip II in September 1592. MacGauran was eager to obtain Spanish military aid to combat English forces in Ireland. Philip II wanted Ireland as an ally in the Anglo-Spanish War, but would only promise support if Ireland proved itself by launching prior military action. MacGauran sought Irish lords willing to openly defy the Crown, and in December a conference of seven Catholic bishops met in Tyrconnell. The bishops saw O'Donnell as their main hope, and declared he was "fittest for the part" and thus to be "their leader or general". On 29 March [N.S. 8 April] 1593, O'Donnell addressed Irish nobles living in Spain: "I and the other chiefs who have united with me and are striving to defend ourselves, cannot hold out long against the power of the Crown of England without the aid of his Grace the Catholic King.... We have thought it well to send the Archbishop of Tuam [James O'Hely] to treat of this matter with his Majesty".

Maguire's revolt

Captain Willis was appointed by FitzWilliam as Sheriff of Fermanagh against Maguire's will. In early April 1593, Willis entered Fermanagh with at least 100 men and began violently pillaging and raiding. This exacerbated resentment towards the Crown, and after Willis' first offensive, O'Donnell met with MacGauran, Maguire, Brian Oge O'Rourke and Theobald, Richard and John Bourke at Enniskillen Castle on 28 April [N.S. 8 May]. MacGauran advised that the noblemen sign a letter addressed to Philip II which emphasised their oppression and which requested urgent reinforcements from the Spanish army. Archbishop O'Hely was tasked with delivering the confederates' messages: two letters from O'Donnell, one letter from MacGauran, and the 8 May letter signed by the confederates.

The Irish confederacy formed following a meeting at Hugh Maguire's stronghold, Enniskillen Castle.

Maguire obtained reinforcements from Tyrone's brother and foster-brothers, who were likely involved on Tyrone's behalf, and forced Willis and his men from Fermanagh. Maguire's revolt marked the start of the Nine Years' War.

Historians have debated on O'Donnell's position within the confederacy. Historians Nicholas Canny, Michael Finnegan, John J. Silke and Darren McGettigan credit O'Donnell as the confederacy's driving force until Tyrone's break into open rebellion. Historians Hiram Morgan and James O'Neill have disputed this by emphasising that Tyrone was a more important figure who hid his allegiance to the confederacy for strategic reasons. The Sheriff of Monaghan alleged that Tyrone attended the meeting at Enniskillen Castle, though Tyrone did not sign MacGauran's letter. Around August 1593, Maguire stated to a spy that Tyrone had pushed him into rebellion and "promised to assist him & bear him owt in his warre". O'Hely reached the Spanish court by September 1593 where he met with Juan de Idiáquez, the royal secretary. In Idiáquez's notes to Philip II, he notes that the early confederates wanted Tyrone to join them in open rebellion, though it appears Tyrone refused to publicly defy the Crown without reassurance that Spanish reinforcements would arrive.

Secret rebellion

Catholic bishops began to spread the Aodh Eangach prophecy to advance the Irish rebellion. Maguire and O'Rourke continued to rebel by attacking English forces. O'Donnell aided the growing rebellion by sending MacSweeney gallowglass, but publicly he feigned neutrality. This was because he lacked sufficient forces to combat a direct assault from English forces; he also faced pressure from his father-in-law to likewise appear publicly loyal to the Crown. Bingham put Maguire and O'Rourke under heavy pressure, and O'Donnell used their chiefdoms as a buffer between Bingham's forces and Tyrconnell. O'Donnell had some influence over Maguire, giving him advice and sheltering his creaghts on Tyrconnell's borders. MacGauran was killed on 23 June [N.S. 3 July] 1593 whilst accompanying Maguire on a raid. In September, O'Donnell sent his mother to Scotland to secure further Scottish troops.

Signatures of the founding members of the Irish confederacy. Left column, top to bottom (clergymen): Edmund MacGauran, Redmond O'Gallagher, Richard Brady, Cornelius O'Devany, Patrick MacCaul, Niall O'Boyle. Right column, top to bottom (noblemen): Hugh Maguire, Theobald Bourke, Richard Bourke, John Bourke, Brian Oge O'Rourke.

Maguire's rebellious activity provoked a large-scale military expedition led by Marshal Henry Bagenal, which culminated at the Battle of Belleek in October. Tyrone fought on Bagenal's side ostensibly to prove his loyalty to the Crown. O'Donnell was in nearby Ballyshannon when the battle was taking place, but he was ordered by Tyrone not to reinforce Maguire. The battle was a ploy to make the confederacy seem weaker than it actually was, thus diverting English attention away from Ireland. O'Donnell partially disobeyed Tyrone's order and sent 60 horsemen, 60 swordsmen and 100 gallowglass under the command of Niall Garve. Historian James O'Neill has theorised that O'Donnell intentionally dispatched Niall Garve to Belleek with the hope that he would die in the slaughter, thus easily eliminating a potential enemy. Bagenal's forces won the battle. Despite the successful ploy, the battle was damaging to O'Donnell. Many of the gallowglass were killed and Niall Garve survived. To placate the Crown's victorious army, O'Donnell sent 115 cattle to the English camp as a gift.

By November 1593, Bingham had received intelligence that O'Donnell was secretly assisting Maguire and O'Rourke. The Crown demanded that Tyrone discipline O'Donnell and bring him under control, and in March 1594, Tyrone and O'Donnell met with government commissioners near Dundalk. O'Donnell professed that "his ancestors had always been loyal to her majesty, and so he would continue but stood in danger of his life and feared practices would be used against him". Tyrone submitted a list of his and O'Donnell's grievances, but the talks ended in confusion when O'Donnell threatened to kill some of Tyrone's English friends. Afterwards government commissioners surmised that a confederacy had been established between the Ulster lords. In March 1594, Philip II sent a Spanish ship—containing O'Hely, Spanish experts and Irish émigrés—to Ireland on a reconnaissance mission, but the crew died when it was shipwrecked off the coast of Santander.

Open rebellion

William Russell served as Lord Deputy from 1594 to 1597.

O'Donnell was aware that Tyrconnell would become an easy target if Maguire and O'Rourke's territories were occupied by the English. In February 1594, O'Donnell demolished castles in Belleek and Bundrowes to prevent English forces from taking them, and he concentrated his forces at Ballyshannon on his mother's advice. That same month, Captain John Dowdall captured Enniskillen Castle, Maguire's stronghold, after a nine-day siege. O'Donnell rushed to Maguire's aid, assembling an army and joining Maguire to retake the castle. O'Donnell stated he "would not leave that siege until he had eaten the last cow in his country". The castle was blockaded by 11 June, and by late July the English soldiers were suffering from food shortages. O'Donnell's decision to join the siege of Enniskillen brought his rebellion into the open.

O'Donnell encountered resistance from his family, with both his brother Rory and his father Hugh MacManus opposing his choice to go to war. Frustrated with Tyrone's loyalist facade, O'Donnell warned Tyrone that he "must consider [him] his enemy, unless he came to his aid in such a pinch". Tyrone subsequently sent reinforcements under his brother Cormac MacBaron O'Neill to the Battle of the Ford of the Biscuits. O'Donnell continued to negotiate through his father-in-law; in August, Tyrone presented the new Lord Deputy, William Russell, with a lengthy document of O'Donnell's grievances and demands, titled "A note of such oppressions and indirect courses as hath been held in Tirconnell and other places". O'Donnell requested a general pardon for himself and his followers, as well as "good security" for Maguire, O'Rourke and rebels in County Monaghan. Russell ignored these demands and resupplied Enniskillen castle with 1,200 Irish Army soldiers—comprising most of the troops at his disposal. The English relief mission was successful but ominously peaceful—Russell lost communication with his spies as they had all been captured by confederate soldiers. By early 1595, Tyrone had finally joined O'Donnell in open rebellion with an assault on the Blackwater Fort.

Expansion into Connacht

O'Donnell launched raids against Richard Bingham, Lord President of Connacht, who had persecuted Connacht's Gaelic population.

In 1595, O'Donnell began to expand his rebellion into Connacht. His ancestors (particularly his grandfather Manus O'Donnell) had ruled over Lower Connacht, and Hugh Roe O'Donnell increasingly demanded the restoration of these lands. Richard Bingham had persecuted Connacht's Gaelic population since the mid-1580s, causing many refugees to flee to Tyrconnell. O'Donnell aided the refugees and recruited many of them as swordsmen. O'Donnell resented Bingham and was "easily tempted" by the refugees, who urged him to attack Bingham's administration. O'Donnell invaded Connacht on 3 March 1595 with 400 men. From Rathcroghan, the province's ancient royal capital, he launched large raids into Longford and Roscommon. In June 1595, the castle of Sligo, which was key to securing control over the province, was betrayed to O'Donnell "in a stroke of luck"; Bingham's government collapsed. O'Donnell reestablished brehon law and asserted suzerainty over north Connacht. According to Ó Cléirigh, O'Donnell "spared no one over fifteen years of age who could not speak Irish".

By 1595, O'Donnell and his wife were facing difficulties; Rose had not born him children. In order to increase his influence in southern Connacht, O'Donnell had hopes of a marriage alliance with Lady Margaret Burke, daughter of the neutral 3rd Earl of Clanricarde. With Tyrone's consent, Rose and O'Donnell separated, purportedly over her "barrenness". However the government became aware of his plan to reportedly "rob her from her parents by surprise or force", and in December Margaret was placed in protective custody. Additionally Clanricarde stated that he would "rather see [Margaret's] burial than her marriage to [O'Donnell] were he a good subject". Tyrone sent his trusted secretary Henry Hovenden to Tyrconnell to advise O'Donnell, and O'Donnell eventually took Rose back. His choice to remain in a barren marriage is representative of his dependence on Tyrone.

Peace talks

Negotiations with the Crown

O'Donnell lived under the reign of English monarch Elizabeth I (1558–1603), who asserted herself as "Queen of Ireland".

Tyrone and O'Donnell sought to delay the war in order to buy time for the arrival of Spanish troops, and in September 1595, Tyrone sent overtures of submission to the Crown. Tyrone convinced O'Donnell to submit to the authorities and agree to a ceasefire whilst the settlement could be negotiated. He tendered his submission in October, expressing his "inward sorrow and most harty repentance". A cessation of arms was signed on 27 October 1595. O'Donnell took advantage of the truce to intervene in Connacht politics. Accompanied by Cormac MacBaron and Tyrone's son Conn, he led a large force of troops into Mayo in December. During Christmas-time, O'Donnell stage-managed the election of Connacht exile Tibbot MacWalter Kittagh as the Lower MacWilliam Bourke. Further elections organised by O'Donnell, spanning four counties, were indicative of his growing power in Connacht.

