Hugh O'Neill, Earl of Tyrone

Hugh O'Neill
Extract of a fresco depicting Hugh O'Neill, painted c. 1610 by Giovanni Battista Ricci
Chief of the Name O'Neill
Reign	15 September 1595 – 20 July 1616
Inauguration	15 September 1595
Predecessor	Turlough Luineach O'Neill
Successor	Dormant
Earl of Tyrone[a]
Tenure	30 June 1585 – 28 October 1614
Predecessor	Conn Bacagh O'Neill, 1st Earl of Tyrone
Successor	Attainted in 1614[b]
3rd Baron Dungannon
Tenure	12 April 1562 – 10 May 1587[3]
Predecessor	Brian O'Neill, 2nd Baron Dungannon
Successor	Hugh O'Neill, 4th Baron Dungannon
Born	c. 1550[c] Oneilland, Tír Eoghain, Ireland (present-day County Armagh)
Died	(1616-07-20)20 July 1616 (aged about 66) Rome, Papal States
Burial	21 July 1616[4] San Pietro in Montorio, Rome
Spouse	Katherine/Feodora O'Neill ​ ​ (ann. 1574)​ Siobhán O'Donnell ​ ​ (m. 1574; died 1591)​ Mabel Bagenal ​ ​ (m. 1591; died 1595)​ Catherine Magennis ​ (m. 1597)​
Issue Detail	Conn Mac An Iarla Rose Alice, Countess of Antrim Hugh, 4th Baron Dungannon Henry Shane, 3rd Earl of Tyrone Brian Conn Ruadh
House	O'Neill dynasty
Father	Matthew O'Neill, 1st Baron Dungannon
Mother	Siobhán Maguire
Signature

Hugh O'Neill, Earl of Tyrone^[a] (Irish: Aodh Mór Ó Néill;^[d] c. 1550 – 20 July 1616) was an Irish lord and key figure of the Nine Years' War. Known as the "Great Earl",^[12] he led the confederacy of Irish lords 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.

Throughout 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.^[13] 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. 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 reinforcements from Spain until the arrival of the 4th Spanish Armada in 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—and possibly believing his arrest for treason was imminent—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 aggressive and warlike ally Hugh Roe O'Donnell, Tyrone was cautious and deliberate.^[14] A consummate liar, he is considered an enigma to historians due to the elaborate bluffs he employed to mislead his opponents.^[15] 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 the last inaugurated Chief of the Name of the O'Neill clan. He had four wives, many concubines and various children.^[16]

Hugh O'Neill was born c. 1550^[c] in the barony of Oneilland, Tír Eoghain (present-day northern County Armagh)—possibly in a crannog such as Marlacoo.^[19][e] The O'Neill dynasty were Tír Eoghain's ruling Gaelic Irish noble family,^[21] and claimed descent from Niall Ruadh of the Cenél nEógain, who was a descendant of legendary high king Niall of the Nine Hostages.^[22] Hugh was the second son of Feardorcha "Matthew" O'Neill, 1st Baron Dungannon (c. 1510–1558) and his wife Siobhán Maguire (died 1600).^[23] Hugh's paternal grandparents were clan chief Conn Bacagh O'Neill, 1st Earl of Tyrone (c. 1484–1559) and Alison Kelly of Dundalk, a blacksmith's wife.^[24] Siobhán was a daughter of Cúconnacht Maguire, Lord of Fermanagh (c. 1480–1537).^[25] Hugh had three brothers: Brian, Cormac MacBaron and Art MacBaron.^[26] During his youth, Hugh was fostered by the O'Hagan and O'Quinn families.^[27]

Family tree

Hugh O'Neill with one of his wives and selected relatives Alison Kelly Conn 1st Earl Tyrone c. 1484–1559 Sorcha O'Neill Mathew 1st Baron Dungannon c. 1510–1558 d.v.p. Siobhán Maguire d. 1600 Shane O'Neill c. 1530–1567 Art MacBaron d. 1618 Brian 2nd Baron Dungannon d. 1562 de jure Earl of Tyrone Hugh Earl Tyrone c. 1550–1616 Siobhán O'Donnell d. 1591 Owen Roe O'Neill c. 1585–1649 Alice O'Neill 1583–c. 1665 Hugh 4th Baron Dungannon c. 1585–1609 d.v.p. Henry 5th Baron Dungannon c. 1586–1610 de jure, d.v.p. Legend XXX Subject of the article XXX Earl of Tyrone 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.^[28] 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,^[29] who employed the ambivalent status of Matthew's paternity to affirm his own claim to the chieftaincy. 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.^[30] 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.^[31]

Shane had Matthew killed in 1558,^[32] placing Hugh and his elder brother Brian^[33] in a dangerous situation. The Dublin Castle administration hoped to use the support of the MacBarons to curb the MacShanes' growing power in Ulster.^[34] At some point between May and August 1558, English statesman Henry Sidney organised the retrieval of the two boys, and for a brief time they stayed at his Dublin residence.^[33]

Hugh and his brother Brian became wards of the Crown. 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.^[35] 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 administration once they came of age and took their places in the Gaelic nobility.^[36]

Giles Hovenden, Hugh's foster father, was an English settler with a pre-existing business connection with Conn Bacagh.^[37] Hugh was raised by Giles's wife Joan Walshe, and she continued to care for Hugh after Giles's death.^[38] Hugh would remain close with his adoptive family throughout the rest of his life.^[35] His foster brother Henry became his chief advisor^[39] and accompanied him on his flight in 1607.^[40] Brothers Henry and Richard led Hugh's troops in the late 1580s.^[41]

Growing up in the Pale amongst English people, Hugh gained a knowledge of English customs and politics. He was able to secure allies such as the Earls of Ormonde and Leicester.^[42] He would have received a basic education, either by attending grammar school or from private lessons.^[43]

Brian was assassinated in 1562 by Shane's tanist Turlough Luineach O'Neill,^[44] and Hugh succeeded him as 3rd Baron Dungannon and heir to the earldom.^[45] Four years later, war broke out between Shane and the Crown. 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.^[43]

In June 1567, Shane was killed by Scots supporting the MacDonnells of Antrim.^[46] Hugh's wardship formally ended when he sued out his livery the following November.^[47] Lord Deputy Sidney brought Hugh, together with a delegation of heirs of Irish clans, to visit the royal court in London to seek permission for the restructuring of Ulster.^[48] This was young Hugh's first visit to England. He finally returned to Ulster in early 1568^[49] having been granted territory in Oneilland. Sidney intended to keep Turlough from crossing south past the River Blackwater, thus creating further discord within the O'Neill family.^[50]

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 (Cormac MacBaron and Art MacBaron had remained in Ulster). According to Sidney, these families "much repined that the great and regal estate of the O'Neill... should be so broken and dismembered".^[47] As he had spent the previous ten years raised as an Englishman, Hugh would have been considered an outsider by these families.^[51] He 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.^[52] The same year, Hugh established his most important and longlasting alliance by remarrying to Siobhán O'Donnell, daughter of chief Hugh McManus O'Donnell.^[53] The O'Donnell and O'Neill clans had traditionally been mortal enemies for centuries.^[54] Hugh O'Neill gained good standing with the 1st Earl of Essex (the English leader of an Ulster colonisation scheme) after joining him in attacks on Turlough.^[55] Essex commended Hugh as "the only man of Ulster... to be trusted and used".^[56] By the early 1570s, Hugh was using his combined support from the Pale and Ulster to put Turlough under heavy pressure.^[47]

