# Hugh Roe O'Donnell

Hugh Roe O'Donnell II (Irish: Aodh Ruadh Ó Domhnaill; c. 30 October 1572 – 10 September 1602), also known as Red Hugh O'Donnell, was an Irish clan chief, Lord of Tyrconnell from 1592 until his death in 1602, and senior leader of the Irish confederacy during the Nine Years' War.
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 powerful 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 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 seek reinforcements from King Philip III. Whilst on route to an audience 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. O'Donnell was succeeded by his younger brother Rory.
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 in Valladolid 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. 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 Pre-Christian 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. 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

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. Their practice, since the Reformation in Ireland, had been to grant sanctuary to Catholic priests fleeing from religious persecution. In medieval Ireland, the sons of Irish clan chiefs were typically trained from the age of seven in horse-riding and weaponry.
In his biography of Rob Roy MacGregor, W. H. Murray described the Highland code of conduct as follows: "The abiding principle is cast up from the records of detail: that right must be seen to be done, no man left destitute, the given word honoured, the strictest honour observed to all who have given implicit trust, and that a guest's confidence in his safety must never be betrayed by his host, or vice versa. There was more of like kind, and each held as its kernel the simple ideal of trust honoured... Breaches of it were abhorred and damned... The ideal was applied 'with discretion'. Its interpretation went deeply into domestic life, but stayed shallow for war and politics."

### Fosterage

Children of the Gaelic Irish nobility were traditionally fostered to fellow clans, typically 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".
Family tree :
| | | | | | | | | | | | | Hugh Dubh O'Donnell d. 1537 | Hugh Dubh O'Donnell d. 1537 | Hugh Dubh O'Donnell d. 1537 | Hugh Dubh O'Donnell d. 1537 | Hugh Dubh O'Donnell d. 1537 | Hugh Dubh O'Donnell d. 1537 |
| | | | | | | Manus O'Donnell 1490–1563 | Manus O'Donnell 1490–1563 | Manus O'Donnell 1490–1563 | Manus O'Donnell 1490–1563 | Manus O'Donnell 1490–1563 | Manus O'Donnell 1490–1563 | | | | | | | Hugh McHugh Dubh O'Donnell c. 1537–1618 | Hugh McHugh Dubh O'Donnell c. 1537–1618 | Hugh McHugh Dubh O'Donnell c. 1537–1618 | Hugh McHugh Dubh O'Donnell c. 1537–1618 | Hugh McHugh Dubh O'Donnell c. 1537–1618 | Hugh McHugh Dubh O'Donnell c. 1537–1618 | | |
| | | | | | | | | | | | | | | | | | | | | | | Calvagh O'Donnell c. 1515–1566 | Calvagh O'Donnell c. 1515–1566 | Calvagh O'Donnell c. 1515–1566 | Calvagh O'Donnell c. 1515–1566 | Calvagh O'Donnell c. 1515–1566 | Calvagh O'Donnell c. 1515–1566 |
