Hugh O'Neill, Earl of Tyrone

Hugh O'Neill Aodh Ó Néill
Hugh O'Neill, part of a fresco in the Vatican (see Portraits)
An Ó Néill, King of Tír Eoghain
Reign	1595–1616
Predecessor	Turlough Luineach O'Neill
Successor	Title Dormant
Earl of Tyrone
Reign	1585–1613
Predecessor	Conn Bacagh O'Neill, 1st Earl of Tyrone
Successor	Title attainted in 1613[a]
3rd Baron Dungannon
Reign	1562–1587
Predecessor	Brian O'Neill, 2nd Baron Dungannon
Successor	Hugh O'Neill, 4th Baron Dungannon
Born	c. 1550[b] Oneilland, Tír Eoghain, Ireland (present-day County Armagh)
Died	20 July 1616 (aged about 66) Rome, Papal States
Burial	21 July 1616[4] San Pietro in Montorio, Rome
Spouse	Katherine/Feodora O'Neill ​ ​ (m. 1569; div. 1574)​ Siobhán O'Donnell ​ ​ (m. 1574; died 1591)​ Mabel Bagenal ​ ​ (m. 1591; died 1595)​ Catherine Magennis ​ ​ (m. 1597)​
Issue	Conn, Rose, Alice, Hugh, Henry, Shane, Conn Ruadh and others
House	O'Neill dynasty (MacBaron branch)
Father	Feardorcha "Matthew" O'Neill, 1st Baron Dungannon

Hugh O'Neill, Earl of Tyrone^[c] (Irish: Aodh Mór Ó Néill;^[d] c. 1550 – 20 July 1616) was a Gaelic Irish lord and key figure of the Nine Years' War. Known as the "Great Earl",^[6][7] he led the confederacy of Irish clans against the English Crown in resistance to the Tudor conquest of Ireland under Queen Elizabeth I.

He was born into the O'Neill clan, Tír Eoghain's ruling noble family, during a violent succession conflict which saw his father assassinated. At the age of eight he was relocated to the Pale where he was raised by an English family. Although the Crown hoped to mold him into a puppet ruler sympathetic to the English government, by the 1570s he had built a strong network of both British and Irish contacts which he utilised for his pursuit of political power.

Through the early 1590s, Tyrone secretly supported rebellions against the Crown's advances into Ulster whilst publicly maintaining a loyal appearance. He regularly deceived government officials via bribes and convoluted disinformation campaigns. Via his web of alliances and the heavy taxation of his subjects, he could arm and feed over 8,000 men, making him well-prepared to resist English incursions. In 1591 he caused a stir when he eloped with Mabel Bagenal, younger sister of the Marshal of the Queen's Irish Army.^[14] During the Battle of Belleek Tyrone fought alongside his brother-in-law Henry Bagenal whilst covertly commanding the very troops they were fighting against. After years of playing both sides, he finally went into open rebellion in early 1595 with an assault on the Blackwater Fort. Despite victories at the Battle of the Yellow Ford and Battle of Curlew Pass, the confederacy began to suffer upon the arrival of Lord Deputy Mountjoy and commander Henry Docwra in Ulster. Tyrone was not able to secure Spanish reinforcements until late 1601. The confederacy was decisively defeated at the Siege of Kinsale, and Tyrone surrendered to Mountjoy in 1603 with the signing of the Treaty of Mellifont.

Due to increasing hostility against Tyrone and his allies, in 1607 he made the "snap decision" to flee with his countrymen to continental Europe in what is known as the Flight of the Earls. He settled in Rome where he was granted a small pension by Pope Paul V. Despite his plans to return to and retake Ireland, he died during his exile.

In comparison to his "warlike and arrogant" ally Hugh Roe O'Donnell, Tyrone was cautious and deliberative.^[15][16] A consummate liar, he is considered an enigma to historians due to the elaborate bluffs he employed to mislead his opponents.^[17][18][19] Although wartime propaganda promoted Tyrone as a "Catholic crusader", historians believe his motivations were primarily political rather than religious - though he apparently underwent a genuine conversion around 1598. He also held the title 3rd Baron Dungannon, and in 1595 he became Chief of the Name of the O'Neill clan. He had four wives, many concubines and various children.^[1][20]

Hugh O'Neill was born c. 1550^[b] in the barony of Oneilland, Tír Eoghain (present-day northern County Armagh)—possibly in a crannog such as Marlacoo.^[21] The O'Neill dynasty were Tír Eoghain's ruling Gaelic Irish noble family,^[22][23] and claimed descent from Niall Ruadh of the Cenél nEógain, who was a descendant of legendary high king Niall of the Nine Hostages.^[24][25][26] Hugh was the second son of Feardorcha "Matthew" O'Neill, 1st Baron Dungannon (c. 1520–1558) and his wife Siobhán Maguire (died 1600).^[5][27][28] Hugh's paternal grandparents were clan chief Conn Bacagh O'Neill, 1st Earl of Tyrone (c. 1480–1559) and Alison Kelly of Dundalk, a blacksmith's wife.^[29][28][30] Siobhán was a daughter of Cúconnacht Maguire, Lord of Fermanagh (1480–1537).^[27][31] Hugh had three brothers: Brian, Cormac MacBaron and Art MacBaron.^[32][28] During their youth, Hugh and Brian were fostered by the O'Hagan and O'Quinn families.^[33][34][23]

Family tree

Hugh O'Neill with one of his wives, his father, and selected relatives[e] Alison Kelly Conn 1st Earl Tyrone c. 1480–1559 Sorcha O'Neill Mathew 1st Baron Dungannon c. 1520–1558 d.v.p. Siobhán (Joan) Maguire Shane O'Neill c. 1530–1567 Art MacBaron d. 1618 Brian 2nd Baron Dungannon d. 1562 de jure Hugh Earl Tyrone c. 1550–1616 Siobhán O'Donnell d. 1591 Owen Roe O'Neill c. 1585–1649 Hugh 4th Baron Dungannon c. 1585–1609 d.v.p. Randal 1st Earl Antrim d. 1636 Alice O'Neill 1583–c. 1665 Legend XXX Subject of the article XXX Earl of Tyrone XXX Earls of Antrim XXX Baron Dungannon d.v.p. = decessit vita patris (predeceased his father)

During Hugh's childhood, a rivalry formed between his uncle Shane and his father Matthew.^[37] Matthew was born from an affair between Conn Bacagh and Alison, but was accepted by Conn Bacagh as his son and tanist. This affronted Shane, a younger legitimate son of Conn Bacagh, who employed the ambivalent status of Matthew's paternity to affirm his own claim to the chieftaincy.^[38][28] Shane asserted that Matthew's father was actually Alison's husband John Kelly, which would render Matthew illegitimate in both Irish and English systems of succession.^[39] In the ensuing conflict, the O'Neill family split into rival septs—the "MacShanes" (Shane's immediate family) and the "MacBarons" (Matthew's immediate family). The English encouraged this conflict as it weakened the powerful O'Neill clan.^[37]

Matthew was killed in 1558^[40] by the O'Donnelly clan, Shane's foster family,^[41][42] placing his sons Brian and Hugh in a dangerous situation. The continuing support for their claims came from the English administration in Dublin Castle, which was anxious to use the support of the MacBarons to break the independent power of the O'Neill lords of Ulster.^[43][34] At some point between May and August 1558, English statesman Sir Henry Sidney organised the retrieval of the two boys, and for a brief time they stayed at his Dublin residence.^[34]

Hugh O'Neill and his elder brother Brian became wards of the Crown.^[44][37] They were moved into the care of the Anglo-Irish Hovenden family and were raised at their household in Balgriffin, County Dublin—a property formerly belonging to Conn Bacagh.^[37][45] The Crown sought to keep the children safe from harm and to raise them in the English manner, so that they would be more sympathetic to the English administration once they came of age and took their places in the Gaelic nobility.^[43]

Giles Hovenden, Hugh's foster father, was an English settler with a pre-existing business connection with Conn Bacagh.^[46] Hugh was raised by Giles's wife Joan Walshe, and she continued to care for Hugh after Giles's death.^[34][37] Hugh would remain close with his adoptive family throughout the rest of his life.^[37] His foster brother Henry became his chief advisor^[47] and accompanied him on his flight in 1607.^[48] Brothers Henry and Richard led Hugh's troops in the late 1580s, though another brother Walter died opposing the Irish confederacy in battle.^[49]

Growing up in the Pale amongst English people, Hugh gained a knowledge of English customs and politics, mainly through his attendance at the Irish Parliament and the court in England. He was able to secure allies such as the Earls of Ormonde and Leicester.^[45][50] He would have received a basic education, either by attending grammar school or from private lessons.^[51]

In 1562, Brian was assassinated by Shane's tanist Turlough Luineach O'Neill, and Hugh succeeded him as Baron Dungannon.^[52][34][53] Four years later, war broke out between Shane and the Crown.^[51] It was previously considered unlikely that a MacBaron could sway Shane's dominance in Ulster, but in light of these events, the English government began to view Hugh as a significant contender who could bring Ulster under loyalist control. On the contrary, Hugh's main concern was the ruthless pursuit of political and military power, and he intended to remain autonomous and independent.^[45][51]

In June 1567, Shane was killed by Scots supporting the MacDonnells of Antrim.^[41][7] Hugh's wardship formally ended the following November when he sued out his livery,^[37] returning to Ulster in 1568^[54] under the protection of Lord Deputy Sidney.^[7] Sidney granted Hugh territory in Oneilland, intending to keep Turlough from crossing south past the River Blackwater, thus creating further discord within the O'Neill family.^[55]