On 30 June 1585,^[57] he attended the Irish House of Lords in Dublin, 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.^[58] This was apparently done to suppress his desire for O'Neill chieftainship.^[59] From 1587, the Crown grew suspicious of Tyrone and began attempts at curbing his growing power.^[60] Although Elizabeth I asserted herself as "Queen of Ireland"^[61] and recognised Tír Eoghain as an earldom, it was in practice a sovereign entity and the most powerful Gaelic polity in Ireland. In the mid-1590s, 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. In 1597, Tyrone countered that the queen had given him only what he was owed, and he "ascribed the things which he had gotten to his own scratching in the world than Her Majesty's goodness". During this period, Tyrone regularly bribed government officials, developed alliances with Gaelic clans, and relied on his extensive web of connections.^[62]

Per an arrangement with the Crown, Tyrone 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.^[63] Tyrone wrote to Lord Deputy Arthur Grey on 3 September 1580 that he had been driven by Turlough to take refuge in the woods, and that unless he was relieved he would be compelled to submit to him. Later that year Tyrone was given a troop of horse.^[64] During the Second Desmond Rebellion in Munster, he fought with the English forces against Gerald FitzGerald, 14th Earl of Desmond.^[65] In January 1582, Tyrone captured John Cusack of Alliston-read, who had assisted rebel William Nugent.^[64] In December 1582, he was given temporary use of government footsoldiers to defend the Pale's northern border.^[66] In 1584 he assisted John Perrot against the MacDonnells of Antrim.^[65]

The government quickly became dependant on Tyrone's defence of the Pale. Though the Pale gentry disliked Tyrone, his services were seen as necessary to maintain order in Ireland. In December 1580, Arthur Grey praised Tyrone as "the only Irish nobleman that hath done any service and drawn blood since my coming".^[66] Tyrone was nicknamed "The Queen's O'Neill" for his loyalty to the Crown.^[67] Nevertheless, he feared that the Dublin government might weaken his power by appointing a sheriff in Tír Eoghain.^[42]

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.^[68] The Armada ship La Trinidad Valencera sank in Kinnagoe Bay, Inishowen.^[69] Tyrone sent his mercenary forces to Inishowen to massacre the Spanish survivors, with the intent of keeping in the English government's good graces.^[70] However, Tyrone's response to the Armada is unclear as he himself assisted three noblemen and many commoners^[41] from the Armada shipwrecks at Streedagh Strand in County Sligo.^[71][72] He may have been playing a double game.^[41] Tyrone rescued ordinary seaman Pedro Blanco of La Juliana, who was kept on as his footman throughout the whole of the Nine Years' War,^[72] and also helped stranded nobleman Don Antonio Manrique escape Ulster.^[41] Ultimately about a dozen Spaniards remained in Ireland,^[73] as despite their desire to return home, Philip II of Spain believed they would be of better use as emissaries for Tyrone.^[72]

Tyrone further developed his alliance with the O'Donnell clan—by 1587 his daughter Rose was betrothed to tanist Hugh Roe O'Donnell,^[74] which outraged Turlough.^[75] Via this alliance, Tyrone was able to secure Scottish mercenaries to fight the MacShanes.^[76] Lord Deputy Perrot feared this alliance would threaten government control of Ulster, so in September 1587 he had young O'Donnell kidnapped by merchants. O'Donnell was imprisoned in Dublin Castle, along with two MacShanes, Art and Henry. Tyrone lobbied for O'Donnell's release,^[77] describing the ordeal as "the most prejudice that might happen unto me".^[78]

The O'Donnell clan's military power was key to Tyrone ambitions to overthrow Turlough.^[79] In summer 1590, Conn MacShane O'Neill alleged that Tyrone "did lay down a plot and practised the escape of Hugh Roe" from prison.^[80] O'Donnell made a failed prison break attempt in January 1591.^[81] The same month, Tyrone's wife Siobhán (Hugh Roe's elder half-sister) died.^[82] Around January 1592, Tyrone successfully aided O'Donnell's (and ironically, the MacShanes') escape by bribing officials—most likely Lord Deputy FitzWilliam.^[83] Henry MacShane split from the others in Dublin; O'Donnell and Art MacShane 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^[84] and was inaugurated as O'Donnell clan chief in April 1592.^[85] Art MacShane died in the mountains, fueling speculation that Tyrone had O'Byrne's party kill Art MacShane when they found him. It is more likely however that Art MacShane died of exposure.^[86] Henry was later reincarcerated by Tyrone in Ulster.^[87]

In the north, Tyrone also had to contend with his "grievous enemy" Nicholas Bagenal, the Marshal of Her Majesty's Irish Army.^[88] In 1589 Nicholas Bagenal described Tyrone "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] In autumn 1590, Gaelic 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.^[91] Tyrone, who had owned part of MacMahon's lands under brehon law, was passed over in favour of Henry Bagenal.^[92] Furthermore, Tyrone's authority was directly challenged when Henry was named chief commissioner of Ulster on 18 May 1591.^[93]

Soon afterwards, Tyrone began to woo Mabel, Henry's younger sister.^[94] This was only months after the similarly-timed deaths of Nicholas Bagenal (in February) and Tyrone's late wife Siobhán (in January).^[95] Tyrone professed his love and asked for Mabel's hand in marriage. Alarmed, Henry 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] After a dinner at Turvey, the Earl distracted Barnewall while his ally William Warren escorted Mabel to Warren's house in Drumcondra.^[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] 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.^[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.^[100] Mabel has been dubbed the "Helen of the Elizabethan Wars", a sobriquet that historians decry as being overly simplistic.^[101] Historians believe that Tyrone would have recognised the advantages of marrying into the powerful Bagenal family.^[102] The marriage was his attempt to merge the Bagenals' interests with his own^[103] and to neutralise Henry Bagenal's growing power.^[104]

Henry Bagenal was outraged. He refused to pay his sister's £1000 dowry, even two years after the marriage, and had Tyrone's previous divorce investigated,^[105] though it was found to be valid.^[106] Because of this dramatic episode and their roles as opposing commanders during the Nine Years' War, Bagenal and Tyrone have been called "arch-enemies",^[107] "nemeses"^[108] and "arch-rivals".^[109]

The aging 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.^[42]

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, the ancient ceremonial site where the O'Neill chiefs were traditionally inaugurated. It turned out that Turlough had not died but had only fallen into a brief coma from alcohol poisoning.^[110] Tyrone's constant disputes with Turlough were utilised by the government to weaken the O'Neill clan.^[47] 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.^[111]