| Hugh McManus O'Donnell c. 1520–1600 | Hugh McManus O'Donnell c. 1520–1600 | Hugh McManus O'Donnell c. 1520–1600 | Hugh McManus O'Donnell c. 1520–1600 | Hugh McManus O'Donnell c. 1520–1600 | Hugh McManus O'Donnell c. 1520–1600 | | | | | Fiona "Iníon Dubh" MacDonald | Fiona "Iníon Dubh" MacDonald | Fiona "Iníon Dubh" MacDonald | Fiona "Iníon Dubh" MacDonald | Fiona "Iníon Dubh" MacDonald | Fiona "Iníon Dubh" MacDonald | | | Hugh MacEdegany d. 1588 illegitimate | Hugh MacEdegany d. 1588 illegitimate | Hugh MacEdegany d. 1588 illegitimate | Hugh MacEdegany d. 1588 illegitimate | Hugh MacEdegany d. 1588 illegitimate | Hugh MacEdegany d. 1588 illegitimate | | | Conn O'Donnell d. 1583 | Conn O'Donnell d. 1583 | Conn O'Donnell d. 1583 | Conn O'Donnell d. 1583 | Conn O'Donnell d. 1583 | Conn O'Donnell d. 1583 |
| Donal O'Donnell d. 1590 | Donal O'Donnell d. 1590 | Donal O'Donnell d. 1590 | Donal O'Donnell d. 1590 | Donal O'Donnell d. 1590 | Donal O'Donnell d. 1590 | Hugh Roe O'Donnell 1572–1602 | Hugh Roe O'Donnell 1572–1602 | Hugh Roe O'Donnell 1572–1602 | Hugh Roe O'Donnell 1572–1602 | Hugh Roe O'Donnell 1572–1602 | Hugh Roe O'Donnell 1572–1602 | | | Nuala O'Donnell c. 1575–c. 1630 | Nuala O'Donnell c. 1575–c. 1630 | Nuala O'Donnell c. 1575–c. 1630 | Nuala O'Donnell c. 1575–c. 1630 | Nuala O'Donnell c. 1575–c. 1630 | Nuala O'Donnell c. 1575–c. 1630 | | | | | | | Niall Garve O'Donnell c. 1569–1626 | Niall Garve O'Donnell c. 1569–1626 | Niall Garve O'Donnell c. 1569–1626 | Niall Garve O'Donnell c. 1569–1626 | Niall Garve O'Donnell c. 1569–1626 | Niall Garve O'Donnell c. 1569–1626 |
| XXX | XXX | XXX | XXX | XXX | XXX | Subject of the article | Subject of the article | Subject of the article | Subject of the article | Subject of the article | Subject of the article | XXX | XXX | XXX | XXX | XXX | XXX | King of Tyrconnell | King of Tyrconnell | King of Tyrconnell | King of Tyrconnell | King of Tyrconnell | King of Tyrconnell | XXX | XXX | XXX | XXX | XXX | XXX | Succession Challenger | Succession Challenger | Succession Challenger | Succession Challenger | Succession Challenger | Succession Challenger | XXX | XXX | XXX | XXX | XXX | XXX | Foster-father of Hugh Roe | Foster-father of Hugh Roe | Foster-father of Hugh Roe | Foster-father of Hugh Roe | Foster-father of Hugh Roe | Foster-father of Hugh Roe |
Ultimately Hugh Roe's fosterage did not engender much loyalty in his foster-families. Hugh 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".
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. According to O'Clery, 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 6 October [O.S. 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 two fellow hostages were imprisoned in Dublin Castle's Bermingham Tower.
   "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."
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. Tyrone's men captured thirty Spanish officers from the Spanish Armada's September 1588 shipwreck in Inishowen, and handed them over to Hugh MacManus so he could offer the government to exchange them for his son. This was unsuccessful. 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 FitzWilliam 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 Bermingham Tower, 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. 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. Niall Garve subsequently took over as head of the "MacCalvagh" branch.
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 14 September [O.S. 3 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. 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