Now returned to his province of birth, Hugh began engaging the support of neighbouring Irish Gaelic families, including the O'Hagans, the O'Quinns and his own family the MacBarons. According to Sidney, these families "much repined that the great and regal estate of the O'Neill... should be so broken and dismembered".^[37] As he had spent the previous ten years raised as an Englishman, Tyrone would have been considered an outsider by these families.^[54] Hugh married the daughter of favoured noble Brian McPhelim O'Neill, but in 1574 he hastily annulled the marriage when his father-in-law was implicated in a bloody conflict and tried for treason.^[56] The same year, Hugh established his most important and longlasting alliance by marrying Siobhán O'Donnell, daughter of chief Hugh McManus O'Donnell.^[57] The O'Donnell and O'Neill clans had traditionally been mortal enemies for centuries.^[58] Hugh O'Neill gained good standing with the 1st Earl of Essex after joining him in an abortive attack on Turlough.^[37] Essex praised Hugh as "the only man in Ulster to be trusted".^[59] By the early 1570s, Hugh was using his combined support from the Pale and Ulster to put Turlough under heavy pressure.^[37]

In 1585 he attended the Irish House of Lords in Dublin,^[7] where he was recognised as the Earl of Tyrone. In 1587, he successfully persuaded Elizabeth I to grant him letters patent to the lands of Tír Eoghain.^[23] This was apparently done to suppress his desire for O'Neill chieftainship.^[60] From 1587, the Crown grew suspicious of Tyrone and began attempts at curbing his growing power. Elizabeth I characterised Tyrone as "a creature of our own"—a noble raised as an Englishman who had nonetheless turned his back on the English court in favour of political independence. During this period, Tyrone regularly bribed government officials and relied on his extensive web of connections.^[61][45][62]

Per an arrangement with the Crown, Hugh agreed to defend the Pale's borders from fellow Ulstermen in exchange for soldiers. This arrangement allowed him to extend his influence over southeastern Ulster.^[37] In 1580, during the Second Desmond Rebellion in Munster, Hugh fought with the English forces against Gerald FitzGerald, 14th Earl of Desmond. In 1584 he assisted Sir John Perrot against Sorley Boy, the first Chief of Clan MacDonnell of the Glens.^[7][45] Lord Deputy Arthur Grey praised him as "the only Irish nobleman that hath done any service and drawn blood since my coming".^[63] Tyrone was nicknamed "The Queen's O'Neill" for his loyalty to the Crown.^[64] Nevertheless, he feared that the Dublin government might weaken his power by appointing a sheriff in Tír Eoghain.^[45]

In late 1588, 23 ships of the Spanish Armada were lost on Ireland's coast. Lord Deputy William FitzWilliam ordered the execution of Spanish survivors.^[65] Tyrone's response to the Armada is unclear - his mercenary forces massacred survivors in Inishowen, though Tyrone himself rescued various crew members in County Sligo.^[66] Tyrone may have been playing a "double game",^[67][68] as is common throughout his career.^[7]

The Armada ship La Trinidad Valencera sank in Kinnagoe Bay, Inishowen.^[69] Tyrone's mercenary forces, commanded by his Hovenden foster-brothers, proceeded to Inishowen upon hearing of the presence of Spanish fugitives there.^[69][67] Tyrone's instructions to the Hovendens are unknown;^[70] ultimately his forces committed the largest single massacre of Armada survivors in Inishowen.^[65] FitzWilliam was suspicious of the Earl's activities and refused to believe this news, but it is confirmed in the report of a Spanish escapee,^[67] improving FitzWilliam's opinion of Tyrone.^[71]

Historians John Marshall, Hiram Morgan and Matthew McGinty characterised Tyrone as reluctantly ordering the massacre to keep in the English government's good graces.^[70][37][71] Contemporary sources seem to imply that the massacre was carried out on the actions of the O'Donnell clan,^[72][73] who counselled O'Neill's troops,^[65] though this is possibly misdirection by Tyrone.^[67] Government officials reported that Tyrone heavily reprimanded Hugh McManus O'Donnell for betraying the Spaniards and their refuge, and he contemptuously told O'Donnell to seek dwelling in another country.^[65][70][68]

On 25 September, the ships La Lavia, La Juliana and the Santa Maria de Vison became shipwrecked at Streedagh Strand in County Sligo.^[74][75] Tyrone himself assisted three sick officers and many commoners.^[65][67] One of the latter included ordinary seaman Pedro Blanco of La Juliana, who was kept on as Tyrone's footman and manservant throughout the whole of the Nine Years' War.^[65][76] Tyrone also helped stranded nobleman Don Antonio Manrique escape Ulster.^[67] Ultimately about a dozen Spaniards remained in Ireland.^[75] Despite their desire to return home, Philip II of Spain believed they would be of better use as interpreters and emissaries for Tyrone.^[76]

It seems Tyrone never recruited any of these Spaniards as soldiers. His decision may have been affected by the hostility the English had towards Lord Brian O'Rourke for recruiting many Spanish survivors into his military.^[65]

Tyrone further developed his alliance with the O'Donnell clan—by 1587 his daughter Rose was betrothed to tanist Hugh Roe O'Donnell.^[77] Via this alliance, Tyrone was able to secure Scottish mercenaries to fight the MacShanes. In turn, he supported O'Donnell in a succession dispute within his own kingdom.^[45]

Lord Deputy Perrot ordered young O'Donnell's kidnapping in 1587 in hopes of destroying the O'Neill-O'Donnell alliance. O'Donnell was imprisoned in Dublin Castle, along with two MacShanes, Art and Henry.^[78] Tyrone was outraged, describing the ordeal as "the most prejudice that might happen unto me",^[79] and lobbied fruitlessly for his son-in-law's release.^[37]

In January 1591, Hugh Roe O'Donnell made a failed prison break attempt.^[78][80] The same month, Tyrone's wife Siobhán (Hugh Roe's elder half-sister) died.^[81] In December 1591 Tyrone successfully aided Hugh Roe O'Donnell's (and ironically, the MacShanes') escape.^[45][78] He had bribed FitzWilliam—one of the most corrupt Lord Deputies of Tudor Ireland^[82][71]—with £1,000^[f] to aid in O'Donnell's escape.^[83][84] Henry split from the others in Dublin; O'Donnell and Art fled to the Wicklow Mountains to seek shelter with Tyrone's ally Fiach McHugh O'Byrne. O'Byrne's search party found the two men buried in snow and close to death. O'Donnell recovered from frostbite^[85] and was inaugurated as O'Donnell clan chief in May 1592.^[86] Art died in the mountains, fueling speculation that Tyrone had O'Byrne's party kill Art when they found him.^[45][87] It is more likely however that Art died of exposure.^[78][87]

In the north, Tyrone also had to contend with his "grievous enemy" Sir Nicholas Bagenal, the Marshal of Her Majesty's Irish Army.^[37][88] Around 1589 Nicholas Bagenal described Tyrone as "as so allied by kindred in blood and affinity as also by marriages and fosters and other friendships as if he should be ill-disposed might hap put the crown of England to more charges than the purchase of Ulster should be worth".^[89] On 24 October 1590, his son Henry Bagenal succeeded him as Marshal.^[90][91]

In autumn 1590, Lord Hugh Roe MacMahon was executed on FitzWilliam's orders; MacMahon's land was confiscated, divided and allotted to English servitors rather than the Gaelic Irish.^[92] Tyrone, who had owned part of MacMahon's lands under brehon law, was passed over in favour of Henry Bagenal.^[37] Furthermore, Tyrone's authority was directly challenged when Henry Bagenal was named chief commissioner of Ulster on 18 May 1591.^[93][91]

Soon afterwards, Tyrone began to woo Mabel, the Marshal's younger sister.^[91] This was only months after the similarly-timed deaths of Henry Bagenal's father and Tyrone's late wife.^[89][88] Tyrone professed his love and asked for Mabel's hand in marriage. Alarmed, Bagenal kept Mabel out of Tyrone's reach by sending her to live with his brother-in-law Patrick Barnewall in Turvey. Nevertheless, Tyrone found excuses to visit Mabel, and in July he convinced her to elope.^[94][88]

After a dinner at Turvey, the Earl distracted Barnewall while his ally William Warren escorted Mabel to Warren's house in Drumcondra.^[95][96] Tyrone wanted a Protestant ceremony so that the marriage would be recognised by English law, and so Protestant Bishop of Meath Thomas Jones was summoned.^[97][98] Jones was reluctant to perform the marriage, but after being assured of Mabel's free consent, and for the sake of her reputation, the couple were married on 3 August 1591.^[94][88][98]

Jerrold Casway notes that this "whirlwind courtship" is unlike Tyrone's other marriages, which otherwise always had political motives.^[99] It is possible Tyrone's judgment was impaired by his feelings.^[94][100] Mabel was young and attractive, and clearly enamoured by the attention she received from Tyrone.^[88] She has been simplistically dubbed the "Helen of the Elizabethan Wars".^{[101][102][103]} Historians believe that Tyrone would have recognised the advantages of marrying into the powerful Bagenal family.^{[94][104][105]}

Henry Bagenal was outraged at the marriage.^[14] He refused to pay his sister's dowry,^[106] even two years after the marriage,^[101] and also had Tyrone's previous divorce investigated, though it was found to be valid.^[107] Because of this dramatic episode and their roles as opposing commanders during the Nine Years' War, Bagenal and Tyrone have been called "arch-enemies",^[108] "nemeses"^[109] and "arch-rivals".^[110]

The aging chief Turlough had yet to choose a tanist, and the position was contested by Tyrone and his MacShane cousins. Tír Eoghain's population favoured the MacShanes, but outside the kingdom they were disliked due to their father's cruelty towards the various smaller neighbouring kingdoms. Furthermore, the MacShanes had lost a valuable ally in their kin, the FitzGeralds of Desmond, following their defeat in the Desmond Rebellions.^[45]

