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Hugh Roe O'Donnell II (; 20 October 1572 – 30 August 1602), also known as Red Hugh O'Donnell, was an Irish

clan chief The Scottish Gaelic word means children. In early times, and possibly even today, Scottish clan members believed themselves to descend from a common ancestor, the founder of the clan, after whom the clan is named. The clan chief (''ceannard ci ...

and senior leader of the Irish confederacy during the

Nine Years' War The Nine Years' War was a European great power conflict from 1688 to 1697 between Kingdom of France, France and the Grand Alliance (League of Augsburg), Grand Alliance. Although largely concentrated in Europe, fighting spread to colonial poss ...

. He was Lord of

Tyrconnell Tyrconnell (), also spelled Tirconnell and Tirconaill, was a kingdom of Gaelic Ireland. It is associated geographically with present-day County Donegal, which was officially named ''County Tirconaill'' between 1922 and 1927. At times it also i ...

from 1592 until his death in 1602. He was born into the powerful O'Donnell clan of Tyrconnell (present-day

County Donegal County Donegal ( ; ) is a Counties of Ireland, county of the Republic of Ireland. It is in the Provinces of Ireland, province of Ulster and is the northernmost county of Ireland. The county mostly borders Northern Ireland, sharing only a small b ...

). By the age of fourteen, he was recognised as his clan's

tanist Tanistry is a Gaelic system for passing on titles and lands. In this system the Tanist (; ; ) is the office of heir-apparent, or second-in-command, among the (royal) Gaelic patrilineal dynasties of Ireland, Scotland and Mann, to succeed to ...

and engaged to the daughter of the prominent

Earl of Tyrone The Earl of Tyrone is a title created three times in the Peerage of Ireland, and once in the Spanish nobility. It was created for the final time in 1746 for Marcus Beresford, 1st Viscount Tyrone, son-in-law of the last de Poer earls. His son wa ...

. The English-led Irish government feared that an alliance between Tyrone and the O'Donnell clan would threaten

the Crown The Crown is a political concept used in Commonwealth realms. Depending on the context used, it generally refers to the entirety of the State (polity), state (or in federal realms, the relevant level of government in that state), the executive ...

's control over

Ulster Ulster (; or ; or ''Ulster'') is one of the four traditional or historic provinces of Ireland, Irish provinces. It is made up of nine Counties of Ireland, counties: six of these constitute Northern Ireland (a part of the United Kingdom); t ...

, so in 1587

Lord Deputy The Lord Deputy was the representative of the monarch and head of the Irish executive (government), executive under English rule, during the Lordship of Ireland and then the Kingdom of Ireland. He deputised prior to 1523 for the Viceroy of Ireland ...

John Perrot Sir John Perrot (7 November 1528 – 3 November 1592) was a member of the Welsh gentry who served as Lord Deputy of Ireland under Queen Elizabeth I of England during the Tudor conquest of Ireland. It was formerly speculated that he was an ille ...

arranged Hugh Roe's kidnapping. The government subsequently backed

regime change Regime change is the partly forcible or coercive replacement of one government regime with another. Regime change may replace all or part of the state's most critical leadership system, administrative apparatus, or bureaucracy. Regime change may ...

in Tyrconnell. After four years' imprisonment in

Dublin Castle Dublin Castle () is a major Government of Ireland, Irish government complex, conference centre, and tourist attraction. It is located off Dame Street in central Dublin. It is a former motte-and-bailey castle and was chosen for its position at ...

, 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 Kilmacrennan ( or ), also Kilmacrenan, is a village, townland and civil parish in County Donegal, Ireland. The village population was 888, as of the 2022 census. The village's population has increased steadily over the last decade with many n ...

on 23 April N.S. 3 May">Old_Style_and_New_Style_dates.html" ;"title="/nowiki>Old Style and New Style dates">N.S. 3 May/nowiki> 1592. Along with his father-in-law Tyrone, Hugh Roe O'Donnell led a confederacy of Irish lords in the Nine Years' War, motivated to prevent

English incursions into their territory and to end Catholic Church in Ireland">Catholic The Catholic Church (), also known as the Roman Catholic Church, is the List of Christian denominations by number of members, largest Christian church, with 1.27 to 1.41 billion baptized Catholics Catholic Church by country, worldwid ...

religious persecution">persecution Persecution is the systematic mistreatment of an individual or group by another individual or group. The most common forms are religious persecution, racism, and political persecution, though there is naturally some overlap between these term ...

under

Elizabeth I Elizabeth I (7 September 153324 March 1603) was List of English monarchs, Queen of England and List of Irish monarchs, Ireland from 17 November 1558 until her death in 1603. She was the last and longest reigning monarch of the House of Tudo ...

. Throughout the war, O'Donnell expanded his territory into

Connacht Connacht or Connaught ( ; or ), is the smallest of the four provinces of Ireland, situated in the west of Ireland. Until the ninth century it consisted of several independent major Gaelic kingdoms (Uí Fiachrach, Uí Briúin, Uí Maine, C ...

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 The siege of Kinsale (), also known as the battle of Kinsale, was the ultimate battle in England's conquest of Gaelic Ireland, commencing in October 1601, near the end of the reign of Queen Elizabeth I, and at the climax of the Nine Years' War� ...

, O'Donnell travelled to

Habsburg Spain Habsburg Spain refers to Spain and the Hispanic Monarchy (political entity), Hispanic Monarchy, also known as the Rex Catholicissimus, Catholic Monarchy, in the period from 1516 to 1700 when it was ruled by kings from the House of Habsburg. In t ...

to acquire reinforcements from King Philip III. The promised reinforcements were continually postponed, and whilst preparing for a follow-up meeting with the king, O'Donnell died of a sudden illness at the Castle of Simancas, aged 29. His body was buried inside the Chapel of Wonders at the Convent of St. Francis in

Valladolid Valladolid ( ; ) is a Municipalities of Spain, municipality in Spain and the primary seat of government and ''de facto'' capital of the Autonomous communities of Spain, autonomous community of Castile and León. It is also the capital of the pr ...

. O'Donnell's premature death disheartened an already withering Irish resistance; Tyrone ended the Nine Years' War in 1603 with the

Treaty of Mellifont The Treaty of Mellifont (), also known as the Articles of Mellifont, was signed in 1603, ending the Nine Years' War (Ireland), Nine Years' War which took place in Ireland from 1593 to 1603. End of war Following the English victory in the Battl ...

. Fiercely patriotic and militarily aggressive, O'Donnell is considered a

folk hero A folk hero or national hero is a type of hero – real, fictional or mythology, mythological – with their name, personality and deeds embedded in the popular consciousness of a people, mentioned frequently in Folk music, folk songs, folk tales ...

and a symbol of

Irish nationalism Irish nationalism is a nationalist political movement which, in its broadest sense, asserts that the people of Ireland should govern Ireland as a sovereign state. Since the mid-19th century, Irish nationalism has largely taken the form of cult ...

. He has drawn comparisons to

El Cid Rodrigo Díaz de Vivar ( – 10 July 1099) was a Castilian knight and ruler in medieval Spain. Fighting both with Christian and Muslim armies during his lifetime, he earned the Arabic honorific ("the Lord" or "the Master"), which would evolve i ...

and

William Wallace Sir William Wallace (, ; Norman French: ; 23 August 1305) was a Scottish knight who became one of the main leaders during the First War of Scottish Independence. Along with Andrew Moray, Wallace defeated an English army at the Battle of St ...

. In 2020, an unsuccessful

archaeological dig In archaeology, excavation is the exposure, processing and recording of archaeological remains. An excavation site or "dig" is the area being studied. These locations range from one to several areas at a time during a project and can be condu ...

for his remains drew international media attention. Since 2022, the city has annually reenacted his 1602

funeral procession A funeral procession is a procession, usually in motor vehicles or by foot, from a funeral home or place of worship to the cemetery or crematorium. In earlier times the deceased was typically carried by male family members on a bier or in a cof ...

in period costumes.

Early life

Family background

Hugh Roe O'Donnell was born 20 October N.S. 30 October">Old_Style_and_New_Style_dates.html" ;"title="/nowiki> N.S. 30 October/nowiki> 1572, the eldest son of Irish lord

Hugh MacManus O'Donnell and his second wife, Scottish aristocrat Iníon Dubh">Fiona "Iníon Dubh" MacDonald. He was born into the ruling branch of the O'Donnell clan, a

Gaelic Irish The Gaels ( ; ; ; ) are an Insular Celtic ethnolinguistic group native to Ireland, Scotland, and the Isle of Man. They are associated with the Gaelic languages: a branch of the Celtic languages comprising Irish, Manx, and Scottish Gaeli ...

noble dynasty based in

, a kingdom geographically associated with present-day

. He had three younger brothers, Rory Rory is a given name of Gaelic origin. It is an anglicisation of the /''Ruaidhrí'' and /''Ruaraidh'' and is common to the Irish, Highland Scots and their diasporas. for the given name "Rory". The meaning of the name is "red king", composed ...

, Manus and

Cathbarr (ordered oldest to youngest), and several sisters, Nuala O'Donnell">Nuala Nuala ( , ) or Fionnuala is an Irish feminine given name, derived from Irish mythology - being either a diminutive form of Fionnuala ("fair shoulder"), the daughter of Lir, or an alternate name for Úna (perhaps meaning "lamb"), wife of Finvar ...

, Margaret and Mary Mary may refer to: People * Mary (name), a female given name (includes a list of people with the name) Religion * New Testament people named Mary, overview article linking to many of those below * Mary, mother of Jesus, also called the Blesse ...
. He also had older half-siblings from his father's previous relationships, including

Donal and Siobhán O'Donnell">Siobhán Siobhán is a female name of Irish origin. The most common anglicisations are Siobhan (identical to the Irish spelling but omitting the acute accent over the 'a'), Shavawn, Shebahn, Shevaun and Shivaun. A now uncommon spelling variant is Siubh ...

. Paternally Hugh Roe claimed descent, via the lineage of Conall Gulban of the

Cenél Conaill Cenél is a surname. Notable people with the surname include: *Cenél Conaill, the name of the "kindred" or descendants of Conall Gulban, son of Niall Noígiallach defined by oral and recorded history *Cenél nEógain (in English, Cenel Eogan) is ...

, from the semi-legendary High King of Ireland, 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 Clan MacDonald of Dunnyveg, also known as Clan Donald South, ''Clan Iain Mor, Clan MacDonald of Islay and Kintyre, MacDonalds of the Glens (Antrim)'' and sometimes referred to as ''MacDonnells'', is a Scottish clan and a branch of Clan Donald. T ...

and from

Somerled Somerled (died 1164), known in Middle Irish as Somairle, Somhairle, and Somhairlidh, and in Old Norse as Sumarliði , was a mid-12th-century Norse-Gaelic lord who, through marital alliance and military conquest, rose in prominence to create the ...

, the first

Lord of the Isles Lord of the Isles or King of the Isles ( or ; ) is a title of nobility in the Baronage of Scotland with historical roots that go back beyond the Kingdom of Scotland. It began with Somerled in the 12th century and thereafter the title was ...

. He was also descended from

King of Scots The monarchy of the United Kingdom, commonly referred to as the British monarchy, is the form of government used by the United Kingdom by which a hereditary monarch reigns as the head of state, with their powers regulated by the British cons ...

Robert the Bruce Robert I (11 July 1274 – 7 June 1329), popularly known as Robert the Bruce (), was King of Scots from 1306 until his death in 1329. Robert led Kingdom of Scotland, Scotland during the First War of Scottish Independence against Kingdom of Eng ...

and his grandson Robert II, the first

Stuart Stuart may refer to: People *Stuart (name), a given name and surname (and list of people with the name) * Clan Stuart of Bute, a Scottish clan *House of Stuart, a royal house of Scotland and England Places Australia Generally *Stuart Highway, ...

king of Scotland. Hugh Roe's father, Hugh MacManus, had ruled as

and Lord of Tyrconnell since 1566. He was a wary politician who alternated between alliances with the

O'Neill clan The O'Neill dynasty ( Irish: ''Ó Néill'') are a lineage of Irish Gaelic origin that held prominent positions and titles in Ireland and elsewhere. As kings of Cenél nEógain, they were historically one of the most prominent family of the Nor ...