After three years and three months in English 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 25 January [O.S. 15 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 returned to Dublin Castle, more heavily shackled, and checked by the chief gaoler twice a day.

### Second escape attempt

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. 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.
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. Since 1954 (and as an official event since 2006), the escape is commemorated each January in the Art O'Neill Challenge, an ultramarathon endurance event in which participants recreate the same journey from Dublin to Glenmalure on foot.
Unusually, the state papers do not reference Hugh Roe's escape until his safe return to Ulster. This could point to corruption or embarrassment on the part of government officials. 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". 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.

## 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. 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 Chief Hugh Maguire of 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

Hugh Roe arrived in a Tyrconnell which had suffered much repression and turmoil in his absence. A few months before Hugh Roe's return, Willis and Connill's forces raided Donegal in the dead of night, killed thirty people, 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. Hugh Roe made expelling the English forces his first order of business, and he summoned and rallied his family's followers to Ballyshannon. Even nobles in Tyrconnell who previously favoured the Crown had become resentful by this time.
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 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. The peace terms stipulated that Willis and his soldiers were forbidden to take any stolen cattle or other looted property with them as they crossed back into Connacht. Afterwards the clergy returned to the abbey.

### Inauguration

After the expulsion of Willis's forces in February, Hugh Roe returned to Ballyshannon where his big toes were amputated due to frostbite. He remained in recovery from February to April. In April, before an assembly of fellow nobles in Kilmacrennan, Hugh MacManus abdicated in favour of Hugh Roe. This was accepted by the nobility present. The abdication, though apparently voluntary, 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.
19-year-old Hugh Roe O'Donnell was inaugurated as Chief of the O'Donnell clan on 3 May [O.S. 23 April] 1592. The ceremony, which involved the O'Donnell clan's ornamental inauguration stone (the "Rock of Doon"), was held at Kilmacrennan Friary. Hugh Roe was the last ruler of Tyrconnell to be inaugurated with the traditional ceremony, with the exception of Niall Garve's controversial inauguration in 1603. Hugh Roe's younger brother Rory was appointed as tanist. Hugh Roe's great-grandfather, also named Hugh Roe O'Donnell, was clan chief from 1461 to 1505; historian Francis Martin O'Donnell thus distinguishes them using the regnal numbers I and II.
Theologian Timothy T. O'Donnell described the traditions of the ceremony, which was both civil and religious in nature: "It began with the religious rites in the church of the nearby monastery and holy well singing Psalms and hymns in honor of Christ and St. Columba for the success of the prince's sovereignty. Standing on the rock surrounded by nobles and his clansmen, the Prince received an oath in which he promised to preserve the Church and the laws of the land. The Prince also vowed to deliver the succession of the realm peacefully to his Tanist (his successor). O'Ferghil, the hereditary warden and abbot of Kilmacrenan, performed the religious ceremony of the inauguration of the O'Donnell. O'Gallagher was the Prince's marshal and O'Clery was the ollamh, or scholarly lawyer who presented to him the book containing the laws and customs of the land and the straight, white wand symbolizing the moral rectitude demanded of his judgments and rule." O'Donnell would have turned "thrice from left to right and thrice from right to left, in honor of the Holy Trinity", after which O'Ferghil would have led the spectators in loudly proclaiming Hugh Roe as The O'Donnell.
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.

### Rise in power

Immediately after his inauguration, Hugh Roe O'Donnell and Tyrone mounted raids against Tyrone's rival Turlough Luineach. Turlough Luineach had provided assistance to O'Donnell's rivals, such as Niall Garve. O'Donnell would have desired revenge and felt a need to assist his new ally Tyrone. For Tyrone, a key reason for maintaining his alliance with the O'Donnell clan was to defeat Turlough Luineach and take control of Tír Eoghain. In June 1592, Hugh Roe O'Donnell renewed the O'Donnell 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.
O'Donnell dispatched letters to the state informing of his inauguration and giving justification for attacking Turlough Luineach. He sarcastically offered to submit to FitzWilliam in person if he was lent £800 or £900. FitzWilliam recognised the necessity of conciliating with O'Donnell. He reprimanded O'Donnell for his arrogance but promised, if they could meet at Dundalk by 16 July [O.S. 6 July], to pardon his escape and lend him £200. 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 and gain government recognition.
Bribery was probably involved in the meeting, which took place in a church on 12 August [O.S. 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 O'Donnell was concerned for her safety. After the meeting, the two Hughs feasted at Dungannon where they further discussed their developing alliance. The submission to FitzWilliam put O'Donnell temporarily in favour with the government, and he took advantage of this to crush his opponents.
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

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 promised support, as he wanted Ireland as an ally in the Anglo-Spanish War, but only if Ireland proved itself by launching prior military action. Thus MacGauran sought powerful Irish lords willing to openly rebel against the Crown. He organised a conference of seven Catholic bishops in Tyrconnell that December. 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 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 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.
Maguire managed to obtain reinforcements from Tyrone's brother and foster-brothers, who were likely involved on Tyrone's behalf. Similarly to O'Donnell, Maguire besieged Willis and his men in a church and planned to starve them out, but Tyrone intervened and negotiated their safe rescue. 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 continued to rebel by attacking English forces. He was joined by O'Rourke who had been fighting Bingham since his late father's expulsion from West Breifne in 1590. O'Donnell aided the growing rebellion by sending MacSweeney gallowglass, but publicly he feigned neutrality. O'Donnell chose to conceal his rebellion because he lacked sufficient 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 3 July [O.S. 23 June] 1593 whilst accompanying Maguire on a raid. In September, O'Donnell sent his mother to Scotland to secure further Scottish troops.
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

