Hugh O'Neill, Earl of Tyrone

Hugh O'Neill was born {{circa|1550}}{{Efn|name=birthdate|Until the early twentieth century, historians assumed Tyrone's birthdate to be within the 1540s. Modern historians believe he was born circa 1550, based on the discovery of a 1562 letter stating Tyrone to be 12 years old. Paul Walsh placed Tyrone's birthdate between July 1550 and July 1551.{{Cite journal |last=Graham |first=John K. |date=1938 |title=The Birth-Date of Hugh O'Neill, Second Earl of Tyrone |url=https://www.jstor.org/stable/30006560 |journal=Irish Historical Studies |volume=1 |issue=1 |pages=58–59 |jstor=30006560 |issn=0021-1214}}}} in the barony of Oneilland, Tír Eoghain (present-day northern County Armagh)—possibly in a crannog such as Marlacoo.{{Cite AV media |url=https://www.youtube.com/watch?v=VA-4bb08WCk |title=Hugh O'Neill with Dr. Hiram Morgan |date=13 May 2022 |last=Morgan |first=Hiram |type=Video |language=en |time=0:08 |access-date=11 May 2024 |via=YouTube}}{{Efn|Micheline Kerney Walsh stated that Hugh O'Neill was born in Dungannon, which is in present-day County Tyrone.{{sfn|Walsh|1996|pp=7, 19}}}} The O'Neill dynasty were Tír Eoghain's ruling Gaelic Irish noble family,{{sfn|Morgan|2005|p=38}} and claimed descent from Niall Ruadh of the Cenél nEógain, who was a descendant of legendary high king Niall of the Nine Hostages.{{harvnb|O'Hart|1892|pp=718–724|ps=. Demonstrates lineage from Niall Ruadh to Hugh O'Neill}}; {{harvnb|Connolly|2007|p=84|ps=. "Cenél nEógain were the most powerful grouping within the northern Uí Néill, claiming descent from Eógan, eldest son of Niall Noígiallach."}}{{citation needed|date=April 2025}} Hugh was the second son of Feardorcha "Matthew" O'Neill, 1st Baron Dungannon ({{circa|1510}}–1558) and his wife Siobhán Maguire (died 1600).{{harvnb|Canny|2004|p=837}}: Hugh's parents Matthew and Siobhán; {{harvnb|Walsh|1930|p=22}}: Siobhán's date of death; {{harvnb|O'Byrne|2009b|ps=, 1st paragraph}}: Matthew's lifespan. Hugh's paternal grandparents were clan chief Conn Bacagh O'Neill, 1st Earl of Tyrone ({{circa|1484}}–1559) and Alison Kelly of Dundalk, a blacksmith's wife.{{harvnb|O'Byrne|2009b|ps=, 1st paragraph: Matthew's parents}}; {{harvnb|O'Byrne|2009c|ps=, 1st paragraph: Conn Bacagh's lifespan.}} Siobhán was a daughter of Cúconnacht Maguire, Lord of Fermanagh ({{circa|1480}}–1537).{{Cite journal |last=Morley |first=Vincent |date=October 2009 |title=Mág Uidhir (Maguire), Cú Chonnacht Óg ('an Comharba') |url=https://www.dib.ie/biography/mag-uidhir-maguire-cu-chonnacht-og-comharba-a5370 |url-status=live |journal=Dictionary of Irish Biography |doi=10.3318/dib.005370.v1 |archive-url=https://web.archive.org/web/20240603191334/https://www.dib.ie/biography/mag-uidhir-maguire-cu-chonnacht-og-comharba-a5370 |archive-date=3 June 2024 |access-date=12 August 2024|url-access=subscription }} Hugh had three brothers: Brian, Cormac MacBaron and Art MacBaron.{{harvnb|O'Hart|1892|p=723}}. states that Cormac MacBaron and Art MacBaron were not Siobhan's sons, making them half-brothers of Hugh and Brian. {{harvnb|O'Byrne|2009b}}. states that all four boys were Siobhan's sons, thus making them all full-brothers. During his youth, Hugh was fostered by the O'Hagan and O'Quinn families.{{sfnm|1a1=Morgan|1y=1993|1p=96|2a1=Canny|2y=2004|2p=837}}{{Chart top|width=auto|collapsed=no|align=right|clear=right|Family tree}}