In January 1590, Tyrone organised the execution of his MacShane cousin Hugh Gavelagh, who had exposed to FitzWilliam that the Earl was making treasonous dealings with the Spanish.^[112] When the MacShanes refused to submit to Tyrone in exchange for Gavelagh's life, Tyrone had Gavelagh hanged at Dungannon by public executioners.^[113][f] Tyrone proceeded to London where he sufficiently defended himself against England's Privy Council by alleging that Gavelagh was guilty of various crimes.^[49] Tyrone was placed under house arrest but released by letters of commendation from FitzWilliam and the Dublin government.^[113]

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.^[120] The Earl had effectively become the ruler of Tír Eoghain.^[121]

By late 1592, the Crown's advances into Gaelic territory, as well as the recent executions of chieftains MacMahon (in 1590) and Brian O'Rourke (in 1591) had created a fierce resentment in the Gaelic nobility and Irish Catholic clergy.^[122] In early April 1593, English captain Humphrey Willis was appointed by FitzWilliam as Sheriff of Fermanagh; he entered the kingdom with at least 100 men and began pillaging and raiding, to the fury of Fermanagh's chieftain Hugh Maguire. Morgan states that this was a blatant move to weaken Tyrone's power by subjugating Maguire.^[123]

After Willis' first offensive,^[123] a meeting took place at Enniskillen Castle on 8 May, with O'Donnell, Maguire and Brian Oge O'Rourke present.^[109] The Sheriff of Monaghan alleged that Tyrone also attended the meeting.^[124] The noblemen were assembled by Edmund MacGauran,^[125] a Catholic Archbishop recently returned from Spain with promises that Philip II would support oppressed Irish Catholics if they proved themselves by launching prior military action.^[126] MacGauran advised that the noblemen sign a letter addressed to Philip II which emphasised their oppression and which requested urgent reinforcements from the Spanish army. Tyrone did not sign MacGauran's letter.^[127] Catholic Archbishop James O'Hely was tasked with delivering the confederates' messages—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."^[129]

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.^[130] Tyrone often used his relatives and followers to make war on his behalf and it is unlikely they would have assisted Maguire without Tyrone's permission.^[131] Willis and his men in a church took refuge in a church for about a week until Tyrone intervened and negotiated their safe rescue out of Fermanagh.^[109] This conflict is considered to mark the start of the Nine Years' War.^[132]

Subsequently Maguire launched raids across Connacht. Tyrone's nephews—sons of his brother Art MacBaron—also engaged in campaigns against loyalist clans.^[133]

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.^[134][g] Hiram Morgan represents Tyrone as a master strategist who was complicit in rebellion from the start^[135][136] but feigned loyalty to the Crown for strategic reasons.^[137] James O'Neill agrees that Tyrone was the chief architect of the rebellion, and states that the conflict in Fermanagh allowed Tyrone to divert English forces and thus suppress English clients in east Ulster.^[138] 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.^[42] Nicholas Canny similarly states that Tyrone aspired to be the "queen's man in Ulster", was passed over in favour of Henry Bagenal,^[103] and reluctantly pushed into rebellion to prevent his followers defecting to his brother Cormac MacBaron.^[139] 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.^[140] 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".^[141] McGettigan and Morgan disagree over Tyrone's prominence in the confederacy.^{[142][143][137]}

By the beginning of the Nine Years' War, Tyrone had formally allied with O'Donnell and Maguire via their marriages to his daughters.^[144][42] O'Donnell married Tyrone's daughter Rose in December 1592,^[145] and Maguire married Tyrone's daughter Margaret around May 1593.^[146] Around August 1593, Maguire stated to a spy that Tyrone had pushed him into rebellion and "promised to assist him and bear him out in his war".^[147] By April 1594, Geoffrey Fenton noted that the confederates "have secretly contracted a strong league amongst themselves, leaving out the name of the earl... to be an instrument to work for them when opportunity would serve".^[148] The English government had their suspicions that Tyrone was plotting against them, but he repeatedly proved his loyalty in battles against Irish uprisings.^[135] Per Idiáquez's notes to Philip II, the early confederates operated under the understanding that Tyrone belonged to their cause but publicly hid his true allegiance.^[129]

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.^[149] 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.^[150]

By late April, there were more allegations against Tyrone from Irish lords Hugh McHugh Dubh O'Donnell and Hugh Magennis. 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.^[151] When Elizabeth I was later briefed on the proceedings, she concluded that Tyrone should have been arrested.^[152]

Tyrone met with Maguire in early August—within weeks Maguire launched raids into Monaghan.^[153]

Maguire's attacks provoked a large-scale military expedition to be led by Bagenal.^[154] Tyrone was able to deflect the past allegations and prove his loyalty to the Crown by agreeing to assist Bagenal.^[155] On 26 September he joined Bagenal and his army at Enniskillen, but the Earl had brought far fewer troops than he had promised.^[156] 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.^[157]

Their combined forces moved on Maguire's positions on 10 October. O'Donnell was in nearby Ballyshannon when the battle was taking place, but he was ordered by Tyrone not to reinforce Maguire.^[158] It was estimated that 300 Irish soldiers were killed.^[159] Though Maguire's forces were not directly engaged, FitzWilliam was convinced Maguire's revolt had been stopped. 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.^[160] Tyrone protested against Bagenal's accusation by claiming that Bagenal and FitzWilliam were conspiring to rob him of the honour he was due.^[161]

More allegations emerged in 1594. Captain Willis, Sir Edward Herbert and Joan Kelly claimed Tyrone was ordering the Irish raids. He would apparently meet with confederate soldiers at Slieve Beagh under the pretense that he was going hunting. In March, it appeared that Tyrone was behind the burning of Bagenal's lands.^[162] The same month, following talks with Tyrone and other Ulster lords, government commissioners surmised that a confederacy had been established between the Ulster lords, and that Tyrone was the leader.^[163] Despite pressure from Tyrone to feign neutrality,^[164] O'Donnell joined Maguire in besieging Enniskillen Castle in early 1594. This signaled to the government O'Donnell's status as a confederate commander.^[165] O'Donnell pushed Tyrone into supplying further soldiers to the confederacy, by warning that "he must consider [Tyrone] his enemy, unless he came to his aid in such a pinch". Tyrone subsequently sent reinforcements under Cormac MacBaron to the Battle of the Ford of the Biscuits.^[166]

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 six days later to tender his submission. Tyrone admitted his failure to prevent the treasons of his followers, but the meeting was interrupted with Bagenal accusing Tyrone of disloyalty to the Crown. Most of the councillors were friendly with the earl, and to Bagenal's frustration, Russell allowed Tyrone to leave in safety. The queen was furious that Tyrone had not been arrested and she scolded Russell in private, denouncing it "as foul an oversight as ever committed in that kingdom".^[167]

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.^[168] The evidence against Tyrone became too great to ignore, and the government deemed an immediate attack essential.^[169] A considerable royal force arrived in Waterford on 19 March, but Tyrone had already managed to invade and burn Louth on 17 February.^[170]

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,^[42][166] such as his brother Cormac MacBaron.^[135]

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.^[171] 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.^[172]

In a report to the Lord Deputy, veteran soldier John 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. Ralph Lane recorded 31 killed and 103 wounded, though he later admitted to concealing the true number of wounded and dead.^[173] The Irish victory shocked the English and was a severe setback early in the war. On 24 June, Tyrone was proclaimed a traitor at Dundalk.^[174] The queen's advisor Lord Burghley 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.^[175]