It is clear that Tyrone aspired to the position of O'Neill clan chief. In March 1583, news spread that Turlough had died. Tyrone rushed to Tullyhogue Fort,^[66] the ancient ceremonial site where the O'Neill chiefs were traditionally inaugurated.^[111] It turned out that Turlough had not died but had only fallen into a brief coma from alcohol poisoning.^[37]

Tyrone's constant disputes with Turlough were fomented by the English with a view to weakening the clan.^[7] In 1584, Tyrone and Turlough were at Strabane to celebrate Easter together. The Dublin government was extremely alarmed at this news and feared that the O'Neill rivalry may be dissolving. By 1587, Turlough had established an alliance with the MacShanes. In 1588 Tyrone and Hugh McManus O'Donnell launched an attack on Turlough, but they were defeated at Carricklea to the satisfaction of Perrot.^[37]

In January 1590, Tyrone organised the execution of his MacShane cousin Hugh Gavelagh,^[112] who had exposed to FitzWilliam that the Earl was making treasonous dealings with the Spanish.^[113][114] Tyrone reputedly hanged Gavelagh over a tree with his bare hands^[115]—though other sources claim the executioner was from Meath or Cavan, given Tír Eoghain's population were sympathetic to the MacShanes.^{[114][116][117]} Tyrone proceeded to London where he sufficiently defended himself against England's Privy Council by alleging that Gavelagh was guilty of various crimes.^[118][40] Tyrone was placed under house arrest but released by letters of commendation from FitzWilliam and the Dublin government.^[37]

After Hugh Roe O'Donnell's inauguration as O'Donnell clan chief, Tyrone and O'Donnell executed a pincer movement against Turlough. With an overwhelming alliance against him, in May 1593 Turlough was forced to surrender his lordship of Tír Eoghain and name Tyrone as his tanist. Turlough would receive a pension of £2,000 and the right to officially remain O'Neill chief until his death.^[53] The Earl had effectively become the ruler of Tír Eoghain.^[45][119]

It is certain Tyrone was involved in the events in Fermanagh and Connacht during 1593-4, but historians disagree as to his true motivations during this period.^[120][121] Hiram Morgan represents Tyrone as a master strategist who was complicit in rebellion from the start^[122] but feigned loyalty to the Crown for strategic reasons.^[123] James O'Neill agrees that Tyrone was the chief architect of the rebellion.^[124] According to John Dorney, Tyrone originally distanced himself from the rebellions because he hoped to be appointed Lord President of Ulster by Elizabeth I, but she recognised Tyrone's ambitions to usurp her as Ireland's sovereign and refused to grant him provincial presidency or similar powers.^[45] Nicholas Canny similarly states that Tyrone aspired to be the "queen's man in Ulster", was passed over in favour of Henry Bagenal,^[105] and reluctantly pushed into rebellion to prevent his followers defecting to his brother Cormac MacBaron.^[122] Michael Finnegan suggests that Tyrone wanted to prevent war with the English, trying in vain to restrain his Irish allies, but was dragged into the war because his association with O'Donnell had corrupted his loyalist reputation.^[125] Darren McGettigan downplays Tyrone's role, stating that "while [Tyrone] was crucial to the confederacy, he did not build it, and may have been carried along by events and his own success, much more than some historians realise".^[126] McGettigan and Morgan disagree over Tyrone's prominence in the confederacy.^[127][123]

The English government had their suspicions that Tyrone was plotting against them, but he repeatedly proved his loyalty in battles against Irish uprisings.^[122] His fellow Gaelic chiefs understood that Tyrone belonged to their cause but publicly hid his true allegiance.^[128] By this time, Tyrone had formally allied with chiefs O'Donnell and Hugh Maguire via their marriages to his daughters.^[129][45] O'Donnell married daughter Rose in December 1592,^[130] and Maguire married daughter Margaret^[131] around May 1593.^[132]

In spring 1593, English captain Humphrey Willis was appointed by FitzWilliam as Sheriff of Fermanagh;^[133] he entered Fermanagh with at least 100 men and began pillaging and raiding, to the fury of Fermanagh's chieftain Hugh Maguire.^[134] Morgan believes this was a blatant move to weaken Tyrone's power by subjugating Maguire.^[133] Maguire managed to obtain reinforcements which included 100 men led by Tyrone’s brother Cormac MacBaron and 120 men under the commands of Tyrone's O’Hagan foster-brothers.^[135] Tyrone often used his relatives and followers to make war on his behalf^[37] and it is unlikely they would have assisted Maguire without Tyrone's permission.^[136] Maguire besieged Willis and his men in a church and planned to starve them out, but Tyrone intervened and negotiated their rescue safely out of Fermanagh.^[137][110] This conflict is considered to mark the start of the Nine Years' War.^[138][139]

After a meeting on 8 May 1593, Maguire, O'Donnell and Brian Oge O'Rourke signed a letter addressed to Philip II of Spain^[110] requesting urgent reinforcements from the Spanish army. They tasked Catholic Archbishop of Tuam James O'Hely with delivering their message^[140]—he met with Juan de Idiáquez, the royal secretary.^[128] Idiáquez's notes to Philip II reveal Tyrone's relationship with the emerging confederacy:

"The Irish archbishop of Tuam says that it will be of great importance for the success of the confederacy of Irish Catholics, that Your Majesty should write very affectionately to the earl of Tyrone, whose name is O’Neill to induce him to enter into the confederacy openly. He already belongs to it secretly, and he should be assured that Your Majesty’s aid shall not fail them. The archbishop begs Your Majesty to order a letter to be written to the earl to that effect."^[141]

Subsequently Maguire launched raids across Connacht. Tyrone's nephews—sons of his brother Art MacBaron—also engaged in campaigns against loyalist clans.^[142]

On 14 May 1593, Phelim MacTurlough O'Neill, a client of Henry Bagenal, was assassinated by the O'Hagans, Tyrone's foster family. This murder permitted Tyrone to annex Killetra, which he had been attempting since the late 1580s.^[143] Tyrone was charged with involvement in the assassination. He swore his innocence, blamed it solely on the O'Hagans as a revenge murder, and accused the administration of manipulating the evidence against him. FitzWilliam had his doubts, but the council were satisfied.^[144]

By late April, there were more allegations against Tyrone from Irish lords Hugh McHugh Dubh O'Donnell and Sir Hugh Magennis. According to the Sheriff of Monaghan, a large group of Irish noblemen including Tyrone, Maguire and O'Donnell had taken treasonous oaths in support of Spain. FitzWilliam summoned Tyrone to Dublin, but Tyrone refused and made excuses, so the council went to Dundalk to confront him in person. During the proceedings, which occurred 14–28 June, the main charge was foreign conspiracy. FitzWilliam and Bagenal favoured the Earl's arrest. Three councillors were already well-disposed to Tyrone; the rest felt threatened by his power in Dundalk. Certain councillors feared Tyrone's arrest would only exacerbate the growing conflict in the north and could lead to a Gaelic invasion of the Pale. Ultimately Tyrone managed to avoid arrest.^[145] When Elizabeth I was later briefed on the proceedings, she concluded that Tyrone should have been arrested.^[146]

Tyrone met with Maguire in early August—within weeks Maguire launched raids into Monaghan.^[147]

Maguire's attacks provoked a large-scale military expedition to be led by Bagenal.^[148] Tyrone was able to deflect the past allegations and prove his loyalty to the Crown by agreeing to assist Bagenal.^[37][149] On 26 September he joined Bagenal and his army at Enniskillen, but the Earl had brought far fewer troops than he had promised.^[150] The two commanders detested each other and there was a nervous awkwardness between their troops. Bagenal proposed several plans of attack but these were all vetoed by Tyrone. On 7 October, they marched separately to the ford near Belleek.^[151]

Their combined forces moved on Maguire's positions on 10 October in what is known as the Battle of Belleek.^[150] Hugh Roe O'Donnell was in nearby Ballyshannon when the battle was taking place, but he was ordered by Tyrone not to reinforce Maguire.^[152] It was estimated that 300 of Maguire's men were killed.^[153] Though Maguire's forces were not directly engaged, FitzWilliam was convinced Maguire's revolt had been stopped.^[154] During the battle Tyrone was speared in the leg; the wound served as physical proof of his loyalty to the authorities in Dublin. Bagenal remain suspicious of his brother-in-law and later received intelligence that Tyrone had advised Maguire prior to the battle.^[155] Tyrone protested against Bagenal's accusation by claiming that Bagenal and FitzWilliam were conspiring to rob him of the honour he was due.^[156]

More allegations emerged in 1594. Captain Willis, Sir Edward Herbert and Joan Kelly claimed Tyrone was ordering the Irish raids. In March, it appeared that Tyrone was behind the burning of Bagenal's lands.^[157] The same month, government commissioners surmised that a confederacy had been established between the Ulster lords, and that Tyrone was the leader.^[37][158] Tyrone was involved in the Battle of the Ford of the Biscuits, which occurred on 7 August.^[159] O'Donnell pushed Tyrone into supplying further soldiers, by warning that "he must consider [Tyrone] his enemy, unless he came to his aid in such a pinch".^[160]

FitzWilliam was succeeded as Lord Deputy by William Russell, who was sworn in on 11 August. To the surprise of the council, Tyrone appeared in Dublin four days later to tender his submission. Russell allowed Tyrone to leave in safety, but he later realised his mistake and unsuccessfully shifted blame to the council. The queen was furious.^{[161][156][37]}

On 16 February 1595 Tyrone's brother Art MacBaron assaulted and captured the English-held Blackwater Fort in Blackwatertown. More significant however was the presence of Tyrone at the assault.^[162] The evidence against Tyrone became too great to ignore, and the government deemed an immediate attack essential.^[156] Sir John Norris was ordered to Ireland at the head of a considerable force for the purpose of subduing Tyrone. Tyrone anticipated this and struck the first blow by invading and burning Louth. When Norris arrived at Waterford on 4 May 1595, Tyrone had already succeeded in taking the Blackwater Fort.^[163]