In January 1596, O'Donnell and Tyrone entered into face-to-face negotiations with government commissioners. The two confederates refused to meet the commissioners anywhere except in the open fields, thus negotiations were conducted in the countryside near Dundalk. O'Donnell demanded his ancestral claims of lands in Sligo, exemption from the jurisdiction of a sheriff, and a pardon for Connacht men including O'Rourke and MacWilliam Bourke. Similarly to Tyrone he demanded religious liberty of conscience. The queen warily accepted O'Donnell's claims to lands in Connacht. On 28 January, the commissioners presented O'Donnell with a list of twelve articles. These urged him to disperse his forces, to shire Tyrconnell, to stop aiding O'Rourke and Maguire, to re-edify Sligo Castle, to pay annual rents to the Crown as his father had done, and to confess the extent of his dealings with Spain. O'Donnell agreed to most articles, with some exceptions. He refused to give hostages or make a personal submission. A compromise was created, and O'Donnell agreed to terms on 30 January. A hollow peace was signed on 24 April 1596, and further negotiations to develop a peace treaty were almost complete by May.

Relations with Spain

In May, three Spanish ships arrived at Tyrconnell with the aim of encouraging the confederates and assessing Ireland's military situation. Spanish captain Alonso Cobos arrived in Killybegs and was invited by O'Donnell to Lifford, where he was staying. O'Donnell refused to go further into conversation without Tyrone present "because there was one above him naming [Tyrone], which if he would consent unto it he would do the same". O'Donnell called the confederates to Lifford and in the meantime, he entertained Cobos and his men for three nights. When the confederates arrived at Lifford, a subsequent dinner took place. The confederates upheld their allegiance to Spain and pleaded for Philip II to re-establish Catholicism across Ireland.

O'Donnell sought to make Albert VII Ireland's new Catholic sovereign.

Later on, a secret talk between Cobos and O'Donnell, Tyrone, and Cormac MacBaron occurred in a small house beside Lifford's castle. Hugh Boye MacDavitt of Inishowen, a war veteran who had served in the Low Countries, served as their interpreter. After the meeting, the confederates jointly agreed to abandon the peace treaty and become vassals of Philip II. Tyrone and O'Donnell also petitioned Philip II to make Albert VII, Archduke of Austria, the new Catholic monarch of Ireland. O'Donnell and his father-in-law began to deliberately derail peace negotiations and provoke war in previously peaceful parts of the country. They developed a sophisticated "good cop, bad cop" routine which they used to stall peace talks. Additionally, O'Donnell was ashamed at the sparse nature of his residence and set about purchasing "linen and pewter and all other necessaries fit to entertain the Spaniards".

The confederate lords of Connacht refused to discuss peace talks with government commissioners until the arrival of O'Donnell, who was apparently delayed by dealings with Redshanks. When O'Donnell arrived that June, he refused to hand over English hostages until his terms were met. Tyrone sent Hovenden to ostensibly aid O'Donnell in pacifying Connacht, but the government intercepted a letter revealing that Hovenden was intentionally stalling negotiations so that Tyrone would have to be brought in as an arbitrator; this he eventually was. The commissioners were in a weak position due to Elizabeth I's health issues. Soon after, O'Donnell met with Tyrone, O'Rourke and MacWilliam Bourke at Strabane. Together, they issued a letter to Munster's population demanding they adhere to Catholicism and join the confederacy. In October, Cobos was sent back to Ireland to brief the confederates on the impending 2nd Spanish Armada. Cobos's briefing motivated O'Donnell to make extensive preparations for the arrival of Spanish troops in Tyrconnell. After much delay, the Armada sailed from Lisbon in late October 1596, though it ended in disaster when a sudden storm claimed over 3,000 lives.

Elizabeth I reopened negotiations in Dundalk. Ó Cléirigh states that Elizabeth offered to forfeit Ulster to the confederates (with the exception of land from Dundalk to the Boyne). O'Donnell was apparently instrumental in the confederacy's rejection of this offer—he was possibly motivated by Philip II's recently renewed interest in Ireland. O'Donnell's relationships to Spain and England were complicated by the fact that aging monarchs Philip II and Elizabeth I were both in ill health at the time.

Renewal of hostilities

Clifford's presidency

Conyers Clifford succeeded Bingham as Connacht's Lord President. After his death at the Battle of Curlew Pass, his severed head was carried by O'Donnell as a trophy.

Elizabeth I suspended Bingham from the presidency of Connacht. Conyers Clifford, a distinguished soldier favoured by the Irish, was made Connacht's chief commissioner in December 1596. O'Donnell again raided into Connacht in January 1597, sacking Athenry and plundering the suburbs of Galway city. He was supported by competitors to the Clanricarde title. Clifford responded by forcing MacWilliam Bourke from Mayo. O'Donnell reinstalled MacWilliam Bourke, but Clifford forced him out again in June.

Thomas Burgh took over as Lord Deputy in May 1597. Burgh refused to entertain the confederates' excuses and ordered prompt military attacks on both Tyrone and O'Donnell. In July, the English launched a two-pronged assault in Ulster; Clifford assembled 1,500 men at Boyle and led them into Tyrconnell as the western arm of the assault. Clifford's army besieged Ballyshannon castle for five days, but it was successfully defended by O'Donnell's garrison of eighty men, which included Spaniards. Once O'Donnell himself arrived, Clifford's army, which had exhausted its supplies, retreated to Sligo, abandoning three pieces of ordnance and losing many men. On 4 September 1597, Clifford was appointed as Connacht's new Lord President.

Lord Deputy Burgh died from illness in October. Despite the confederacy's advantageous position, Tyrone renewed peace negotiations. He submitted to authorities on 22 December and promised to renounce his Gaelic titles and rebellious activities. O'Donnell heavily criticised Tyrone for agreeing to a cessation, pointing out that the confederate forces were strong across Leinster, Connacht and Ulster. O'Donnell declared that he would break the cessation, though he never did.

Clifford changed tactics following the defeat at Ballyshannon. He encouraged confederates to change sides by promising them royal grants. In February 1598, founding confederacy member O'Rourke submitted at Boyle. By April, Clifford had lured further confederates Conor McDermot, O'Connor Don and Shane MacManus Oge (O'Donnell's cousin). In response, O'Donnell executed six of McDermot and O'Connor Don's pledges. He detained Shane MacManus Oge upon the latter's secret return to Tyrconnell. O'Donnell also killed sixteen of Mulmurry MacSweeney na dTuath's men when MacSweeney na dTuath was linked to Shane MacManus Oge. O'Donnell's younger brother Rory was also engaged by Clifford, and he resolved to serve against his brother. When this news reached O'Donnell, he had Rory clamped in chains—the brothers' relationship eventually improved and by 1600 Rory was once again fighting alongside his older brother. O'Donnell captured O'Rourke's brother Teigue and forced him to marry his sister Mary, in order to formalise an alliance and antagonise O'Rourke. By June 1598, O'Rourke had rejoined the confederacy in fear.

Battle of the Yellow Ford

Main article: Battle of the Yellow Ford

Government commissioners abandoned negotiations by spring 1598, recognising that O'Donnell and Tyrone were intentionally impeding the peace process. Tyrone was granted a pardon in April 1598. However he felt that the Crown would eventually supersede his authority in Ulster. When the truce expired in June, Tyrone besieged the Blackwater Fort. Bagenal encouraged for a relief exercise to be sent to the fort.

The Battle of the Yellow Ford was the greatest confederate victory during the Nine Years' War.

Tyrone called O'Donnell and Maguire to assemble their combined forces, numbering 5,000 men. The confederates made extensive plans to obstruct Bagenal's army, preparing deep trenches in the ground outside Armagh. Prior to the attack, the confederates made a speech "to incite their people to acts of valour". On 14 August, Bagenal's army was attacked by O'Donnell, Tyrone and Maguire's combined forces. O'Donnell attacked from the left and Tyrone from the right simultaneously. Bagenal was killed and roughly 2,000 men (half his army) were lost. O'Donnell's men ran out of ammunition and the English survivors fled to Armagh. More than 300 English soldiers deserted to the confederacy.

The battle was the greatest victory by Irish forces against England, and it sparked a general revolt throughout the country, particularly in Munster. News of the battle spread across western Europe, prompting Philip II to send a congratulatory letters to O'Donnell and Tyrone. Unfortunately for the confederacy, Philip II died in September and was succeeded by his son Philip III. Following the battle, O'Donnell purchased Ballymote Castle from Clan MacDonagh and made it his primary residence. He sent Sean O'Doherty, Donough MacSweeney Banagh and MacWilliam Bourke to successfully attack the O'Malleys in County Mayo. In December, O'Donnell led another successful raid into Clanricarde.

The confederates' victory unravelled much of Clifford's success in Connacht, leaving loyalist Donough O'Connor Sligo (lord of Lower Connacht) as his only Gaelic Irish ally. The Irish victory at the Yellow Ford was highly distressing to the English Privy Council, and after much hesitation Elizabeth I appointed her royal favourite Robert Devereux, 2nd Earl of Essex, as the new Lord Deputy. He arrived at Dublin in April 1599. Despite the generous resources afforded to him, Essex's campaign was a major failure on account of his poor generalship.

Battle of Curlew Pass

Main article: Battle of Curlew Pass

The Gaelic Chieftain (1999) by Maurice Harron, located near Boyle, commemorates the Battle of Curlew Pass.

In July 1599, Essex sent O'Connor Sligo to confront O'Donnell. In response, O'Donnell quickly laid siege to O'Connor Sligo's stronghold, Collooney Castle. Essex then ordered Clifford to relieve O'Connor Sligo, and Clifford subsequently led an expedition of 1,400 men towards Collooney Castle. O'Donnell left Niall Garve to continue the siege and he took up a position in the Curlew Mountains, where he remained for two months, deliberately provoking Clifford. In August, Clifford finally gave in and marched his troops into the Curlew Mountains. O'Donnell made a dramatic speech and prepared his men.

Once O'Donnell's brothers had lured Clifford's army into a prepared position, O'Donnell and O'Rourke (who was camped nearby) ambushed Clifford's forces in a swift battle. The English panicked and were routed back to Boyle Abbey. 240 English soldiers were killed, including Clifford who was stabbed by a pike. After the battle, O'Rourke decapitated Clifford and gave the head to O'Donnell. When O'Donnell presented Clifford's severed head to O'Connor Sligo, the latter surrendered Collooney Castle. The queen and her secretary of state Robert Cecil were shocked by the Irish victory. The victory is viewed as a highlight of O'Donnell's career, though contemporary sources credit O'Rourke and Conor McDermot with the battle's success.

O'Donnell forced O'Connor Sligo to join the confederacy, and he gave O'Connor Sligo "large numbers" of oxen, horses, cattle and corn to re-establish himself in lower Connacht. However he threatened O'Connor Sligo with imprisonment on an island in Lough Eske if he did not cooperate. By this time Iníon Dubh had been in Scotland for two months gathering redshanks—as Clifford's forces had been easily defeated, O'Donnell notified his mother that the redshanks were unnecessary, and she returned to Tyrconnell in January 1600 with gunpowder instead. O'Donnell followed the victory at Curlew Pass with a successful battle at the Ballaghboy Pass.