Upon Turlough's death, Tyrone travelled to Tullyhogue Fort where he was officially inaugurated as O'Neill clan chief on 15 September.^[176] Tyrone was the last inaugurated chief of the O'Neill clan,^[177] and he appointed Cormac MacBaron as his tanist.^[178] 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."^[179]

Tyrone and O'Donnell opened communications with Philip II and his general Juan del Águila. In letters to the king—intercepted by English forces in September—they promoted themselves as champions of the Roman Catholic Church.^[180] 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.^[181] In fact Philip II had sent a ship to Ireland in March 1594 for the purpose of gathering intelligence, but the crew died in a shipwreck off Biscay.^[182]

Tyrone sought to delay the war in order to buy time for the arrival of Spanish troops.^[183] 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.^[184] After the discovery of the confederacy's letters to Spain, Elizabeth I emphasised the urgency of completing negotiations to her commissioners.^[185] Tyrone wore down commissioners by repeatedly objecting to their conditions. He eventually signed a cessation of arms on 27 October.^[184] This pardoned certain confederates and give them local autonomy. It also acknowledged a tolerance of Catholicism.^[186] The confederacy proved to be unsatisfied with the terms,^[187] but ultimately Tyrone successfully managed to defer all-out war for more than two years.^[188]

Tyrone's wife Mabel died in December 1595.^[189] The same month, Tyrone's partnership with O'Donnell came under strain as Rose had not born O'Donnell children. With Tyrone's consent, O'Donnell separated from Rose in hopes of a marriage alliance with the daughter of the neutral 3rd Earl of Clanricarde.^[190] This plan came to naught. Tyrone sent his secretary Henry Hovenden into Tyrconnell to handle the situation,^[191] and O'Donnell eventually took Rose back.^[192]

Further negotiations to develop a peace treaty were almost complete by May.^[193] In April 1596, Philip II had three ships sent to Ireland to exhort the confederates to continue the war against England.^[194] Spanish captain Alonso Cobos arrived at Tyrconnell in May and dined with the confederates at Lifford.^[195] Following a secret talk between Cobos and Tyrone, O'Donnell and Cormac MacBaron, 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.^[196] 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 government that Tyrone intended the war to encompass all of Ireland.^[197]

Tyrone declared to the government that he and O'Donnell had rejected further meetings with the Spanish, and he submitted Philip II's letter as a show of transparency. However, Philip II soon learned of Tyrone's maneuver and was indignant at this breach of trust. In defense, Tyrone shifted blame onto his secretary.^[179] Tyrone's strategy became more combative once he received promises that a large-scale Spanish military expedition would be incoming. He imported regular shipments of munitions and his ally Fiach McHugh O'Byrne engaged in a series of skirmishes against Lord Deputy Russell's troops. Tyrone intentionally gave the government the impression that peace was imminent as misdirection from the impending Spanish expedition.^[198] 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.^[199]

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.^[200] On 22 May, Thomas Burgh, 3rd Baron Burgh, took over as Lord Deputy. Burgh refused to entertain Tyrone's excuses and launched a two-pronged attack on Tyrone and O'Donnell's territories.^[201] On 6 June, royal 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.^[200] Burgh died from illness in October.^[202]

It was anticipated that Tyrone would seize this opportunity to overrun the Pale. Instead, he requested a truce to facilitate peace negotiations.^[203] 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.^[204] Tyrone presented a document of grievances which listed offences committed by the government against the Irish.^[205] 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.^[204]

In early 1598, administrator Conyers Clifford induced various confederates (most notably founding member Brian Oge O'Rourke) to leave the confederacy and fight for the Crown. Many of the turncoats rejoined the confederacy in fear after O'Donnell executed their men. O'Rourke's betrayal "did amaze Tyrone"—he became paranoid and temporarily arrested various confederate clan chiefs, including Hugh Maguire.^[206]

Government commissioners abandoned negotiations by spring 1598, recognising that O'Donnell and Tyrone were intentionally impeding the peace process.^[207] When the truce expired in June, Tyrone resumed hostilities by besieging the Blackwater Fort. Bagenal, motivated by his animosity towards Tyrone, advocated to lead an army to relieve 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. The confederates had prepared ditches in the ground to obstruct the enemy.^[208] Half of Bagenal's 4,000 men were killed, including Bagenal himself,^[209] who was struck by a bullet after lifting his visor.^[210]

The confederacy's success at the battle was the greatest victory by Irish forces against England,^[211] and it sparked a general revolt throughout the country, particularly in Munster. Tyrone has been criticised for failing to immediately capitalise on his victory, however it is possible he sustained heavy losses from the battle.^[205] One estimate puts Irish losses at the battle of the Yellow Ford at around 200 killed.^[212] News of the battle spread across western Europe, prompting Philip II to send a congratulatory letter to the confederates. Unfortunately for Tyrone, Philip II died the following month; he was succeeded by his son Philip III.^[213]

After much hesitation, Elizabeth I selected her royal favourite Robert Devereux, 2nd Earl of Essex, as the new Lord Deputy; he reluctantly took on the role.^[214] Essex had an existing connection with Ireland and Tyrone, as his father Walter Devereux was one of Tyrone's early allies.^[215] 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".^[216]

Essex landed in Ireland on 15 April 1599 with an expeditionary force of 17,000 troops and 1,500 horses—the largest English army dispatched to the country.^[217] Despite his resources, Essex's campaign proved to be a failure. He led months of ill-managed operations in the south of Ireland, lost hundreds of soldiers to disease, desertion and warfare (particularly the Battle of Curlew Pass),^[218] and executed every tenth officer for cowardice.^[219] The confederates felt the English threat had weakened enough that they could safely travel with their wives—Tyrone's fourth wife Catherine Magennis, whom he had married in August 1597, was present at his camp in June 1599 during her first pregnancy.^[220] Towards the end of July, Essex received letters from the queen with peremptory orders to travel northwards and attack Tyrone with all speed.^[221]

Tyrone lightly skirmished with Essex's forces as they approached the borders of Ulster.^[222] Essex's numbers had dwindled to only 4,500^[223] and Tyrone, whose army far outnumbered Essex's, refused to give battle.^[224] Tyrone sent his counsellor Henry O'Hagan on 5 September to request a parley,^[225] and Essex stubbornly agreed only after Tyrone had asked three times.^[222]

On 7 September, at the ford of Bellaclinthe on the River Lagan, Tyrone met Essex for a half-hour parley.^[226] Tyrone waded his horse into the river whilst Essex stayed on the bank.^[227] Tyrone 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. He once again demanded liberty of conscience, to Essex's contempt, and also demanded a single treaty wherein the Crown would restore confiscated Irish lands to their former owners.^[228] Essex was not familiar with Tyrone's wily nature and gullibly accepted these proposals.^[229] Because their parley was conducted privately, out of earshot of their armies,^[227] Essex was later accused of conspiring with Tyrone to seize the thrones of England and Ireland.^[223] These accusations are far-fetched and obviously defamatory.^[228][h]