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{{Tree chart| |AlcFG|y|CnnT1|y|SrcON|boxstyle=border-width: 1px; border-radius: 0.5em;

|AlcFG=Alison
Kelly

|CnnT1=Conn
1st Earl
Tyrone
{{circa|1484}}–1559|boxstyle_CnnT1=border-width: 1px; border-radius: 0.5em; background: lavender;

|SrcON=Sorcha
O'Neill}}

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{{Tree chart| | | |MttD1|y|JoanM| |ShnON|boxstyle=border-width: 1px; border-radius: 0.5em;

|MttD1=Mathew
1st Baron
Dungannon
{{circa|1510}}–1558
d.v.p.|boxstyle_MttD1=border-width: 1px; border-radius: 0.5em; background: beige;

|JoanM=Siobhán
Maguire
d. 1600

|ShnON=Shane
O'Neill
{{circa|1530}}–1567}}

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{{Tree chart|ArtON| |BrnD2| |Sbjct|y|SbhOD|boxstyle=border-width: 1px; border-radius: 0.5em;

|ArtON=Art
MacBaron
d. 1618

|BrnD2=Brian
2nd Baron
Dungannon
d. 1562
de jure Earl of Tyrone|boxstyle_BrnD2=border-width: 1px; border-radius: 0.5em; background: beige;|Sbjct=Hugh
Earl
Tyrone
{{circa|1550}}–1616|boxstyle_Sbjct=border: 2px solid red; border-radius: 0.5em; background: lavender;

|SbhOD=Siobhán
O'Donnell
d. 1591}}

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|OwnON=Owen
Roe
O'Neill
{{circa|1585}}–1649

|HghON=Hugh
4th Baron
Dungannon
{{circa|1585}}–1609
d.v.p.|boxstyle_HghON=border-width: 1px; border-radius: 0.5em; background: beige;

|RndA1=Henry
5th Baron
Dungannon
{{circa|1586}}–1610
de jure, d.v.p.|boxstyle_RndA1=border-width: 1px; border-radius: 0.5em; background: beige;

|Alice=Alice
O'Neill
1583–{{circa|1665}}}}

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|Bk1Bx=XXX|boxstyle_Bk1Bx=background: lavender; border-radius: 0.5em; border-width: 1px; color: lavender;

|Bk1Tx=Earl of
Tyrone|boxstyle_Bk1Tx=border: 0 solid white; text-align: left;

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Dungannon|boxstyle_Bk3Tx=border: 0 solid white; text-align: left;

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During Hugh's childhood, a rivalry formed between his uncle Shane and his father Matthew.{{harvnb|Morgan|2014}}, 1st paragraph. 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,{{Sfnm|1a1=Brady|1y=2015|1p=29|2a1=O'Byrne|2y=2009b|2ps=, 1st paragraph.}} 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.{{Sfn|Brady|2015|p=29}} 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.{{sfn|Morgan|2014|ps=, 1st–3rd paragraph.}}

Matthew was killed in 1558 by the O'Donnelly clan (Shane's foster family),{{harvnb|Brady|2009a|ps=, 3rd paragraph: Shane had Matthew assassinated by the O'Donnellys in 1558}}; {{harvnb|Brady|2015|p=28|ps=: the O'Donnelly clan was Shane's foster family.}} placing his sons Brian and Hugh in a dangerous situation. The Dublin Castle administration hoped to use the support of the MacBarons to curb the MacShanes' growing power in Ulster.{{sfnm|1a1=Marshall|1y=1907|1pp=6–7|2a1=Canny|2y=2022|2p=40}} 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.{{sfn|Canny|2022|p=40}}

Hugh and his elder 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.{{harvnb|Morgan|2014}}, 2nd paragraph. 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.{{sfn|Marshall|1907|pp=6–7}}

Giles Hovenden, Hugh's foster father, was an English settler with a pre-existing business connection with Conn Bacagh.{{Sfn|Morgan|1993|pp=92–93, 214}} Hugh was raised by Giles's wife Joan Walshe, and she continued to care for Hugh after Giles's death.{{sfnm|1a1=Morgan|1y=2014|1ps=, 1st paragraph|2a1=Canny|2y=2022|2p=40}} Hugh would remain close with his adoptive family throughout the rest of his life. His foster brother Henry became his chief advisor{{Sfnm|1a1=Marshall|1y=1907|1pp=4, 7|2a1=Morgan|2y=1994|2p=5}} and accompanied him on his flight in 1607.{{sfn|Hegarty|2010|pp=22–23}} Brothers Henry and Richard led Hugh's troops in the late 1580s, though another brother Walter died opposing the Irish confederacy in battle.{{sfn|Marshall|1907|pp=8–10}}

