Hugh Roe O'Donnell

Hugh Roe O'Donnell II also known as Red Hugh O'Donnell, was an Irish clan chief and leader of the confederacy of Irish lords during the Nine Years' War (1593–1603).

He was born into the powerful O'Donnell clan of Tyrconnell (present-day County Donegal). By the age of fourteen, he was recognised as his clan's tanist (heir) and engaged to the daughter of prominent lord Hugh O'Neill, Earl of Tyrone. The English-led Irish government feared this alliance would threaten their control over Ulster, so Lord Deputy John Perrot had O'Donnell kidnapped by wine merchants at Rathmullan in 1587. After four years' imprisonment in Dublin Castle, O'Donnell escaped in December 1591 with the help of Tyrone's bribery, and was subsequently inaugurated as clan chief at Kilmacrennan on 23 April 1592.

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

After a crushing defeat at the Siege of Kinsale, O'Donnell travelled to Habsburg Spain to acquire reinforcements from King Philip III. The promised reinforcements 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. O'Donnell's premature death disheartened an already withering Irish resistance; Tyrone ended the Nine Years' War in 1603 with the Treaty of Mellifont.

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

Early life

Family background

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

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

Hugh Roe O'Donnell's father, Hugh McManus, had ruled as clan chief and Lord of Tyrconnell since 1566. In 1569, Hugh McManus married Iníon Dubh of Clan MacDonald of Dunnyveg, as part of a marriage alliance which gave the O'Donnell clan access to the formidable Scottish mercenary forces known as Redshanks. Iníon Dubh pushed the O'Donnell clan further into opposition with the English, and in 1574 the clan established an alliance with the ascendant O'Neill clansman Hugh O'Neill (future Earl of Tyrone) through his marriage to Siobhán.

Education and fosterage

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

Children of the Gaelic Irish nobility were traditionally fostered to fellow clans in the hopes of developing political alliances. Hugh Roe O'Donnell was fostered by four families of differing political alignments: Clans Sweeney na dTuath and O'Cahan, as well as two rival O'Donnell branches led by Hugh McHugh Dubh O'Donnell and Conn O'Donnell. Conn's father Calvagh was a prior ruler of Tyrconnell, and Hugh Roe was removed from his care when he turned against Hugh McManus in 1581. Conn died two years later and Hugh Roe's succession seemed assured. Nevertheless, Conn's sons, particularly Niall Garbh, 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, who gave him much independence.

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

O'Donnell saw his first military action in 1584 along with his father's chief advisor Eoin O'Gallagher against Clan O'Rourke of West Breifne. Even before reaching the age of fifteen, O'Donnell had become well known across Ireland. Some of his contemporaries came to associate him with Aodh Eangach, a prophesised 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, O'Donnell was betrothed to the Earl of Tyrone's daughter Rose. In addition to Tyrone's earlier marriage to Siobhán, this betrothal further cemented a growing alliance between two clans who had been mortal enemies for centuries. As tanist (heir) of the O'Donnell clan, Hugh Roe O'Donnell was widely considered to be his father's most likely successor. Tyrone described him as "the stay that his father had for the quieting of his inhabitance".

Imprisonment and escape

Capture at Rathmullan

The English government feared the emergence of a powerful O'Neill-O'Donnell alliance, cemented by O'Donnell's marriage to Rose, that 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. O'Donnell's father had also failed to pay his promised annual rents, and hostages were often kept for policy reasons. Ultimately the government decided that O'Donnell must not be allowed to succeed as clan chief. In May 1587, Lord Deputy John Perrot proposed to Lord Burghley that he could capture O'Donnell or his parents by sending a boat with wines.

thumb|Lord Deputy [[John Perrot authorised O'Donnell's kidnapping.|alt=A color portrait of a middle-aged man in early modern English costume]]In September, Hugh McManus was summoned to a conference with Perrot. Meanwhile the ship Matthew, captained by Dublin merchant Nicholas Barnes, was dispatched to Rathmullan on Lough Swilly, where fourteen-year-old Hugh Roe O'Donnell was sojourning with his foster-father MacSweeney na dTuath. Hostages were offered in O'Donnell's stead to no avail.

Imprisonment

O'Donnell arrived in Dublin on 25 September; Queen Elizabeth I was informed the next day. The four hostages were imprisoned in Dublin Castle, most likely in one of the gate towers. Within three months, Tyrone was lobbying the Queen for O'Donnell's release. In 1588, he offered a bribe of £1000 to William FitzWilliam, Perrot's successor as Lord Deputy, plus £300 to newly-appointed officials. Tyrone was later accused of offering a further £1000 to Dublin Castle's constable. In spring 1588, Iníon Dubh offered Perrot a bribe of £2000 plus sureties and hostages for her son's release. After the Spanish Armada's September 1588 shipwreck in Inishowen, Hugh McManus unsuccessfully offered the government thirty captured Spanish officers in exchange for his son. In 1590, FitzWilliam indicated a willingness to release O'Donnell, but this came to naught.

During his time in Dublin Castle, O'Donnell had little interaction with the outside world beyond conversations with fellow political prisoners, particularly the Anglo-Irish Munster lords imprisoned during the Desmond Rebellions. Witnessing first-hand the brutality inflicted by the Dublin government on Irish rebels, he became embittered and distrustful of English authority. Ironically, O'Donnell learnt English during his imprisonment, though commissioners reported in March 1593 he "could hardly speak it". This period in Dublin is seen as the defining event of his short life.

O'Donnell's imprisonment, coupled with his father's premature senility, exacerbated a long-running succession dispute which had consumed Tyrconnell since October 1580. Iníon Dubh effectively took over Tyrconnell and ruled in her husband's name, pushing for O'Donnell's succession by spreading the Aodh Eangach prophecy. On her orders, her redshanks killed challengers Hugh MacEdegany and Donal O'Donnell in 1588 and 1590 respectively. She also bought off Niall Garbh with a political marriage to her daughter Nuala in an effort to temper his hostility. Further disruptions developed as the government appointed various administrators who pillaged Tyrconnell, such as William Mostian, John Connill and Humphrey Willis. In 1594, O'Donnell estimated Tyrconnell had suffered £20,000 worth of damages (equivalent to £5,500,000 in May 2025). This chaos created mass resentment towards the English government, even from the typically pro-English portion of the population.

First escape attempt

thumb|O'Donnell was imprisoned in [[Dublin Castle's Bermingham Tower.|alt=A color photograph of a cylindrical stone tower painted blue]]

O'Donnell made his first escape attempt in January 1591 with a number of companions.