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 (Old Style), 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 [Tyrone] his enemy, unless he came to his aid in such a pinch". Tyrone subsequently sent reinforcements under his brother Cormac MacBaron 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

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 (Old Style) 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

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 (Old Style). 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 (Old Style), 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 (Old Style). A hollow peace was signed on 24 April 1596 (Old Style), 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.
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 with the aging Elizabeth I in poor health. 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

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 on 22 May 1597 (Old Style). 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 (Old Style), 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 (Old Style) 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

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.
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 (Old Style), whilst crossing the River Callan, 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 the south. 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

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 and was subsequently imprisoned. O'Donnell later carried the head around as a trophy. 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

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. The Calendar of State Papers makes reference to "some breach between Tirone and O Donnell about Tirone's daughter" on 2 April 1596 (Old Style). 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 on account of her "barronness". The divorce was most likely against Tyrone's wishes. Rose remarried to Tyrone's principal vassal Donnell Ballagh O'Cahan by 1599.
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 (Old Style) 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 (Old Style) 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 11 March [O.S. 1 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. Despite these actions, the Spanish government failed to send the confederacy the resources they desired. O'Donnell was reportedly "like a madman when he saw no kind of news, neither of men nor money to come".

## Forced from Tyrconnell
### Henry Docwra

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 (Old Style). 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. The confederates' failure to drive away Docwra's forces led to further tension between O'Donnell and Tyrone.

### Defection of Niall Garve

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 had special instructions to win him over. He opened secret communications with Niall Garve. 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 September 1600, Hugh Roe O'Donnell left Ulster for a raid in Thomond, entrusting Niall Garve in charge of besieging Derry.{{Sfnm|1a1=Clavin|1y=2009|2a1=McGurk|2y=2006|2p=94} The following month, 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 [Hugh Roe O'Donnell] and all his country". Fearing O'Donnell's revenge, Niall Garve—alongside his three brothers and various followers—quickly defected to the English. They joined Docwra on 3 October (Old Style). O'Donnell was in Thomond when he received news, and he immediately hurried to secure Lifford Castle to retain control over Lough Foyle. He was shocked 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 (Old Style), taking it from O'Donnell's brother Rory.
   "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."
Nuala separated from Niall Garve due to his defection. According to a 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 would indicate 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

O'Donnell and Rory tried in vain to retake Lifford Castle with minor skirmishes. O'Donnell lost about 20 men on 17 October (Old Style). He attacked again one week later, but Niall Garve retaliated by leading a calvary charge of mixed Irish and English forces out to battle. During the battle, Niall Garve and his ally Cornelius O'Gallagher stabbed O'Donnell's brother Manus in the shoulder. Manus was taken to Donegal where he died from his wounds on 22 October (New Style). O'Donnell's father Hugh MacManus died shortly afterwards, allegedly from his grief, on 7 December (New Style). 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, Hugh Roe had put a price of £300 on Niall's head. Shortly after, Cornelius O'Gallagher was captured by O'Donnell and hanged. Niall Garve appeared to make later efforts to rejoin the confederacy, but his murder of Manus made this near-impossible.
O'Donnell made further plans to cement his alliances beyond Ulster. O'Donnell schemed to marry Joan FitzGerald (step-daughter to O'Connor Sligo and sister of the loyalist 1st Earl of Desmond). In November 1600 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.