A more formal meeting occurred later that day with six witnesses on each side attending. Ultimately an informal truce of six weeks was arranged. Essex left Ireland on 24 September and was quickly placed under house arrest and removed from his post.^[231] Tyrone broke off the truce upon hearing of Essex's arrest, though English statesman Robert Cecil was weary of the war and remained intent on peace.^[223] Following a failed uprising, Essex was eventually executed for treason on 25 February 1601.^[232]

On 5 November 1599, in a strong position after Essex's failed campaign,^[233] Tyrone issued a public proclamation declaring a holy war against non-Catholics.^[234] He sent a list of 22 proposed terms for a peace agreement to Queen Elizabeth, including a request on the status of future Lord Deputies. This amounted to accepting English sovereignty over Ireland as a reality while hoping for tolerance and a strong Irish-led administration.^[235][236] 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.^[237]

Tyrone's main goal was now to win over Ireland's English-speaking Catholic population (the "Old English").^[238] 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.^[239] He declared that "if [he] had to be king of Ireland without having the catholic religion, [he] would not the same accept".^[240] Tyrone gained a token of encouragement from Pope Clement VIII, who entitled him "Captain General of the Catholic Army in Ireland".^[241] In late 1599 and early 1600, the Earl was in Munster on pilgrimage.^[242] He supported the claim of James FitzThomas Fitzgerald (the Súgán Earl) to the Earldom of Desmond, and recognised Florence MacCarthy as the MacCarthy Mor at Inniscarra.^[233] However, the Munster expedition ended in failure when in early March, confederacy commander Maguire was shot and killed by royal forces during a reconnaissance mission near Cork. Maguire's death was a major loss to the confederacy and prompted Tyrone to abruptly return to Ulster.^[243] 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.^[244]

In April 1600, a Spanish ship arrived in Ireland bearing considerable supplies of munitions for the confederacy.^[245] Tyrone stimulated the Irish-Spanish alliance by sending his son Henry to Spain in April 1600.^[246] At this time controversial Jesuit James Archer operated as his representative at the Spanish court.^[247]

In February 1600, Charles Blount, 8th Baron Mountjoy, Essex's successor as Lord Deputy, arrived in Ireland.^[248] Mountjoy posed a major threat to Tyrone as he began immediately revitalising and restoring confidence in the royal army.^[249] He assigned commanders George Carew and Henry Docwra to north-west Ulster and Munster respectively.^[250] In May 1600 the Crown achieved a strategic breakthrough when Docwra, at the head of a considerable army, took up a position at Tyrone's rear in Derry. Docwra persuaded several unsatisfied confederacy members to defect to the Crown. These Irish turncoats, particularly Niall Garve O'Donnell, Arthur O'Neill and Sean O'Doherty, emboldened the royal troops and allowed Docwra to significantly weaken Tyrone's forces.^[251]

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.^[252][253] Upset with setbacks, Tyrone 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.^[254] In October 1601, a long-awaited armada from Spain occupied the port town of Kinsale under Spanish commander Juan del Águila.^[255] Tyrone was displeased at the small size of the force and the fact that they had landed in the south—moving his army there would mean leaving Ulster unprotected.^[256] Mountjoy rushed to contain the Spanish,^[257] but it was not until the beginning of November that Tyrone was able to put his army in motion. Tyrone and O'Donnell marched separately from the north, through territories defended by Carew, in the depths of a severe winter, gaining little support en route. Tyrone's army united with O'Donnell's at Bandon on 15 December.^[258]

The Irish presence at Kinsale trapped the English army between the confederates and the Spaniards.^[259] Juan del Águila urged for a prompt combined attack on the English, but Tyrone and O'Donnell were apparently conflicted in their preferred strategy.^[260] According to 17th-century Irish sources, the brash O'Donnell convinced Tyrone to attack against his better judgement; this account is not unanimously accepted by historians.^[261] It is possible the story was retroactively developed to excuse the defeat at Kinsale, or perhaps was an attempt by biographer Lughaidh Ó Cléirigh to enhance O'Donnell's role in the war.^[262] O'Donnell had previously induced Tyrone into a full frontal assault in 1597, so this narrative is not out of the question.^[261] Morgan claims it was the pressure from the beleaguered Spaniards that wore down Tyrone,^[263] and that the confederates also had their reputations on the line.^[257] In any case, Tyrone abandoned his characteristically cautious military approach and resolved to make an immediate joint attack.^[264]

On the morning of 24 December 1601, Tyrone's force of 4,000 men took their position. Mountjoy spotted the soldiers and ordered an immediate attack.^[265] Tyrone retreated but Mountjoy's cavalry routed the fleeing soldiers. 1,200 men were killed and another 800 were wounded. The battle was a disaster for Tyrone and nullified years of his wartime success.^[257] He was strongly in favour of attempting another siege but was unable to persuade his surviving soldiers.^[266] The defeat at Kinsale was a fatal blow to the confederacy.^[267]

O'Donnell left for Spain to seek further military assistance from Philip III. The confederate commanders separately returned to their territories. In the haste to leave Munster, 140 of Tyrone's men drowned while passing the Blackwater.^[268] Meanwhile the Crown's army swept the country. English forces began to close in on Tyrone—Mountjoy from the south, and Dowcra and Arthur Chichester from the north.^[269] Mountjoy destroyed the traditional O'Neill inauguration stone at Tullyhogue.^[270] 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.^[269]

English forces destroyed crops and livestock in Ulster in 1601–1602,^[271] particularly 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 in July 1602,^[272] which drastically weakened the Earl's power.^[273] In June 1602 Tyrone destroyed his capital at Dungannon and retreated into the woods of Glenconkeyne.^[274] Despite O'Donnell's petitioning to Philip III, the promised Spanish fleet was repeatedly delayed due to a lack of resources.^[275] O'Donnell died in Simancas of a sudden illness on 30 August.^[276] The Spanish government subsequently abandoned plans to support the confederacy and instead sought a peace treaty with England.^[277]

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.^[278] Whilst in Glenconkeyne, exactly a year after the defeat at Kinsale, Tyrone wrote to Philip III asking for a Spanish warship to be sent to Ulster.^[279] The royal army's use of scorched earth tactics led to famine across 1602–1603,^[269] with conditions so extreme that the local population were reduced to cannibalism.^[257] In January 1603, Mountjoy admitted to Cecil that capturing the Earl would be up to chance, as despite his efforts he could not convince anyone to betray Tyrone.^[280]

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.^[280] However with the queen on her deathbed, Mountjoy reopened negotiations with Tyrone in early 1603.^[281] Tyrone made his submission to Mountjoy on 30 March at Mellifont Abbey. The queen had died on 24 March but Mountjoy concealed this news until the negotiations had concluded.^[282] 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.^[42] These were particularly generous terms.^[283] On 8 April Tyrone renewed his submission before Mountjoy and the council in Dublin.^[284] This was where Tyrone heard of the queen's death;^[280] he apparently wept with frustration.^[42] After Tyrone's submission, the remaining confederates followed suit. This marked the end of the Nine Years' War.^[285]