, his long-established rivals in

, and the English government, which controlled the area around Dublin (

the Pale The Pale ( Irish: ''An Pháil'') or the English Pale (' or ') was the part of Ireland directly under the control of the English government in the Late Middle Ages. It had been reduced by the late 15th century to an area along the east coast s ...

). In 1569 Hugh MacManus married Iníon Dubh of

, 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

) via his marriage to Siobhán.

Education and fosterage

The

Franciscan The Franciscans are a group of related organizations in the Catholic Church, founded or inspired by the Italian saint Francis of Assisi. They include three independent Religious institute, religious orders for men (the Order of Friars Minor bei ...

friars at

Donegal Abbey Donegal Abbey (Irish: ''Mainistir Dhún na nGall'') is a ruined Franciscan Priory in Donegal in Ireland. It was constructed by the O'Donnell dynasty in the fifteenth century and remained a center of Classical Christian education even after its ...

were the spiritual counselors of the ruling O'Donnells, and were also the educators of the dynasty's children. In medieval Ireland, the sons of Irish clan chiefs were typically trained from the age of seven in horse-riding and weaponry. Children of the Gaelic Irish nobility were traditionally fostered to fellow clans 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 The O'Cahan ( Irish: ''Ó Catháin'' 'descendants of Cahan') were a powerful sept of the Northern Uí Néill's Cenél nEógain in medieval Ireland. The name is presently anglicized as O'Kane, Kane and Keane. The O'Cahan's originated in Lagga ...

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

Rise to prominence

Hugh Roe saw his first military action in 1584, with his father's chief advisor Eoin O'Gallagher, against Clan

O'Rourke O'Rourke () is an Irish Gaelic clan based most prominently in what is today County Leitrim. The family were the historic rulers of Breifne and later West Breifne until the 17th century. The O'Rourke Clan Chief was at odds with the O'Reilly Chie ...

West Breifne The Kingdom of West Breifne (Irish: ''Breifne Ua Ruairc'') or Breifne O'Rourke was a historic kingdom of Ireland that existed from 1256 to 1605, located in the area that is now County Leitrim. It took its present boundaries in 1583 when West Br ...

. Even before reaching the age of fifteen, Hugh Roe had become well known across Ireland. Biographer

Lughaidh Ó Cléirigh Lughaidh Ó Cléirigh (fl. 1603 – 1616), sometimes anglicised as Lewey O'Clery, was an Irish Gaelic poet and historian. He is best known today as the author of ''Beatha Aodha Ruaidh Uí Dhomhnaill'', a biography of Red Hugh O'Donnell. Life Bo ...

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 A rose is either a woody perennial plant, perennial flowering plant of the genus ''Rosa'' (), in the family Rosaceae (), or the flower it bears. There are over three hundred Rose species, species and Garden roses, tens of thousands of cultivar ...

. 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

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 The Lord Deputy was the representative of the monarch and head of the Irish executive (government), executive under English rule, during the Lordship of Ireland and then the Kingdom of Ireland. He deputised prior to 1523 for the Viceroy of Ireland ...

, Welsh statesman

, hatched a plan to kidnap the young noble. In May 1587, Perrot proposed to

Lord Burghley William Cecil, 1st Baron Burghley (13 September 15204 August 1598), was an English statesman, the chief adviser of Queen Elizabeth I for most of her reign, twice Secretary of State (1550–1553 and 1558–1572) and Lord High Treasurer from ...

that he could capture " ugh MacManus his wife (who is a great bringer in of Scots), and perhaps his son ugh Roe by sending thither a boat with wines".

In September, 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 Rathmullan () is a seaside village and townland on the Fanad Peninsula in County Donegal, Ireland. It is situated on the western shore of Lough Swilly, north-east of Ramelton and east of Milford. Rathmullan was the point of departure duri ...

Lough Swilly Lough Swilly () in Ireland is a glacial fjord or sea inlet lying between the western side of the Inishowen Peninsula and the Fanad Peninsula, in County Donegal. Along with Carlingford Lough and Killary Harbour it is one of three glacial fjords ...

, where fourteen-year-old Hugh Roe was sojourning with his foster-father MacSweeney na dTuath. The ship was anchored and the crew went on shore under the guise of ordinary merchants selling wine. Hugh Roe heard of the merchant ship and arrived with several young companions. Barnes claimed that he had no wine left unsold except for what was left on the ship, and invited Hugh Roe aboard. Chief Donnell MacSweeney Fanad (Hugh Roe's host) was ashamed that the young noble had missed out on the wine and unwittingly encouraged him to take a small boat to the ''Matthew''. Chief MacSweeney Fanad, Chief MacSweeney na dTuath and Eoin O'Gallagher accompanied Hugh Roe onto the ''Matthew''. Once on board, Hugh Roe and his compatriots were conducted into a secured cabin and plied with food and wine. Whilst they were enjoying themselves, the hatches were fastened and their weapons were removed. MacSweeney Fanad was released in exchange for his eldest son Donnell Gorm MacSweeney Fanad. O'Gallagher likewise gave his nephew Hugh O'Gallagher. MacSweeney na dTuath was also released upon giving "his eldest son" (actually a young peasant dressed in his son's clothes) as a hostage. Hostages were offered in Hugh Roe's stead to no avail, and the ship set sail for Dublin.

Imprisonment

Hugh Roe arrived in Dublin on 25 September; Queen

was informed the next day. Perrot ascertained that the peasant was not MacSweeney na dTuath's son and dismissed him. Hugh Roe and his fellow hostages were imprisoned in

, most likely one of the gate towers.. Within three months, Tyrone was lobbying the queen for Hugh Roe's release. In 1588, he offered a bribe of £1000 to William FitzWilliam (Perrot's successor as Lord Deputy) plus £300 to newly-appointed officials. Tyrone was later accused of offering a further £1000 to Dublin Castle's constable. In spring 1588, Iníon Dubh offered Perrot a bribe of £2000, plus sureties and hostages, for her son's release. After the

Spanish Armada The Spanish Armada (often known as Invincible Armada, or the Enterprise of England, ) was a Spanish fleet that sailed from Lisbon in late May 1588, commanded by Alonso de Guzmán, Duke of Medina Sidonia, an aristocrat without previous naval ...

's September 1588 shipwreck in

Inishowen Inishowen () is a peninsula in the north of County Donegal in Ireland. Inishowen is the largest peninsula on the island of Ireland. The Inishowen peninsula includes Ireland's most northerly point, Malin Head. The Grianan of Aileach, a ringfor ...

, Hugh MacManus offered the government thirty captured Spanish officers in exchange for his son. FitzWilliam refused due to "the dangers that might grow unto this miserable realm by letting loose the reins unto so harebrain and ungracious an imp". In 1590 he indicated a willingness to release Hugh Roe, but this came to naught. The English attempted to convert Hugh Roe and his fellow

Catholic The Catholic Church (), also known as the Roman Catholic Church, is the List of Christian denominations by number of members, largest Christian church, with 1.27 to 1.41 billion baptized Catholics Catholic Church by country, worldwid ...

hostages to

Protestantism Protestantism is a branch of Christianity that emphasizes Justification (theology), justification of sinners Sola fide, through faith alone, the teaching that Salvation in Christianity, salvation comes by unmerited Grace in Christianity, divin ...

by bringing them to a Protestant service, but the boys shouted over the hymns and music so the service could not be heard. They did not desist even when carried out of the church and sent back to their cell, and were never again summoned. During his time in Dublin Castle, Hugh Roe had little interaction with the outside world beyond conversations with fellow political prisoners (particularly the Anglo-Irish

Munster Munster ( or ) is the largest of the four provinces of Ireland, located in the south west of the island. In early Ireland, the Kingdom of Munster was one of the kingdoms of Gaelic Ireland ruled by a "king of over-kings" (). Following the Nor ...

lords imprisoned from the

Desmond Rebellions The Desmond Rebellions occurred in 1569–1573 and 1579–1583 in the Irish province of Munster. They were rebellions by the Earl of Desmond, the head of the FitzGerald dynasty in Munster, and his followers, the Geraldines and their allies, ...

). 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 " 'Donnellhad been listening to tories about the Englishduring 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 Leinster ( ; or ) is one of the four provinces of Ireland, in the southeast of Ireland. The modern province comprises the ancient Kingdoms of Meath, Leinster and Osraige, which existed during Gaelic Ireland. Following the 12th-century ...

and of the province of unster.. The English tell you lies now, and they will attack you when they find you unprepared". Ironically, Hugh Roe learnt to speak English during his imprisonment. This period in Dublin is seen as the defining event of his short life.

Chaos in Tyrconnell

Hugh MacManus became prematurely senile, and Hugh Roe's imprisonment exacerbated a long-running succession dispute which had consumed Tyrconnell since October 1580. The dispute was bloody; three of Conn's sons were violently killed in the conflict. Iníon Dubh effectively took over Tyrconnell and ruled in her husband's name. She pushed successfully for Hugh Roe to become her husband's successor by spreading the Aodh Eangach prophecy and by directing her Redshanks to kill any challengers. Hugh MacEdegany, an illegitimate son of Calvagh O'Donnell, was the first major challenger. He was assassinated on Iníon Dubh's orders during a visit to her residence, Mongavlin Castle, in May 1588, leaving Niall Garve as head of the "MacCalvagh" branch. Ulster Early 16th Century

Further disruptions developed as the government appointed various administrators in Tyrconnell who ransacked and pillaged the kingdom. Perrot appointed William Mostian as Sheriff of Tyrconnell—he quickly carried out eight cattle raids, ransacking Donegal Abbey and murdering its guardian. Later the same year, FitzWilliam gave Captain John Connill charge of Tyrconnell after being bribed with two Spanish gold chains. Connill assisted the opponents of the ruling O'Donnells. He was later joined by Captain Humphrey Willis and two hundred soldiers. At one point Connill befriended then captured Hugh MacManus, but he was freed by Niall Garve. Another brutal administrator was Captain Bowen, a notorious torturer who fried the soles of his victims' feet. This chaos created mass resentment towards the English government. Hugh Roe's elder half-brother Donal became the Crown's favored candidate for the chiefdom, and shortly after the Armada's shipwreck, FitzWilliam knighted and appointed Donal as Sheriff. FitzWilliam also imprisoned important Tyrconnell nobles Sean O'Doherty (Lord of Inishowen) and Eoin O'Gallagher, believing them to possess Spanish treasure from the Armada. O'Gallagher's imprisonment also had political motivations as he was a major adherent of Hugh Roe during the succession dispute. Donal made an effort to depose his father, backed by Connill's troops. Iníon Dubh, backed by her Redshanks and the clans of the

who remained loyal to her husband, crushed Donal at the Battle of Doire Leathan on 3 September N.S. 14 September">Old_Style_and_New_Style_dates.html" ;"title="/nowiki>Old Style and New Style dates">N.S. 14 September/nowiki> 1590. Willis (who replaced Donal as Sheriff) and Connill exploited the ensuing chaos. They took control of western Tyrconnell and began raiding into the east, accompanied by a Captain Fuller. Their forces also ransacked southern Tyrconnell and forced many of the population to flee to the mountains. Iníon Dubh bought off Niall Garve with a political marriage to her daughter Nuala O'Donnell">Nuala Nuala ( , ) or Fionnuala is an Irish feminine given name, derived from Irish mythology - being either a diminutive form of Fionnuala ("fair shoulder"), the daughter of Lir, or an alternate name for Úna (perhaps meaning "lamb"), wife of Finvar ...
, 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 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 Fiach mac Aodha Ó Broin (anglicised as Feagh or Fiach MacHugh O'Byrne) (1534 – 8 May 1597) was Chief of the Name of Clann Uí Bhroin (Clan O'Byrne) and Lord of Ranelagh during the Elizabethan wars against the Irish clans. Background Dur ...

, of Clan O'Byrne, to take Hugh Roe to his house in

Glenmalure Glenmalure () is a 20-kilometre long U-shaped glacial valley in the Wicklow Mountains in Ireland. Glenmalure is an important base for climbing in the Wicklow mountains, and particularly accessing the massif of Lugnaquilla, and contains one of ...