Quarrels with Tyrone

O"Donnell's partnership with Tyrone became strained over the former's divorce, their differing military approaches, and the division of resources from Spain.

By the late 1590s, O'Donnell's relationship with his father-in-law was coming under strain, not least because of the breakdown of O'Donnell's marriage to Rose. It was reported in April 1597 that O'Donnell had recently renewed his alliance with Tyrone, and that "their league of friendship is more apparently confirmed... by O'Donnell's receiving of the earl's base daughter" in marriage. By 1598, it was reported O'Donnell had divorced Rose, most likely against Tyrone's wishes. She remarried to Tyrone's principal vassal Donnell Ballagh O'Cahan by 1599. O'Donnell reportedly divorced Rose due to her "barronness", though the historian Morwenna Donnelly has questioned this truthfulness of this explanation, considering that O'Donnell did not immediately remarry to ensure an heir.

The confederacy leaders argued over the division of money and munitions sent from Spain. Tyrone typically demanded the superior portion; when munitions arrived in 1596, Tyrone took twenty firkins of gunpowder compared to O'Donnell receiving fifteen. This came to a head in mid-1599, when O'Donnell debated over the division of a delivery brought by Barrionuevo. O'Donnell felt he was owed more resources in view of his recent victories, as well as his riskier approach to warfare. According to a spy's report, "Tyrone and O'Donnell fell into some contention about receiving of the said munition and treasure, Tyrone challenging the disposal of the whole, as chief and general of the common service, and O'Donnell claiming as great a right in it as he, as he affirmed, as deeply engaged therein as he. In the end the assembly there (by mediation of an Irish bishop from Rome with them) overruled the disposition of the whole for Tyrone". A treaty of equality was established between the two men, which decreed that "one had no pre-eminence over the other and that in walking and travelling together whichever was the elder should be on the right hand".

Tyrone refused to fight Essex's dwindling forces; instead the two men parleyed on 7 September 1599 and a six-week truce was organised. O'Donnell was furious at Tyrone's decision to negotiate with Essex, as he wanted to avoid any association with English officials in favour of soliciting aid from the Spanish. He declared that he would travel into Connacht, but Tyrone forbid him on account of the truce. O'Donnell admitted that he would burn the entire Pale if not for Tyrone preventing him. Essex left Ireland on 24 September and was shortly afterwards removed from his post. Essex's downfall briefly put the confederacy in a strong position. In February 1600, Charles Blount, 8th Baron Mountjoy, arrived in Ireland as the new Lord Deputy. Mountjoy posed a major threat to the confederacy as he immediately began revitalising and restoring confidence in the royal army.

On 1 March [N.S. 11 March] 1600, Hugh Maguire was shot and killed whilst on reconnaissance near Cork. His lordship was contested by rival claimants Cúconnacht Maguire (his younger half-brother) and Connor Roe Maguire (his loyalist-leaning cousin). Tyrone favoured Connor Roe's accession, perhaps to ensure Connor Roe's loyalism was kept in check. O'Donnell favoured Cúconnacht, and a debate ensued on how to resolve the succession crisis. At a banquet at Tyrone's house in Dungannon, with Tyrone and both claimants present, O'Donnell addressed Cúconnacht as the new Maguire clan chief. O'Donnell's fait accompli affronted Tyrone and created further tension between the confederates.

In April 1600, a Spanish ship arrived in Ireland bearing considerable supplies of money and ammunition for the confederacy, as well as letters from Philip III. Tyrone and O'Donnell stimulated the Irish-Spanish alliance by sending pledges to Spain; Tyrone sent his son Henry, and O'Donnell sent the sons of O'Doherty and O'Gallagher.

Forced from Tyrconnell

Defection of Niall Garve

Commander Henry Docwra enticed Niall Garve to defect from the confederacy, which greatly weakened O'Donnell's power in Tyrconnell.

In May 1600, English commander Henry Docwra established an English garrison in Derry. O'Donnell made a substantial attempt to weaken Docwra's forces on 29 July. O'Donnell captured at least 60 horses and Docwra was nearly killed by Hugh McHugh Dubh. O'Donnell later made a failed night attack on the garrison. Despite the poor conditions at the Derry garrison—desertion and disease was rife—Docwra managed to maintain his position, which led to further tension between O'Donnell and Tyrone.

The prospects of Docwra's mission depended on winning over disaffected confederates, Niall Garve being the most important. Niall Garve's grievances were well-known to the government on account of his overtures, and Docwra began secretly communicating with him. By August, Niall Garve had sent through his list of demands, the principal of which was to rule Tyrconnell in the same manner as his grandfather Calvagh. Docwra promised to obtain him a royal grant of Tyrconnell if he defected and served against his cousin.

In June 1600, Hugh Roe O'Donnell left Ulster to plunder south Connacht and north Munster, entrusting Niall Garve to besiege Derry. O'Donnell did the same again in September when he left for a raid in Thomond. Whilst O'Donnell was in Ballymote, Niall Garve and his followers murdered Niall Garve's uncle Neachtan in a drunken rage. Neachtan was "a man of great authority with [O'Donnell] and all his country". Fearing O'Donnell's revenge, Niall Garve—alongside his three brothers and about 100 soldiers—quickly defected to the English. They joined Docwra on 3 October. O'Donnell was in Thomond when he received the news, and he immediately hurried to secure Lifford Castle to retain control over Lough Foyle. According to Willis, O'Donnell was "dumb-stricken" to hear of Niall Garve's betrayal and could not drink or sleep for three days. Niall Garve and an English force stormed Lifford Castle on 9 October, taking it from O'Donnell's brother Rory. O'Donnell wrote angrily to Tyrone, "charging him with many oversights, that he lay too long at the Moyry, that he spent his munition, lost his best men, and wasted his victuals there to no purpose".

"O'Donnell hath of late hanged many of good account . . . he dasht owt the brains of Neil Garve's childe (of [four] yeares olde) againste a post, beinge in the mother's custody, his owne naturall sister."

—Report by Henry Docwra, February 1601

O'Donnell's sister Nuala separated from Niall Garve due to his defection. According to a February 1601 report by Docwra, O'Donnell was so outraged by his brother-in-law's defection that he ordered mass hangings of Niall Garve's followers, and personally killed Niall Garve and Nuala's four-year-old son (his own nephew) by bashing the child's brains out against a post. This accusation is considered contentious among historians. Docwra's biographer John McGurk acknowledges the uncertainty of the report's truthfulness, and notes that it is unclear where Docwra received this intelligence. He points out that Docwra's "blunt" personality indicates that he reported current affairs accurately, and also admits that infanticide was a feature of warfare in the early modern period. Morgan notes that since this is a contemporary account, it should not be dismissed out of hand.

Battle of Lifford

Main article: Battle of Lifford

The confederacy suffered—and eventually surrendered—under the deputyship of Charles Blount, 8th Baron Mountjoy.

O'Donnell tried in vain to retake Lifford from Niall Garve, with minor skirmishes occurring around the castle. He lost about 20 men on 17 October 1600. He attacked again on 24 October, but Niall Garve retaliated by leading a cavalry charge of mixed Irish and English forces out to battle. During the battle, Niall Garve speared O'Donnell's brother Manus in the shoulder. Manus was taken to Donegal where he died from his wounds. O'Donnell's father Hugh MacManus died shortly afterwards, apparently from grief, on 27 November [N.S. 7 December]. They were buried beside each other at Donegal Abbey, as was customary for the ruling O'Donnell branch.

Docwra was pleased that the outcome of the battle had exacerbated the feud between O'Donnell and Niall Garve: "I think there needeth no better hostages for his fidelity, for he hath slain with his own hands (in fight and open view of our men that saw him) O'Donnell's second brother... His love and credit with the people is little inferior to O'Donnell's and may easily be more, if he be backed and strengthened by Her Majesty..." By December 1600, O'Donnell had put a price of £300 on Niall Garve's head. It appears Niall Garve made later efforts to rejoin the confederacy, but his murder of Manus made this near-impossible. His defection allowed Docwra to mobilise the Crown's forces beyond Lough Foyle into Tyrconnell, Inishowen and even Tír Eoghain. In addition to his skill as a guide across Tyrconnell, Niall Garve informed Docwra of his cousin's tactics.

Political alliances collapse

O'Donnell made further plans to cement his alliances beyond Ulster. In November 1600, he schemed to marry Joan FitzGerald (step-daughter to O'Connor Sligo and sister of the loyalist 1st Earl of Desmond). A servant met with Joan in Limerick "alleging that O'Donnell was a great Lord, and very rich, and that if he would prove good, he were a fit marriage for the best lady in the country". Joan rejected the match; additionally Lord President of Munster George Carew placed her under house arrest as a precaution.

O'Donnell became frustrated by the Spanish government's failure to send the military resources he desired. When a Spanish ship arrived around the time of the new year, O'Donnell was "like a madman when he saw no kind of news, neither of men nor money to come: presently swore he would go himself to Spain and would have gone indeed, if the Captain of the Spaniards had suffered him".

Sean O'Doherty, Lord of Inishowen, died on 27 January 1601, leading to a succession dispute. The O'Doherty clan preferred Sean's eldest son Cahir (then aged about 14) as the successor, but O'Donnell was bribed into inaugurating Sean's half-brother (and his own first cousin) Phelim Og O'Doherty. This decision outraged Cahir's foster family and they opened negotiations with Docwra to secure the lordship. O'Donnell attempted revenge by invading Inishowen with 1,500 men, but 40 of his men were killed and he retreated.

Both Docwra and O'Donnell's conduct of war was vicious; soldiers and civilians on either side were summarily executed (including Bishop Redmond O'Gallagher). In February 1601, Docwra noted that O'Donnell was regularly hanging individuals of otherwise good standing at the slightest cause for suspicion. When O'Donnell discovered that O'Connor Sligo was plotting with Mountjoy in early 1601, he imprisoned O'Connor Sligo in Lough Eske Castle's prison. Docwra plundered and garrisoned Rathmullan. By April, the list of O'Donnell's allies preparing to submit to Docwra included Tadhg Og O'Boyle, Owen Og MacSweeney (son of O'Donnell's late foster-father), Chief Donough MacSweeney Banagh, Chief Donnell MacSweeney Fanad and his son Donnell Gorm MacSweeney Fanad. By the end of 1601, only the immediate families of O'Donnell and Hugh McHugh Dubh remained loyal to the confederacy. Ballyshannon Castle became a safe haven to masses of women and children. Others took refuge in Lower Connacht. In late October 1601, O'Donnell's mother Iníon Dubh, plus one of his sisters, were taken prisoner in Collooney Castle.

