Sir Niall Garbh O'Donnell (; – 1626) was an Irish nobleman and soldier who alternately rebelled against and supported English rule in Ireland. During the Nine Years' War he defected from the Irish confederacy and sided with the Crown against his cousin Hugh Roe O'Donnell, with the aim of restoring the lordship of Tyrconnell to his own branch of the O'Donnell clan.

Although Niall's paternal grandfather Calvagh ruled Tyrconnell, in 1557 the lordship was seized by Niall's half-uncle Hugh McManus O'Donnell. Following a violent succession conflict, Hugh McManus's son Hugh Roe—Niall's younger cousin—succeeded to the lordship in 1592. A long lasting bitterness ensued between the two cousins.

Niall initially fought for Hugh Roe and the Irish confederacy, but in 1600 he entered secret negotiations with English commander Henry Docwra. The government hoped to harness Niall's feud against Hugh Roe and promised him the lordship of Tyrconnell for his military assistance. Niall defected in October bringing many followers with him. Niall's skills in guerrilla warfare emboldened the royal troops and allowed Docwra to significantly weaken Irish forces in Ulster. However, Niall's desire to rule Tyrconnell as a sovereign entity was incompatible with the Plantation of Ulster, and after the war ended, the majority of Tyrconnell's land was granted back to Hugh Roe's immediate family.

Niall was inaugurated as the O'Donnell clan chief in April 1603. Following years of land rights disputes, he turned against the Crown in 1608. He covertly instigated fellow spurned loyalist Cahir O'Doherty to launch a rebellion in Derry, but he was quickly implicated and put on trial for treason. Faced with a sympathetic jury that would almost certainly acquit, the government sent Niall to the Tower of London in 1609, where he remained until his death seventeen years later.

Early life (1569–1586) Niall Garbh O'Donnell was born into the O'Donnell clan, the ruling Gaelic Irish noble family of Tyrconnell. He was the fourth son of Conn O'Donnell, head of the O'Donnells' MacCalvagh branch, and Rose O'Neill, daughter of O'Neill clan chief Shane O'Neill. Niall's brothers included Naghtan, Calvagh Oge, Manus, Hugh Boye, Conn Oge, Donal, and Cathbharr. His sisters were Róise, Elizabeth, Siobhan and Máire.

Niall's sobriquet "Garbh" meant "rough". According to historian Paul Walsh, this epithet was traditional with O'Donnell clansmen named Niall, and has no special significance in his case; his ancestor, who ruled Tyrconnell from 1422 to 1439, was also named Niall Garbh. As a child, Niall was fostered to the MacLeans of Scotland's Western Isles.

Niall's paternal grandfather, Calvagh O'Donnell, ruled Tyrconnell in the mid-1560s. In 1557, Calvagh's half-brother Hugh McManus turned against the family.The Editors of Encyclopaedia Britannica (29 March 2024). "Hugh O'Donnell". Encyclopedia Britannica. Archived from the original on 1 July 2024. His allies imprisoned Conn, Calvagh's son and tanist. When Calvagh died in 1566, Hugh McManus easily established himself as the new Lord of Tyrconnell.. "Calvagh, however, died in the same year, and as his son Conn was a prisoner in the hands of Shane O'Neill, his half-brother Hugh MacManus was inaugurated The O'Donnell in his place. Hugh, who in the family feud with Calvagh had allied himself with O'Neill..." Conn and his descendants, particularly Niall, looked to the English-led Irish government as a means of restoring their branch of the family to power. This branch established themselves in Lifford, between the River Finn and Lough Swilly, and were constantly at odds with the ruling O'Donnells. The MacCalvagh family estate, which Niall inherited, totalled 12,900 acres of land and included Finn Castle (now Castlefin), where he was probably born. His father Conn died in March 1583; his mother Rose died in 1585.

Succession dispute (1587–1593)

In 1587, Hugh McManus's son and tanist Hugh Roe O'Donnell was kidnapped on the orders of the Lord Deputy and imprisoned in Dublin Castle. Hugh McManus became prematurely senile, and a long-running succession dispute broke out within the greater O'Donnell family over who would succeed him. Three of Niall's brothers died during the conflict: Naghtan in 1582, Calvagh Oge in 1588, and Manus in 1589.

Hugh McManus's Scottish wife Iníon Dubh effectively took over leadership of Tyrconnell and used her Scottish redshanks to eliminate rival claimants and defend Hugh Roe's claim to the chieftaincy. On her orders, her redshanks killed Calvagh's son Hugh MacEdegany in May 1588. After Hugh MacEdegany's death, Niall took over as the head of the MacCalvagh faction. Niall had a significant following within Tyrconnell, but he was apparently not powerful enough to provoke an assault from Iníon Dubh.

Niall was supported by his neighbour Turlough Luineach O'Neill of Tír Eoghain, who had succeeded Niall's maternal grandfather Shane as O'Neill clan chief. In turn, Niall supported Turlough in attacks against the latter's rival Hugh O'Neill, Earl of Tyrone, who had formed an alliance with the ruling O'Donnell branch. On 1 May 1589, Niall fought alongside Turlough and defeated Tyrone in battle.

Royal forces took advantage of the clan's internal conflict and began pillaging and raiding across Tyrconnell. At one point Hugh McManus was kidnapped by Captain John Connill, but he was rescued by Niall. Despite the continued looting by government troops, Tyrconnell's nobility remained obsessed with their succession conflict. Iníon Dubh temporarily bought off Niall with a political marriage to her daughter Nuala, his first cousin once-removed, in an attempt to temper his hostility. Niall used his marriage to ingratiate himself with the ruling O'Donnell branch, and by 1592, he was in a strong position to claim Tyrconnell's lordship.