. According to O'Sullivan Beare, O'Byrne and his clansmen immediately set out to rescue Hugh Roe, but their inability to cross a flooded river prevented them from reaching Castlekevin in time. English officer George Carew was dispatched to Castlekevin on 15 January N.S. 25 January">Old_Style_and_New_Style_dates.html" ;"title="/nowiki>Old Style and New Style dates">N.S. 25 January/nowiki> and Hugh Roe was surrendered and returned to Dublin Castle in chains. Ó Cléirigh states the Privy Council of Ireland">Privy Council were pleased with Hugh Roe's recapture: "they made little or no account of all the hostages and pledges who escaped from them, and they were thankful for the visit which restored him to them again". Hugh Roe was lodged in Dublin Castle's record tower (the Bermingham Tower), shackled more heavily than before,. and checked by the chief gaoler twice a day.

Second escape attempt

Around January 1592, Hugh Roe made a successful escape attempt with his fellow prisoners Henry MacShane O'Neill and Art MacShane O'Neill. After years of lobbying and bribery, Tyrone had finally succeeded in bribing officials to help facilitate Hugh Roe's escape. FitzWilliam, considered one of Tudor Ireland's most corrupt Lord Deputies, was most likely the recipient of this bribe, though this has never been conclusively proven. A 17th-century account by Donegal priests alleged that Tyrone successfully bribed FitzWilliam with £1,000 (equivalent to £287,000 in March 2024). In summer 1590,

Conn MacShane O'Neill Con(n) MacShane O'Neill (1565–1630) was an Irish flaith or Prince of Ulster Ulster (; or ; or ''Ulster'') is one of the four traditional or historic provinces of Ireland, Irish provinces. It is made up of nine Counties of Ireland, coun ...

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 Winter clothing are clothes used for protection against the particularly cold weather of winter. Often they have a good water resistance, consist of multiple layers to protect and insulate against low temperatures. Winter clothes are especially o ...

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 enrywho was the oldest of the party...

he others He or HE may refer to: Language * He (letter), the fifth letter of the Semitic abjads * He (pronoun), a pronoun in Modern English * He (kana), one of the Japanese kana (へ in hiragana and ヘ in katakana) * Ge (Cyrillic), a Cyrillic letter cal ...

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 The Wicklow Mountains (, archaic: '' Cualu'') form the largest continuous upland area in Ireland. They occupy the whole centre of County Wicklow and stretch outside its borders into the counties of Dublin, Wexford and Carlow. Where the mountai ...

at which point they sought shelter in a cave, traditionally said to be along the slopes of

Conavalla Conavalla () at , is the 69th–highest peak in Ireland on the Arderin scale, and the 85th–highest peak on the Vandeleur-Lynam scale.Mountainviews, (September 2013), "A Guide to Ireland's Mountain Summits: The Vandeleur-Lynams & the Arderins" ...

. 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 Hypothermia is defined as a body core temperature below in humans. Symptoms depend on the temperature. In mild hypothermia, there is shivering and mental confusion. In moderate hypothermia, shivering stops and confusion increases. In severe ...

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

Gardiner Gardiner may refer to: Places Settlements ;Canada * Gardiner, Ontario ;United States * Gardiner, Maine * Gardiner, Montana * Gardiner (town), New York ** Gardiner (CDP), New York * Gardiner, Oregon * Gardiner, Washington * West Gardiner, ...

, and the Treasurer, and inquire who they are that have been touched by it".

Accession as clan chief

Return to Ulster

For a few days after his rescue, Hugh Roe was tended to in a hidden cabin in Glenmalure. Hugh Roe and O'Byrne swore oaths to mutually assist each other if they came under English attack, and Hugh Roe promised to make Tyrone and Chief Hugh Maguire of

Fermanagh Historically, Fermanagh (), as opposed to the modern County Fermanagh, was a kingdom of Gaelic Ireland, associated geographically with present-day County Fermanagh. ''Fir Manach'' originally referred to a distinct kin group of alleged Laigin or ...

swear similar oaths. Turlough Boye O'Hagan, a trusted emissary of Tyrone, arrived to escort Hugh Roe back to Ulster; they set out immediately. Hugh Roe's feet were frostbitten so he had to be lifted up and off of his horse. He was escorted across the Liffey by a band of horsemen (which included Felim O'Toole). He proceeded northwards under O'Hagan's guidance and crossed the Boyne on a small ferry kept by a "poor little fisherman", whilst his attendant led their horses through

Drogheda Drogheda ( , ; , meaning "bridge at the ford") is an industrial and port town in County Louth on the east coast of Ireland, north of Dublin. It is located on the Dublin–Belfast corridor on the east coast of Ireland, mostly in County Louth ...

. At

Mellifont Mellifont Abbey (, literally 'the Big Monastery'), was a Cistercian abbey located close to Drogheda in County Louth, Ireland. It was the first abbey of the order to be built in Ireland. In 1152, it hosted the Synod of Kells-Mellifont. After i ...

, he rested one night at the house of English ally Garret Moore, travelled through

Dundalk Dundalk ( ; ) is the county town of County Louth, Ireland. The town is situated on the Castletown River, which flows into Dundalk Bay on the north-east coast of Ireland, and is halfway between Dublin and Belfast, close to and south of the bor ...

and the Fews, and on the third day reached

Armagh Armagh ( ; , , " Macha's height") is a city and the county town of County Armagh, in Northern Ireland, as well as a civil parish. It is the ecclesiastical capital of Ireland – the seat of the Archbishops of Armagh, the Primates of All ...

. The next day Hugh Roe arrived at

Dungannon Dungannon (, ) is a town in County Tyrone, Northern Ireland. It is the second-largest town in the county (after Omagh) and had a population of 16,282 at the United Kingdom Census 2011, 2021 Census. The Dungannon and South Tyrone Borough Counci ...

, 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 Sir Turlough Lynagh O'Neill (also known as Turlough Luineach) ( Irish: ''An Ridire Toirdhealbhach Luineach mac Néill Chonnalaigh Ó Néill''; – September 1595) was an Irish Gaelic lord of Tír Eoghain in early modern Ireland. He was inau ...

, Tyrone's rival in

Tír Eoghain Tír Eoghain (), also known as Tyrone, was a kingdom and later earldom of Gaelic Ireland, comprising parts of present-day County Tyrone, County Armagh, County Londonderry and County Donegal (Raphoe). The kingdom represented the core homeland of ...

. Hugh Roe remained at Tyrone's residence for four days, hidden in a secret chamber to avoid corrupting Tyrone's loyalist public image. Afterwards, Hugh Roe was received by Maguire in Fermanagh. Maguire conveyed Hugh Roe across

Lough Erne Lough Erne ( , ) is the name of two connected lakes in County Fermanagh, Northern Ireland. It is the second-biggest lake system in Northern Ireland and Ulster, and the fourth biggest in Ireland. The lakes are widened sections of the River E ...

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 Ballyshannon () is a town in County Donegal, Republic of Ireland, Ireland. It is located at the southern end of the county where the N3 road (Ireland), N3 from Dublin ends and the N15 road (Ireland), N15 crosses the River Erne. The town was inc ...

Attack on English occupation

Tyrconnell had suffered much repression and turmoil in Hugh Roe's absence. Not long before his return, Willis and Connill's forces raided Donegal in the dead of night and occupied Donegal Abbey as a

garrison A garrison is any body of troops stationed in a particular location, originally to guard it. The term now often applies to certain facilities that constitute a military base or fortified military headquarters. A garrison is usually in a city ...

. Ballyshannon Castle and

Donegal Castle Donegal Castle () is a castle situated in the centre of Donegal Town in County Donegal in Ulster, the northern province in Ireland. The castle was the stronghold of the O'Donnell clan, Lords of Tír Conaill and one of the most powerful Gaeli ...

were the two major strongholds in Tyrconnell not yet deprived by the Crown. Even nobles in Tyrconnell who previously favoured the Crown had become resentful by this time. Hugh Roe made expelling the English forces his first order of business, and he rallied his family's followers to Ballyshannon. Donegalcastle

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

Inauguration

On 23 April N.S. 3 May">Old_Style_and_New_Style_dates.html" ;"title="/nowiki>Old Style and New Style dates">N.S. 3 May/nowiki> 1592 at

Friary, 19-year-old Hugh Roe O'Donnell was inaugurated as O'Donnell clan chief before an audience of his family and their supporters. The inauguration ceremony was part-religious and part-secular, and involved the O'Donnell clan's ornamental inauguration stone. Hugh MacManus's apparently voluntary abdication was "stage-managed" by Iníon Dubh, who remained the "head of advice and counsel" in Tyrconnell. Following his abdication, Hugh MacManus spent his final years living in retirement among the Franciscans at Donegal Abbey and doing penance for his sins. Hugh Roe's younger brother Rory was appointed as tanist. Kilmacrenan Friary W 2012 09 19

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

Rise in power

Immediately after his inauguration, Hugh Roe O'Donnell and Tyrone mounted raids against Turlough Luineach, who had provided assistance to O'Donnell's rivals such as Niall Garve. O'Donnell desired revenge and sought to assist his new ally Tyrone, whose alliance with O'Donnell was primarily founded on using the latter's military power to take control of Tír Eoghain. In June 1592, O'Donnell renewed his clan's interest in north

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

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 Lifford (, historically anglicised as ''Liffer'') is the county town of County Donegal, Ireland, the administrative centre of the county and the seat of Donegal County Council, although the town of Letterkenny is often mistaken as holding this ...

'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

Portrait of Philip II of Spain by Sofonisba Anguissola - 002b

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 Sir Brian O'Rourke (; c. 1540 – 1591) was first king and then lord of West Bréifne in the west of Ireland from 1566 until his execution in 1591. He reigned during the later stages of the Tudor conquest of Ireland and his rule was marked by ...

(1591) had created a fierce resentment in the Gaelic nobility and Irish Catholic clergy. Catholic priests were suffering harassment and imprisonment from English authorities, and Spain had been a refuge to the Irish Catholic clergy since the 1570s. Archbishop Edmund MacGauran returned from Spain having met with King Philip II in September 1592. MacGauran was eager to obtain Spanish military aid to combat English forces in Ireland. Philip II wanted Ireland as an ally in the Anglo-Spanish War, but would only promise support if Ireland proved itself by launching prior military action. MacGauran sought Irish lords willing to openly defy the Crown, and in December a conference of seven Catholic bishops met in Tyrconnell. The bishops saw O'Donnell as their main hope, and declared he was "fittest for the part" and thus to be "their leader or general". On 29 March N.S. 8 April">Old_Style_and_New_Style_dates.html" ;"title="nowiki/>Old Style and New Style dates">N.S. 8 April1593, 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 The Archbishop of Tuam ( ; ) is an Episcopal polity, archbishop which takes its name after the town of Tuam in County Galway, Republic of Ireland, Ireland. The title was used by the Church of Ireland until 1839, and is still in use by the Cathol ...
James O'Hely">nowiki/>Seamus Ó hÉilidhe">James O'Helyto 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 Tibbot na Long Bourke, 1st Viscount Mayo, Theobald, Richard and John Bourke at Enniskillen Castle on 28 April N.S. 8 May">Old Style and New Style dates">N.S. 8 May MacGauran advised that the noblemen sign a letter addressed to Philip II which emphasised their oppression and which requested urgent reinforcements from the Spanish army. Archbishop O'Hely was tasked with delivering the confederates' messages: two letters from O'Donnell, one letter from MacGauran, and the 28 April letter signed by the confederates. Enniskillen_Castle_05

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

. 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 and bear him out in his war". O'Hely reached the Spanish court by September 1593 where he met with Juan de Idiáquez, the royal secretary. In Idiáquez's notes to Philip II, he notes that the early confederates wanted Tyrone to join them in open rebellion, though it appears Tyrone refused to publicly defy the Crown without reassurance that Spanish reinforcements would arrive.

Secret rebellion

Catholic bishops began to spread the Aodh Eangach prophecy to advance the Irish rebellion. Maguire and O'Rourke continued to rebel by attacking English forces. O'Donnell aided the growing rebellion by sending MacSweeney

gallowglass The Gallowglass (also spelled galloglass, gallowglas or galloglas; from meaning "foreign warriors") were a class of elite mercenary warriors who were principally members of the Norse-Gaelic clans of Ireland and Scotland between the mid 13th ...