Siege of Donegal

Main article: Siege of Donegal

The ruins of Donegal Abbey in 2009

On 18 March 1601, the government recognised Niall Garve as the rightful chief of the O'Donnell clan. Hugh Roe O'Donnell marched on Lifford in April 1601, forcing Niall Garve and his forces to temporarily retreat to Derry. Following the Earl of Clanricarde's death in May, O'Donnell concentrated his forces at Ballymote in anticipation of an attack from Clanricarde's successor. This allowed Niall Garve to take Donegal Abbey in August and occupy it as a garrison, installing 500 English troops. His hold over Donegal was his greatest blow against O'Donnell; it virtually prevented O'Donnell from entering Tyrconnell and led to a month-long siege. The siege climaxed on 26 September when a fire in the garrison's store detonated several barrels of gunpowder and caused the abbey to collapse. O'Donnell hurriedly ordered his men to attack, leading to a chaotic engagement amidst the burning abbey. Niall Garve's defeat seemed certain, but the loyalist forces held out until a relief force arrived and forced O'Donnell to call off the attack. 330 of Niall Garve's troops were killed during the battle, including his brother Conn Oge.

Niall Garve was so unsettled by his losses at the siege that, with Docwra's permission, he began negotiating with O'Donnell to became his tanist. Niall Garve's conditions (which included "that [Hugh Roe O'Donnell] and [Niall Garve] should be bound and sworn never to come in sight of one another") were so numerous that O'Donnell discarded negotiations.

Siege of Kinsale

Further information: 4th Spanish Armada and Siege of Kinsale

Spanish general Juan del Águila fought with O'Donnell at Kinsale.

Throughout 1601, Philip III was focused on dispatching an armed expedition to Ireland to improve his position in the Anglo-Spanish War. Under the command of General Juan del Águila, the 4th Spanish Armada finally landed and was besieged by English forces inside the port town of Kinsale—virtually the opposite end of Ireland from Ulster—on 21 September [N.S. 1 October] 1601. O'Donnell was energised by the news of the Spanish expedition's long-awaited arrival and he called his forces to abandon their sieging of Niall Garve's forces. He set out for Kinsale from Ballymote in late October with about 2,000 men. Tyrone's forces began their separate march a week after O'Donnell. O'Donnell's army marched through Connacht to Ath Croch near Shannon Harbour, where they were joined by Chief John Og McCoughlan and Captain Richard Tyrrell. O'Donnell's men carried two garrons loaded with Spanish silver on their march; this was to impress his wealth and wisdom upon locals he encountered. Marching onwards they reached Druim-Saileach in County Tipperary, where the troops stopped for twenty days to plunder the neighbouring territories. O'Donnell visited Holy Cross Abbey on Saint Andrew's Day where he venerated its relic of the True Cross. He also dispatched an expedition to Ardfert, which included his nephew Donal Oge (son of his late half-brother Donal), to recover the territory of confederacy ally Thomas Fitzmaurice. Carew attempted to intercept O'Donnell on 7 November but O'Donnell eluded him by passing through a defile in the Slieve Felim Mountains. O'Donnell's forces regrouped in Connelloe, County Limerick, and finally united with Tyrone at Bandon on 15 December.

Map of the Siege of Kinsale

The Crown's army was trapped in Kinsale between the Irish and the Spaniards. It appears Tyrone and O'Donnell had previously agreed to starve out the English, but Juan del Águila urged for a prompt combined attack. Near-contemporary writers Ó Cléirigh and O'Sullivan Beare allege that O'Donnell was convinced by Juan del Águila and naively urged Tyrone to attack. This account is not unanimously accepted by historians. McGurk, Silke, McGettigan and Cyril Falls concur; Morgan and G. A. Hayes-McCoy disagree. O'Donnell had previously induced Tyrone into a full frontal assault during a campaign in 1598, so this narrative is not out of the question. Morgan claims that the pressure from the beleaguered Spaniards that wore down Tyrone, and that both O'Donnell and Tyrone had their reputations at stake. Whatever the cause, Tyrone uncharacteristically agreed to a combined attack on both English camps.

At dawn on 24 December [N.S. 3 January 1602] 1601, Tyrone's forces of 4,000 men took their position. Mountjoy spotted the soldiers and ordered an immediate attack. Tyrone retreated but Mountjoy's cavalry charge routed the confederate soldiers; 1,200 were killed and 800 were wounded. O'Donnell was too far off to aid Tyrone. The sight of butchered Irish forces demoralised O'Donnell's soldiers, and many fled despite O'Donnell's commands to stay and fight. O'Donnell's forces were lightly engaged but Tyrone's forces suffered the greatest losses. The defeat at Kinsale was a fatal blow for the confederacy and destroyed what remained of O'Donnell's military strength. Niall Garve was left as the de facto ruler of Tyrconnell.

Travel to Spain

Meeting with Philip III

The defeated confederates gathered at Innishannon. Tyrone was strongly in favour of attempting another siege, but was unable to convince O'Donnell, who was in a state of nervous breakdown. According to Ó Cléirigh, his followers "were greatly afraid that he would bring on his death, through the suffering which seized him, so that he did not sleep nor eat in comfort for three days and three nights after". He became determined to travel to Spain to secure reinforcements from Philip III. A factor in his decision was that, having been forced from Tyrconnell, O'Donnell had no property in Ulster to return to. Tyrone disagreed with O'Donnell's plan but could not stop him. Before the confederate commanders returned to Ulster, O'Donnell appointed Rory as commander of his forces.

O'Donnell left Castlehaven on 27 December [N.S. 6 January 1602] 1601 with General Pedro de Zubiaur. He was accompanied by Archbishop Florence Conroy, Maurice MacDonough Ultach, Redmond Burke and Captain Hugh Mostian. They arrived in Luarca on 3 January [N.S. 13 January] after travelling through a stormy passage. As Philip III was in the province of Leon at the time, the group headed to A Coruña. On 6 January [N.S. 16 January] they were welcomed to A Coruña by Luis de Carillo, the governor of Galicia and Conde de Caracena, who was a political supporter of the confederacy's cause. He offered the group the hospitality of his seaside house. O'Donnell was also taken to sightsee the Farum Brigantium, where the legendary sons of Milesius left for Ireland.

O'Donnell travelled to Spain to seek assistance from King Philip III.

Philip III agreed to meet with O'Donnell on the recommendation of his advisors, and O'Donnell was escorted to Zamora with a dozen Irishmen to meet the Spanish king. When he arrived in the King's presence, O'Donnell knelt before him and vowed not to rise until three requests were granted:

1. To send a Spanish army (with O'Donnell) to Ireland;
2. To make O'Donnell the most powerful noble in Ireland, once it had been conquered by Spain;
3. To protect the rights of his clan and his successors.

Philip III agreed and bade O'Donnell to rise. During O'Donnell's time at the Spanish court, he met with Tyrone's son Henry (also his own nephew) and was treated for a bubonic plague sore by Tyrconnell physician Nial O'Glacan. He also spent much of his time working with Archbishop Mateo de Oviedo to assemble a case against Juan del Águila. The Spanish Council of State reported to the King that "[O'Donnell's] zeal and loyalty should be highly praised... He should be assured that His Majesty regards the Irish Catholics as his subjects." Philip III granted O'Donnell a generous pension and ordered him to return to La Coruña to supervise the planned naval reinforcements.

Cancelled naval expedition

O'Donnell returned to La Coruña on 16 February [N.S. 26 February], by which time he received news of Juan del Águila's surrender, which was not unexpected. O'Donnell wrote to the King two days later, begging him to focus his attention on sending the discussed naval expedition to Ireland. Although O'Donnell would have been content with a small-scale expedition sent to Tyrconnell, Philip III wanted to send a large fleet—three times the size of the 4th Armada—to ensure military success and restore his damaged reputation. Due to the time it would take to assemble a force of this size, O'Donnell was left anxiously waiting in Spain. Meanwhile, the confederacy disintegrated as English forces travelled across Ulster destroying crops and livestock. In June 1602 Tyrone burned Dungannon and retreated into Glenconkeyne. O'Donnell kept in contact with Ireland during this time—he wrote to one confederate "if there is anything bad it may be concealed from the Spaniard, but not from me".

Throughout 1602 O'Donnell was placated with promises that the Spanish fleet was being gradually assembled. He insistently asked to return to court to discuss the military situation. In March, O'Donnell was alarmed by the Duke of Lerma's suggestion that O'Donnell could be sent back to Ireland with only one ship and 50,000 ducats. On 10 June [N.S. 20 June] O'Donnell wrote to Philip III: "I am weary of seeing how I am wasting my time here, and I fear that things are going on badly at home". By July it became clear that, due to delays, the envisioned fleet would not be ready until the next year. On 23 July [N.S. 2 August], the ships already prepared at La Coruña were sent to the New World on unrelated missions. Fr. Ludovico Mansoni, Papal Nuncio to Ireland, reported that O'Donnell was gripped "by an extreme melancholia and disgust which took hold of him when buoyed up by hope as a result of the promises and letters he had received... he saw the whole [Spanish] army suddenly diverted... without even a mention being made of Ireland". Mansoni credited this anguish with causing O'Donnell's early death. Philip III permitted O'Donnell to meet with him, and O'Donnell left La Coruña on 26 July [N.S. 5 August] to go to Simancas.

Death and burial

O'Donnell died at the Castle of Simancas on 30 August 1602.

O'Donnell arrived at the Castle of Simancas on around 31 July [N.S. 10 August]. Within weeks he had developed a fever, and by 14 August [N.S. 24 August] he was extremely ill. He was attended by Irish doctor John Noonan; the guilty king also sent his own physician, Álvarez, to the castle. O'Donnell was aware he was dying, and indicated that he was "fearful of death, as is natural to my creaturely condition". He received the last rites and was attended by Archbishop Conroy and two Franciscans, Maurice MacDonough Ultach and Maurice MacSean Ultach.

O'Donnell made his will on 28 August [N.S. 7 September], whilst on his deathbed. He dictated his will in Irish, but Conroy translated it into Castilian Spanish for the notary. O'Donnell was in an extremely weak physical condition and could only blot the page when attempting to sign his signature. He warned against news of his death reaching Ireland before Spanish reinforcements arrived, as he believed the news would demotivate the confederacy and lead to a peace treaty with England. O'Donnell was content to be a vassal of the Spanish king if the Gaelic chiefs could keep their power over Ireland, which would effectively make Ireland a Spanish colony. O'Donnell bequeathed "all [his] estates, lands, lordships and vassals" to his younger brother Rory.

After over two weeks of bedridden suffering, Hugh Roe O'Donnell died at the Castle of Simancas on 30 August [N.S. 9 September] 1602. He was 29 years of age, and left no children. The same evening, O'Donnell's body was taken to Valladolid in a four-wheeled hearse "with blazing torches and bright flambeaux of beautiful waxlights blazing all round on each side of it". His elaborate funeral procession was attended by Philip III, state officers and council members. Per his will, O'Donnell was buried in the Convent of St. Francis, in the Chapel of Wonders.