Hugh Roe escaped prison and returned to Tyrconnell in early 1592; Tyrone bribed officials in Dublin to secure his release. Hugh McManus abdicated in favour of Hugh Roe, who was inaugurated as clan chief on 23 April 1592. Niall was incensed at his cousin's successful assertion of the lordship. He was conspicuously absent from the inauguration ceremony, and was instead in Dublin unsuccessfully attempting to secure support from the government.

Soon after Hugh Roe's inauguration, Hugh Roe and Tyrone attacked Turlough, forcing him to surrender in May 1593. In July 1592, Lord Deputy William FitzWilliam agreed to conditionally overlook Hugh Roe's anti-royalist activities, one condition being that Hugh Roe's rivals be treated fairly. Despite his promise to FitzWilliam, Hugh Roe quickly subjugated his rivals. A significant claimant, Hugh Dubh O'Donnell, submitted to Hugh Roe after many of his followers were beheaded. These beheadings intimidated Niall to submit to Hugh Roe "wholly through fear... by the point and edge of the sword". Niall was forced to turn over control of Lifford's castle, though his ambitions to seize the lordship remained.

Irish confederacy (1593–1599) Niall fought for the Irish confederacy, which was led by Hugh Roe and Tyrone, during the early years of the Nine Years' War. Hugh Roe sent him to assist commander Hugh Maguire in 1592. On Hugh Roe's orders, he commanded 60 horsemen, 60 swordsmen and 100 gallowglass to the Battle of Belleek in October 1593. This was one of the first major battles of the war but was secretly planned to result in an Irish failure. This would divert English attention away from Ireland and make the Irish confederacy seem weaker than it actually was. As part of the plan, Hugh Roe was ordered by Tyrone not to send reinforcements. Historian James O'Neill has theorised that Hugh Roe intentionally dispatched Niall to Belleek with the hope that he would die in the slaughter, thus easily eliminating a potential enemy.

Niall's continued belligerence led him to be detained in February 1594. He was only released when he gave one of his brothers to Hugh Roe as a pledge of good behaviour. In late 1597, Niall told two of Hugh Roe's enemies, imprisoned in Donegal, that he would join the English if their forces were sent there. In 1597 and 1598, Hugh Roe sent Niall on military expeditions into Connacht. From at least 1598, Tyrone had his doubts about the sincerity of Niall's loyalty. Hugh Roe was seemingly more trusting of Niall, as he left him in charge of the siege of Collooney castle in July 1599. Niall presumably fought at the Battle of Curlew Pass in August 1599.

Defection (1600–1602)

Arrival of Henry Docwra In May 1600, royal commander Henry Docwra established an English garrison in Derry. The government believed that the divisions within the major Irish clans could be exploited in order to win Gaelic support for the Crown. The prospects of Docwra's mission counted on luring disaffected confederates. Niall had already made overtures to the government, and Docwra had instructions to win him over. They began secretly communicating. By August, Niall had sent through his list of demands, the principal of which was to rule Tyrconnell like his grandfather Calvagh. Docwra promised to obtain Niall a royal grant of Tyrconnell if he served against his cousin.

In September, Hugh Roe left Ulster for a raid in Thomond, entrusting Niall to besiege Derry. While Hugh Roe was in Ballymote, Niall and his followers murdered Niall's uncle Neachtan in a drunken rage. Neachtan was "a man of great authority with [Hugh Roe] and all his country". Fearing Hugh Roe's revenge, Niall—alongside his three brothers and about 100 soldiers—quickly defected to the English. They joined Docwra on 3 October. Hugh Roe's supporters were aware of Niall's communication with Docwra, which forced Niall into leaving for Derry before he was fully ready. He brought over 200 men with him to Docwra, but would have brought more if not for the shortness of time. His brothers Hugh Boy, Conn Oge and Donal defected with him.

Niall was one of many disgruntled Gaelic Irish noblemen who defected on Docwra's promises, including Arthur O'Neill, Sean O'Doherty and Cahir O'Doherty.

Battle of Lifford Accompanied by royal forces, Niall marched to Lifford's castle, which had been left in the control of Hugh Roe's tanist and younger brother Rory. The Crown loyalists successfully stormed Lifford on 9 October. Hugh Roe was shocked at Niall's betrayal and rushed back to Ulster. The confederates tried in vain to retake Lifford from Niall, with minor skirmishes occurring around the castle. Hugh Roe lost about 20 men on 17 October.

The siege climaxed in the Battle of Lifford on 24 October, when Hugh Roe attacked the castle. Niall retaliated by leading a cavalry charge of mixed Irish and English forces out to battle. During the battle, Niall fatally wounded Hugh Roe's younger brother Manus in the shoulder. Rory and Niall subsequently engaged in single combat against each other, though both men survived the battle. Docwra was pleased that the feud between Niall and Hugh Roe had been exacerbated, as it pushed Niall further into opposition with the confederacy. He wrote: "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) [Hugh Roe]'s second brother, and there have passed beside many arguments of extreme and irreconcible hatred between them." By December 1600, Hugh Roe had put a price of £300 on Niall's head. Apparently Niall later made efforts to return to the Irish confederacy, but this was obviously difficult due to his murder of Manus.

From Lifford, Niall and his brothers made several raids into Tír Eoghain, and captured Newtown from the O'Neills. Men, women and children were killed, and 500 cows were pillaged and taken back to Lifford.

Partnership with royal forces