, but publicly he feigned neutrality. This was because he lacked sufficient forces to combat a direct assault from English forces; he also faced pressure from his father-in-law to likewise appear publicly loyal to the Crown. Bingham put Maguire and O'Rourke under heavy pressure, and O'Donnell used their chiefdoms as a buffer between Bingham's forces and Tyrconnell. O'Donnell had some influence over Maguire, giving him advice and sheltering his creaghts on Tyrconnell's borders. MacGauran was killed on 23 June N.S. 3 July">Old_Style_and_New_Style_dates.html" ;"title="/nowiki>Old Style and New Style dates">N.S. 3 July/nowiki> 1593 whilst accompanying Maguire on a raid. In September, O'Donnell sent his mother to Scotland to secure further Scottish troops. IrishConfederacySignatures8May1593

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

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. A letter from O'Donnell was later found on the corpse of a Redshank captain killed in the battle. 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, 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 Loyalism, in the United Kingdom, its overseas territories and its former colonies, refers to the allegiance to the British crown or the United Kingdom. In North America, the most common usage of the term refers to loyalty to the British Cr ...

facade, O'Donnell warned Tyrone that he "must consider imhis enemy, unless he came to his aid in such a pinch". Tyrone subsequently sent reinforcements under his brother

Cormac MacBaron O'Neill Sir Cormac MacBaron O'Neill (d.1613) was an Irish soldier and landowner of the Elizabethan and early Stuart eras. He was part of the O'Neill dynasty, one of the most prominent Gaelic families in Ireland. Biography O'Neill was the son of M ...

to the

Battle of the Ford of the Biscuits The Battle of the Ford of the Biscuits () took place in Fermanagh, Ireland on 7 August 1594, during the Nine Years' War. A column of almost 650 English troops led by Sir Henry Duke was ambushed and defeated by a Gaelic Irish force under Hugh ...

. 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 County Monaghan ( ; ) is a Counties of Ireland, county in Ireland. It is in the Provinces of Ireland, province of Ulster and is part of Border Region, Border strategic planning area of the Northern and Western Region. It is named after the town ...

. Russell ignored these demands and resupplied Enniskillen castle with 1,200

Irish Army The Irish Army () is the land component of the Defence Forces (Ireland), Defence Forces of Republic of Ireland, Ireland.The Defence Forces are made up of the Permanent Defence Forces – the standing branches – and the Reserve Defence Forces. ...

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 Manus O'Donnell ( Irish: ''Maghnas Ó Domhnaill'' or ''Manus Ó Domhnaill''; 1490 – 9 February 1563) was a Gaelic Irish lord and King of Tyrconnell. After his father Hugh Dubh's death in 1537, Manus succeeded as Tyrconnell's ruler.The Edi ...

) had ruled over Lower Connacht, and Hugh Roe O'Donnell increasingly demanded the restoration of these lands. Richard Bingham had persecuted Connacht's Gaelic population since the mid-1580s, causing many refugees to flee to Tyrconnell. O'Donnell aided the refugees and recruited many of them as swordsmen. O'Donnell resented Bingham and was "easily tempted" by the refugees, who urged him to attack Bingham's administration. O'Donnell invaded Connacht on 3 March 1595 with 400 men. From

Rathcroghan Rathcroghan () is a complex of archaeological sites near Tulsk in County Roscommon, Ireland. It is identified as the site of Cruachan, the traditional capital of the Connachta, the prehistoric and early historic rulers of the western territory ...

, the province's ancient royal capital, he launched large raids into Longford and

Roscommon Roscommon (; ; ) is the county town and the largest town in County Roscommon in Republic of Ireland, Ireland. It is roughly in the centre of Ireland, near the meeting of the N60 road (Ireland), N60, N61 road (Ireland), N61 and N63 road (Irelan ...

. In June 1595, the castle of

Sligo Sligo ( ; , meaning 'abounding in shells') is a coastal seaport and the county town of County Sligo, Ireland, within the western province of Connacht. With a population of 20,608 in 2022, it is the county's largest urban centre (constituting 2 ...

, 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 Early Irish law, also called Brehon law (from the old Irish word breithim meaning judge), comprised the statutes which governed everyday life in Early Medieval Ireland. They were partially eclipsed by the Norman invasion of 1169, but underwe ...

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 argaret'sburial than her marriage to 'Donnellwere 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. 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 Freedom of thought is the freedom of an individual to hold or consider a fact, viewpoint, or thought, independent of others' viewpoints. Overview Every person attempts to have a cognitive proficiency by developing knowledge, concepts, theo ...

. The queen warily accepted O'Donnell's claims to lands in Connacht. On 28 January, the commissioners presented O'Donnell with a list of twelve articles. These urged him to disperse his forces, to

shire Shire () is a traditional term for an administrative division of land in Great Britain and some other English-speaking countries. It is generally synonymous with county (such as Cheshire and Worcestershire). British counties are among the oldes ...

Tyrconnell, to stop aiding O'Rourke and Maguire, to re-edify Sligo Castle, to pay annual rents to the Crown as his father had done, and to confess the extent of his dealings with Spain. O'Donnell agreed to most articles, with some exceptions. He refused to give hostages or make a personal submission. A compromise was created, and O'Donnell agreed to terms on 30 January. A hollow peace was signed on 24 April 1596, and further negotiations to develop a peace treaty were almost complete by May.

Relations with Spain

In May, three Spanish ships arrived at Tyrconnell with the aim of encouraging the confederates and assessing Ireland's military situation. Spanish captain Alonso Cobos arrived in

Killybegs Killybegs () is a town in County Donegal, Ireland. It is the largest fishing port in the country and on the island of Ireland. It is located on the south coast of the county, north of Donegal Bay, near Donegal Town. Its Irish name means 'littl ...

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 yrone 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. Rubens - arquiduquealbertoVII01

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 A vassal or liege subject is a person regarded as having a mutual obligation to a lord or monarch, in the context of the feudal system in medieval Europe. While the subordinate party is called a vassal, the dominant party is called a suzerai ...

of Philip II. Tyrone and O'Donnell also petitioned Philip II to make

Albert VII, Archduke of Austria Albert VII (; 13 November 1559 – 13 July 1621) was the ruling Archduke of Austria for a few months in 1619 and, jointly with his wife, Isabella Clara Eugenia, sovereign of the Habsburg Netherlands between 1598 and 1621. Prior to this, he had ...

, the new Catholic monarch of Ireland. O'Donnell and his father-in-law began to deliberately derail peace negotiations and provoke war in previously peaceful parts of the country. They developed a sophisticated "good cop, bad cop" routine which they used to stall peace talks. Additionally, O'Donnell was ashamed at the sparse nature of his residence and set about purchasing "linen and pewter and all other necessaries fit to entertain the Spaniards". The confederate lords of Connacht refused to discuss peace talks with government commissioners until the arrival of O'Donnell, who was apparently delayed by dealings with Redshanks. When O'Donnell arrived that June, he refused to hand over English hostages until his terms were met. Tyrone sent Hovenden to ostensibly aid O'Donnell in pacifying Connacht, but the government intercepted a letter revealing that Hovenden was intentionally stalling negotiations so that Tyrone would have to be brought in as an arbitrator; this he eventually was. The commissioners were in a weak position due to Elizabeth I's health issues. Soon after, O'Donnell met with Tyrone, O'Rourke and MacWilliam Bourke at

Strabane Strabane (; ) is a town in County Tyrone, Northern Ireland. Strabane had a population of 13,507 at the 2021 United Kingdom census, 2021 census. This article contains quotations from this source, which is available under th Open Government Li ...

. 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 The Second Spanish Armada also known as the Spanish Armada of 1596Wernham pp. 139–140 was a naval operation that took place during the Anglo–Spanish War. Another invasion of England or Ireland was attempted in the autumn of 1596 by King Phi ...

. 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 Lisbon ( ; ) is the capital and largest city of Portugal, with an estimated population of 567,131, as of 2023, within its administrative limits and 3,028,000 within the Lisbon Metropolitan Area, metropolis, as of 2025. Lisbon is mainlan ...

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 Athenry (; ) is a town in County Galway, Ireland, which lies east of Galway city. Some of the attractions of the medieval town are its town wall, Athenry Castle, its priory and its 13th-century street-plan. The town is also well known by virt ...

and plundering the suburbs of

Galway city Galway ( ; , ) is a City status in Ireland, city in (and the county town of) County Galway. It lies on the River Corrib between Lough Corrib and Galway Bay. It is the most populous settlement in the province of Connacht, the List of settleme ...

. He was supported by competitors to the Clanricarde title.. Clifford responded by forcing MacWilliam Bourke from Mayo. O'Donnell reinstalled MacWilliam Bourke, but Clifford forced him out again in June. Thomas Burgh took over as Lord Deputy in May 1597. Burgh refused to entertain the confederates' excuses and ordered prompt military attacks on both Tyrone and O'Donnell. In July, the English launched a two-pronged assault in Ulster; Clifford assembled 1,500 men at Boyle and led them into Tyrconnell as the western arm of the assault. Clifford's army besieged Ballyshannon castle for five days, but it was successfully defended by O'Donnell's garrison of eighty men, which included Spaniards. Once O'Donnell himself arrived, Clifford's army, which had exhausted its supplies, retreated to Sligo, abandoning three pieces of ordnance and losing many men. On 4 September 1597, Clifford was appointed as Connacht's new Lord President. Lord Deputy Burgh died from illness in October. Despite the confederacy's advantageous position, Tyrone renewed peace negotiations. He submitted to authorities on 22 December and promised to renounce his Gaelic titles and rebellious activities. O'Donnell heavily criticised Tyrone for agreeing to a cessation, pointing out that the confederate forces were strong across Leinster, Connacht and Ulster. O'Donnell declared that he would break the cessation, though he never did. Clifford changed tactics following the defeat at Ballyshannon. He encouraged confederates to change sides by promising them royal grants. In February 1598, founding confederacy member O'Rourke submitted at Boyle. By April, Clifford had lured further confederates Conor McDermot, O'Connor Don and Shane MacManus Oge (O'Donnell's cousin). In response, O'Donnell executed six of McDermot and O'Connor Don's pledges. He detained Shane MacManus Oge upon the latter's secret return to Tyrconnell. O'Donnell also killed sixteen of Mulmurry MacSweeney na dTuath's men when MacSweeney na dTuath was linked to Shane MacManus Oge. O'Donnell's younger brother Rory was also engaged by Clifford, and he resolved to serve against his brother. When this news reached O'Donnell, he had Rory clamped in chains—the brothers' relationship eventually improved and by 1600 Rory was once again fighting alongside his older brother. O'Donnell captured O'Rourke's brother Teigue and forced him to marry his sister

Mary Mary may refer to: People * Mary (name), a female given name (includes a list of people with the name) Religion * New Testament people named Mary, overview article linking to many of those below * Mary, mother of Jesus, also called the Blesse ...

, 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 A peace process is the set of political sociology, sociopolitical negotiations, agreements and actions that aim to solve a specific armed conflict. Definitions Prior to an armed conflict occurring, peace processes can include the prevention of ...

. 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. BattleoftheYellowFord

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

. Prior to the attack, the confederates made a speech "to incite their people to acts of valour". On 14 August, Bagenal's army was attacked by O'Donnell, Tyrone and Maguire's combined forces. O'Donnell attacked from the left and Tyrone from the right simultaneously. Bagenal was killed and roughly 2,000 men (half his army) were lost. O'Donnell's men ran out of ammunition and the English survivors fled to Armagh. More than 300 English soldiers deserted to the confederacy. The battle was the greatest victory by Irish forces against England, and it sparked a general revolt throughout the country, particularly in Munster. News of the battle spread across

western Europe Western Europe is the western region of Europe. The region's extent varies depending on context. The concept of "the West" appeared in Europe in juxtaposition to "the East" and originally applied to the Western half of the ancient Mediterranean ...

, 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 Ballymote Castle (Irish: ''Caisleán Bhaile an Mhóta'') is a large rectangular keepless castle, built around 1300. It is located in the townland of Carrownanty on the outskirts of Ballymote in southern County Sligo, Ireland. This area was known ...