On 30 May 1603, Tyrone sailed to Holyhead with Mountjoy and Niall Garve O'Donnell on their journey to meet Elizabeth's successor James I.^[286] As Tyrone traveled through Wales, widows of British soldiers hurled "dirt and stones at the Earl... and [reviled] him with bitter words".^[287] Tyrone and Rory O'Donnell (Hugh Roe O'Donnell's younger brother)^[288] arrived at London on 4 June^[289] and presented themselves at Hampton Court.^[252] James I confirmed Tyrone in his title and core estates with a new patent. Tyrone was also bold enough to request the lord presidency of Ulster, but was only allowed lieutenancy of Tír Eoghain and Armagh.^[290] Rory was created 1st Earl of Tyrconnell.^[291] Many English courtiers were greatly incensed at the gracious reception the confederates received. 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". Tyrone even went hunting with the new king.^[285][i] 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.^[285]

Tyrone returned to Ireland in September 1603^[293] and began rebuilding his estates, an easy task under the reserved government of Mountjoy's successor George Carey.^[285] O'Cahan's surrender to Docwra was under the promise that he would own his land independently under English law.^[294] However, the Treaty of Mellifont's terms allowed Tyrone to retain his authority over these lands. 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, and was further frustrated by the harsh various levies and taxes Tyrone imposed to rebuild his wealth.^[295]

Arthur Chichester became Lord Deputy in February 1605.^[296] 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. Chichester was also antagonistic to Tyrone,^[297] forcing him to attend Protestant services and accusing him of plotting with Spain.^[42] It became clear to Tyrone that the restoration of his earldom meant little.^[298] Tyrone's marriage became strained and in December 1605 he considered divorcing from Catherine. Chichester sent officer Toby Caulfield to recruit Catherine as a double agent, but she dismissed this out of hand.^[299]

Tyrone lost his support from the council when Mountjoy died in April 1606.^[300] 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.^[301] Attorney-General for Ireland 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.^[302] Montgomery also encouraged O'Cahan to leave his wife, Tyrone's daughter Rose (former wife of Hugh Roe O'Donnell),^[303] noting that "the breach between [O'Cahan] and his landlord [Tyrone] will be the greater by means of [Tyrone's] daughter".^[304] In March 1607 O'Cahan repudiated his marriage to Rose^[305] and before the end of the year he had married another woman,^[306] whilst still retaining Rose's dowry^[304] against Tyrone's wishes.^[307] It is clear that government officials were harnessing O'Cahan's hostility to orchestrate Tyrone's undoing.^[302] Additionally, Tyrone's continued correspondence with Spain broke his promises made at Mellifont.^[279]

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.^[289] 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.^[302] Tyrone's violent behaviour towards O'Cahan greatly damaged his cause, and it was ordered that two-thirds of the lands should remain in O'Cahan's possession. The government, unable to come to a definite conclusion on the remaining third, referred the matter to the king's decision.^[289][308] Tyrone was ordered to present himself in London at the beginning of Michaelmas term (late September).^[309]

In 1607, the Earl of Tyrconnell exposed a plot to seize Dublin Castle, hopefully with Tyrone's involvement, during a conversation with Richard Nugent, Lord Delvin.^[310][311] By September, Tyrconnell's supposed plot was known to the government.^[311] Information reached Tyrone that the government intended to imprison him, or possibly execute him, once he got to London; it is unclear from where he obtained this intelligence.^[309] Historians are undecided on whether this plot actually existed and if the government intended to arrest Tyrone.^[312] The exact cause of Tyrone's flight is a matter of controversy among historians,^[313] though he certainly believed that his arrest was imminent.^[314] A group of confederate allies, including clan chief Cuconnacht Maguire, seaman John Rath, Tyrconnell's secretary Matthew Tully and nobleman Donagh O'Brien, sent a French vessel to Ulster to facilitate an escape.^[315] Tyrconnell already planned to leave the country and flee to Spain, and he convinced Tyrone to come with him.^[311] Tyrone was at Slane with Chichester when news of the vessel's arrival reached him.^[316] He seemed to have come to an immediate snap decision.^[317] Attorney-General Davies recollected that Tyrone left Slane in an unusually solemn manner, farewelling every servant and child in the house.^[318]

At midday on 14 September 1607,^[319] Tyrone and Tyrconnell embarked at Rathmullan on a voyage bound for A Coruña. Accompanying them were their extended families and retainers, numbering about ninety-nine people.^[320] The Flight is seen to symbolically mark the collapse of Gaelic Irish society.^[321] 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".^[322] The ship was driven by storms and contrary winds into port at Quillebeuf in Normandy. Henry IV of France refused English demands to hand over the refugees and—though denying them from proceeding to Spain—permitted them passage to the Spanish Netherlands.^[323] Despite the earls' petitioning, Philip III would not allow the refugees to enter Spain for fear of violating the 1604 Anglo-Spanish peace treaty.^[324] Spain was on the verge of bankruptcy and could not afford another war with England.^[325] In mid-December, the refugees received news that Archduke Albert VII wanted them to leave his states. On 28 February 1608, Tyrone and his companions (now reduced to thirty-two people on horseback plus the women in a coach) left Leuven to travel southwards.^[326] The nobles left their younger children behind in Leuven under the care of Irish Franciscans at St Anthony's College.^[327]

On 29 April, Tyrone and Tyrconnell were welcomed into Rome by a large procession of cardinals. The two earls met Pope Paul V the next day.^[328] The journey to Rome was recorded in great detail by writer and passenger Tadhg Ó Cianáin.^[329] In November 1607 the flight was proclaimed as treasonous by James I.^[330] A bill of attainder was passed against Tyrone by the Parliament of Ireland on 28 October 1614.^[1]

The pope granted Tyrone a monthly pension of a hundred crowns,^[331] a house (on Borgo Vecchio) rent-free, together with an allowance of bread and wine for ten persons.^[332] Philip III offered a sum of 700 ducats a month for the group of about 50 refugees. The earls were displeased with the small size of their pension and their reduced lifestyles.^[333] Catherine became highly distressed by the Roman climate and her separation from her children, though Tyrone forbade her from relocating to Leuven.^[327] 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.^[334] In July 1608 Tyrconnell died of a fever, and by 1610, Tyrone's eldest sons Hugh and Henry had also died. Tyrone continued to petition Philip III for his assistance, including for help during O'Doherty's rebellion, but had no success.^[335]

Tyrone quickly became disillusioned with his exile and yearned to return to his position in Ireland.^[336] For the rest of his life, he did not give up the possibility of returning to Ireland.^[337] English spies were monitoring Tyrone during this period. In 1613 the English Crown briefly discussed with Tyrone a potential reconciliation, but this fell apart as the political situation changed.^[338] 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".^[339] 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".^[340]

It has been alleged that Tyrone became blind in his last years, but this is probably propaganda spread by Chichester. Tyrone remained in good health throughout 1615 but he became seriously ill in January 1616.^[341] He died in Rome on 20 July.^[342]

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 O'Sullivan Beare, 1st Count of Berehaven], from the Groyne [A Coruña]; Raymond Burke, from Lisbon; one who calls himself Desmond from Bayonne in Galicia; and the Archbishop of Tuam, from Alcalá, with many others of less note, but captains and of good quality."^[343]