### Siege of Donegal

On 10 August 1601, the monks of Donegal Abbey carefully removed all sacred objects and fled by ship from their enclosure shortly before Niall Garve O'Donnell seized control of the monastery buildings and fortified them with earthenworks, which he built with the assistance of Tudor navy engineers, who also helped him to repair the dilapidated buildings of Donegal Castle for the expected siege by Hugh Roe's forces.
According to the history of Donegal Abbey, "Meanwhile, O'Donnell arrived, pitched his camp at Carrig, within two thousand paces of Donegal, and resolved to give Nial and his followers no rest, night or day, as long as they remained within the desecrated walls. A series of hand to hand conflicts, in which Nial's people suffered severely, ensued; and in the course of a fortnight many of the revolted Irish, repenting their treason, deserted in twos and threes to our Prince's camp."
According to the history of Donegal Abbey, "Cooped up in the monasteries, so vigilantly watched by O'Donnell that they could not come out into the open country to lift preys, Nial's people began to mutiny; when on the night of Michaelmas, the powder stored in the monastery of Donegal took fire, whether accidentally or by the special interposition of Heaven I know not, and exploded with a terrible crash, that was heard far out at sea, may, scared the wild deer in the coverts of Barnesmore. Oh, the appalling spectacle! Hundreds of the besieged were blown to atoms; others, among the rest Nial's own brother, were crushed to death by masses of the rent masonry; and all that night, while the woodwork blazed like a red volcano, in whose glare friend and foe were distinctly visible to each other, O'Donnell's swordsmen pressed the survivors back across the trenches into the flames, where upwards of a thousand of them perished miserably. Nor should it be forgotten that a ship, laden with munitions for the besieged, ran in a rock, and went to pieces that very night, just as she was entering the bay of Donegal. Next morning Nial proceeded unobserved by O'Donnell's troops, along the strand to Magherabeg, and returned, under cover of the guns of the English war vessel, with the soldiers he had left in that place, determined to maintain himself to the last among the smoldering ruins. O'Donnell immediately shifted his camp nearer to Donegal, and continued the siege till October; when, being informed that the Spaniards had landed at Kinsale, he struck his tents and marched to their assistance."

### Siege of Kinsale

As 1601 began, Philip III of Spain 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 expedition finally landed and was besieged by the English Army inside the city of Kinsale—virtually the opposite end of Ireland from Ulster—in September 1601. Seeking to break the siege and rescue their Spanish allies, O'Donnell led his army in a hard march during the extremely bitter winter conditions of 1601, often covering over 40 miles a day, to join Tyrone and his warriors at Kinsale, arriving in early December 1601.
En route, true to his family arms and Constantinian motto In Hoc Signo Vinces and in anticipation of the battle to come, Red Hugh visited and venerated the relic of the True Cross, the Holy rood, on the Feast of St. Andrew, on 30 November 1601 at Holy Cross Abbey, and removed a portion of it.
From there he dispatched an expedition to Ardfert in County Kerry, to win a quick victory and successfully recover the territory of his ally, James Fitzmaurice, Lord of Kerry, who had lost it and his 9-year-old son, to Sir Charles Wilmot. Red Hugh also left some O'Donnell clansmen behind in Ardfert to defend Clanmaurice country, notably his nephew Donal Oge (son of his late half-brother Donal) who appears in the FitzMaurice pardon of 16 July 1604.
At the Siege of Kinsale on 6 January (Old Style: 24 December 1601) 1602, the combined forces of Irish clans were defeated by Baron Mountjoy. O'Donnell and his clansmen arrived as the defeated Irish clans were withdrawing with heavy losses from the field and he tried in vain to rally them, but in the end, Clan O'Donnell escaped the battle without serious losses. The defeat at Kinsale, for which O'Donnell unjustly blamed himself, would prove every bit as devastating for Gaelic Ireland as the Battle of Culloden would be for their fellow Gaels in Scotland in 1746.
Juan del Águila then surrendered Kinsale on terms and departed with his forces for Spain. Based almost certainly upon Jesuit lay brother and future Irish Catholic Martyr Dominic Collins' tactical assessments, Irish Jesuit priest and Spanish Royal Army military chaplain Fr. James Archer immediately engaged in recrimination. He accused Spanish expeditionary force commander Juan del Águila of cowardice, vacillation, and dereliction of duty for both refusing to heed the advice of the local Irish clans and refusing to sally forth and meet his Ulster allies at the critical point. Archer concluded, "[He] has the reputation in other parts of being a brave soldier, but [in Ireland he was] cowardly and timorous."