Cause of death

George Carew believed that the merchant James Blake poisoned O'Donnell, but it is more likely he died from a tapeworm infection.

According to a now-debunked popular legend, O'Donnell was poisoned by James Blake, a Galway merchant hired as a spy for the English government. Blake approached Lord President Carew with an offer to travel to Spain to assassinate O'Donnell. In a ciphered letter dated 28 May 1602, George Carew informed Mountjoy that "James Blake...took a solemn oath to do service...and is gone into Spain with a determination (bound with many oaths) to kill O'Donnell". O'Donnell was aware that Blake was a security threat and he warned the king's ministers not to trust him "with any secret information".

Despite Blake's oath to Carew, on 19 August [N.S. 29 August] at Valladolid he outlined a detailed plan to the Duke of Lerma for a Spanish expedition aimed at retaking Galway from English control. Given Blake's apparent pro-Spanish sentiments, historians Frederick M. Jones and Micheline Kerney Walsh have questioned whether he was truly an English spy, and speculate that Blake was a Spanish agent who proposed the mission as a means of securing safe passage to Spain. Another ciphered letter was sent from Carew to Mountjoy on 9 October: "O'Donnell is dead... he is poisoned by James Blake, of whom your lordship hath been formerly acquainted... He never told the President in what manner he would kill him, but did assure him it should be effected". There is no evidence that Blake was successful in his promised assassination; when Carew heard of O'Donnell's death, he would have naturally assumed that Blake was responsible.

Historians dismiss the theory that O'Donnell was poisoned. It is more likely he died of illness. Prior to his death he "vomited a worm fourteen measures long, a thing unheard of by the doctors and regarded by them as extraordinary". It was also reported that "a kind of snake or serpent was found within him". This could indicate a tapeworm infection or a cancerous tumour.

End of the Nine Years' War

The English government recognised Rory O'Donnell (Hugh Roe O'Donnell's younger brother) as the successive ruler of Tyrconnell.

With O'Donnell's death, Spanish plans to send further assistance to the confederacy were abandoned. At this time the Spanish court was dominated by the Duke of Lerma who sought peace with England. The Spanish Council of State ignored O'Donnell's request to withhold notice of his death, believing that the confederates "should be undeceived, so that they may be able to make the best terms [with the English] they can, bad as the consequences may be".

Mountjoy sent Rory news of O'Donnell's death and stated that "the war was at an end by his death". Rory convened a council of his advisors. The faction advocating for peace prevailed, though some of Hugh Roe O'Donnell's supporters still refused to believe he was dead. In December, Rory surrendered to Mountjoy at Athlone. Tyrone went into hiding for several months, but eventually surrendered by signing the Treaty of Mellifont on 30 March 1603, which ended the Nine Years' War. Furthermore, the Treaty of London in 1604 ended the Anglo-Spanish War. The historian John McCavitt has stated that "had [O'Donnell] lived... It could have changed the course of Irish history forever."

Legacy

Succession

Following their surrender, Tyrone and Rory were confirmed in their titles and core estates by King James I. Rory was created hereditary Earl of Tyrconnell and granted most of Tyrconnell's lands, which greatly incensed Niall Garve. Per the terms of his surrender, Rory was required to give up his Gaelic titles and thus was not traditionally inaugurated as the O'Donnell clan chief. Niall Garve had himself inaugurated as clan chief in Kilmacrennan.

Hugh Roe O'Donnell was the last undisputed chief of the O'Donnell clan. Rory died of illness in 1608, and the following year Niall Garve, along with his son Naghtan, was imprisoned in the Tower of London for life for his role in O'Doherty's rebellion. Rory had only one son, Hugh Albert, Baron of Donegal, who died without issue, making the subsequent line of succession unclear. Today, branches of the O'Donnell clan which can trace their pedigree to the ruling O'Donnell clan live in Newport, Larkfield and Castlebar, as well as in Spain and Austria.

Historiography

Beatha Aodh Ruadh Ó Domhnaill

Hugh Roe O'Donnell was highly praised by seventeenth-century Irish chroniclers, such as Philip O'Sullivan Beare and the Four Masters, as well as in Irish bardic poetry. Most notably, the Classical Gaelic biography Beatha Aodh Ruadh Ó Domhnaill (Irish: The Life of Red Hugh O'Donnell), written between 1616 and 1627 by Lughaidh Ó Cléirigh, is a highly important source about O'Donnell's life and times. It begins with O'Donnell's birth and ends with his death and funeral in Spain.

Monument to the Four Masters, located by the Drowes River near Kinlough, where the Annals were compiled.

Beatha is essentially a eulogy of Hugh Roe O'Donnell, placing him as the central figure of the Nine Years' War and minimising Tyrone's involvement. Ó Cléirigh was motivated to write the biography when Spanish interest in Ireland was renewed during the Anglo-Spanish War (1625-1630). Ó Cléirigh places O'Donnell at the forefront of the confederacy with the hope that another O'Donnell clansman would retake Ireland. Ó Cléirigh lionises O'Donnell; he claims that Hugh McHugh Dubh submitted willingly to Hugh Roe, when it reality it took O'Donnell beheading followers to obtain a submission. Beatha is written in a deliberately archaic style which further venerates O'Donnell. It was typical for Irish scribes to take liberties to gratify their patrons. They frequently omitted details which would be disagreeable to their patrons or scandalous to the Church.

As a result, Beatha has distorted historical interpretation. According to Paul Walsh, "O'Neill, if not eliminated, is certainly reduced in stature... if one were to read only the Life, [one could say] that O'Donnell and O'Neill were of equal importance". Beatha "is an immense panegyric of a young chief who had just expired in a foreign land, and it cannot be expected to be quite impartial, especially when dealing with Red Hugh's enemies." Ó Cléirigh's portrayal of Niall Garve would have been particularly biased.

It is possible that Ó Cléirigh attended O'Donnell's inauguration and participated in O'Donnell's expeditions, and he may have kept notes. His description of O'Donnell's last days and funeral is based on the recollections of the two friars both named Maurice Ultach. Sections of the Annals of the Four Masters which pertained to O'Donnell's life were adapted from Beatha.

Gaelic Revival

The dramatic content of O'Donnell's short life, which includes his escape from prison and his early overseas death, has "enabled much mythologising of his life and character". He is considered an archetypal hero whose personal struggles against Tudor England served as an allegory to represent Ireland's incarceration, escape from British rule and spirit of resistance. Seventeenth-century annalists and eighteenth-century Catholic authors in Ireland typically admired O'Donnell over Tyrone. During the nineteenth-century Gaelic revival, O'Donnell was embraced as a Celtic national hero, to the exclusion of Tyrone, whose "Machiavellian" nature and partially-English cultural identity were viewed as incompatible with Irish nationalism.

The Neophytes, a Belfast acting troupe, dressed for a 1902 performance of the masque Hugh Roe O'Donnell in Kilkenny. O'Donnell's life has been mythologised and depicted in various mediums.

Modern reappraisal

James MacGeoghegan rehabilitated Tyrone's reputation in the eighteenth century. Twentieth-century historians, such as John Mitchel, Seán Ó Faoláin and Hiram Morgan, restored Tyrone to the status he was formerly afforded by contemporary English commentators, and gave him more prominence as the Irish confederacy's leader. In most modern depictions of the Nine Years' War, O'Donnell is portrayed as the junior partner and thus his reputation has been overshadowed by Tyrone's.

The Aodh Ruadh Ó Domhnaill Guild was formed in 1977 to seek O'Donnell's cause for canonization as a saint of the Catholic Church. The historian James Kelly states that, in opposition to the image of O'Donnell as a Catholic martyr, "it can be argued [that] O'Donnell was first and foremost a traditional Gaelic chieftain intent on affirming the regional authority of his clan and the dynastic aspirations of his immediate family... it was the threat posed by the expanding presence of the English Crown that constituted the major threat to Red Hugh's ambitions". Morgan considers O'Donnell to be "too Catholic and too violent for today's Ireland", and also calls O'Donnell "a counter-reformation Irish dynast living in the world of Machiavelli's Prince rather than the cattle-raid of Cooley".

Commemoration

Ballyshannon Castle, Hugh Roe O'Donnell's key residence, was demolished in 1720. Donegal Castle was granted to Sir Basil Brooke in 1616. It was eventually restored in the 1990s and it is now open to the public as a tourist attraction. O'Donnell's birthday has been celebrated in County Donegal.

A large cross in honour of Art MacShane O'Neill stands near the site of his death and burial in the Wicklow Mountains. Since 1954 (and as an official event since 2006), O'Donnell and Art MacShane's escape is commemorated each January in the Art O'Neill Challenge, an ultramarathon endurance event in which participants retrace the same 55km journey from Dublin to Glenmalure on foot.

A sculpture by Maurice Harron, titled The Gaelic Chieftain, was unveiled in 1999 near Boyle. Overlooking the N4, the sculpture depicts O'Donnell on horseback and commemorates his victory at the battle of Curlew Pass.

O'Donnell's will became lost for a period, but in 1983 it was discovered by Donegal priest John J. Silke in the archives of Simancas. In 1991, a commemorative plaque was erected at the Castle of Simancas. As of 2023, plans are afoot to erect statues of O'Donnell in both Lifford and Simancas. It has also been proposed that the two towns be twinned. The proposed twinning was passed by the Donegal County Council in March 2024, and as of April is yet to be validated by Simancas.

Following an unsuccessful dig for O'Donnell's remains, Valladolid has reenacted O'Donnell's funeral procession in 2022, 2023 and 2024, on the instigation of chairman of the Hispano-Irish Society, Carlos Burgos. The reenactors wear period costumes and carry an empty casket draped with an Irish tricolour. It is based on historical records of the real funeral.

Search for remains

But he never said
And -- it seemed odd -- he
Never had heard
The aspirated name
Of the centuries-dead
Bright-haired young man
Whose grave I sought
(...)

They brought
His blackening body
Here
To rest
Princes came
Walking
Behind it
And all Valladolid knew
And out to Simancas all knew
Where they buried Red Hugh.

Excerpt from Thomas MacGreevy's 20th-century poem Aodh Ruadh Ó Domhnaill, which describes a search for O'Donnell's grave

The Convent of St. Francis was later secularised and O'Donnell's body was disinterred; its current location is unknown. The Chapel of Wonders was sold and destroyed in 1836 during a wave of monastic expropriations, and its exact location was lost. In 2019, Donegal man and retired soldier Brendan Rohan visited Valladolid and persuaded city authorities to conduct a dig for O'Donnell's grave. The following year, a week-long excavation of Valladolid's Constitution Street revealed the walls of what was believed to be the Chapel of Wonders underneath a four-storey building. On 22 May 2020, archaeologists began a dig inside the chapel's remains.