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 County Mayo (; ) is a Counties of Ireland, county in Republic of Ireland, Ireland. In the West Region, Ireland, West of Ireland, in the Provinces of Ireland, province of Connacht, it is named after the village of Mayo, County Mayo, Mayo, now ge ...

. 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 Royal may refer to: People * Royal (name), a list of people with either the surname or given name * A member of a royal family or royalty Places United States * Royal, Arkansas, an unincorporated community * Royal, Illinois, a village * Roy ...

Robert Devereux, 2nd Earl of Essex Robert Devereux, 2nd Earl of Essex (; 10 November 1565 – 25 February 1601) was an English nobleman and a favourite of Queen Elizabeth I. Politically ambitious, he was placed under house arrest following a poor campaign in Ireland during th ...

, 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 The Curlew Mountains () are a range of low-lying hills situated between Boyle and Castlebaldwin in northeastern Connacht. Toponymy The assignation of the name ''Curlew'' to the mountains may not relate the Curlew bird, but rather to the whic ...

, 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 Boyle Abbey () is a ruined Cistercian friary located in Boyle, County Roscommon, Ireland. It was founded by Saint Malachy in the year 1161 but not consecrated until 1218 (work was interrupted by the Anglo-Norman invasion of Ireland and it wa ...

. 240 English soldiers were killed, including Clifford who was stabbed by a pike. After the battle, O'Rourke decapitated Clifford and gave the head to O'Donnell. When O'Donnell presented Clifford's severed head to O'Connor Sligo, the latter surrendered Collooney Castle. The queen and her secretary of state Robert Cecil were shocked by the Irish victory. The victory is viewed as a highlight of O'Donnell's career, though contemporary sources credit O'Rourke and Conor McDermot with the battle's success. O'Donnell forced O'Connor Sligo to join the confederacy, and he gave O'Connor Sligo "large numbers" of oxen, horses, cattle and corn to re-establish himself in lower Connacht. However he threatened O'Connor Sligo with imprisonment on an island in Lough Eske if he did not cooperate. By this time Iníon Dubh had been in Scotland for two months gathering redshanks—as Clifford's forces had been easily defeated, O'Donnell notified his mother that the redshanks were unnecessary, and she returned to Tyrconnell in January 1600 with gunpowder instead. O'Donnell followed the victory at Curlew Pass with a successful battle at the Ballaghboy Pass.

Quarrels with Tyrone

By the late 1590s, O'Donnell's relationship with his father-in-law was coming under strain,. not least because of the breakdown of O'Donnell's marriage to Rose. It was reported in April 1597 that O'Donnell had recently renewed his alliance with Tyrone, and that "their league of friendship is more apparently confirmed... by O'Donnell's receiving of the earl's base daughter" in marriage. By 1598, it was reported O'Donnell had divorced Rose, most likely against Tyrone's wishes. She remarried to Tyrone's principal vassal Donnell Ballagh O'Cahan by 1599. O'Donnell reportedly divorced Rose due to her "barronness", though the historian Morwenna Donnelly has questioned this truthfulness of this explanation, considering that O'Donnell did not immediately remarry to ensure an heir. The confederacy leaders argued over the division of money and munitions sent from Spain. Tyrone typically demanded the superior portion; when munitions arrived in 1596, Tyrone took twenty firkins of gunpowder compared to O'Donnell receiving fifteen. This came to a head in mid-1599, when O'Donnell debated over the division of a delivery brought by Barrionuevo. O'Donnell felt he was owed more resources in view of his recent victories, as well as his riskier approach to warfare. According to a spy's report, "Tyrone and O'Donnell fell into some contention about receiving of the said munition and treasure, Tyrone challenging the disposal of the whole, as chief and general of the common service, and O'Donnell claiming as great a right in it as he, as he affirmed, as deeply engaged therein as he. In the end the assembly there (by mediation of an Irish bishop from Rome with them) overruled the disposition of the whole for Tyrone". A treaty of equality was established between the two men, which decreed that "one had no pre-eminence over the other and that in walking and travelling together whichever was the elder should be on the right hand". Tyrone refused to fight Essex's dwindling forces; instead the two men parleyed on 7 September 1599 and a six-week truce was organised. O'Donnell was furious at Tyrone's decision to negotiate with Essex, as he wanted to avoid any association with English officials in favour of soliciting aid from the Spanish. He declared that he would travel into Connacht, but Tyrone forbid him on account of the truce. O'Donnell admitted that he would burn the entire Pale if not for Tyrone preventing him. Essex left Ireland on 24 September and was shortly afterwards removed from his post. His downfall briefly put the confederacy in a strong position. In February 1600,

Charles Blount, 8th Baron Mountjoy Charles Brooke Blount, 1st Earl of Devonshire, KG (pronounced ''Blunt''; 15633 April 1606), was an English nobleman and soldier who served as Lord Deputy of Ireland under Elizabeth I, and later as Lord Lieutenant of Ireland under James I. He wa ...

, arrived in Ireland as the new Lord Deputy. Mountjoy posed a major threat to the confederacy as he immediately began revitalising and restoring confidence in the royal army. On 1 March N.S. 11 March">Old_Style_and_New_Style_dates.html" ;"title="nowiki/> N.S. 11 March1600, Hugh Maguire was shot and killed whilst on reconnaissance near Cork (city)">Cork "Cork" or "CORK" may refer to: Materials * Cork (material), an impermeable buoyant plant product ** Stopper (plug), or "cork", a cylindrical or conical object used to seal a container *** Wine cork an item to seal or reseal wine Places Ireland * ...
. His lordship was contested by rival claimants Cúconnacht Maguire (his younger half-brother) and Connor Roe Maguire (died 1625)">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

, 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 Henry may refer to: People and fictional characters * Henry (given name), including lists of people and fictional characters * Henry (surname) * Henry, a stage name of François-Louis Henry (1786–1855), French baritone Arts and entertainmen ...

, and O'Donnell sent the sons of O'Doherty and O'Gallagher.

Forced from Tyrconnell

Defection of Niall Garve

In May 1600, English commander Henry Docwra established an English garrison in

Derry Derry, officially Londonderry, is the second-largest City status in the United Kingdom, city in Northern Ireland, and the fifth-largest on the island of Ireland. Located in County Londonderry, the city now covers both banks of the River Fo ...

. O'Donnell made a substantial attempt to weaken Docwra's forces on 29 July. O'Donnell captured at least 60 horses and Docwra was nearly killed by Hugh McHugh Dubh. O'Donnell later made a failed night attack on the garrison. Despite the poor conditions at the Derry garrison—desertion and disease was rife—Docwra managed to maintain his position, which led to further tension between O'Donnell and Tyrone. The prospects of Docwra's mission depended on winning over disaffected confederates, Niall Garve being the most important. Niall Garve's grievances were well-known to the government on account of his overtures, and Docwra began secretly communicating with him. By August, Niall Garve had sent through his list of demands, the principal of which was to rule Tyrconnell in the same manner as his grandfather Calvagh. Docwra promised to obtain him a royal grant of Tyrconnell if he defected and served against his cousin. In September O'Donnell left Ulster for a raid in

Thomond Thomond ( Classical Irish: ; Modern Irish: ), also known as the Kingdom of Limerick, was a kingdom of Gaelic Ireland, associated geographically with present-day County Clare and County Limerick, as well as parts of County Tipperary around Nena ...

, entrusting Niall Garve to besiege Derry. Whilst O'Donnell was in

Ballymote Ballymote () is a market town in southern County Sligo, Ireland. It is around 20 km south of Sligo town in the province of Connacht, which is in the north-west of Republic of Ireland, Ireland. Ballymote lies in the Barony (Ireland), barony ...

, Niall Garve and his followers murdered Niall Garve's uncle Neachtan in a drunken rage. Neachtan was "a man of great authority with 'Donnelland all his country". Fearing O'Donnell's revenge, Niall Garve—alongside his three brothers and about 100 soldiers—quickly defected to the English. They joined Docwra on 3 October. O'Donnell was in Thomond when he received the news, and he immediately hurried to secure Lifford Castle to retain control over

Lough Foyle Lough Foyle, sometimes Loch Foyle ( or "loch of the lip"), is the estuary of the River Foyle, on the north coast of Ireland. It lies between County Londonderry in Northern Ireland and County Donegal in the Republic of Ireland. Sovereignty over t ...

. According to Willis, O'Donnell was "dumb-stricken" to hear of Niall Garve's betrayal and could not drink or sleep for three days. Niall Garve and an English force stormed Lifford Castle on 9 October, taking it from O'Donnell's brother Rory. O'Donnell wrote angrily to Tyrone, "charging him with many oversights, that he lay too long at the Moyry, that he spent his munition, lost his best men, and wasted his victuals there to no purpose". O'Donnell's sister

Nuala Nuala ( , ) or Fionnuala is an Irish feminine given name, derived from Irish mythology - being either a diminutive form of Fionnuala ("fair shoulder"), the daughter of Lir, or an alternate name for Úna (perhaps meaning "lamb"), wife of Finvar ...

separated from Niall Garve due to his defection. According to a February 1601 report by Docwra, O'Donnell was so outraged by his brother-in-law's defection that he ordered mass hangings of Niall Garve's followers, and personally killed Niall Garve and Nuala's four-year-old son (his own nephew) by bashing the child's brains out against a post. This accusation is considered contentious among historians. Docwra's biographer John McGurk acknowledges the uncertainty of the report's truthfulness, and notes that it is unclear where Docwra received this intelligence. He points out that Docwra's "blunt" personality indicates that he reported current affairs accurately, and also admits that

infanticide Infanticide (or infant homicide) is the intentional killing of infants or offspring. Infanticide was a widespread practice throughout human history that was mainly used to dispose of unwanted children, its main purpose being the prevention of re ...

was a feature of warfare in the

early modern period The early modern period is a Periodization, historical period that is defined either as part of or as immediately preceding the modern period, with divisions based primarily on the history of Europe and the broader concept of modernity. There i ...

. Morgan notes that since this is a contemporary account, it should not be dismissed out of hand.

Battle of Lifford

O'Donnell tried in vain to retake Lifford from Niall Garve, with minor skirmishes occurring around the castle. He lost about 20 men on 17 October 1600. He attacked again on 24 October, but Niall Garve retaliated by leading a cavalry charge of mixed Irish and English forces out to battle. During the battle, Niall Garve speared O'Donnell's brother Manus in the shoulder. Manus was taken to Donegal where he died from his wounds. O'Donnell's father Hugh MacManus died a few weeks afterwards, apparently from grief. They were buried beside each other at Donegal Abbey, as was customary for the ruling O'Donnell branch. Docwra was pleased that the outcome of the battle had exacerbated the feud between O'Donnell and Niall Garve: "I think there needeth no better hostages for his fidelity, for he hath slain with his own hands (in fight and open view of our men that saw him) O'Donnell's second brother... His love and credit with the people is little inferior to O'Donnell's and may easily be more, if he be backed and strengthened by Her Majesty..." By December 1600, O'Donnell had put a price of £300 on Niall Garve's head. It appears Niall Garve made later efforts to rejoin the confederacy, but his murder of Manus made this near-impossible.. His defection allowed Docwra to mobilise the Crown's forces beyond Lough Foyle into Tyrconnell,

and even Tír Eoghain. In addition to his skill as a guide across Tyrconnell, Niall Garve informed Docwra of his cousin's tactics.

Political alliances collapse

O'Donnell made further plans to cement his alliances beyond Ulster. In November 1600, he schemed to marry Joan FitzGerald (step-daughter to O'Connor Sligo and sister of the loyalist 1st Earl of Desmond). A servant met with Joan in

Limerick Limerick ( ; ) is a city in western Ireland, in County Limerick. It is in the Provinces of Ireland, province of Munster and is in the Mid-West Region, Ireland, Mid-West which comprises part of the Southern Region, Ireland, Southern Region. W ...

"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 The post of Lord President of Munster was the most important office in the English government of the Irish province of Munster from its introduction in the Elizabethan era for a century, to 1672, a period including the Desmond Rebellions in Munste ...