If Tyrone did not go into open rebellion once the English encroached onto Tír Eoghain, he could have risked estranging his followers and allowing another O'Neill clansman to oust him,^[45][164] such as his brother Cormac MacBaron.^[122][165]

In May 1595, 1,750 English troops led by Bagenal were ambushed near Clontibret by an army led by Tyrone. The English column had been sent to relieve the besieged English garrison in Monaghan. The battle spanned multiple days as Bagenal's forces attempted to outrun Tyrone's.^[166] During the battle, Tyrone entered a melee with a cornet who had thrown him off his horse. An O'Cahan (possibly Donnell Ballagh O'Cahan) severed the cornet's arm then Tyrone stabbed him under the corslet.^{[167][168][169]}

In a report to the Lord Deputy, Norris warned that the proficiency of the Irish rebels was far greater than expected: "their number greater, their arms better, and munition more plenty". The discipline and co-ordination of Tyrone's pike and shot technique caused extreme concern. Bagenal recorded 31 killed and 103 wounded,^[170] though it is likely casualties were much higher.^[171] The Irish victory shocked and demoralised the English and was a severe setback early in the war.^[37][172]

On 24 June Tyrone was proclaimed a traitor at Dundalk.^[163] The queen's advisor William Cecil advised a compromise, writing that Elizabeth "would be content to see what was in the traitor's heart, and what he would offer". Tyrone insisted on a general pardon but this was refused.^[173]

Turlough Luineach died in September, making Tyrone officially O'Neill clan chief under brehon law.^[37][53] According to Norris, "the coming to the place of [clan chief] hath made [Tyrone] much prouder and harder to yield to his duty, and he flattereth himself much with the hope of foreign assistance."^[174]

Tyrone and O'Donnell opened communications with Philip II and his general Juan del Águila. In letters to the king—intercepted by Russell—they promoted themselves as champions of the Roman Catholic Church, claiming liberty of conscience as well as political liberty for the Gaelic Irish.^[175][176] They also offered Philip II the kingdom of Ireland in return for military support. It had long been suspected that Tyrone was in league with the Spanish but this was the English government's first piece of hard evidence.^[177] In fact Philip II had sent a ship to gather intelligence in March 1594, but the crew died in a shipwreck off Biscay.^[178]

Tyrone sought to delay the war in order to buy time for the arrival of Spanish troops.^[179] In September 1595, he sent overtures of submission to the Crown, and a ceasefire was enacted whilst the settlement could be negotiated. This timing was advantageous to the Crown, as the queen's Irish Army was facing shortages of manpower and supplies.^[180] The discovery of the confederacy's letters to Spain affected negotiations, but ultimately the government was willing to accept Tyrone's assurances.^[176] After much deliberation and negotiation,^[37] a cessation of arms was signed by Tyrone on 27 October.^[180] This pardoned certain confederates and give them local autonomy. It also acknowledged a tolerance of Catholicism.^[37] The confederacy proved to be unsatisfied with the terms,^[181] but this policy was a success in that Tyrone managed to defer English attempts on his territory for more than two years.^[182][175] Tyrone's wife Mabel died a few months after the cessation.^[94]

According to Dunlop, "for the next two years it is impossible to describe the relations between Tyrone and the government as those either of settled peace or open war".^[176] In April 1596, Philip II anxiously exhorted Tyrone to continue the war with England.^[183] Tyrone thereafter chose to temporize with the authorities, professing his loyalty to the crown whenever circumstances required.^[175] A hollow peace was signed on 24 April.^[176] Further negotiations to develop a peace treaty were almost complete by May.^[184] Spanish captain Alonso Cobos met with Tyrone, O'Donnell and Cormac MacBaron in early May. After the meeting, the Irishmen agreed to abandon the peace treaty and become vassals of Philip II. Tyrone and O'Donnell also petitioned Philip II to make Albert VII, Archduke of Austria the new monarch of Ireland.^[185] After these developments, Tyrone and O'Donnell began to deliberately derail peace negotiations and provoke war in previously peaceful parts of the country. It became clear to the English that Tyrone intended the war to be not just a war for Ulster, but for all of Ireland.^[184][186]

Tyrone's strategy became more combative once he had received promises that a large-scale Spanish military expedition would be incoming. He imported regular shipments of munitions and his ally Fiach O'Byrne engaged in a series of skirmishes against Lord Deputy Russell's troops. Tyrone intentionally gave the English government the impression that peace was imminent as misdirection from the impending Spanish expedition.^[187] After much delay, the 2nd Spanish Armada finally sailed from Lisbon in October 1596. Unfortunately for Tyrone, the armada ended in failure when it was met with a sudden storm which claimed over 3,000 lives.^[188]

In a parley with Norris at Dundalk in January 1597, Tyrone admitted to writing letters to Spain but placed the blame partly on O'Donnell. He agreed to a further parley in March but made excuses to postpone it. On 22 May, Thomas Burgh, 3rd Baron Burgh took over as Lord Deputy. Burgh refused to entertain Tyrone's excuses and on 6 June, English forces launched a surprise attack on Tyrone between Newry and Armagh. Tyrone withdrew across the Blackwater. On 14 July Burgh captured the Blackwater fort. Tyrone "hanged twenty of his knaves that were appointed for the defence of the sconce", and returned to besiege the fort. Burgh died from illness in October.^[189]

It was anticipated that Tyrone would seize this opportunity to overrun the Pale. Instead, on 22 December, he submitted himself to the Earl of Ormonde at Dundalk, and "upon the knees of his heart professed most hearty penitence for his disloyalty, and especially his foul relapses thereinto". He promised to renounce the title of O'Neill clan chief, to refrain from putting obstacles in the way of victualling the Blackwater fort, and not to correspond with Spain or any other foreign nation.^[190] Tyrone presented a document of grievances which listed offences committed by the government against the Irish.^[37] Ormonde transmitted this petition, in which liberty of conscience was foremost, to Elizabeth I. On these terms a truce for eight weeks, subsequently renewed to 7 June 1598, was concluded.^[190]

Tyrone's pardon was granted on 11 April 1598. However the Earl felt that the Crown would eventually supersede his authority in Ulster. When the truce expired in June, Tyrone resumed hostilities.^[190][191] He besieged the Blackwater fort and threatened to starve out the inhabitants.^[190][37]

Motivated by his animosity towards Tyrone, Bagenal encouraged a relief exercise to be sent to the fort. On 14 August, whilst crossing the River Callan, Bagenal's army was attacked by the combined forces of Tyrone, O'Donnell and Maguire. Tyrone had prepared ditches in the ground to obstruct the enemy.^[191] Half of Bagenal's 4,000 men were killed, including Bagenal himself,^[192][193] who was struck by a bullet after lifting his visor.^[194]

The confederacy's success at the battle was the greatest victory by Irish forces against England,^[37][6] and it sparked a general revolt throughout the country, particularly the south.^[195] Tyrone has been criticised for failing to immediately capitalise on his victory,^[196] as he let three months elapse before launching a major attack into Munster.^[197] However, it is possible Tyrone sustained heavy losses from the battle.^[37] One estimate puts Irish losses at the battle of the Yellow Ford at around 200 killed.^[198] News of the battle spread across western Europe, prompting Philip II to send a congratulatory letter to the confederates. Unfortunately for Tyrone,^[199] Philip II died the following month; he was succeeded by his son Philip III.^[200][201]

After much hesitation, Elizabeth I selected Robert Devereux, 2nd Earl of Essex as her new Lord Deputy. Essex, a recently-disgraced favourite of the queen, reluctantly took on the role to strengthen his reputation.^[202] Essex had an existing connection with Ireland and Tyrone, as his father Walter Devereux was one of Tyrone's early allies.^[203] In a letter prior to his arrival in Ireland, he declared his intentions as Lord Deputy: "by God, I will beat Tyrone in the field, for nothing worthy of her Majesty's honour hath yet been achieved".^[202]

Essex landed in Ireland on 15 April 1599 with an expeditionary force of 16,000 troops and 1,500 horses^[204]—the largest English army dispatched to the country.^[37] The situation in Ireland was practically unaltered since the battle of the Yellow Ford.^[205] Despite his resources, Essex's Irish campaign proved to be a failure. He led months of ill-managed operations in the south of Ireland, lost three-quarters of his forces to disease and desertion, and executed of hundreds of his troops for cowardice.^[206] The confederates felt the English threat had weakened enough that they could safely travel with their wives—Tyrone's fourth wife Catherine Magennis,^[207] whom he had married circa 1597,^[208] was present at his camp in June 1599 during her first pregnancy.^[207] Towards the end of July, Essex received letters from the queen with peremptory orders to travel northwards and attack Tyrone with all speed.^[209]

Tyrone skirmished with Essex's forces as they approached the borders of Ulster, but this was nothing like a general engagement.^[210] Essex's numbers had dwindled to only 4,500 and Tyrone, whose army far outnumbered Essex's, refused to give battle.^[211] Tyrone sent his counsellor Henry O'Hagan to request a parley.^[212] Essex stubbornly agreed only after Tyrone had asked three times.^[213]

On 7 September 1599, at a ford on the River Lagan, Tyrone met Essex for a half-hour parley.^[214] Tyrone waded his horse into the river whilst Essex stayed on the bank.^[215] Tyrone doffed his cap, saluting Essex "with a great deal of reverence".^[216] He praised Essex's late father and claimed he was willing to obtain peace from the new Lord Deputy. Tyrone would not give anything in writing, claiming that he feared Spain would cease their alliance with Ireland if evidence appeared that he was negotiating with England. Tyrone once again demanded liberty of conscience, to Essex's contempt. He also demanded a single treaty wherein the Crown would restore confiscated Irish lands to their former owners.^[217] Essex was not familiar with Tyrone's wily nature and gullibly accepted these proposals.^[218] Because their parley was conducted privately, out of earshot of their armies,^[219] Essex was later accused of using the parley to conspire with Tyrone.^[216] These accusations are far-fetched and obviously defamatory.^[220]