A number of modern descendants of O'Donnell's kin were "lined up for DNA tests" to confirm O'Donnell's identity if his remains were found. There was call for repatriation of O'Donnell's remains if discovered, even though O'Donnell himself asked to be buried in the Convent of St. Francis in his will. It was hoped his skeleton would be easy to identify due to his two missing big toes. However many of the skeletons discovered were in a state of decay and did not have any existing feet. Eventually twenty skeletons were discovered during the dig, though DNA testing showed they were from an earlier period. The site has been used for burials for hundreds of years, making O'Donnell's discovery near-impossible.

In March 2021, archaeologists believed the Chapel of Wonders extended further beneath the dig site, and went into negotiations to resume the excavation. The search ended in October 2021. By September 2022, McCavitt had come across an inscription on an early 17th-century tombstone about O'Donnell. According to McCavitt, if O'Donnell's burial place still exists, it would have been marked by such a gravestone.

As of 2024, O'Donnell's grave has not been discovered, though the media attention garnered by the dig has promoted Hispano-Irish relations. The dig was spearheaded by the local Hispanic-Irish Association. As of October 2023, the investigation is not closed. If discovered intact, O'Donnell's remains may provide insight into his health, nutrition and diet. Tests may also determine his specific cause of death.

Character

Personality

[O'Donnell's] voice was musical. In action he was quick and decisive. He loved justice and was stern with evildoers. He was resolute, faithful to his word and steadfast in time of trial. Maintaining a rigorous military discipline, he led by example in battle. To all he was courteous and affable. He was not married. He was gracious, without pretension.

— Fr. Donagh O'Mooney

Described as "fiery and flamboyant", Hugh Roe O'Donnell was a highly charismatic individual. 17th-century sources opined on his great powers of command, and stated that the look of amiability on his face captivated onlookers. He also had an aggressive and bellicose personality and could not always control his impulses. As Edward Alfred D'Alton put it, "the ordinary Irish chief... boasted much, and talked much, and did little, and... heedlessly rushed into war without estimating his difficulties or his resources".

In his youth, a bardic poet claimed that O'Donnell was arrogant and in need of maturity. Thomas Lee warned the government that because of O'Donnell's youth, he could become radicalised by his imprisonment. Indeed, O'Donnell's four years in prison instilled within him a profound anti-English stance which shaped his aggressive military approach. The bardic poet Maolmuire mac Con Uladh Mic an Bhaird addressed a composition to O'Donnell in 1590, urging O'Donnell to "show fortitude in his adversity", but also indicating that the period in prison would lead O'Donnell to cultivate the discipline and solemnity "appropriate to kingship". Particularly because he had not committed any offence, O'Donnell saw his imprisonment as unjust and villainising. His distrust of English people affected the 1596 peace talks, and is why he was more committed to an alliance with Spain than Tyrone was. O'Donnell's insolence was remarked on by English officials, who described him as the "firebrand of all the rebels". McGettigan notes that O'Donnell was "only anti-English on a political level", as he willingly purchased English goods and firearms for his own purposes. Jane Ohlmeyer describes O'Donnell as "a wily negotiator, an effective and pragmatic power broker, and a brave soldier".

Personal relationships

Morwenna Donnelly notes that it is unusual that O'Donnell had no further marriages after his divorce from Rose. Excluding his rejected proposal to Joan FitzGerald, he appeared uninterested in securing an heir. Despite his desirable status as a prominent and powerful lord, O'Donnell had no known mistresses or illegitimate children. This is in stark contrast to Tyrone, who had four wives, many concubines and various children. Donnelly suggests that O'Donnell remained single because he coveted Donnell Gorm's wife, Honora MacSweeney na dTuath (daughter of O'Donnell's foster-father). Another explanation for O'Donnell's celibacy comes from the Franciscan Donagh O'Mooney, who stated that O'Donnell sought to join the Franciscan clergy if he survived the war. O'Mooney also stated that O'Donnell was "not married", possibly in keeping with clerical celibacy.

Partnership with Tyrone

Mountjoy called the two confederate leaders "the two vipers of the kingdom".

Historians have debated on whether O'Donnell or his father-in-law held a more influential position within the confederacy in its early years. Many of Tyrone's contemporaries who knew Tyrone, such as John Perrot, considered O'Donnell to be the junior partner in the confederacy. In 1596, a list of the confederates drawn up by Alonso Cobos' secretary was altered to place Tyrone's name above O'Donnell's. By 1599, O'Donnell saw his partnership with Tyrone as one of two equals, as evident from their treaty of equality.

O'Donnell and Tyrone had contrasting temperaments, which often caused disputes over military tactics. In contrast to Tyrone, who was known for bribing or elaborately bluffing his way out of trouble, O'Donnell was uncompromising and preferred military solutions over negotiations. Tyrone attempted to restrain O'Donnell from openly attacking English forces in the early stages of the war. O'Donnell's absence from the Battle of Beleek (per Tyrone's request) suggests that Tyrone had a level of control over his son-in-law. English Privy Councillor Geoffrey Fenton stated that Tyrone could "command and rule" O'Donnell at will. That being said, Canny and Silke suggest that Tyrone's failure to manage O'Donnell led to the former's decision to reluctantly go into open rebellion.

By 1596, the pair had developed a sophisticated double-act as O'Donnell played the "bad cop" to Tyrone's "good cop" during their negotiations with the government. They used the absence of one of them to delay and stall further negotiations. Spanish emissaries noted that the pair "acted like one man and were respected by the rest". Throughout the war the two leaders got on remarkably well, and Morgan notes that O'Donnell probably learned the virtue of patience from his father-in-law. Their partnership was under heavy strain by the war's end, and it is possible that their differences in temperament led to the disastrous failure at Kinsale. O'Donnell warned against Tyrone violating their agreements after his death: "in case the Earl O'Neill (though I know and believe he will not do so) should wish to violate the agreement and settlements arranged and made between him and me and our heirs, I hereby beg his Majesty to uphold my brother [Rory] in his rights and to retain him in his service".

The age difference between the two men may have been a source of conflict; Tyrone was O'Donnell's senior by 22 years. Unlike Tyrone, who was raised in the Pale and had received generous assistance from the government during his early years in Ulster, O'Donnell had a traditional Gaelic upbringing and associated the government with his time in captivity.

Generalship

John Derricke's The Image of Irelande (1581) depicts a battle between Irish forces and the Crown's army.

Tyrone and O'Donnell's military approaches were representative of their personalities. Tyrone typically won out in arguments over military strategy, though not always. Donnelly and Lucius Emerson argued that O'Donnell's success early in the war indicate a leader wise beyond his years. Donnelly stated that "any statement of Red Hugh which seeks to imply that a dynamic temperament was not under control of a keen and realistic mind, is a superficial one. Within eighteen months, young and totally inexperienced, he had radically changed the situation in West Ulster; what he effected could only have been accomplished by a highly disciplined man with balanced judgment". O'Donnell's notes on the Battle of Moyry Pass show that he could develop complex battle plans, as he stated that it was better to attack Mountjoy's forces when they were deep in Irish territory, away from reinforcements, and in poor weather.

McGettigan praises O'Donnell's leadership abilities and vision, but McCavitt notes that his failure to foresee Niall Garve's betrayal displays clear flaws in his foresight. The pitfalls of O'Donnell's aggressive approach are evident—he lost over 100 confederate soldiers in an ill-fated 1598 assault on the Blackwater Fort, and his poor foresight may have led to the defeat at Kinsale. Morgan states that credit for the victory at Curlew Pass should go to O'Rourke and McDermot rather than O'Donnell. He describes O'Donnell as a "gung-ho leader" whose military successes were limited.

Physical appearance

There are no surviving portraits or visual representations of Hugh Roe O'Donnell made in his lifetime. Donagh O'Mooney described him as "above middle height, strong, handsome, well-built and of pleasing appearance". He presumably had red hair, as adjectives such as ruadh (Irish for red) were commonly employed in Irish names to refer to hair colour. This epithet would have differentiated him from kinsmen also named "Hugh O'Donnell". After losing his big toes to frostbite, Hugh Roe O'Donnell would have hobbled around or travelled on horseback for the rest of his life. If discovered intact, O'Donnell's skeleton would reveal his stature and height, and technology might allow researchers to recreate his facial features.

Although O'Donnell was fiercely patriotic, he had no aversion to foreign dress. He was described in 1601 as wearing English clothing and even going to mass in a "fine English gown". Historian Francis Martin O'Donnell suggests that Hugh Roe O'Donnell dressed in Spanish clothing, as his grandfather Manus was known for preferring continental fashion over traditional Gaelic clothing.

Ancestry

Ancestors of Hugh Roe O'Donnell

8. Hugh Dubh O'Donnell, Lord of Tyrconnell 4. Manus O'Donnell, Lord of Tyrconnell 2. Hugh MacManus O'Donnell, Lord of Tyrconnell 10. Conn Bacagh O'Neill, 1st Earl of Tyrone 5. Siobhán O'Neill 1. Hugh Roe O'Donnell 12. Alexander Carragh MacDonnell, 5th of Dunnyveg 6. James MacDonald, 6th of Dunnyveg 13. Catherine MacDonald 3. Fiona MacDonald 14. Colin Campbell, 3rd Earl of Argyll 7. Agnes Campbell 15. Jean Gordon

In popular culture

Poetry

• In his 1861 poem Eirinn a' Gul ("Ireland Weeping"), Scottish Gaelic poet William Livingston laments the loss of the heroism displayed by O'Donnell, Tyrone and Maguire.
• James Clarence Mangan's poem Ceann Salla dramatises O'Donnell's last words on his deathbed.
• Thomas MacGreevy's 20th-century poem Aodh Ruadh Ó Domhnaill describes a search for O'Donnell's grave.

Music

• Róisín Dubh, which is one of Ireland's most popular political songs, is addressed in O'Donnell's voice to his wife Rose. The song is reputed to have originated in the rebel encampments during the Nine Years War, and has also been attributed to a Tyrconnellian poet under O'Donnell's reign. Conversely, music scholar Donal O'Sullivan claims there is no evidence it was composed that early. The most popular version of Róisín Dubh was adapted by James Clarence Mangan from a fragmentation of an existing romantic poem to Rose. Although superficially a love song, it has been described as a patriotic song that covertly hides its nationalism via allegory.
• In 1843, the Young Irelander Michael Joseph MacCann wrote the song O'Donnell Abú in tribute to O'Donnell, drawing on the tradition of romantic nationalism which was popular during the era.
• Hugh Roe O'Donnell is the subject of the Irish ballad If These Stones Could Speak, as featured on the Phil Coulter album Highland Cathedral.
• For Seville Expo '92, composer Bill Whelan composed The Seville Suite to commemorate the 390th anniversary of O'Donnell's arrival in Galicia. The suite was commissioned by the Taoiseach's office and was performed by a 50-piece orchestra at the Teatro de la Maestranza on 4 October 1992.