George Carew placed her under house arrest as a precaution. O'Donnell became frustrated by the Spanish government's failure to send the military resources he desired. When a Spanish ship arrived around the time of the new year, O'Donnell was "like a madman when he saw no kind of news, neither of men nor money to come: presently swore he would go himself to Spain and would have gone indeed, if the Captain of the Spaniards had suffered him". Sean O'Doherty, Lord of Inishowen, died on 27 January 1601, leading to a succession dispute. The O'Doherty clan preferred Sean's eldest son

Cahir Cahir (; ) is a town in County Tipperary in Ireland. It is also a civil parish in the barony of Iffa and Offa West. Location and access For much of the twentieth century, Cahir stood at an intersection of two busy national roadways: the Dubli ...

(then aged about 14) as the successor, but O'Donnell was bribed into inaugurating Sean's half-brother (and his own first cousin) Phelim Og O'Doherty. This decision outraged Cahir's foster family and they opened negotiations with Docwra to secure the lordship. O'Donnell attempted revenge by invading Inishowen with 1,500 men, but 40 of his men were killed and he retreated. Both Docwra and O'Donnell's conduct of war was vicious; soldiers and civilians on either side were

summarily executed In civil and military jurisprudence, summary execution is the putting to death of a person accused of a crime without the benefit of a free and fair trial. The term results from the legal concept of summary justice to punish a summary offense, a ...

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

Siege of Donegal

On 18 March 1601, the government recognised Niall Garve as the rightful chief of the O'Donnell clan. Hugh Roe O'Donnell marched on Lifford in April 1601, forcing Niall Garve and his forces to temporarily retreat to Derry. Following the Earl of Clanricarde's death in May, O'Donnell concentrated his forces at Ballymote in anticipation of an attack from Clanricarde's successor. This allowed Niall Garve to take Donegal Abbey in August and occupy it as a garrison, installing 500 English troops. His hold over Donegal was his greatest blow against O'Donnell; it virtually prevented O'Donnell from entering Tyrconnell and led to a month-long siege. The siege climaxed in late September when a fire in the garrison's store detonated several barrels of gunpowder and caused the abbey to collapse. O'Donnell hurriedly ordered his men to attack, leading to a chaotic engagement amidst the burning abbey. Niall Garve's defeat seemed certain, but the loyalist forces held out until a relief force arrived and forced O'Donnell to call off the attack. 330 of Niall Garve's troops were killed during the battle, including his brother Conn Oge. Niall Garve was so unsettled by his losses at the siege that, with Docwra's permission, he began negotiating with O'Donnell to became his tanist. Niall Garve's conditions (which included "that ugh Roe O'Donnelland iall Garveshould be bound and sworn never to come in sight of one another") were so numerous that O'Donnell discarded negotiations.

Siege of Kinsale

Throughout 1601, Philip III was focused on dispatching an armed expedition to Ireland to improve his position in the Anglo-Spanish War. Under the command of General

Juan del Águila Juan Del Águila (d'Aguila) y Arellano (Ávila, Spain, Ávila, 1545 – A Coruña, August 1602) was a Habsburg Spain, Spanish general. He commanded the Spanish expeditionary Tercio troops in Kingdom of Sicily, Sicily then in Brittany (1584� ...

, the

4th Spanish Armada The Fourth Spanish Armada, also known as the Last Armada, was a military expedition sent to Ireland that took place between August 1601 and March 1602 towards the end of Anglo-Spanish War (1585–1604), Anglo-Spanish war. The armada – the fou ...

finally landed and was besieged by English forces inside the port town of

Kinsale Kinsale ( ; ) is a historic port and fishing town in County Cork, Ireland. Located approximately south of Cork (city), Cork City on the southeast coast near the Old Head of Kinsale, it sits at the mouth of the River Bandon, and has a populatio ...

—virtually the opposite end of Ireland from Ulster—on 21 September N.S. 1 October">Old_Style_and_New_Style_dates.html" ;"title="/nowiki>Old Style and New Style dates">N.S. 1 October1601. O'Donnell was energised by the news of the Spanish expedition's long-awaited arrival and he called his forces to abandon their sieging of Niall Garve's forces. He set out for Kinsale from Ballymote in late October with about 2,000 men. Tyrone's forces began their separate march towards Kinsale a week after O'Donnell. O'Donnell's army marched through Connacht to Ath Croch near Shannon Harbour, where they were joined by Chief John Og McCoughlan and Captain Richard Tyrrell. O'Donnell's men carried two garrons loaded with Spanish silver on their march; this was to impress his wealth and wisdom upon locals he encountered. Marching onwards they reached Druim-Saileach in

County Tipperary County Tipperary () is a Counties of Ireland, county in Republic of Ireland, Ireland. It is in the Provinces of Ireland, province of Munster and the Southern Region, Ireland, Southern Region. The county is named after the town of Tipperary (tow ...

, where the troops stopped for twenty days to plunder the neighbouring territories. O'Donnell visited

Holy Cross Abbey Holy Cross Abbey ''(Mainistir na Croise Naofa)'' was a Cistercian monastery in Holycross near Thurles, County Tipperary, Ireland, situated on the River Suir. It takes its name from a relic of the True Cross or Holy Rood. History A supposed f ...

Saint Andrew's Day Saint Andrew's Day, also called the Feast of Saint Andrew or Andermas, is the feast day of Andrew the Apostle. It is celebrated on 30 November, during Scotland's Winter Festival. Saint Andrew is the disciple in the New Testament who introduc ...

where he venerated its relic of the

True Cross According to Christian tradition, the True Cross is the real instrument of Jesus' crucifixion, cross on which Jesus of Nazareth was Crucifixion of Jesus, crucified. It is related by numerous historical accounts and Christian mythology, legends ...

. He also dispatched an expedition to

Ardfert Ardfert () is a village and Civil parishes in Ireland, civil parish in County Kerry, Ireland. Historically a religious centre, the economy of the locality is driven by agriculture and its position as a dormitory town, being only from Tralee. T ...

, which included his nephew Donal Oge (son of his late half-brother Donal), to recover the territory of confederacy ally Thomas Fitzmaurice. Carew attempted to intercept O'Donnell on 7 November but O'Donnell eluded him by passing through a defile in the

Slieve Felim Mountains The Slieve Felim Mountains () are a mountain range in Munster, Ireland. They cover parts of County Limerick and County Tipperary. Historically, the name "Slieve Felim" meant the whole mountainous area between Murroe, Silvermines, Borrisoleigh and ...

. O'Donnell's forces regrouped in Connelloe,

County Limerick County Limerick () is a western Counties of Ireland, county in Republic of Ireland, Ireland. It is in the Provinces of Ireland, province of Munster and is located in the Mid-West Region, Ireland, Mid-West which comprises part of the Southern Reg ...

, and finally united with Tyrone at Bandon on 15 December. Kinsale-1601-02

The Crown's army was trapped in Kinsale between the Irish and the Spaniards. It appears Tyrone and O'Donnell had previously agreed to starve out the English, but Juan del Águila urged for a prompt combined attack. Near-contemporary writers Ó Cléirigh and O'Sullivan Beare allege that O'Donnell was convinced by Juan del Águila and naively urged Tyrone to attack. This account is not unanimously accepted by historians. McGurk, Silke, McGettigan and

Cyril Falls Cyril Bentham Falls CBE (2 March 1888 – 23 April 1971) was a British military historian, journalist, and academic, noted for his works on the First World War. He was born in Ireland and spent most of his life in England. Early life Falls was ...

concur; Morgan and G. A. Hayes-McCoy disagree. O'Donnell had previously induced Tyrone into a full frontal assault during a campaign in 1598, so this narrative is not out of the question. Morgan claims that the pressure from the beleaguered Spaniards that wore down Tyrone, and that both O'Donnell and Tyrone had their reputations at stake. Whatever the cause, Tyrone uncharacteristically agreed to a combined attack on both English camps. At dawn on 24 December N.S. 3 January 1602">Old_Style_and_New_Style_dates.html" ;"title="/nowiki>Old Style and New Style dates">N.S. 3 January 16021601, Tyrone's forces of 4,000 men took their position. Mountjoy spotted the soldiers and ordered an immediate attack. Tyrone retreated but Mountjoy's cavalry charge routed the confederate soldiers; 1,200 were killed and 800 were wounded. O'Donnell and his rearguard had become lost in the heavy morning fog and were too far off to aid Tyrone. The sight of butchered Irish forces demoralised O'Donnell's soldiers, and many fled despite O'Donnell's commands to stay and fight. O'Donnell's forces were lightly engaged but Tyrone's forces suffered the greatest losses. The defeat at Kinsale was a fatal blow for the confederacy and destroyed what remained of O'Donnell's military strength. Niall Garve was left as the de facto ruler of Tyrconnell.

Travel to Spain

Meeting with Philip III

The defeated confederates gathered at

Innishannon Innishannon or Inishannon () is a large village on the main Cork (city), Cork–Bandon, County Cork, Bandon road (N71 road (Ireland), N71) in County Cork, Republic of Ireland, Ireland. Situated on the River Bandon, the village has grown d ...

. Tyrone was strongly in favour of attempting another siege, but was unable to convince O'Donnell, who was in a state of

nervous breakdown A mental disorder, also referred to as a mental illness, a mental health condition, or a psychiatric disability, is a behavioral or mental pattern that causes significant distress or impairment of personal functioning. A mental disorder is ...

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

Castlehaven Castlehaven () is a civil parish in County Cork, Ireland. It is located in West Cork, approximately 45 miles south-west of Cork City on the coast. The civil parish includes the town of Castletownshend and the hamlets of Rineen and Tragumna. Th ...

on 27 December N.S. 6 January 1602">Old_Style_and_New_Style_dates.html" ;"title="/nowiki>Old Style and New Style dates">N.S. 6 January 16021601 with General Pedro de Zubiaur. He was accompanied by Archbishop Florence Conroy, Muiris mac Donnchadh Ulltach Ó Duinnshléibhe, Maurice MacDonough Ultach, Redmond Burke, Baron Leitrim, Redmond Burke and Captain Hugh Mostian. They arrived in

Luarca Luarca (Ḷḷuarca in Asturian language, Asturian and coofficially) is a parish and the principal town in the Municipalities of Spain, municipality of Valdés, Asturias, Valdés in Asturias, Spain. Luarca (town) is a fishing and pleasure port. L ...

on 3 January N.S. 13 January">Old_Style_and_New_Style_dates.html" ;"title="/nowiki>Old Style and New Style dates">N.S. 13 Januaryafter travelling through a stormy passage. As Philip III was in the province of Province of León">Leon Leon, Léon (French) or León (Spanish) may refer to: Places Europe * León, Spain, capital city of the Province of León * Province of León, Spain * Kingdom of León, an independent state in the Iberian Peninsula from 910 to 1230 and again fro ...
at the time, the group headed to A Coruña. They were welcomed to A Coruña by Luis de Carillo, the governor of Galicia and Conde de Caracena, who was a political supporter of the confederacy's cause. He offered the group the hospitality of his seaside house. O'Donnell was also taken to sightsee the Farum Brigantium, where the legendary sons of Milesius left for Ireland. Philip III agreed to meet with O'Donnell on the recommendation of his advisors, and O'Donnell was escorted to Zamora with a dozen Irishmen to meet the Spanish king. When he arrived in the king's presence, O'Donnell knelt before him and vowed not to rise until three requests were granted: Philip III agreed and bade O'Donnell to rise. During O'Donnell's time at the Spanish court, he met with Tyrone's son Henry (also his own nephew) and was treated for a bubonic plague sore by Tyrconnell physician Nial O'Glacan. He also spent much of his time working with Archbishop Mateo de Oviedo to assemble a case against Juan del Águila. The

Spanish Council of State The Council of State (), is the supreme consultative council of the Spanish Government. The current Council of State was established in 1980 according to the article 107 of the Constitution of 1978. The institution of the Council of State, under ...

reported to the King that " 'Donnell'szeal and loyalty should be highly praised... He should be assured that His Majesty regards the Irish Catholics as his subjects." Philip III granted O'Donnell a generous pension and ordered him to return to A Coruña to supervise the planned naval reinforcements.