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.^[344] 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".^[345] This explains the brevity of the inscription on Tyrone's tomb.^[346] Allegedly, his bones were moved seven years after burial, and his hands were found to be perfectly intact.^[347] The original tombstone was lost in 1849 during the Risorgimento. In 1989 Tomás Ó Fiaich laid a new marble plaque with the same inscription.^[348][349]

Upon news of Tyrone's death, the court poets of Ireland engaged in the contention of the bards.^[350][351] His presence in Europe was a constant source of concern for the English, and his death came as a welcome relief.^[352] The Annals of the Four Masters, compiled in 1636,^[353] 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".^[352] Conversely, because Tyrone had deserted his people in 1607, his own generation expressed little admiration for him.^[354]

Historian James MacGeoghegan rehabilitated Tyrone's image in the seventeenth century.^[355] 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.^[356] Mitchel also credited Tyrone with the development of modern Irish nationalism and the concept of the first independent Irish state.^[357] 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,^[358] whose traditional Celtic upbringing, sensational prison break saga and tragic early death made him a Gaelic Irish martyr and national hero.^[142][359]

Seán Ó Faoláin's biography The Great O'Neill (1942) is the most influential modern work on Tyrone.^[360] It attracted a large readership but is today considered inaccurate and overdramatised.^[361][263] 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.^[362] Hiram Morgan's book Tyrone's Rebellion (1993), which focuses on Tyrone's life up to 1596,^[363] restored the Earl to the status he was formerly afforded by contemporary English commentators.^[358] Tyrone now overshadows O'Donnell in most modern depictions of the Nine Years' War.^[142] Morgan judges Tyrone more harshly than Ó Faoláin,^[352] and compared to other historians, he portrays Tyrone as loyal to the confederacy from the beginning.^[135][136] Generally speaking, present-day historians see Tyrone as a more compelling figure than O'Donnell.^[142] Tyrone's self-serving reasons for entering the war are also recognised.^[364]

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.^[42] In his day, he was one of the richest lords in Ireland.^[365]

Tyrone introduced a "military revolution" to Ireland with his use of firepower and field fortifications in Irish warfare.^[347] His revenue allowed him to purchase muskets, pikes and ammunition from Britain.^[42] Firearms were the primary weapon in Tyrone's army.^[173] 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.^[366][194] Across late 1594 and early 1595, he bought £8,000 worth of gunpowder, lead and firearms from Scotland.^[366]

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,^[42] including pike and shot.^[173] Many of his soldiers were being trained by veterans returned from the Spanish army.^[131] Tyrone also had several Spanish and English military advisors in his pay, the Spanish ones having been sent by Philip II.^[42]

Tyrone's forces were very poor at siege warfare, as evident by their many failures to capture the occupied Blackwater fort.^[367] Tyrone had not been formally trained in regular warfare, hence why most of his successful battles were fought guerilla-style.^[368] Nevertheless with only small forces he was able to defeat the best English generals sent by Elizabeth I and exhaust her resources.^[369] 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".^[355] Henry IV of France declared Tyrone to be one of the best generals of his time.^[370]

Wartime propaganda depicted Tyrone as a "Catholic crusader", though many of his contemporaries had their doubts regarding the sincerity of his religious convictions.^[371] It is generally believed that his preoccupations were political rather than religious.^[43][372] In response to Tyrone framing the Nine Years' War as one of religious freedom, the 2nd Earl of Essex quipped "thou carest for religion as much as my horse".^[223]

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.^[43] In fact, his background gave him the advantage of having allies from both British and Irish backgrounds.^[373]

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.^[374] 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.^[375] Tyrone celebrated Easter 1584 per the Pope's new Gregorian calendar.^[376]

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.^[377] In fact, during 1596 peace negotiations the religious nature of his demands came as a surprise to the Dublin government;^[378] though he was willing to drop his demand for liberty of conscience.^[379] His wartime appeals to Spain typically highlighted the persecution Ireland suffered as a fellow Catholic nation.^[380]

Historians Nicholas Canny and Thomas O'Connor argue that Tyrone underwent a genuine religious conversion in the late 1590s.^[381] 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.^[382] In the same year Tyrone went on pilgrimage to Holycross in Munster.^[242] 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.^[383] Lombard did not meet Tyrone until the latter arrived in Rome, so most of his writings are based on reports from hundreds of miles away.^[384] During his exile, Tyrone interacted with the Pope and partook in traditional pilgrimages,^[334] but his religious views were apparently less dogmatic. This hints that Lombard may have exaggerated Tyrone's devoutness.^[385] Ultimately, Tyrone left no personal record of his faith.^[386]

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.^[388] Tyrone's charm extended even to Queen Elizabeth; letters patent reference him as "one Her Majesty would not willing deny any favour, knowing his devotion to her".^[389] 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.^[390][391] Historians have remarked on Tyrone's cultural fluency, which was highly unusual for Gaelic lords of the era. Tyrone's ability to speak English (unlike his Irish brethren) gave him a clear advantage in dealings with English politicians.^[392]

Tyrone's two-faced nature was well-known; as Attorney-General John 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'".^[393] Tyrone was also a skilled negotiator; he typically played the "good cop" to O'Donnell's "bad cop" during meetings with the government.^[367] O'Donnell was more aggressive and militaristic whereas Tyrone favoured negotiation with their enemies.^[394] He avoided impulsive decisions^[352] 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.^[395] John McGurk described O'Neill as having the "rare gift of patience and the ability to inspire loyalty among erstwhile feuding chieftains".^[396]

However, Tyrone was also a ruthless politician not opposed to murdering his opponents for political gain. 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.^[368] 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.^[397] 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.^[367] 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.^[354] Like his chieftain predecessors, Tyrone spent his life focused primarily on the pursuit and retention of power.^[367]

"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".^[398]

— Description of Tyrone by William Camden, Elizabeth I's official historian

In his late teens, he married a daughter of Brian McPhelim O'Neill of Clandeboye^[399]—possibly named Katherine^[400] or Feodora.^[401] Brian was in the queen's favour and initially appeared to be a useful ally against Turlough Luineach O'Neill. 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.^[52] Thus, the children of this marriage were considered illegitimate by English society.^[402] Tyrone's first wife later married Niall MacBrian Faghartach O'Neill.^[403]

Their children include:

• A daughter who married Ross McMahon^[404] shortly before February 1579. Towards the end of 1579, her father intended to remarry her to Philip O'Relieghe.^[405] After the execution of her father-in-law Hugh Roe MacMahon in 1590,^[406] Tyrone was denied the dowry he was owed from the marriage.^[407]
• Conn^[404] (died December 1601),^[408] known as Conn Mac An Iarla,^[409] who served as an important captain to Tyrone throughout the war. Conn was wounded near Kilmallock in 1600 and died in December the following year. His son Feardorcha took part in the Flight of the Earls.^[408]