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.{{Cite web |last=Dorney |first=John |date=10 January 2019 |title=Hugh O'Neill and the Nine Years' War 1594–1603 |url=https://www.theirishstory.com/2019/01/10/hugh-oneill-and-nine-years-war-1594-1603/ |url-status=live |archive-url=https://web.archive.org/web/20190401062313/https://www.theirishstory.com/2019/01/10/hugh-oneill-and-nine-years-war-1594-1603/ |archive-date=1 April 2019 |website=The Irish Story}}{{Sfn|Morgan|1993|pp=92–93}} He would have received a basic education, either by attending grammar school or from private lessons.{{Sfn|Morgan|1993|p=214}}

Brian was assassinated in 1562 by Shane's tanist Turlough Luineach O'Neill,{{harvnb|Brady|2009b|ps=, 1st paragraph.}} and Hugh succeeded him as 3rd Baron Dungannon and heir to the earldom.{{Sfnm|1a1=Canny|1y=2004|1p=837|2a1=Canny|2y=2022|2p=40}} Four years later, war broke out between Shane and the Crown.{{Sfn|Morgan|1993|p=214}} 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.{{Sfn|Morgan|1993|p=214}}

File:Reputed Portrait of Hugh O'Neill.webp, is a "Victorian fantasy".]]

In June 1567, Shane was killed by Scots supporting the MacDonnells of Antrim.{{Sfn|Brady|2015|p=|pp=82–83}} Hugh's wardship formally ended the following November when he sued out his livery. 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.{{sfn|Canny|2004|p=837}} This was young Hugh's first visit to England. He finally returned to Ulster in early 1568{{sfn|Walsh|1996|p=20}} 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.{{sfn|Morgan|2005|p=41}}

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".{{harvnb|Morgan|2014}}, 3rd paragraph. As he had spent the previous ten years raised as an Englishman, Hugh would have been considered an outsider by these families.{{sfn|McGinty|2013a|p=16}} 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.{{Sfn|Casway|2016|pp=70–71}} The same year, Hugh established his most important and longlasting alliance by remarrying to Siobhán O'Donnell, daughter of chief Hugh McManus O'Donnell.{{Sfnm|1a1=Walsh|1y=1930|1p=17|2a1=McGinty|2y=2013a|2pp=14, 18–19|3a1=Morgan|3y=2014|3ps=, 3rd paragraph.}} The O'Donnell and O'Neill clans had traditionally been mortal enemies for centuries.{{sfnm|1a1=Morgan|1y=1993|1p=135|2a1=Walsh|2y=1930|2p=37}} Hugh O'Neill gained good standing with the 1st Earl of Essex (leader of an Ulster colonisation scheme) after joining him in attacks on Turlough{{harvnb|Morgan|2014}}, 3rd paragraph: Tyrone gained good standing with Essex; {{harvnb|Falls|1997|p=230}}: Essex was leader of colonisation scheme. and Brian McPhelim.{{sfn|Dunlop|1895|p=188}} Essex commended Hugh as "the only man of Ulster... to be trusted and used".{{Sfn|Canny|2004|p=838}} By the early 1570s, Hugh was using his combined support from the Pale and Ulster to put Turlough under heavy pressure.

In 1585 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.{{sfnm|1a1=Cokayne|1y=1896|1p=449|2a1=Morgan|2y=2005|2p=42}} This was apparently done to suppress his desire for O'Neill chieftainship.{{Sfn|O'Hart|1892|p=724}} From 1587, the Crown grew suspicious of Tyrone and began attempts at curbing his growing power.{{Sfnm|1a1=Morgan|1y=1993|1p=85|2a1=McGettigan|2y=2005|2pp=41–42}} Although Elizabeth I asserted herself as "Queen of Ireland",{{Sfn|Morgan|2004|p=297}} Tír Eoghain 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.{{Sfn|Morgan|1993|p=85}}

File:Walter Devereux, 1st Earl of Essex from NPG.jpg was an early English ally to Tyrone.]]