Cancelled naval expedition

O'Donnell returned to A Coruña on 16 February N.S. 26 February">Old_Style_and_New_Style_dates.html" ;"title="nowiki/>Old Style and New Style dates">N.S. 26 February by which time he received news of Juan del Águila's surrender, which was not unexpected. O'Donnell wrote to the King two days later, begging him to focus his attention on sending the discussed naval expedition to Ireland. Although O'Donnell would have been content with a small-scale expedition sent to Tyrconnell, Philip III wanted to send a large fleet—three times the size of the 4th Armada—to ensure military success and restore his damaged reputation. Due to the time it would take to assemble a force of this size, O'Donnell was left anxiously waiting in Spain. Meanwhile, the confederacy disintegrated as English forces travelled across Ulster destroying crops and livestock. In June 1602 Tyrone burned Dungannon and retreated into Glenconkeyne">Burning of Dungannon">burned Dungannon and retreated into Glenconkeyne. O'Donnell kept in contact with Ireland during this time—he wrote to one confederate "if there is anything bad it may be concealed from the Spaniard, but not from me". Throughout 1602 O'Donnell was placated with promises that the Spanish fleet was being gradually assembled. He insistently asked to return to court to discuss the military situation. In March, O'Donnell was alarmed by the Duke of Lerma's suggestion that O'Donnell could be sent back to Ireland with only one ship and 50,000 ducats. On 10 June N.S. 20 June">Old Style and New Style dates">N.S. 20 JuneO'Donnell wrote to Philip III: "I am weary of seeing how I am wasting my time here, and I fear that things are going on badly at home". By July it became clear that, due to delays, the envisioned fleet would not be ready until the next year. On 23 July N.S. 2 August">Old_Style_and_New_Style_dates.html" ;"title="/nowiki>Old Style and New Style dates">N.S. 2 August the ships already prepared at A Coruña were sent to the New World on unrelated missions. O'Donnell's companions reported that he was gripped "by an extreme melancholia and disgust which took hold of him when buoyed up by hope as a result of the promises and letters he had received... he saw the whole panisharmy suddenly diverted... without even a mention being made of Ireland". Philip III permitted O'Donnell to meet with him, and O'Donnell left A Coruña on 26 July N.S. 5 August">Old_Style_and_New_Style_dates.html" ;"title="/nowiki>Old Style and New Style dates">N.S. 5 Augustto go to Simancas.

Death and burial

O'Donnell arrived at the Castle of Simancas on around 31 July N.S. 10 August">Old_Style_and_New_Style_dates.html" ;"title="/nowiki>Old Style and New Style dates">N.S. 10 August/nowiki>. By 14 August N.S. 24 August] he was extremely ill. He was attended by Irish doctor John Noonan; the guilty king also sent his own physician, Álvarez, to the castle. O'Donnell was aware he was dying, and indicated that he was "fearful of death, as is natural to my creaturely condition". He received the

last rites The last rites, also known as the Commendation of the Dying, are the last prayers and ministrations given to an individual of Christian faith, when possible, shortly before death. The Commendation of the Dying is practiced in liturgical Chri ...

and was attended by Archbishop Conroy and two Franciscans, Maurice MacDonough Ultach and Maurice MacSean Ultach. O'Donnell made his will on 28 August N.S. 7 September">Old_Style_and_New_Style_dates.html" ;"title="/nowiki>Old Style and New Style dates">N.S. 7 September/nowiki>, whilst on his deathbed. He dictated his will in Irish, but Conroy translated it into Castilian Spanish for the notary. O'Donnell was in an extremely weak physical condition and could only blot the page when attempting to sign his signature. He warned against news of his death reaching Ireland before Spanish reinforcements arrived, as he believed the news would demotivate the confederacy and lead to a peace treaty with England. O'Donnell was content to be a vassal of the Spanish king if the Gaelic chiefs could keep their power over Ireland, which would effectively make Ireland a Spanish colony. O'Donnell bequeathed "all isestates, lands, lordships and vassals" to his younger brother Rory. After over two weeks of bedridden suffering, Hugh Roe O'Donnell died at the Castle of Simancas on 30 August N.S. 9 September">Old_Style_and_New_Style_dates.html" ;"title="/nowiki>Old Style and New Style dates">N.S. 9 September/nowiki> 1602. He was 29 years of age, and left no children. The same evening, his body was taken to

in a four-wheeled hearse "with blazing torches and bright flambeaux of beautiful waxlights blazing all round on each side of it". The elaborate procession was attended by Philip III, state officers and council members. His funeral rites were performed in Valladolid on the morning of 1 September N.S. 11 September]. Per his will, O'Donnell was buried in the Convent of St. Francis, in the Chapel of Wonders.

Cause of death

A now-debunked popular legend claims that O'Donnell was poisoned by James "Spanish" Blake, James Blake, a Galway merchant hired as a spy for the government. Blake approached Lord President Carew with an offer to travel to Spain to assassinate O'Donnell. In a ciphered letter dated 28 May 1602, 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. Despite Blake's oath to Carew, on 19 August N.S. 29 August">Old_Style_and_New_Style_dates.html" ;"title="nowiki/>Old Style and New Style dates">N.S. 29 Augustat Valladolid he outlined a detailed plan to the Duke of Lerma for a Spanish expedition aimed at retaking Galway from English control. Given Blake's apparent pro-Spanish sentiments, historians Frederick M. Jones and Micheline Kerney Walsh have questioned whether he was truly an English spy, and speculate that Blake was a Spanish agent who proposed the mission as a means of securing safe passage to Spain. Another ciphered letter was sent from Carew to Mountjoy on 9 October: "O'Donnell is dead... he is ''poisoned'' by ''James Blake'', of whom your lordship hath been formerly acquainted... He never told the ''President'' in what ''manner'' he would ''kill'' him, but did assure him it ''should'' be effected". After O'Donnell's death, Blake was arrested in Valladolid on suspicion of being an English spy. Despite two months of interrogation he was never suspected of poisoning O'Donnell. None of O'Donnell's companions (nor his physicians) suspected foul play; at the time, his companions credited his anguish over the diplomatic situation with causing his early death. There is no evidence that Blake was successful in his promised assassination; when Carew heard of O'Donnell's death, he would have naturally assumed that Blake was responsible. Historians dismiss the theory that O'Donnell was poisoned. It is more likely he died of illness. Prior to his death he vomited a worm ten 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 Eucestoda, commonly referred to as tapeworms, is the larger of the two subclasses of flatworms in the class Cestoda (the other subclass being Cestodaria). Larvae have six posterior hooks on the scolex (head), in contrast to the ten-hooked Ce ...

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 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 ith the Englishthey can, bad as the consequences may be". Mountjoy sent Rory news of O'Donnell's death and stated that "the war was at an end by his death". Rory convened a council of his advisors. The faction advocating for peace prevailed, though some of Hugh Roe O'Donnell's supporters still refused to believe he was dead. In December, Rory surrendered to Mountjoy at

Athlone Athlone (; ) is a town on the border of County Roscommon and County Westmeath, Republic of Ireland, Ireland. It is located on the River Shannon near the southern shore of Lough Ree. It is the second most populous town in the Midland Region, Ir ...

. Tyrone went into hiding for several months, but eventually surrendered by signing the

on 30 March 1603, which ended the Nine Years' War. Furthermore, the Treaty of London in 1604 ended the Anglo-Spanish War. The historian John McCavitt has stated that "had 'Donnelllived... It could have changed the course of Irish history forever."

Legacy

Succession

Following their surrender, Tyrone and Rory were confirmed in their titles and core estates by King

James I James I may refer to: People *James I of Aragon (1208–1276) * James I of Sicily or James II of Aragon (1267–1327) * James I, Count of La Marche (1319–1362), Count of Ponthieu * James I, Count of Urgell (1321–1347) *James I of Cyprus (1334� ...

. Rory was created hereditary

Earl of Tyrconnell Earl of Tyrconnell is a title that has been created four times in the Peerage of Ireland. It was first created in 1603, for Rory O'Donnell, 1st Earl of Tyrconnell, formerly king of Tyrconnell, along with the subsidiary title Baron Donegal. The 1 ...

and granted most of Tyrconnell's lands, which greatly incensed Niall Garve. Per the terms of his surrender, Rory was required to give up his Gaelic titles and thus was not traditionally inaugurated as the O'Donnell clan chief. Niall Garve had himself inaugurated as clan chief in Kilmacrennan. Hugh Roe O'Donnell was the last undisputed chief of the O'Donnell clan. Rory died of illness in 1608, and the following year Niall Garve (along with his son Naghtan) was imprisoned in the

Tower of London The Tower of London, officially His Majesty's Royal Palace and Fortress of the Tower of London, is a historic citadel and castle on the north bank of the River Thames in central London, England. It lies within the London Borough of Tower Hamle ...

for life for his role in O'Doherty's rebellion. Rory had only one son, Hugh Albert, Baron of Donegal, who spent most of his life in

continental Europe Continental Europe or mainland Europe is the contiguous mainland of Europe, excluding its surrounding islands. It can also be referred to ambiguously as the European continent, – which can conversely mean the whole of Europe – and, by som ...

and 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 Castlebar () is the county town of County Mayo, Ireland. Developing around a 13th-century castle of the de Barry family, from which the town got its name, the town now acts as a social and economic focal point for the surrounding hinterland. Wi ...

, as well as in Spain and

Austria Austria, formally the Republic of Austria, is a landlocked country in Central Europe, lying in the Eastern Alps. It is a federation of nine Federal states of Austria, states, of which the capital Vienna is the List of largest cities in Aust ...

Historiography

''Beatha Aodh Ruadh Ó Domhnaill''

Hugh Roe O'Donnell was highly praised by seventeenth-century Irish chroniclers, such as Philip O'Sullivan Beare and the Four Masters, as well as in

Irish bardic poetry Bardic poetry is the writings produced by a class of poets trained in the bardic schools of Ireland and the Gaelic parts of Scotland, as they existed down to about the middle of the 17th century or, in Scotland, the early 18th century. Most of t ...

. Most notably, the Classical Gaelic biography ''Beatha Aodh Ruadh Ó Domhnaill'' ('), written between 1616 and 1627 by

, 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. Ó Cléirigh was motivated to write the biography when Spanish interest in Ireland was renewed during the Anglo-Spanish War (1625–1630), Anglo-Spanish War (1625-1630). Ó Cléirigh places O'Donnell at the forefront of the confederacy with the hope that another O'Donnell clansman would retake Ireland.. Ó Cléirigh lionises O'Donnell; he claims that Hugh McHugh Dubh submitted willingly to Hugh Roe, when it reality it took O'Donnell beheading followers to obtain a submission. ''Beatha'' is written in a deliberately archaic style which further venerates O'Donnell. It was typical for Irish scribes to take liberties to gratify their patrons. They frequently omitted details which would be disagreeable to their patrons or scandalous to the Church. As a result, ''Beatha'' has distorted historical interpretation. According to Paul Walsh, "O'Neill, if not eliminated, is certainly reduced in stature... if one were to read only the Life, [one could say] that O'Donnell and O'Neill were of equal importance". ''Beatha'' "is an immense panegyric of a young chief who had just expired in a foreign land, and it cannot be expected to be quite impartial, especially when dealing with Red Hugh's enemies." Ó Cléirigh's portrayal of Niall Garve would have been particularly biased. It is possible that Ó Cléirigh attended O'Donnell's inauguration and participated in O'Donnell's expeditions, and he may have kept notes. His description of O'Donnell's last days and funeral is based on the recollections of the two friars both named Maurice Ultach. Sections of the ''Annals of the Four Masters'' which pertained to O'Donnell's life were adapted from ''Beatha''.

Gaelic Revival

The dramatic content of O'Donnell's short life, which includes his escape from prison and his early overseas death, has "enabled much mythologising of his life and character". He is considered an archetypal hero whose personal struggles against Tudor England served as an allegory to represent Ireland's incarceration, escape from British rule in Ireland, 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

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, counter-reformation Irish dynast living in the world of The Prince, Machiavelli's ''Prince'' rather than the Táin Bó Cúailnge, cattle-raid of Cooley".

Commemoration

Ballyshannon Castle, Hugh Roe O'Donnell's key residence, was demolished in 1720.