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

• Rose^[j] (fl. 1587 – 1607), who was betrothed to Hugh Roe O'Donnell by 1587.^[74] They married in December 1592^[145] and separated in 1595.^[163] Despite reconciling in April 1597, by the following year they had divorced,^[414] putting Tyrone's partnership with O'Donnell under strain.^[415] In 1599 she remarried to Donnell Ballagh O'Cahan to strengthen ties between O'Cahan and Tyrone, but O'Cahan repudiated the marriage in March 1607^[416] and remarried to another woman.^[306]
• A daughter who married her first cousin Henry McArt O'Neill, son of Art MacBaron O'Neill^[417]

Hugh married Siobhán O'Donnell (died January 1591) in June 1574,^[418] beginning his enduring alliance with the O'Donnells of Tyrconnell.^[419] The 1st Earl of Essex announced the marriage on 14 June 1574.^[420]

Hugh decided to ally with Turlough in 1579 with the hopes of becoming the O'Neill clan's tanist. He repudiated his marriage to Siobhán, who had not yet born him a male heir, and prepared to marry one of Turlough's daughters.^[421] In February 1579 it was reported that Hugh and Turlough "knit up such a league of friendship",^[422] with Tyrone accompanying Turlough on various hostings. However this alliance (and the engagement) was soon called off.^[421] Hugh was bought off by a government commission^[58] who convinced Hugh that Turlough would probably die soon enough due to his age and ill health.^[64] This episode apparently convinced Hugh that his "fate was tied to that of O'Donnell" and he solidified his alliance with the O'Donnell clan by reconciling with Siobhán. However it is possible that his reconciliation with Siobhán was a calculated move to keep in the government's favour.^[422]

They had two sons and multiple daughters:

• Margaret (fl. 1598) who married Richard Butler, 3rd Viscount Mountgarret^[423] shortly before 8 October 1596^[424]—possibly in October 1595.^[425]
• Sarah (fl. 1595–1602), who married Arthur Roe Magennis, 1st Viscount Iveagh^[426] in 1590.^[427] Through Sarah, Tyrone is an ancestor to the Anglo-Irish Wellesley family.^[428][429]
• Mary (fl. 1608), who married Brian McHugh Og MacMahon.^[430] According to historian George Hill, Mary is the same woman who married Ross McMahon.^[405][431]
• Alice^[432] (1583^[433] – c. 1665^[434]) who married Randal MacDonnell, 1st Earl of Antrim in 1604.^[435] She was younger than her sisters Sarah and Mary, and older than her brother Hugh.^[436]
• Hugh, 4th Baron Dungannon (c. 1585 – September 1609); he died in Rome and was buried in San Pietro in Montorio on 24 September.^[437]
• Henry (c. 1586 – 25 August 1610); he became colonel of the first Irish regiment in the Spanish army.^[438]

Tyrone was betrothed to Mabel Bagenal (c. 1571 – December 1595) in July 1591. They married on 3 August 1591 and had no offspring together.^[439]

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".^[189] Casway believes that despite the romantic circumstances of their courtship, the marriage "probably ran its course" and Tyrone would have continued with his concubines.^[440] 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".^[441][442] Mabel died in December 1595, aged 24 years old.^[189]

Tyrone married Catherine Magennis (died March 1619) around August 1597.^[443] He jilted the daughter of Angus MacDonald, 8th of Dunnyveg, to marry Catherine instead.^[444] 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".^[445] Catherine reluctantly accompanied Tyrone on his flight. His will did not sufficiently provide for her, and she died penniless in Naples.^[446] She had three surviving sons:

• Shane (October 1599 – 29 January 1641) who was recognised by the Spanish court as the successive Earl of Tyrone ("El Conde de Tyrone"). Per his father's request, he succeeded Henry as colonel of the Irish regiment. Shane fought in the Reapers' War and was killed in Catalonia at the Battle of Montjuïc.^[447]
• 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.^[448]
• Brian (c. 1604 – 16 August 1617), who was found hanged in his room in Brussels with his hands tied behind his back, possibly assassinated.^[449]

Tyrone was known to have various concubines.^[450] He had many illegitimate children or children of unknown maternal origin:

• Margaret O'Neill (fl. 1593–1612), who married Hugh Maguire around May 1593^[146]
• Catherine O'Neill (fl. 1602), who married Henry Oge O'Neill^[451] and had a son, Turlough McHenry O'Neill.^[452] Her husband and son both died in 1608 fighting against O'Doherty's rebellion.^[453]
• A daughter, who married Donnell Oneyle^[454]
• Bridget (fl. 1615) who was with Tyrone in Rome before his death.^[455] She presumably took part in the Flight.^[456]
• A daughter (fl. 1610) who married Brian Art Roe McEny^[457]

According to historian James Kane, the only authenticated likeness of Hugh O'Neill is part of a fresco in the Vatican by Giovanni Battista Ricci. Painted circa 1610 in the Sala Paolina, 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.^[459][460] According to historian Benedict Fearon, Tyrone reputedly sat for a portrait during his last years in Rome.^[458]

An illustration of Tyrone appears in Primo Demaschino's La Spada d'Orione, published in Rome in 1680.^[461] Tyrone's likeness in this illustration was based on the Vatican fresco.^[347] In 1866, C. de Gernon owned two portraits of Tyrone—one in armour, the other in his old age—which both exhibited at the 1866 Exhibition of National Portraits.^{[462][463][464]} The old age portrait was presumably the La Spada d'Orione illustration.^[464]

By the 1990s, the armoured portrait was in the possession of Lord Dunsany. This reputed nineteenth-century portrait, from an original in the Vatican,^[465][466] was based on Tyrone's likeness from the La Spada d'Orione illustration.^[467] William Holl the Younger produced an engraving of Tyrone based on this portrait.^[468] This common image of Tyrone as a stocky armoured figure with cropped hair and a bushy black beard is "almost certainly a Victorian fantasy". Drawings from the 1620s depict Tyrone as a wiry man with a pointed beard and dark eyes.^[469]

The Ulster Museum owns two portraits of Tyrone—both were painted in the 19th century.^[470][471]

• In his 1861 poem Eirinn a' Gul ("Ireland Weeping"), Scottish Gaelic poet William Livingston laments the loss of Irish clan chiefs like Tyrone, O'Donnell and Maguire.^[472]
• 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.^[473]

• Alan Hale Sr. portrayed O'Neill in The Private Lives of Elizabeth and Essex (1939).^[474]
• Tom Adams portrayed O'Neill in the Disney film The Fighting Prince of Donegal (1966), with his name changed to Henry O'Neill.^[475]
• Patrick O'Connell portrayed O'Neill in the BBC drama Elizabeth R (1971), which depicts his riverside parley with the 2nd Earl of Essex.^[476]
• In 2021, it was reported that writer Jack Armstrong was developing a television drama, titled The O'Neill, centered on Tyrone.^[477]

• Tyrone is the central character in Brian Friel's play Making History (1989), which focuses on Tyrone reckoning with his legacy post-Flight. Stephen Rea played Tyrone in the original production by Field Day.^[362] Denis Conway played Tyrone in a 2007 production to mark the 400th anniversary of the Flight of the Earls.^[351]
• Running Beast, a 2007 musical theatre piece by Donal O'Kelly with music by Michael Holohan, is based on Tyrone's career. It commemorated the 400th anniversary of the Flight of the Earls.^[478][479]