Novels

Novels based on O'Donnell's life (particularly centred on his escape from Dublin Castle) include:

• O'Donel of Destiny (1939) by Mary Kiely
• Red Hugh, Prince of Donegal (1957) by Robert T Reilly
• Red Hugh: The Kidnap of Hugh O'Donnell (1999) by Deborah Lisson

Film

• Hugh O'Donnell was portrayed by English actor Peter McEnery in the 1966 Disney adventure film The Fighting Prince of Donegal, which was based on Robert T Reilly's 1957 book Red Hugh, Prince of Donegal.

  

  Peter McEnery portrayed O'Donnell in The Fighting Prince of Donegal (1966).

Theatre

• On 15 August 1902 in Kilkenny, Captain Otway Cuffe staged a single performance of a masque (titled Hugh Roe O'Donnell) recounting O'Donnell's kidnapping, escape and inauguration. The masque was authored by Standish James O'Grady, produced by Francis Joseph Bigger, and performed by the Neophytes, a north Belfast theatre troupe. It was well-received and formed part of the Gaelic revival movement.
• O'Donnell is a major character in Brian Friel's 1989 play Making History, which focuses on Tyrone reckoning with his own legacy. According to historian Jane Ohlmeyer, "Friel portrayed the youthful Red Hugh as fiery, headstrong, quick-witted, passionate, committed to Catholicism, and to the preservation of the values, language, and culture of the Gaelic world into which he had been born and reared." In its original production by Field Day, O'Donnell was played by Peter Gowen.

Other

• Several Gaelic sports clubs in County Donegal are named after Red Hugh O'Donnell, such as Aodh Ruadh CLG in Ballyshannon and Red Hughs GAA Club in Killygordon.

References

Primary sources

• Annals of the Four Masters. CELT: Corpus of Electronic Texts. 2008 [1636].
• Atkinson, Ernest George, ed. (1974). Calendar of the State Papers relating to Ireland, of the reign of Elizabeth, 1596, July – 1597, December. Digitized by the Internet Archive. Kraus Reprint (published 1893).
• Atkinson, Ernest George, ed. (1903). Calendar of the State Papers relating to Ireland, of the reign of Elizabeth, 1600, March – October. via the Internet Archive. Mackie and Co. Ld.
• Brewer, John Sherren; Bullen, William, eds. (1869). Calendar of Carew Manuscripts in the Lambeth Library. Vol III: 1599-1600. (6 vols, 1867–73). London: Longman & Co., et al.
• Brewer, John Sherren; Bullen, William, eds. (1870), The Calendar of the Carew Manuscripts, 1601–1603, London: Longmans, Green, & Co
• Hamilton, Hans Claude, ed. (1974) [1885]. Calendar of the State Papers relating to Ireland, of the reign of Elizabeth, 1588, August—1592, September. Kraus Reprint.
• Mahaffy, Robert Pentland, ed. (1912). Calendar of the State Papers relating to Ireland, 1601-03. His Majesty's Stationery Office.
• Meehan, Charles Patrick (1870). The Rise and Fall of the Irish Franciscan Monasteries, and Memoirs of the Irish Hierarchy in the Seventeenth Century (3rd ed.). Dublin: J. Duffy.
• O'Clery, Lughaidh; O'Clery, Cucogry; Murphy, Denis (1895). Beatha Aodha Ruaidh ui Dhomhnaill. The life of Hugh Roe O'Donnell, prince of Tirconnell (1586-1602). Digitized by the Internet Archive in 2013. Dublin: Fallon & Co.
• O'Sullivan Beare, Philip (1903) [1621]. Chapters towards a History of Ireland in the reign of Elizabeth. Translated by Byrne, Matthew J. CELT: Corpus of Electronic Texts. Archived from the original on 10 March 2024.

Secondary sources

Books

• Ekin, Des (2015). The Last Armada: Queen Elizabeth, Juan del Aguila, and Hugh O'Neill: The Story of the 100-Day Spanish Invasion. Pegasus Books. ISBN 978-1-60598-944-0.
• Lennon, Colm (2005) [1st pub. 1994]. Sixteenth Century Ireland: The Incomplete Conquest (Revised ed.). Dublin: Gill & MacMillan. ISBN 978-0-7171-3947-7.
• McGettigan, Darren (2005). Red Hugh O'Donnell and the Nine Years War. Dublin: Four Courts Press. ISBN 978-1-8518-2887-6. OL 11952048M.
• McGurk, John (2006). Sir Henry Docwra, 1564–1631: Derry's Second Founder. Four Courts Press. ISBN 1-85182-948-2.
• Morgan, Hiram (1993). Tyrone's Rebellion: The outbreak of the Nine Years' War in Tudor Ireland. London: The Boydell Press. ISBN 0-85115-683-5.
• O'Donnell, Timothy T. (2001). Swords Around the Cross: Ireland's Defense of Faith and Fatherland 1594-1603. Front Royal, Virginia: Christendom Press. ISBN 0-931888-78-6.
• O'Donovan, John; Herity, Michael (2000). Ordnance survey letters: Letters containing information relative to the antiquities of the County of Donegal collected during the progress of the Ordnance Survey in 1835. Dublin: Four Masters Press. ISBN 978-1-903538-00-5.
• O'Neill, James (2017). The Nine Years War, 1593-1603: O'Neill, Mountjoy and the Military Revolution. Dublin: Four Courts Press. ISBN 978-1-84682-754-9.
• Starke, Shirley (1984). Red Hugh: The Story of Hugh Roe O'Donnell. Valley City, North Dakota: The Aodh Ruadh Ó Domhnaill Guild.
• Walsh, Paul, ed. (1930). The Will and Family of Hugh O'Neill, Earl of Tyrone [with an Appendix of Genealogies]. Dublin: Sign of the Three Candles.
• Walsh, Micheline Kerney (1996). An exile of Ireland, Hugh O'Neill, Prince of Ulster. Dublin: Four Courts Press. ISBN 978-1-85182-234-8.

Encyclopedias

• Barry, Judy (October 2009b). "Maguire, Hugh". Dictionary of Irish Biography. doi:10.3318/dib.005379.v1. Archived from the original on 18 April 2024. Retrieved 12 May 2024.
• Connolly, S. J., ed. (2007). The Oxford Companion to Irish History (2nd ed.). Oxford: Oxford University Press. doi:10.1093/acref/9780199234837.001.0001. ISBN 978-0-19-923483-7. "Church of Ireland". pp. 95–98. "O'Donnell, Hugh (Aodh Ruadh Ó Domhnaill)". pp. 423–424.{{cite book}}: CS1 maint: postscript (link)
• Clavin, Terry (October 2009). "O'Donnell, Sir Niall Garvach". Dictionary of Irish Biography. doi:10.3318/dib.006345.v1. Archived from the original on 3 January 2024.
• Dunlop, Robert (1894). "O'Donnell, Hugh Roe" . In Lee, Sidney (ed.). Dictionary of National Biography. Vol. 40. London: Smith, Elder & Co. pp. 436–440.
• Dunlop, Robert (1895). "O'Neill, Hugh (1540?-1616)" . In Lee, Sidney (ed.). Dictionary of National Biography. Vol. 42. London: Smith, Elder & Co. pp. 188–196.
• McCormack, Anthony M.; Clavin, Terry (October 2009). "O'Neill, Art". Dictionary of Irish Biography. doi:10.3318/dib.006915.v1. Archived from the original on 13 May 2024.
• McNeill, Ronald John (1911). "1911 Encyclopædia Britannica/O'Donnell" . In Chisholm, Hugh (ed.). Encyclopædia Britannica. Vol. 20 (11th ed.). Cambridge University Press. pp. 6–8.
• Morgan, Hiram (October 2009). "O'Donnell, 'Red' Hugh (Ó Domhnaill, Aodh Ruadh)". Dictionary of Irish Biography. doi:10.3318/dib.006343.v1. Archived from the original on 25 July 2021.
• Morgan, Hiram (September 2014). "O'Neill, Hugh". Dictionary of Irish Biography. doi:10.3318/dib.006962.v1. Archived from the original on 26 September 2023. Retrieved 3 May 2024.
• O'Byrne, Emmett (October 2009a). "MacDonnell (Nic Dhomhnaill), Fiona (Fionnghuala) ('Iníon Dubh')". Dictionary of Irish Biography. doi:10.3318/dib.006337.v1. Archived from the original on 18 April 2024.
• O'Byrne, Emmett (October 2009b). "O'Donnell (Ó Domhnaill), Sir Aodh mac Maghnusa". Dictionary of Irish Biography. doi:10.3318/dib.006332.v1. Archived from the original on 31 March 2022.
• Silke, John J. (2004). "O'Donnell, Hugh [Aodh Ó'Dónaill; known as Red Hugh, Hugh Roe, Aodh Rua], lord of Tyrconnell (1572–1602), chieftain and rebel". Oxford Dictionary of National Biography (online ed.). Oxford University Press. doi:10.1093/ref:odnb/20554. Archived from the original on 4 March 2025. (Subscription or UK public library membership required.)
• Webb, Alfred (1878). A Compendium of Irish Biography. M. H. Gill & Son. "Maguire, Hugh". pp. 324–325. "O'Donnell, Hugh Roe". pp. 391–393.{{cite book}}: CS1 maint: postscript (link)