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

. Since 1954 (and as an official event since 2006), O'Donnell and Art MacShane's escape is commemorated each January in the Art O'Neill Challenge, an ultramarathon endurance event in which participants retrace the same 55km journey from Dublin to Glenmalure on foot. A sculpture by Maurice Harron, titled ''The Gaelic Chieftain'', was unveiled in 1999 near Boyle. Overlooking the N4 road (Ireland), N4, the sculpture depicts O'Donnell on horseback and commemorates his victory at the battle of Curlew Pass. O'Donnell's will became lost for a period, but in 1983 it was discovered by Donegal priest John J. Silke in the archives of Simancas. In 1991, a commemorative plaque was erected at the Castle of Simancas. As of 2023, plans are afoot to erect statues of O'Donnell in both Lifford and Simancas. It has also been proposed that the two towns be Twinned cities, twinned. The proposed twinning was passed by the Donegal County Council in March 2024, and as of April is yet to be validated by Simancas. Following an unsuccessful dig for O'Donnell's remains, Valladolid has Historical reenactment, reenacted O'Donnell's

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 procession.

Search for remains

The Convent of St. Francis was later secularised and O'Donnell's body was disinterred; its current location is unknown. The Chapel of Wonders was sold and destroyed in 1836 during a wave of monastic expropriations, and its exact location was lost. In 2019, Donegal man and retired soldier Brendan Rohan visited Valladolid and persuaded city authorities to conduct a dig for O'Donnell's grave. The following year, a week-long excavation of Valladolid's Constitution Street revealed the walls of what was believed to be the Chapel of Wonders underneath a four-storey building. On 22 May 2020, archaeologists began a dig inside the chapel's remains. A number of modern descendants of O'Donnell's kin were "lined up for DNA tests" to confirm O'Donnell's identity if his remains were found. There was call for repatriation of O'Donnell's remains if discovered, even though O'Donnell himself asked to be buried in the Convent of St. Francis in his will. It was hoped his skeleton would be easy to identify due to his two missing big toes. However many of the skeletons discovered were in a state of decay and did not have any existing feet. Eventually twenty skeletons were discovered during the dig, though DNA testing showed they were from an earlier period. The site has been used for burials for hundreds of years, making O'Donnell's discovery near-impossible. In March 2021, archaeologists believed the Chapel of Wonders extended further beneath the dig site, and went into negotiations to resume the excavation. The search ended in October 2021. By September 2022, McCavitt had come across an inscription on an early 17th-century tombstone about O'Donnell. According to McCavitt, if O'Donnell's burial place still exists, it would have been marked by such a gravestone. As of 2024, O'Donnell's grave has not been discovered, though the media attention garnered by the dig has promoted Ireland–Spain relations, Hispano-Irish relations. The dig was spearheaded by the local Hispanic-Irish Association. As of October 2023, the investigation is not closed. If discovered intact, O'Donnell's remains may provide insight into his health, nutrition and diet. Tests may also determine his specific cause of death.

Character

Personality

Described as "fiery and flamboyant", Hugh Roe O'Donnell was a highly charismatic individual. 17th-century sources opined on his great powers of command, and stated that the look of amiability on his face captivated onlookers. He also had an aggressive and bellicose personality and could not always control his impulses. As Edward Alfred D'Alton put it, "the ordinary Irish chief... boasted much, and talked much, and did little, and... heedlessly rushed into war without estimating his difficulties or his resources". In his youth, a bardic poet claimed that O'Donnell was arrogant and in need of maturity. Thomas Lee warned the government that because of O'Donnell's youth, he could become radicalised by his imprisonment. Indeed, O'Donnell's four years in prison instilled within him a profound anti-English stance which shaped his aggressive military approach. The bardic poet Maolmuire mac Con Uladh Mic an Bhaird addressed a composition to O'Donnell in 1590, urging O'Donnell to "show fortitude in his adversity", but also indicating that the period in prison would lead O'Donnell to cultivate the discipline and solemnity "appropriate to kingship". Particularly because he had not committed any offence, O'Donnell saw his imprisonment as unjust and villainising. His distrust of English people affected the 1596 peace talks, and is why he was more committed to an alliance with Spain than Tyrone was. O'Donnell's insolence was remarked on by English officials, who described him as the "firebrand of all the rebels". McGettigan notes that O'Donnell was "only anti-English on a political level", as he willingly purchased English goods and firearms for his own purposes. Jane Ohlmeyer describes O'Donnell as "a wily negotiator, an effective and pragmatic power broker, and a brave soldier".

Personal relationships

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

Partnership with Tyrone

Historians have debated on whether O'Donnell or his father-in-law held a more influential position within the confederacy in its early years. Many of Tyrone's contemporaries who knew Tyrone, such as John Perrot, considered O'Donnell to be the junior partner in the confederacy. In 1596, O'Donnell described Tyrone as his senior. In 1596, a list of the confederates drawn up by Alonso Cobos' secretary was altered to place Tyrone's name above O'Donnell's. By 1599, O'Donnell saw his partnership with Tyrone as one of two equals, as evident from their treaty of equality. O'Donnell and Tyrone had contrasting temperaments, which often caused disputes over military tactics. In contrast to Tyrone, who was known for bribing or elaborately bluffing his way out of trouble, O'Donnell was uncompromising and preferred military solutions over negotiations. Tyrone attempted to restrain O'Donnell from openly attacking English forces in the early stages of the war. O'Donnell's absence from the Battle of Beleek (per Tyrone's request) suggests that Tyrone had a level of control over his son-in-law. English Privy Councillor Geoffrey Fenton stated that Tyrone could "command and rule" O'Donnell at will. That being said, Canny and Silke suggest that Tyrone's failure to manage O'Donnell led to the former's decision to reluctantly go into open rebellion. By 1596, the pair had developed a sophisticated double-act as O'Donnell played the "bad cop" to Tyrone's "good cop" during their negotiations with the government. They used the absence of one of them to delay and stall further negotiations. Spanish emissaries noted that the pair "acted like one man and were respected by the rest". Throughout the war the two leaders got on remarkably well, and O'Donnell probably learned the virtue of patience from his father-in-law. Their partnership was under heavy strain by the war's end, and it is possible that their differences in temperament led to the disastrous failure at Kinsale. O'Donnell warned against Tyrone violating their agreements after his death: "in case the Earl O'Neill (though I know and believe he will not do so) should wish to violate the agreement and settlements arranged and made between him and me and our heirs, I hereby beg his Majesty to uphold my brother [Rory] in his rights and to retain him in his service". The age difference between the two men may have been a source of conflict; Tyrone was O'Donnell's senior by 22 years. Unlike Tyrone, who was raised in the Pale and had received generous assistance from the government during his early years in Ulster, O'Donnell had a traditional Gaelic upbringing and associated the government with his time in captivity.

Generalship

Tyrone and O'Donnell's military approaches were representative of their personalities. Tyrone typically won out in arguments over military strategy, though not always. Donnelly and Lucius Emerson argued that O'Donnell's success early in the war indicate a leader wise beyond his years. Donnelly stated that "any statement of Red Hugh which seeks to imply that a dynamic temperament was not under control of a keen and realistic mind, is a superficial one. Within eighteen months, young and totally inexperienced, he had radically changed the situation in West Ulster; what he effected could only have been accomplished by a highly disciplined man with balanced judgment". O'Donnell's notes on the Battle of Moyry Pass show that he could develop complex battle plans, as he stated that it was better to attack Mountjoy's forces when they were deep in Irish territory, away from reinforcements, and in poor weather. McGettigan praises O'Donnell's leadership abilities and vision, but McCavitt notes that his failure to foresee Niall Garve's betrayal displays clear flaws in his foresight. The pitfalls of O'Donnell's aggressive approach are evident—he lost over 100 confederate soldiers in an ill-fated 1598 assault on the Blackwater Fort, and his poor foresight may have led to the defeat at Kinsale. Morgan states that credit for the victory at Curlew Pass should go to O'Rourke and McDermot rather than O'Donnell. He describes O'Donnell as a "gung-ho leader" whose military successes were limited.

Physical appearance

There are no surviving portraits or visual representations of Hugh Roe O'Donnell made in his lifetime. Donagh O'Mooney described him as "above middle height, strong, handsome, well-built and of pleasing appearance". He presumably had red hair, "Roe, i.e., Ruadh, from the colour of his complexion or hair."; as adjectives such as ''ruadh'' (Irish for ''red'') were commonly employed in Irish names to refer to hair colour. This epithet would have differentiated him from kinsmen also named "Hugh O'Donnell". After losing his big toes to frostbite, Hugh Roe O'Donnell would have hobbled around or travelled on horseback for the rest of his life. If discovered intact, O'Donnell's skeleton would reveal his stature and height, and technology might allow researchers to recreate his facial features. Although O'Donnell was fiercely patriotic, he had no aversion to foreign dress. He was described in 1601 as wearing English clothing and even going to mass in a "fine English gown". Historian Francis Martin O'Donnell suggests that Hugh Roe O'Donnell dressed in Spanish clothing, as his grandfather Manus was known for preferring continental fashion over traditional Gaelic clothing.

Ancestry

In popular culture

Poetry

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

Music

* ''Róisín Dubh (song), Róisín Dubh'', which is one of Ireland's most popular political songs, is addressed in O'Donnell's voice to his wife

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

Novels

Novels based on O'Donnell's life (particularly centred on his escape from Dublin Castle) include: * ''O'Donel of Destiny'' (1939) by Mary Kiely * ''Red Hugh, Prince of Donegal'' (1957) by Robert T Reilly * ''Red Hugh: The Kidnap of Hugh O'Donnell'' (1999) by Deborah Lisson

Film

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

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 (play), Making History'', which focuses on Tyrone reckoning with his own legacy. According to historian Jane Ohlmeyer, "Friel portrayed the youthful Red Hugh as fiery, headstrong, quick-witted, passionate, committed to Catholicism, and to the preservation of the values, language, and culture of the Gaelic world into which he had been born and reared." In its original production by Field Day Theatre Company, Field Day, O'Donnell was played by Peter Gowen.

Other

* Several Gaelic sports clubs in County Donegal are named after Red Hugh O'Donnell, such as Aodh Ruadh CLG in

and Red Hughs Gaelic Athletic Association, GAA Club in Killygordon.

Notes

References

Citations

Primary sources

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Secondary sources

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External links

The Life of Aodh Ruadh Ó Domhnaill, transcribed from the Book of Lughaidh Ó Clérigh

The O'Donnell Coat of Arms and Family History
{{DEFAULTSORT:O'Donnell, Hugh Roe 1572 births 1602 deaths 16th-century Irish people 17th-century Irish people 16th-century Roman Catholics 17th-century Roman Catholics Irish chiefs of the name Irish escapees Irish people of Scottish descent Irish rebels Irish Roman Catholics Irish Servants of God Kings of Tír Chonaill O'Donnell dynasty, Hugh People of Elizabethan Ireland People of the Nine Years' War (Ireland) 16th-century Irish nobility

Early life

Family background

Education and fosterage

Rise to prominence

Imprisonment and escape

Capture at Rathmullan

Imprisonment

Chaos in Tyrconnell

First escape attempt

Second escape attempt

Accession as clan chief

Return to Ulster

Attack on English occupation

Inauguration

Rise in power

Initial rebellion

Conference of bishops

Maguire's revolt

Secret rebellion

Open rebellion

Expansion into Connacht

Peace talks

Negotiations with the Crown

Relations with Spain

Renewal of hostilities

Clifford's presidency

Battle of the Yellow Ford

Battle of Curlew Pass

Quarrels with Tyrone

Forced from Tyrconnell

Defection of Niall Garve

Battle of Lifford

Political alliances collapse

Siege of Donegal

Siege of Kinsale

Travel to Spain

Meeting with Philip III

Cancelled naval expedition

Death and burial

Cause of death

End of the Nine Years' War

Legacy

Succession

Historiography

''Beatha Aodh Ruadh Ó Domhnaill''

Gaelic Revival

Modern reappraisal

Commemoration

Search for remains

Character

Personality

Personal relationships

Partnership with Tyrone

Generalship

Physical appearance

Ancestry

In popular culture

Poetry

Music

Novels

Film

Theatre

Other

Notes

References

Citations

Primary sources

Secondary sources

Further reading

Primary sources

Secondary sources

See also

External links