## Death in Spain
### Travel to Spain

As the defeated Irish clans gathered in a conference at Innishannon, an outraged and heartbroken Hugh Roe O'Donnell announced his plans to travel to Spain to seek further reinforcements from King Philip III. This announcement devastated his supporters, who suspected, despite O'Donnell's vow he would return before the next spring with twenty thousand more Spanish Royal Army soldiers, that they would never see him again.
O'Donnell left Ireland on 6 January 1602 and sailed to Corunna in Galicia, Spain, where many other Irish clan chiefs were already arriving as refugees with their families. O'Donnell travelled with Archbishop of Tuam Florence Conroy, Maurice MacDonough Ultach, Redmond Burke and Captain Hugh Mostian. They arrived in Luarca on 13 January after travelling through a stormy passage. On arrival O'Donnell was received with great honours by the Governor of Galicia and the Lord Archbishop of Santiago de Compostela, where an Irish College was founded. He was also taken to "visit the Tower of Brigantiums, where according to bardic legends the sons of Milesius left to the Isle of Destiny".
O'Donnell travelled to Valladolid to ask for further assistance from King Philip III. When he arrived in the Royal presence, O'Donnell knelt before the King and vowed not to rise until three requests were granted, "The first is that you send a Spanish Army with me to Ireland. The second is that once you rule Ireland, I will be the most powerful Irish noble there. The third is that you protect the rights of the O'Donnells forever." The King immediately agreed and ordered O'Donnell to rise.
According to Irish historian John McCavitt, "He made sure to position himself with a recognisable aristocratic rank while he also emphasised the Irish's sacrifice for Spain in turning down the chance for peace with England in the hope a further Spanish invasion force would be sent to Ireland."
Tyrconnell physician Nial O'Glacan treated O'Donnell for a bubonic plague sore at the Spanish court. Whilst in Spain, O'Donnell asked to see Tyrone's son Henry who was then studying in Salamanca. Henry was summoned to Zamora. O'Donnell spent less than a week in Zamora before moving on to La Coruña.
During his time at court, O'Donnell also spent much of his time assisting the gathering of evidence for the court martial of Juan del Aguila. After two weeks, however, the King granted O'Donnell a generous pension and reassigned him to supervise naval preparations for another Spanish expeditionary force at Coruña. The Spanish Council of State also reported to the King about O'Donnell, "His zeal and loyalty should be highly praised... He should be assured that His Majesty regards the Irish Catholics as his subjects."
Upon his own arrival on 21 March 1602, Juan del Aguila was met at the quay of Coruña by a livid Hugh Roe O'Donnell, whom del Águila told in a buoyant, positive tone, "Be of good comfort. We will have one more turn at Ireland." O'Donnell's reply is not recorded. The Venetian Ambassador to Spain reported, "[The Spanish authorities] now insist that Águila made a mistake in coming to terms with the English and surrendering to them two places which he held. Some prophesy ill for him, declaring that he has escaped an honourable death in Ireland to meet with a shameful one in Spain."
The 31 July 1602 execution of the Duc de Biron, for allegedly plotting with Spanish backing to assassinate King Henry IV of France, brought France to the brink of entering the war as an ally of England and drastically increased the risk that further Spanish intervention in Ireland would result in French troops being dispatched there as well. Despite this fact, O'Donnell continued being told "anything he wanted to hear" by the Spanish Council of State. At the same time, according to intelligence reports received by George Carew, O'Donnell's reputation remained "great in Spain", while there was widespread "dislike of Don Juan." Feelings regarding both men remained almost identical in Ireland.

### Illness and death

In the middle of 1602, Hugh Roe O'Donnell, suffering from "anguish of heart and sickness of mind", finally left for Valladolid "to go into the King's presence again to learn the cause of the delay." O'Donnell unexpectedly fell ill at the Castle of Simancas.
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. Also present were O'Donnell's secretary Matthew Tully and a physician named Álvarez. Irish doctor John Noonan attended O'Donnell's final illness.
O'Donnell made his will on 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; he 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 10 September 1602. He was 29 years of age, and left no children.

### Burial

In a letter dated 28 September, statesman Thomas Goold informed the Privy Council of O'Donnell's death and funeral. Ó Cléirigh described the elaborate funeral: "His body was then taken to Valladolid, to the King's Court, in a four-wheeled hearse, with great numbers of State officers, of the Council, and of the royal guard all round it, with blazing torches and bright flambeaux of beautiful waxlights blazing all round on each side of it". Per his will, O'Donnell was buried in the Convent of St. Francis in nearby Valladolid, specifically in the Chapel of Wonders (Spanish: Capilla de las Maravilla; also translated as the Chapel of Marvels). The Italian explorer Christopher Columbus was buried in the same convent almost 100 years earlier, and MacWilliam Bourke was buried there in November 1604.