A more formal meeting occurred later on at the same ford, with six witnesses on each side attending.^[221][g] Ultimately an informal truce of six weeks was arranged. Tyrone retired to Tír Eoghain, and a humiliated Essex returned to England to face his queen.^[202] Elizabeth I was displeased by the favourable conditions allowed to Tyrone and by Essex's treatment of him as an equal.^[224] Tyrone broke off the truce on hearing of Essex's arrest, though English statesmen Robert Cecil was weary of the war and remained intent on peace.^[225] Following a failed uprising, Essex was executed for treason on 25 February 1601.^[226][227]

On 5 November 1599, in a strong position after Essex's failed campaign,^[228] Tyrone issued a public proclamation declaring a holy war against England.^[229][37] He sent a list of 22 proposed terms for a peace agreement to Queen Elizabeth, including a request on the status of future English viceroys. This amounted to accepting English sovereignty over Ireland as a reality while hoping for tolerance and a strong Irish-led administration.^[230][231] The Dublin government were frightened upon receiving the proclamation. It was decided that any further meetings would be unseemly and futile, and the proposal was ignored.^[232]

Tyrone's main goal was now to win over Ireland's English-speaking Catholic population (the "Old English").^{[37][233][234]} Despite his previous apathy towards religion, Tyrone began to position himself as a champion for Catholicism in order to rally further Irishmen to his cause.^[45] Tyrone declared that "if [he] had to be king of Ireland without having the catholic religion, [he] would not the same accept".^[210] He gained support from Pope Clement VIII,^[1] who entitled him "Captain General of the Catholic Army in Ireland".^[235] In late 1599 and early 1600, the Earl was in Munster on pilgrimage.^[236] He supported the claim of James FitzThomas Fitzgerald (the Súgán Earl) to the Earldom of Desmond,^[1] and recognised Florence MacCarthy as the MacCarthy Mor at Inniscarra.^[237] However the Munster expedition ended in failure^[238] when in early March,^[239] confederacy commander Maguire was shot and killed by English forces whilst on a nearby reconnaissance mission.^[240] Maguire's death was a major loss to the confederacy and prompted Tyrone to abruptly return to Ulster.^[241] Ultimately Tyrone's religious rhetoric could not abolish the deep distrust the Old English had of the Gaelic Irish, and he looked again to Spanish intervention as a means of winning the war.^[235][37]

Tyrone stimulated the Irish-Spanish alliance by sending his son Henry to Spain in April 1600.^[37] At this time controversial Jesuit James Archer operated as his representative at the Spanish court.^[242] Shortly after Tyrone's return to Ulster, he learnt that a Spanish ship had arrived bearing Archbishop of Dublin Mateo de Oviedo with letters from Philip III. The ship carried considerable supplies of money and ammunition for the confederacy.^[243]

In February 1600, Charles Blount, 8th Baron Mountjoy, Essex's successor as Lord Deputy, arrived in Ireland.^[244][245] He was a protégé of Essex and similarly a favourite at court.^[246] Mountjoy posed a major threat to Tyrone as he began immediately revitalising and restoring confidence in the English army.^[245][241] He assigned veteran soldiers Arthur Chichester and George Carew to Ulster and Munster respectively.^[45]

In May 1600 the English achieved a strategic breakthrough when Sir Henry Docwra, at the head of a considerable army, took up a position at Tyrone's rear in Derry.^[243][1] Docwra persuaded several unsatisfied confederacy members to defect to the English. These Irish soldiers, particularly Niall Garve O'Donnell, emboldened the English troops and allowed Docwra to significantly weaken Tyrone's forces.^[247][248]

In September Mountjoy established his camp at Faughart with the intention of conducting a winter campaign against Tyrone. There was some fighting in the Moyry Pass, where Tyrone had entrenched himself, compelling him to retire to Armagh. A large reward was offered for the Earl's capture, dead or alive.^[1][243] Tyrone was in a desperate position.^[45] Upset with setbacks, he began drinking heavily and took his frustrations out on his wife Catherine.^[99]

As 1601 began, Philip III was focused on dispatching an expedition to Ireland in order to improve his position in the Anglo-Spanish War.^[249] In October 1601, the long-awaited aid from Spain appeared in the form of an army under Spanish commander Don Juan del Águila, which occupied the town of Kinsale in the extreme south of the country.^[1] Tyrone was displeased at the small size of the force^[37] and the fact that they had landed in the south—moving his army there would mean leaving Ulster unprotected.^[235] Mountjoy rushed to contain the Spanish,^[37] but it was not till the beginning of November that Tyrone was able to put his army in motion.^[243] In December his army united with O'Donnell's at Bandon.^[250] The two chieftains reluctantly marched separately from the north, through territories defended by Carew, in the depths of a severe winter. They gained little support en route.^[235]

The Irish presence at Kinsale trapped the English army between them and the Spaniards. Tyrone and O'Donnell seem to have initially agreed on starving out the besiegers, but Juan del Águila urged a prompt combined attack on the English lines.^{[243][235][37]} Contemporary writers Lughaidh Ó Cléirigh and Philip O'Sullivan Beare claim that O'Donnell naively urged Tyrone to attack, but not all modern historians believe these accounts are accurate. John McGurk, J. J. Silke, Cyril Falls and McGettigan concur; Morgan and Gerard Anthony Hayes-McCoy disagree. O'Donnell had previously induced Tyrone into a full frontal assault during a campaign in 1598, so this narrative is not out of the question.^[251] Morgan claims it was the pressure from the beleaguered Spaniards that wore down Tyrone,^[252] and that the Earl also had his reputation on the line.^[37] In any case, Tyrone reluctantly (and uncharacteristically) yielded to the Spanish officers and resolved to make an immediate joint attack.^[243][235]

On the morning of 24 December 1601, Tyrone's force of 5,000 men took their position. As soon as they were spotted, Mountjoy ordered his men to attack. Tyrone retreated but Mountjoy's cavalry routed the fleeing soldiers.^[37][235] 1,200 men were killed and another 800 were wounded.^[37] The battle was a disaster for Tyrone and nullified years of his wartime success.^[253] The Earl was strongly in favour of another attempt, but he was overruled by O'Donnell who laid blame on Juan del Águila.^[243][254] After the failure at Kinsale, the chance of the confederacy winning the war had passed.^[45] In his haste to leave Munster, 140 of Tyrone's men drowned while passing the Blackwater.^[254] According to Carew, a troop of women could have beaten Tyrone's army on its homeward march.^[243]

O'Donnell went to Spain to seek further assistance, where he died soon afterwards of a sudden illness, aged 29.^[255] With a shattered force, Tyrone made his way once more to the north, where he renewed his policy of ostensibly seeking pardon while warily defending his territory.^[1]

The Crown's army swept the country.^[45] The English forces began to close in on Tyrone—Mountjoy from the south, and Dowcra and Chichester from the north.^[256] Mountjoy destroyed the traditional O'Neill inauguration stone at Tullyhogue.^[45] With queen Elizabeth in bad health, Tyrone may have been set on holding out until James VI of Scotland acceded to the English throne—he had diplomatic relations with James earlier in the war.^[256][243]

English forces managed to destroy crops and livestock in Ulster in 1601–1602,^[257] especially in the lands of Tyrone's principal vassal (and son-in-law) Donnell Ballagh O'Cahan. This led to O'Cahan's surrender and withdrawal from Tyrone^[45][169] in July 1602,^[258] which drastically weakened the Earl's power. In June 1602 Tyrone destroyed his capital at Dungannon and retreated into the woods of Glenconkeyne.^[257] Mountjoy continued to pursue Tyrone to no avail. The Earl entered Fermanagh in autumn but was back in Glenconkeyne by December. He was able to rely on fellow Irish lords to provide him with provisions and intelligence.^[259] Whilst in Glenconkeyne, exactly a year after the defeat at Kinsale, Tyrone wrote a letter to Philip III asking for a Spanish warship to be sent to Ulster.^[169] The English army's use of scorched earth tactics led to famine across 1602–1603,^[260] with conditions so extreme that the local population were reduced to cannibalism.^[45][37] In January 1603, Mountjoy admitted to Cecil that capturing the Earl would be up to chance. Despite his efforts, Mountjoy could not convince anyone to betray Tyrone.^[261]

On 22 December 1602, Tyrone offered his submission on his own terms, but this was firmly rejected by the queen. She insisted that Tyrone's title should be stripped from him and that his lands should be reduced.^[261] Early in 1603, Mountjoy opened negotiations with Tyrone.^[1][256] Tyrone made his submission to Mountjoy on 30 March at Mellifont Abbey.^[256][261] The queen had died on 24 March^[262] but Mountjoy concealed this news until the negotiations had concluded.^[263] Had Tyrone known of Elizabeth's death, he would likely have bargained more aggressively. The primary stipulations of the treaty were that the Gaelic chieftains abandon brehon law, dissolve their private armies and swear loyalty only to the English Crown.^[45] These were particularly generous terms.^[261][169] On 8 April Tyrone renewed his submission before Mountjoy and the council in Dublin.^[264] This was where Tyrone heard of the queen's death;^[261] he apparently wept with frustration.^[45] After Tyrone's submission, the remaining confederates followed suit. This marked the end of the Nine Years' War.^[265]