Journals

• Breatnach, Pádraig A. (1986). "An Address to Aodh Ruadh Ó Domhnaill in Captivity, 1590". Irish Historical Studies. 25 (98): 198–213. doi:10.1017/S0021121400026493. ISSN 0021-1214. JSTOR 30008529.
• Canny, Nicholas (7 June 2022). "Hugh O'Neill in Irish historical discourse, c.1550–2021". Irish Historical Studies. 46 (169): 25–51. doi:10.1017/ihs.2022.2. ISSN 0021-1214.
• Casway, Jerrold (2003). "Heroines or Victims? The Women of the Flight of the Earls". New Hibernia Review / Iris Éireannach Nua. 7 (1): 56–74. ISSN 1092-3977. JSTOR 20557855.
• Casway, Jerrold (2016). "Catherine Magennis and the Wives of Hugh O'Neill". Seanchas Ardmhacha: Journal of the Armagh Diocesan Historical Society. 26 (1): 69–79. JSTOR 48568219.
• Concannon, Helena (1920). "'The Woman of the Piercing Wail' (The Lady Nuala O'Donnell)". The Irish Ecclesiastical Record. 16 (5). Digitized by the Internet Archive in 2007. Dublin: Browne and Nolan: 216–240.
• Cowley, Ken (2015). "The Art O'Neill Challenge". History Ireland. 23 (6): 6–7. ISSN 0791-8224. JSTOR 43598734.
• Donnelly, Morwenna (1986). "Red Hugh and Rose O'Neill". Donegal Annual (38): 46–51.
• Finnegan, David (2007). "Niall Garbh O'Donnell and the Rebellion of Sir Cahir O'Doherty" (PDF). Donegal Annual (59): 60–82. Archived (PDF) from the original on 4 February 2024. Retrieved 27 October 2024.
• Jones, Frederick M. (1950). "James Blake and a Projected Spanish Invasion of Galway in 1602". Journal of the Galway Archaeological and Historical Society. 24 (1/2): 1–18. ISSN 0332-415X. JSTOR 25535325.
• Kelly, James (2004). "Review of Red Hugh O'Donnell and the Nine Years War". Studia Hibernica (33): 160–162. ISSN 0081-6477. JSTOR 20495169.
• Manning, Conleth (2017). "'But You Are First to Build a Tower' — the Bermingham Tower, Dublin Castle". Ulster Journal of Archaeology. 74: 145–154. ISSN 0082-7355. JSTOR 26788441.
• McCavitt, John (2007). "Review of Red Hugh O'Donnell and the Nine Years War". Irish Historical Studies. 35 (140): 562–563. doi:10.1017/S0021121400005198. ISSN 0021-1214. JSTOR 20547497.
• McGurk, John (2001). "The Battle of Kinsale, 1601". History Ireland. 9 (3): 16–21. JSTOR 27724898.
• McGurk, John (2007). "The Flight of the Earls: Escape or Strategic Regrouping?". History Ireland. 15 (4): 16–21. ISSN 0791-8224. JSTOR 27725653.
• McGurk, John (February 2008). "Flight of the Earls Special Issue". History Ireland. 16 (1): 7–8. ISSN 0791-8224. JSTOR 27725724.
• Mitchell, Angus (2024). "Hugh Roe O'Donnell: The Great Kilkenny Masque of August 1902". Old Kilkenny Review. 75: 71–89.
• Morgan, Hiram (2002). Ó Riain, Pádraig (ed.). "The Real Red Hugh". Irish Texts Society (12). Published through academia.edu. London: 1–17.
• Morgan, Hiram (2004). "'Never Any Realm Worse Governed': Queen Elizabeth and Ireland". Transactions of the Royal Historical Society. 14: 295–308. ISSN 0080-4401. JSTOR 3679322.
• Morgan, Hiram (June 2007a). "Review of Red Hugh O'Donnell and the Nine Years War; Sir Henry Docwra, 1564-1631: Derry's Second Founder". The English Historical Review. 122 (497): 823–824. doi:10.1093/ehr/cem144. ISSN 0013-8266. JSTOR 4493950.
• Morgan, Hiram (2007b). "Playing the Earl: Brian Friel's "Making History"". History Ireland. 15 (4): 62–63. ISSN 0791-8224. JSTOR 27725661.
• Morgan, Hiram (2013). Peduelo Martin, Eduardo; Rodriguez de Diego, Julia (eds.). "The establishment of the Irish-Spanish relationship" (PDF). Los Irlandeses y la Monarquia Hispanica (1529-1800): Vinculos in Espacio y Tiempo. Madrid: 1–10. Archived (PDF) from the original on 25 May 2024.
• Ó Canann, Tomás G. (2007). "Ó Domhnaill's inauguration, according to Pilib Ó Súilleabháin Bhéarra". The Journal of the Royal Society of Antiquaries of Ireland. 137: 101–116. ISSN 0035-9106. JSTOR 23024262.
• O'Donnell, Eunan (2006). "Reflection on the Flight of the Earls". Donegal Annual. 58: 31–44.
• O'Donnell, Vincent, ed. (1993). "1593". Ó Domhnaill Abú (20): 3–4. ISSN 0790-7389.
• O'Neill, James (April 2015). "Death in the lakelands: Tyrone's proxy war, 1593–4". History Ireland. 23 (2): 14–17. JSTOR 43235412.
• O'Neill, James (2016). "Maguire's revolt but Tyrone's war: proxy war in Fermanagh 1593–4". Seanchas Ardmhacha: Journal of the Armagh Diocesan Historical Society. 26 (1): 42–68. ISSN 0488-0196. JSTOR 48568218.
• O'Neill, James (2020). "Red Hugh O'Donnell, Tirconnell's missing lord—: but for how long?". History Ireland. 28 (4): 6–7. ISSN 0791-8224. JSTOR 26934602.
• Power, Gerald (2010). "Darren McGettigan, Red Hugh O'Donnell and the Nine Years War". Peritia. 21: 382–384. doi:10.1484/J.PERIT.1.102404. ISSN 0332-1592.
• Purcell, Mary (1966). "Red Hugh O'Donnell". The Furrow. 17 (4): 255–257. ISSN 0016-3120. JSTOR 27659140.
• Silke, John J. (1988). "The Last Will of Red Hugh O'Donnell". Studia Hibernica (24): 51–60. doi:10.3828/sh.1988.24.3. ISSN 0081-6477. JSTOR 20496218.
• Walsh, Paul (1922). "Hugh Roe O'Donnell's Sisters". The Irish Ecclesiastical Record. XIX. Dublin: 358–364.
• Walsh, Paul (1929). "The Book of O'Donnell's Daughter". The Irish Ecclesiastical Record. XXXIII. Dublin: 561–575.
• Walsh, Paul (1939). "Historical Criticism of the Life of Hugh Roe O'Donnell". Irish Historical Studies. 1 (3): 229–250. doi:10.1017/S0021121400030819. ISSN 0021-1214. JSTOR 30005953.
• Walsh, Micheline Kerney (1990). "Archbishop Magauran and His Return to Ireland, October 1592". Seanchas Ardmhacha: Journal of the Armagh Diocesan Historical Society. 14 (1): 68–79. doi:10.2307/29742439. ISSN 0488-0196. JSTOR 29742439.

News

• Jones, Sam; Carroll, Rory (27 May 2020). "Spanish dig closes in on burial site of Irish lord Red Hugh O'Donnell". The Guardian. ISSN 0261-3077. Retrieved 2 November 2024.
• McGreevy, Ronan (24 May 2020b). "Archaeologists are 'quite sure' they have found Red Hugh O'Donnell's burial place". The Irish Times. Retrieved 1 July 2024.
• Morgan, Hiram (2 June 2020). "Red Hugh hunt shines light on gung-ho hero". Irish Independent. Archived from the original on 20 October 2023. Retrieved 13 February 2025.
• O'Donnell, Francis Martin (4 June 2020a). "We should avoid being 'holier than Pope' about Red Hugh". Irish Independent. Retrieved 18 February 2025.

Other works

• McGinty, Matthew (August 2013a), The Development and Dynamics of the Relationship between Hugh O'Neill and Red Hugh O'Donnell, pp. 1–69
• McGinty, Matthew (2013b), O'Neill, O'Donnell and the Nine Years War, pp. 1–15, retrieved 3 November 2024

Further reading

Primary sources

• O'Donovan, John, ed. (1856). Annála Rioghachta Éireann. Annals of the Kingdom of Ireland by the Four Masters ... with a Translation and Copious Notes. 7 vols. Translated by O'Donovan (2nd ed.). Dublin: Royal Irish Academy. CELT editions. Full scans at Internet Archive: Vol. 1; Vol. 2; Vol. 3; Vol. 4; Vol. 5; Vol. 6; Indices.
• Calendar of the State Papers relating to Ireland. Full scans at Internet Archive: 1586 – 1588, July; 1588, August – 1592, September; 1592, October – 1596, June; 1596, July – 1597, December; 1598, January – 1599, March; 1599, April – 1600, February; 1600, March – October; 1 November, 1600 – 31 July, 1601; 1601-3
• Dispatches and Letters between Ireland and Spain (PDF), An Chartlann, archived from the original (PDF) on 16 June 2024
• Meehan, Charles Patrick (1868). The fate and fortunes of Hugh O'Neill, earl of Tyrone, and Rory O'Donel, earl of Tyrconnel; their flight from Ireland, their vicissitudes abroad, and their death in exile. Dublin: J. Duffy.
• O'Donovan, John; Kelly, William, eds. (2003) [1849]. Docwra's Derry: A Narration of Events in North-west Ulster 1600-1604. Ulster Historical Foundation. ISBN 978-1-903688-22-9.
• O'Donovan, John, ed. (1854). Annals of the Kingdom of Ireland by the Four Masters from the Earliest Period to the Year 1616. Vol. VI. Digitized by the Internet Archive in 2007 with funding from Microsoft Corporation (2nd ed.). Dublin: Hodges, Smith and Co.

Secondary sources

• Burke, Bernard (1861). Vicissitudes of Families. Ulster King of Arms. Paternoster Row, London: Longman, Green, Longman and Roberts. pp. 125–148.
• Falls, Cyril (1997). Elizabeth's Irish Wars. Syracuse University Press. ISBN 978-0-8156-0435-8.
• Lynch, William (2016) [Originally published 1830]. A View of the Legal Institutions, Honorary Hereditary Offices, and Feudal Baronies established in Ireland. Paternoster Row, London: Longman, Rees, Orme, Brown, and Green. p. 190. ISBN 978-1-357-67945-3.
• Mac Cuinneagáin, Conall (1994). "Aodh Ruadh Ó Domhnaill - what caused his death?". Donegal Annual. 46: 18–22.
• Morgan, Hiram (October 2005). "Gaelic lordship and Tudor conquest: Tír Eoghain, 1541–1603". History Ireland. 13 (5): 38–43. JSTOR 27725334.{{cite journal}}: CS1 maint: url-status (link)
• Murray, Eavan (13 September 2022b). "'I know where it's not...': Historian hints at new clue in hunt for the missing remains of Red Hugh O'Donnell". ISSN 0307-1235. Retrieved 12 May 2025.
• O Domhnaill, Adhamhnan. "Simancas Castle Address". Journal of the County Donegal Historical Society: 94–96.
• O'Donnell, Eunan (2000) [1941]. "Niall Garbh O'Donnell – A man more sinned against than sinning". Journal of the County Donegal Historical Society.
• O'Donnell, Vincent (2001b). "Was Red Hugh married?". Ó Domhnaill Abú (30): 4–7.
• Silke, John J. (1970). Kinsale; the Spanish intervention in Ireland at the end of the Elizabethan wars. Digitized by the Internet Archive in 2022 with funding from Kahle/Austin Foundation. New York: Fordham University Press. ISBN 978-0-8232-0865-4.

See also

• O'Donnell dynasty
• Irish kings
• Tyrconnell
• County Donegal
• Kings of Tir Connaill
• Early Modern Ireland 1536-1691
• Nine Years' War (Ireland)

External links

• The Life of Aodh Ruadh Ó Domhnaill, transcribed from the Book of Lughaidh Ó Clérigh
• The Hugh O'Donnell Guild
• The O'Donnell Coat of Arms and Family History