### Cause of death

Fr. Ludovico Mansoni, Papal Nuncio to Ireland, claimed that O'Donnell's death "was caused 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 and thinking that finally he had secured powerful reinforcements, he saw the whole army suddenly diverted to Africa, without even a mention being made of Ireland".
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 George Carew, then-Lord President of Munster, with an offer to travel to Spain to assassinate O'Donnell. In a ciphered letter dated 28 May 1602 (Old Style), 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 this person with any secret information". Despite Blake's oath to Carew, on 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. Blake was considered unreliable by the English government, and it is now speculated 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 1602 (Old Style): "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 Hugh Roe 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

With O'Donnell's death, Spanish plans to send further assistance to the confederacy were abandoned. At this time the Spanish court was now 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 Hugh Roe 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. Rory surrendered to Mountjoy at Athlone in December. Tyrone went into hiding whilst making overtures of peace to Mountjoy. He eventually surrendered by signing the Treaty of Mellifont on 30 March 1603 (Old Style), which ended the Nine Years' War. McCavitt has stated that "had [O'Donnell] lived... It could have changed the course of Irish history forever."

## Legacy
### O'Donnell clan leadership

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, who had himself controversially inaugurated as clan chief in Kilmacrennan. Hostility towards the Gaelic nobility from English politicians gradually increased over time. In September 1607, Rory and Tyrone, accompanied by their families, household staff, followers and fellow Irish nobles, permanently left Ireland for Catholic Europe in what is known as the Flight of the Earls. The earls' motivations are unclear. They may have been conspiring against the government, and their flight could have been an attempt to evade arrest. Rory and Cathbarr died of fevers shortly after settling in Rome, and Tyrone died of illness in 1616 despite his plans to return to Ireland. Discontented with his treatment by the government, Niall Garve instigated the anti-Crown O'Doherty's rebellion. He was ultimately arrested and was sent to the Tower of London for life; he died there in 1626.
Hugh Roe O'Donnell was the last undisputed chief of the O'Donnell clan. 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. Following the Anglo-Irish Treaty in 1921, the Irish government introduced a policy granting courtesy recognition as Chief of the Name to senior male descendants of the Gaelic nobility. The O'Donnell clan was revived in 1954 as the "O’Donnell Clan Association".

### Views on O'Donnell
#### 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.
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. As a result, it 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.
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 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 and their clan. They frequently omitted details which would be disagreeable to their patrons or scandalous to the Church.
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

Hugh Roe O'Donnell's short life, which involved 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.

#### 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. O'Donnell and Art MacShane's 55 km. escape route from Dublin Castle to Glenmalure is also retraced by long-distance runners (and walkers) every January in the Art O'Neill Challenge. A sculpture by Maurice Harron, titled The Gaelic Chieftain, was unveiled in 1999 near Boyle, County Roscommon. 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 the early 1980s it was discovered by a Donegal priest in the archives of Simancas. In 1991, a plaque was erected at the Castle of Simancas in commemoration of O'Donnell. As of 2023, plans are afoot to erect statues of him 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.

### 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.
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, 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, historian John 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.

### Re-enactment of funeral

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.

## Character
### Personality

Hugh Roe O'Donnell was a highly charismatic individual. Contemporary sources state that he had "great powers of command, and a look of amiability on his countenance that captivated everyone who beheld him". According to the historian Jane Ohlmeyer, historical records show O'Donnell to be "a wily negotiator, an effective and pragmatic power broker, and a brave soldier". He has also been described as "fiery and flamboyant". O'Donnell 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. Captain Thomas Lee warned the government that because of O'Donnell's youth, imprisonment could result in him becoming radicalised. 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 at least one 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 been imprisoned due to any offence, O'Donnell saw his imprisonment as unjust and villainising. His distrust of English people affected the 1596 peace talks, and is the reason why he was far more committed to an alliance with Spain than Tyrone was. O'Donnell's insolence was remarked on by English officials, and he was described as the "firebrand of all the rebels".