At about the end of May, Tyrone sailed to England with Mountjoy and Rory O'Donnell, Hugh Roe O'Donnell's younger brother and successor.^[264][1] They arrived at London on 4 June.^[258] Tyrone and Rory presented themselves to Elizabeth's successor, King James I, at Hampton Court.^[1] The English courtiers were greatly incensed at the gracious reception accorded by James to these notable rebels.^[1][258] Sir John Harington was outraged "to see that damnable rebel Tyrone brought to England, honoured, and well-liked... [He] now smileth in peace at those who did hazard their lives to destroy him".^[266] Tyrone even went hunting with the new king.^[265]

Under a new patent almost as extensive as the one he had been given in 1587, Tyrone was confirmed in his title and core estates.^[267] He was also bold enough to request the lord presidency of Ulster, but was only allowed lieutenancy of Tyrone and Armagh.^[37] Rory was made 1st Earl of Tyrconnell.^[247] Whilst Tyrone was in England, he sent a letter to Philip III offering to take up arms for Spain if peace negotiations between Spain and England failed.^[265]

Tyrone returned to Ireland at the end of August^[258] and began rebuilding his estates, an easy task under the reserved government of Sir George Carey, who had replaced Mountjoy as Lord Deputy.^[265] As part of the Treaty of Mellifont, Tyrone was given authority over O’Cahan,^[268] whom he retained animosity towards due to his desertion during the war.^[45][169] A land rights dispute shortly arose between them, as O'Cahan's surrender to Docwra was under the promise that O'Cahan would retain his land as an independent chieftain. Tyrone maintained that O'Cahan's independence was incompatible with the terms of his own restoration, and insisted on exacting his customary rents from him.^[258] Docwra pleaded for O'Cahan's case before the council, but Mountjoy sided with Tyrone. O'Cahan was forced to yield a third of his ancestral lands to the Earl.^[169]

In February 1605 Arthur Chichester became Lord Deputy.^[269][270] Chichester's attitude towards the Gaelic lords was markedly more aggressive. He abolished brehon law and removed the authority that senior lords had over junior nobles—making O'Cahan a freeholder with new legal rights.^[271][258]

Chichester was also antagonistic to Tyrone, forcing him to attend Protestant services and accusing him of plotting with Spain.^[45] It became clear to Tyrone that the restoration of his earldom meant little.^[169] Tyrone's marriage became strained and in December 1605 he considered divorcing his wife Catherine. Chichester sent officer Toby Caulfield to recruit Catherine as a double agent, but she dismissed this out of hand.^[272][273]

Tyrone lost his support from the council when Mountjoy died in April 1606.^[169][274] George Montgomery, the new Protestant Bishop of Derry, exacerbated the conflict between Tyrone and O'Cahan by encouraging O'Cahan to renew his suit against Tyrone.^[258][274] Attorney-General for Ireland Sir John Davies prepared a case to prove that O'Cahan's lands were legally vested in the Crown, and he also acted as O'Cahan's counsel during the proceedings.^[169] Montgomery also encouraged O'Cahan to leave his wife, Tyrone's daughter Rose (former wife of Hugh Roe O'Donnell), and return to his first wife Mary,^{[37][275][169]} who he was never actually divorced from.^[169][276] Montgomery wrote to Chichester on 4 March 1607: "the breach between [O'Cahan] and his landlord [Tyrone] will be the greater by means of [Tyrone's] daughter, his reputed wife, whom he has resolved to leave, having a former wife lawfully married to him."^[276] O'Cahan later repudiated his marriage to Rose.^[277] Tyrone would ask for Rose's dowry back,^[169] but O'Cahan retained it.^[276] It is clear that government officials were harnessing O'Cahan's hostility to orchestrate Tyrone's undoing.^[169]

Tensions between Tyrone and the English government escalated. Tyrone's continued correspondence with Spain broke his promises made at Mellifont.^[169] In 1607, the 1st Earl of Tyrconnell accidentally exposed a plot, involving Tyrone and Spain, during a conversation with Richard Nugent, Lord Delvin.^[278]

Though the government had no evidence to charge Tyrone with, they suspected his intention to raise up a fresh rebellion, and in April 1607 the Earl was summoned to Dublin to answer O'Cahan's plaint.^[258] O’Cahan had received loans to fund his case. During their meeting in court that May, Tyrone lost his temper. He snatched a document from O'Cahan's hands and tore it up in front of Chichester.^[169] Tyrone's violent behaviour towards O'Cahan greatly damaged his cause. The government, unable to come to any definite conclusion, referred the matter to the king's decision, and Tyrone promised to go to London.^[258]

By September, the supposed plot involving Tyrone and Spain was known to the government.^[278] Historians are undecided on whether this plot actually existed,^{[169][274][279]} and the exact cause of Tyrone's flight is a matter of controversy among historians,^{[280][37][279]} though he certainly believed that his arrest was imminent.^[281] Information reached clan chief Cuconnacht Maguire that the government intended to arrest Tyrone if he went to England. Maguire sent a vessel of eighty tons into the north of Ireland to facilitate an escape.^[258] Tyrconnell already planned to leave, and he convinced Tyrone to flee to Spain with him.^[278][279] Tyrone was at Slane with Chichester when news of the vessel's arrival reached him. He seems to have come to an immediate snap decision; it was afterwards recollected "that he took his leave of the lord deputy in a more sad and passionate manner than he used at other times".^[258] Tyrone left for Dungannon to collect his wife and children.^[282]

"The Flight of the Earls" occurred on 14 September 1607, when Tyrone and Tyrconnell embarked at midnight at Rathmullan on Lough Swilly on a voyage bound for Spain.^[1] Accompanying them were their wives, families and retainers, numbering ninety-nine persons.^[169][283] This effectively marked the collapse of Gaelic Irish society.^[284] Tyrone was clearly agitated during the departure. Due to time constraints, he left his five-year-old son Conn Ruadh behind, to Catherine's distress. According to an English account, "[Catherine] being exceedingly weary slipped down from her horse and weeping said she could go no further." Tyrone responded by threatening her with his sword "if she did not pass on with him and put on a more cheerful countenance".^[282]

Driven by contrary winds to the east, the refugees took shelter in the Seine estuary and were told by the Spanish to pass the winter in the Spanish Netherlands and not to proceed to Spain itself.^[267] The hopes of the earls for military support foundered as Philip III, on the verge of bankruptcy, sought to maintain the recent 1604 peace treaty with England.^[169] Tyrone accepted the offer of Pope Paul V to take up his abode in Rome, and on 28 February 1608 he and his companions, now reduced to thirty-two persons, left Leuven.^[285] Tyrone and his fellow nobles left their younger children behind in Leuven under the care of Irish Franciscans.^[286]

On 29 April,^[278][287] Tyrone and Tyrconnell were welcomed into Rome by a large concourse of ecclesiastics. The two earls met the pope the next day.^[285] The journey to Rome was recorded in great detail by writer Tadhg Ó Cianáin.^[288][258] In November 1607 the flight was proclaimed as treasonous by James I.^[289] A bill of attainder was passed against Tyrone by the Parliament of Ireland in 1613.^[1]

The pope granted Tyrone a monthly pension of a hundred crowns, and a house (on Borgo Vecchio) rent-free, together with an allowance of bread and wine for ten persons. Philip III added four hundred ducats a month.^[285] Compared to his arrangements in Ireland, this was a miserly lifestyle.^[37][290] During his time in Rome, Tyrone attended papal ceremonies, visited catacombs and relics, ascended the Scala Santa on his knees, and made the traditional pilgrimage to the Seven Pilgrim Churches of Rome.^[291] In 1608 Tyrconnell died of a fever,^[278] and by 1610, Tyrone's eldest sons Hugh and Henry had also died.^[292] Tyrone continued to petition Philip III for his assistance, pleading him to "liberate [Catholic Ireland] from heresy and tyranny",^[293] but had no success.^[292]

Tyrone quickly became disillusioned with his exile and yearned to return to his position in Ireland.^[294][291] He did not give up the possibility of return^[295] and toyed variously both with schemes to oust English authority outright and with proposed offers of pardon from London. When the former Crown loyalist Cahir O'Doherty launched his failed rebellion in 1608, it briefly raised hopes of a return.^[296][297] English spies were monitoring Tyrone during this period. In 1613 the English government briefly discussed with Tyrone a potential reconciliation.^[37] Tyrone ceased his petitioning to Philip III by 1614 when he was threatened with losing his pension unless he remained silent. By this time, Tyrone was planning an ambitious return to Ireland with Spanish aid. In March 1615, he declared to Philip III that "rather than live in Rome, he would prefer to go to his land with a hundred soldiers and die there in defence of the Catholic faith and of his fatherland".^[292] In July he bemoaned that he would likely "die within four or six years" and he did not wish to die "without the consolation of dying fighting for my religion and the territories of my forebears".^[298]

In late 1615, Tyrone fell ill with a fever and never recovered.^[291] His eyesight failed him at the start of 1616.^[299] Tyrone died in Rome on 20 July 1616.^[37][300]

His elaborate funeral was paid for by the Spanish ambassador and attended by cardinals, foreign ambassadors, dignitaries, and many Irish nobles. The English ambassador in Madrid, Francis Cottington, reported on Tyrone's funeral: "Upon the news of his death, I observe that all the principal Irish entertained in several parts of this Kingdom are repaired unto this court, as [Donal Cam O'Sullivan Beare, 1st Count of Berehaven], from the Groyne (i.e. la Coruna); Raymond Burke from Lisbon; one who calls himself Desmond from Bayonne in Galicia; and the Archbishop of Tuam, from Alcala, with many others of less note, but captains and of good quality.”^[301]