### Relationship with Tyrone

Historians have debated on whether O'Donnell or his father-in-law held a more influential position within the confederacy. Many of Tyrone's contemporaries who knew Tyrone, such as John Perrot, considered O'Donnell to be the junior partner in the confederacy. From the start, O'Donnell saw his partnership with Tyrone as one of two equals. On his deathbed, he referenced their 1599 treaty "that one had no pre-eminence over the other". O'Donnell also 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".
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. This attitude led to military successes as well as failures. Tyrone attempted to restrain O'Donnell from openly attacking English forces in the early stages of the war. He mostly complied with Tyrone's order to avoid participating in the Battle of Beleek, which suggests that Tyrone had a level of control over his son-in-law. Morgan notes that O'Donnell probably learned the virtue of patience from his father-in-law. Lucius Emerson states that O'Donnell's success early in the war indicate a leader wise beyond his years. 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 emmisaries noted that the pair "acted like one man and were respected by the rest". According to McGettigan, "throughout the war the two leaders got on remarkably well". 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.
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

Tyrone and O'Donnell's differing military strategies complemented each other. In 1598, Tyrone was struggling to seize the Blackwater fort using siege warfare. O'Donnell pushed Tyrone to launch a full frontal assault. The assault was a disaster with over one hundred Irish men lost. Tyrone continued to restrain O'Donnell's aggressive strategy. He forbid O'Donnell from travelling to Connacht during the 1599 cessation. Tyrone also prevented O'Donnell from burning the Pale, so as not to provoke an English counter-attack. Tyrone's strategy typically won out, though not always. The Irish failure at the battle of Kinsale has been attributed to O'Donnell naively urging Tyrone to attack, rather than starving out the English as was the previously agreed-upon strategy. This account by near-contemporary writers Ó Cléirigh and O'Sullivan Beare is not unanimously accepted by historians. McGurk, Silke, McGettigan and Cyril Falls concur; Morgan and Gerard Anthony 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. Juan del Águila was also in favour of an immediate attack. Morgan claims it was the pressure from the beleaguered Spaniards that wore down Tyrone, and that the Earl also had his reputation on the line.
McGettigan praises O'Donnell's leadership abilities. However, McCavitt and Gerald Power note that O'Donnell's failure to forsee Niall Garve's betrayal displays clear flaws in his foresight. Morgan describes O'Donnell as a "gung-ho leader" whose military successes were "limited". Evidence supports this evaluation, though his notes on the Battle of Moyry Pass show that he could develop complex battle plans. O'Donnell stated that it was better to attack Mountjoy's forces when they were deep in Irish territory, away from reinforcements, and in poor weather. Morwenna Donnelly argues 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".

### Physical appearance

There are no surviving portraits or visual representations of Hugh Roe O'Donnell made in his lifetime. Franciscan Donagh O'Mooney, who knew O'Donnell personally, described him as of "middle height, ruddy, of comely face, and beautiful to behold... his voice was like the music of a silver trumpet". O'Donnell probably 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.

## Family tree
### Ancestry

Ancestors of Hugh Roe O'Donnell :

### Family tree
## In popular culture
### Poetry

* In his 1861 poem Eirinn a' Gul ("Ireland Weeping"), Scottish Gaelic poet William Livingston recalls the many stories about his fellow Gaels in Inis Fáil (Ireland) he had heard in the Ceilidh houses of Islay, before that island was emptied by the Highland Clearances. He then lamented the destruction wreaked upon the Irish people by both famine and similar mass evictions ordered by Anglo-Irish landlords. He particularly laments the loss of the chiefs of the Irish clans, who led their clansmen in war and provided "leadership of the old and true Gaelic kind". Mac Dhun Lèibhe comments sadly that the mid-19th century fighters for Irish republicanism had none of the heroic qualities shown by Red Hugh O'Donnell, Hugh O'Neill, and Hugh Maguire during the Nine Years War against Queen Elizabeth I. Sadly, but expressing hope for the future of the Irish people, Mac Dhun Lèibhe closes by asking where are the Irish clan warriors who charged out of the mist and slaughtered the armies of the Stranger at the Battle of the Yellow Ford and the Battle of Moyry Pass.
* James Clarence Mangan's poem Ceann Salla dramatises O'Donnell's last words on his deathbed.

### 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 it is superficially a love song, it has been described as a patriotic song that covertly hides its nationalism via allegory.
* In 1843, Michael Joseph MacCann wrote the song O'Donnell Abu in tribute, 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 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. The film received middling box office returns and contains many historical inaccuracies.

### 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, 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.