He was interred in the church of San Pietro in Montorio, beside his son Hugh, his ally Tyrconnell, and Tyrconnell's brother Cathbarr O'Donnell.^[300] In a letter dated 27 July, the Council of State remarked to Philip III that "as the Earl left no funds for his burial, Cardinal Borja spent what was necessary at the expense of the Embassy... but in doing this he endeavoured to cover such appearances as might cause difficulties in the relations of your Majesty with the King of England". This explains the brevity of the inscription on Tyrone's tomb.^[302][300] The original tombstone was lost in 1849 during the Risorgimento. In 1989 Tomás Ó Fiaich laid a new marble plaque with the same inscription.^[303][300]

Upon news of Tyrone's death, the court poets of Ireland engaged in the contention of the bards.^[304][305] His presence in Europe was a constant source of concern for the English, and his death came as a welcome relief.^[301] The Annals of the Four Masters, compiled in 1636,^[306] praise the Earl: "the person who here died was a powerful, mighty lord, [endowed] with wisdom, subtlety, and profundity of mind and intellect; a warlike, predatory, enterprising lord, in defending his religion and patrimony against his enemies".^[301] Conversely, because Tyrone had deserted his people in 1607, his own generation expressed little admiration for him.^[307]

Historian James MacGeoghegan rehabilitated Tyrone's image in the seventeenth century.^[308] This carried into the nineteenth century when Irish nationalists such as John Mitchel developed a romantic myth around Tyrone, portraying him as a selfless idealist dedicated to the freedom of Gaelic Ireland.^{[309][308][310]} Nevertheless, Tyrone tended to be sidelined in favour of his wartime ally Hugh Roe O'Donnell. Tyrone's "Machiavellian" nature and his partially-English cultural identity are reasons he was not embraced by Irish nationalists in the same way as O'Donnell,^[311][312] whose traditional Celtic upbringing, sensational prison break saga and tragic early death made him a Gaelic Irish martyr and national hero.^[127][313]

Seán Ó Faoláin's biography The Great O'Neill (1942) is the most influential modern work on Tyrone.^[37] It attracted a large readership but is today considered inaccurate and overdramatised.^[314][252] Particularly, Ó Faoláin incorrectly claims that Tyrone grew up in England (instead of the Pale) and he overtly romanticises Tyrone's marriage to Mabel Bagenal.^[315] The Great O'Neill was so popular that it was used by Brian Friel as the basis for his 1988 play Making History,^[37][316] which focuses on Tyrone reckoning with his legacy post-Flight.^[315]

Hiram Morgan's book Tyrone's Rebellion (1993), which focuses on Tyrone's life up to 1596,^[301] restored the Earl to the status he was formerly afforded by contemporary English commentators.^[311] Tyrone now overshadows O'Donnell in most modern depictions of the Nine Years' War.^[127] Morgan judges Tyrone more harshly than Ó Faoláin,^[301] and compared to other historians, he portrays Tyrone as loyal to the confederacy from the beginning.^[122][317] Generally speaking, contemporary historians see Tyrone as a more compelling figure than O'Donnell.^[127] They also recognise Tyrone's self-serving reasons for entering the war^[37][318] and blame Tyrone for expediting Gaelic Ireland's decline.^[309]

Unsatisfied with the tribute or rents entitled to him as O'Neill clan chief, Tyrone heavily increased taxes on his subjects. Like his predecessor Shane O'Neill, Tyrone introduced conscription to all men within his country, regardless of their social class. He also tied the peasantry to the land, effectively making them serfs, increasing the production of materials and guaranteeing his supply of labour. Eventually, he was generating revenue of £80,000 per year. For comparison, in the 1540s the Tudor monarchy's total tax revenue was about £31,000. Although that figure had certainly increased since then, in financial terms Tyrone was in a position to challenge the English administration.^[45]

This revenue allowed him to purchase muskets, pikes and ammunition from Britain.^[45] Firearms were the primary weapon in Tyrone's army.^[170] In 1590, the Crown allowed Tyrone to obtain six tonnes of lead, ostensibly to weatherproof his hall in Dungannon, but he melted the lead into bullets for his army.^[319][183] Across late 1594 and early 1595, he bought £8,000 worth of gunpowder, lead and firearms from Scotland.^[319]

Tyrone could arm and feed over 8,000 men—impressive for a Gaelic lord. They were trained and equipped with the latest European weapons and tactics,^[45] including pike and shot.^[170] Many of his soldiers were being trained by veterans returned from the Spanish army.^[37] Tyrone also had several Spanish and English military advisors in his pay, the Spanish ones having been sent by Philip II.^[45]

Tyrone's forces were very poor at siege warfare, as evident by their many failures to capture the occupied Blackwater fort.^[37] Tyrone had not been formally trained in regular warfare, hence why most of his successful battles were fought guerilla-style.^[320] Nevertheless with only small forces he was able to defeat the best English generals sent by Elizabeth I and exhaust her resources.^[321] Contemporary English sources lamented how Tyrone was "educated in our discipline and naturally valiant [and had become] worthily reputed the best man of war of his nation".^[308] Henry IV of France declared Tyrone to be one of the best generals of his time.^[322][321]

Wartime propaganda depicted Tyrone as a "Catholic crusader", though many of his contemporaries had their doubts regarding the sincerity of his religious convictions.^[323] It is generally believed that his preoccupations were political rather than religious.^[51][45] In response to Tyrone framing the Nine Years' War as one of religious freedom, the 2nd of Earl of Essex quipped "thou carest for religion as much as my horse".^[37]

Tyrone was born to Catholic parents, but raised amongst Protestants since the age of 8. The Hovenden family were the "least Protestant of the New English settlers". Tyrone's education in the Pale certainly would have anglicised him, but would not necessarily have led to an identity crisis.^[51] In fact, his background gave him the advantage of having allies from both British and Irish backgrounds.^[316]

Tyrone feigned support for the Crown through the 1580s and early 1590s. On visits to Dublin, he would attend Protestant services with the Lord Deputy.^[324][325] Tyrone's 1591 marriage ceremony was performed by a Protestant bishop, because Tyrone wanted the marriage recognised under English law.^[97] Mabel later converted to Catholicism.^[94] Tyrone celebrated Easter 1584 per the Pope's new Gregorian calendar.^[325][232]

Once in open rebellion with the Crown, Tyrone publicly declared that his ultimate objective was to support the freedoms of Catholics by establishing the religion throughout Ireland. This proclamation was predominantly to widen support for his confederacy nationally and abroad, rather than as an authentic statement of belief.^[326] In fact, during 1596 peace negotiations the religious nature of his demands came as a surprise to the Dublin government;^[327] though he was willing to drop his demand for liberty of conscience.^[328] His wartime appeals to Spain typically highlighted the persecution Ireland suffered as a fellow Catholic nation.^[65][318]

Historians Nicholas Canny and Thomas O'Connor believe that Tyrone underwent a genuine religious conversion in the late 1590s.^[307][329] It was reported in August 1598 that O’Neill’s men made confession before the battle. O'Connor believes that Tyrone's sentimental address at the 1599 parley of Dungannon is indicative of a "conversion experience" and goes beyond simple propaganda rhetoric. In his address, Tyrone candidly admitted his initially secular motives on entering the war and described Roman Catholicism as the one true religion.^[330] In the same year Tyrone went on pilgrimage to Holycross in Munster.^[331] In a 1600 memorandum to Pope Clement VIII, as part of the "Faith and Fatherland" campaign, Catholic Archbishop Peter Lombard refuted charges against Tyrone's past: "During his tutelage under the English, [he] never thought or professed anything other than what was orthodox in religion". According to Lombard, O’Neill attended daily mass, even in the field, and regularly confessed and received communion. Lombard admitted that Tyrone "was not yet always equally solicitous, earnest and zealous in the cause of religion", and claimed that it was the Earl's wartime experiences and the providential nature of his success on the field that molded him into a militant Catholic figure.^[332] During his exile, Tyrone interacted with the Pope and partook in traditional pilgrimages,^[291] but his religious views were apparently less dogmatic. This hints that Lombard may have exaggerated Tyrone's devoutness.^[333] Ultimately, Tyrone left no personal record of his faith.^[325]

Although Tyrone lacked the magnetism and charisma of his son-in-law Hugh Roe O’Donnell, he was possessed of a considerable charm that produced confidence in others.^[17][322] This allowed him to build a wide range of contacts, including Old English, Gaelic Irish and New English figures, making him one of the most accomplished Irish politicians of his day.^[37][44] Tyrone's two-faced nature was well-known; as Attorney-General Davies put it, "when the earl was in the presence of Englishmen, he was content to be called earl; but when among his followers, he would be highly indignant, nay, offended, if he was not styled 'O'Neill'".^[334] Tyrone was also a skilled negotiator; he typically played the "good cop" to O'Donnell's "bad cop" during meetings with the government.^[37] O'Donnell was more aggressive and militaristic whereas Tyrone favoured negotiation with their enemies.^[16] He avoided impulsive decisions^[301] and was prepared to use English techniques to fight his enemies. According to historian Edward Alfred D'Alton, for these reasons, Tyrone bore little resemblance to the average boastful and talkative Gaelic lord.^[335]

However, Tyrone was also a ruthless politician not opposed to murdering his opponents for political gain.^[37][17] He was willing to put himself in danger during his many travels to Dublin. Tyrone was overly ambitious in his war aims, particularly since he had not been formally trained in warfare.^[320] His habitual brazenness, his inability to win over the Old English and his over-reliance on Spanish intervention are the major factors that led to his defeat in the Nine Years' War.^[37][322] Conversely to D'Alton, Morgan notes that Tyrone's sudden flight from Ireland, leaving many of his people to suffer in the Plantation of Ulster, displays a selfishness that is typical of a Gaelic lord.^[37] Canny calls Tyrone a "forceful, determined and unscrupulous individual, who would allow nothing, and certainly not loyalty to Gaelic institutional life, to hinder his ambitions". Tyrone's disregard for Gaelic tradition and his Gaelic countrymen became evident following the war's end.^[307] Like his chieftain predecessors, Tyrone spent his life focused primarily on the pursuit and retention of power.^[37]

William Camden, Elizabeth I's official historian, described Tyrone:

"He had a strong body, able to endure labour, watching and hunger: his industry was great, his soul large and fit for the weightiest business: much knowledge he had in military affairs, and a profound dissembling heart: in so much as some did prognosticate of him, that he was born either to the very great good or the great hurt of Ireland".^[336]

In his late teens, he married a daughter of Brian McPhelim O'Neill of Clandeboye^[337]—possibly named Katherine^[338][309] or Feodora.^[339] Brian was in the queen's favour and initially appeared to be a useful ally against Turlough Luineach. In 1574, after being incriminated in a violent conflict with English colonists, Brian and his immediate family were imprisoned, tried for treason and executed. Hugh withdrew any association with his father-in-law by annulling the marriage on grounds of consanguinity.^[56] Thus, the children of this marriage were considered illegitimate by English society.^[340] Tyrone's first wife later married Niall MacBrian Faghartach O'Neill.^[341]

Their children include:

• A daughter who married Sir Ross McMahon in c. 1579^[342]
• Conn^[343] (died c. December 1601),^[344] known as Conn Mac An Iarla.^[345] He served as a captain to Tyrone throughout the war. Conn was wounded near Kilmallock in 1600 and died in December the next year. His son Feardorcha took part in the Flight of the Earls.^[344][346]

Children of Tyrone, possibly by his first wife, include:

• Rose^[h] (fl. 1587 – 1607), who was betrothed to Hugh Roe O'Donnell in 1587. They married in December 1592 and separated in 1595 due to her "barrenness".^[350] In 1598 she remarried to Donnell Ballagh O'Cahan to strengthen ties between O'Cahan and Tyrone;^[275] they separated circa 1607.^[277]
• A daughter who married her first cousin Henry McArt O'Neill, son of Art MacBaron O'Neill^[351]

Hugh married Siobhán O'Donnell (died January 1591)^[81] in June 1574,^[352] beginning his enduring alliance with the O'Donnells of Tyrconnell.^[353] The 1st Earl of Essex announced the marriage on 14 June 1574.^[354] In 1579, Hugh repudiated his marriage to Siobhán^[338] and prepared to wed a daughter of Turlough O'Neill, with the aim of becoming the O'Neill tanist.^[37] The government easily dissuaded Hugh as Turlough's age and ill health meant his death was probably soon anyway.^[355][23] Hugh reconciled with his wife.^[37]

They had two sons and multiple daughters:

• Margaret (fl. c. 1596) who married Richard Butler, 3rd Viscount Mountgarret^[299][356] shortly before 8 October 1596^[357]—possibly in October 1595.^[358]
• Sarah (fl. 1595–1602),^[i] who married Sir Arthur Roe Magennis, 1st Viscount Iveagh^[360] sometime before 4 March 1595^[361] - possibly in 1590.^[362] Through Sarah, Tyrone is an ancestor to the Anglo-Irish Wellesley family.^[363][364]
• Mary (fl. 1608), who married Brian McHugh Og MacMahon.^[365] According to historian George Hill, she is the same woman who married Sir Ross McMahon.^[366][367]
• Alice^[368] (1583^[369] – c. 1665^[370]) who married Randal MacDonnell, 1st Earl of Antrim in 1604.^[371] She was younger than her sisters Sarah and Mary, and older than her brother Hugh.^[369]
• Hugh, 4th Baron Dungannon (c. 1585 – 24 September 1609); he died in Rome and was buried in San Pietro in Montorio.^{[372][373][374]}
• Henry (c. 1586 – 25 August 1610); he became a colonel of an Irish regiment in the Archduke's army.^[375]

Tyrone was betrothed to Mabel Bagenal (c. 1571 – December 1595) in July 1591. They married on 3 August 1591 and had no offspring together.^[94]

In May 1593 the couple clashed over the assassination of Phelim MacTurlough O'Neill - "the countess clapping her hands together was sorry, as should seem, of that which happened, to whom the earl in English spoke with vehemency".^[94] Casway believes that despite the romantic circumstances of their courtship, the marriage "probably ran its course" and Tyrone would have continued with his concubines.^[376] According to Tyrone himself, "because I did affect two other gentlewomen, she grew in dislike with me, forsook me, and went unto her brother to complain upon me to the council of Ireland, and did exhibit articles against me".^[377] Mabel died in December 1595, aged around 24 years old.^[94]

Tyrone married Catherine Magennis (died 15 March 1619) around August 1597.^[208][99] He jilted the daughter of Angus MacDonald, 8th of Dunnyveg, to marry Catherine instead.^[378] It was a political marriage intended to bring the previously neutral Magennis family into the confederacy.^[99]

In 1600, with the confederacy facing failure, Tyrone began drinking heavily and took his frustrations out on Catherine. He considered divorcing her in December 1605, but allegedly she confronted him and warned that if he didn't stop his abuse, she "would discover him so far as to infer again to rebellion or to lose his head".^[272] Catherine reluctantly accompanied Tyrone on his flight. Tyrone's will did not sufficiently provide for her, and she died penniless in Naples.^[379] She had three sons:

• Shane (18 October 1599 – 27 January 1641)^[380] who was recognised by the Spanish court as the successive Earl of Tyrone ("El Conde de Tyrone").^[2][3] He entered the Spanish army and was killed in Catalonia.^[381]
• Conn Ruadh (c. 1602 – in or after 1622), also known as Conn na Creige. He was left behind at the time of the flight, was educated at Eton College as a Protestant, and was committed to the Tower of London on 12 August 1622.^[382]
• Brian (c. 1604^[383] – 16 August 1617), who was found hanged in his room in Brussels under suspicious circumstances, possibly murdered by an English assassin.^{[384][169][385]}

Tyrone also had many illegitimate children or children of unknown maternal origin:

• Margaret O'Neill (fl. 1593–1612), who married Hugh Maguire around May 1593^{[131][366][240]}
• Catherine O'Neill (fl. 1602), who married Henry Oge O'Neill.^[386][387] Their son was Turlough McHenry O'Neill.^[388]
• A daughter, who married Donnell Oneyle^[389]
• A daughter (fl. 1615; probably named Bridget) who was with Tyrone before his death^[390]
• A daughter (fl. 1610) who married Brian Art Roe McEny^[391]

According to historian James Kane, the only authenticated likeness of Hugh O'Neill is part of a fresco in the Vatican. Painted circa 1610, the fresco depicts his attendance at the 1608 canonization of Frances of Rome by Pope Paul V. He stands next to the 1st Earl of Tyrconnell, sometimes mistaken for the Spanish ambassador.^[392][393]

An image of Tyrone appears in Charles Patrick Meehan's 1868 book The Fate and Fortunes of Hugh O'Neill, Earl of Tyrone, and Rory O'Donel, Earl of Tyrconnel.^[394] Dunlop believed that this portrait was "made in [Tyrone's] decrepitude at Rome".^[299] Another illustration of Tyrone is from Primo Demaschino’s La Spada d’Orione (Rome, 1680).^[322]

Lord Dunsany owned a reputed nineteenth-century portrait of Tyrone, from an original in the Vatican.^{[395][396][23]} Exhibited at the 1866 Exhibition of National Portraits,^[397][299] it is apparently developed from a "true likeness" of the Earl.^[23] In the late 19th century, William Holl the Younger produced an engraving of Tyrone based on this portrait.^[37]

The Ulster Museum owns two portraits of Tyrone—both were painted in the 19th century.^[398][399]

• In his 1861 poem Eirinn a' Gul ("Ireland Weeping"), Scottish Gaelic poet William Livingston (Scottish Gaelic: Uilleam Mac Dhunlèibhe) laments the loss of the Irish clan chiefs who led their clansmen in war and provided "leadership of the old and true Gaelic kind". Mac Dhunlèibhe comments that the 19th-century fighters for Irish republicanism had none of the heroic qualities shown by Tyrone, Hugh Roe O'Donnell and Hugh Maguire during the Nine Years' War. Expressing hope for the future of the Irish people, Mac Dhunlèibhe closes by asking where the Irish clan warriors are who charged out of the mist and slaughtered the enemy armies at the Battle of the Yellow Ford and the Battle of Moyry Pass.^[400]
• Flint and Mirror, a 2022 novel by John Crowley, depicts Tyrone as a man whose loyalties are magically divided between the Queen of England and the old gods of Ireland.^[401]

• Hugh O'Neill was played by Alan Hale Sr. in The Private Lives of Elizabeth and Essex (1939).^[402]
• Hugh O'Neill was portrayed by Tom Adams in the Disney film The Fighting Prince of Donegal (1966), with a character name change to Henry O'Neill.^[403][404]
• In the 1971 BBC drama Elizabeth R he was played by Patrick O'Connell. The drama depicts his riverside parley with the 2nd Earl of Essex.^[405]
• The BBC Northern Ireland documentary programme You Thought You Knew - The Plantation depicts several events from Tyrone's life via re-enactment.^[406][407]
• In 2021, it was reported that writer Jack Armstrong was developing a television drama, titled The O'Neill, centered on Tyrone.^[408]

• Tyrone is the central character in Brian Friel's play Making History (1989), which is concerned largely with his third marriage to Mabel Bagenal; Friel describes the marriage as a genuine if ill-fated love affair.^[409] In its original production, Tyrone was played by actor Stephen Rea.^[315] In the 2007 production, for the 400th anniversary of the Flight of the Earls, Denis Conway played Tyrone.^[305]
• Running Beast (2007), a musical theatre piece by playwright Donal O'Kelly with music by the composer Michael Holohan, is based on Tyrone's career. It commemorated the 400th anniversary of the Flight of the Earls.^{[410][411][412]}