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.{{harvnb|Morgan|2014}}, 5th paragraph. 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.{{sfn|Dunlop|1895|p=188}} During the Second Desmond Rebellion in Munster, he fought with the English forces against Gerald FitzGerald, 14th Earl of Desmond.{{Sfn|McNeill|1911|p=109}} In January 1582, Tyrone captured John Cusack of Alliston-read, who had assisted rebel William Nugent.{{sfn|Dunlop|1895|p=188}} In 1584 he assisted John Perrot against the MacDonnells of Antrim.{{Sfn|McNeill|1911|p=109}}

The government quickly became dependant on Tyrone's defence of the Pale. Arthur Grey praised Tyrone as "the only Irish nobleman that hath done any service and drawn blood since my coming".{{Sfn|Morgan|1993|p=94}} Tyrone was nicknamed "The Queen's O'Neill" for his loyalty to the Crown.{{sfnm|1a1=Marshall|1y=1907|1p=6|2a1=Morgan|2y=2004|2p=305}} Nevertheless, he feared that the Dublin government might weaken his power by appointing a sheriff in Tír Eoghain.

{{See also|Spanish Armada in Ireland|}}

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.{{sfn|Morgan|2013|page=5}} 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.{{Sfn|O'Neill|2017|p=23}} He may have been playing a "double game",{{Sfn|Morgan|1993|p=106}} as is common throughout his career.{{Harvnb|McNeill|1911|p=109|ps=. "His career was marked by unceasing duplicity, at one time giving evidence of submission to the English authorities, at another intriguing against them in conjunction with lesser Irish chieftains."}}

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The Armada ship La Trinidad Valencera sank in Kinnagoe Bay, Inishowen.{{Sfn|Marshall|1907|pages=8–9}} Tyrone's mercenary forces, commanded by his Hovenden foster-brothers, proceeded to Inishowen upon hearing of the presence of Spanish fugitives there.{{Sfnm|1a1=Marshall|1y=1907|1pp=8–9|2a1=Morgan|2y=1993|2p=106}} Tyrone's instructions to the Hovendens are unknown;{{Sfn|Marshall|1907|p=10}} ultimately his forces committed the largest single massacre of Armada survivors in Inishowen.{{Sfn|Morgan|2013|p=5}} FitzWilliam was suspicious of the Earl's activities and refused to believe this news, but it was confirmed by a Spanish escapee.{{Sfn|Morgan|1993|p=106}} Historians John Marshall, Hiram Morgan and Matthew McGinty characterise Tyrone as reluctantly ordering the massacre to keep in the English government's good graces.{{sfnm|1a1=Marshall|1y=1907|1p=10|3a1=Morgan|3y=2014|3ps=, 8th paragraph.|2a1=McGinty|2y=2013a|2p=24}} Contemporary sources imply that the massacre was carried out on the actions of the O'Donnell clan,{{efn|In a report from Inishowen prior to the massacre, the Hovendens wrote to FitzWilliam: "O'Donnell is willing to serve against [the Spaniards], and hath none of his country as yet come in to him passing thirty horsemen; he hath sent for all his forces, but it is doubtful whether they will come in to him or not".{{sfn|Marshall|1907|p=9}} In the 17th-century, the clergy of Donegal Abbey wrote that "[in retirement, Hugh McManus O'Donnell did] penance for his sins, the weightiest of which was a cruel raid on the wrecked Spaniards of the Armada, whom he slew in Innishowen, at the bidding of deputy Fitzwilliam".{{Cite book|page=13 |last=Meehan |url=https://archive.org/details/RiseAndFallOfTheIrishFranciscan |title=The Rise and Fall of the Irish Franciscan Monasteries |year=1870 |edition=3rd |location=Dublin |first=Charles Patrick |publisher=J. Duffy}}}} who counselled O'Neill's troops,{{Sfn|Morgan|2013|p=5}} though this is possibly misdirection by Tyrone.{{Sfn|Morgan|1993|p=106}} 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.{{Sfnm|1a1=Morgan|1y=2013|1p=5|2a1=Marshall|2y=1907|2p=10}}

On 25 September, the ships La Lavia, La Juliana and the Santa Maria de Vison became shipwrecked at Streedagh Strand in County Sligo.{{cite web |last=McGowan |first=Joe |date=7 September 2010 |title=The Spanish Armada in Sligo |url=http://www.sligoheritage.com/ArchSpanishArmada.htm |url-status=live |archive-url=https://web.archive.org/web/20240526080856/http://www.sligoheritage.com/ArchSpanishArmada.htm |archive-date=26 May 2024 |access-date=21 November 2012 |website=SligoHeritage |publisher=}} Tyrone himself assisted three sick officers and many commoners,{{Sfnm|1a1=Morgan|1y=1993|1p=106|2a1=Morgan|2y=2013|2p=5}} including ordinary seaman Pedro Blanco of La Juliana, who was kept on as his footman and manservant throughout the whole of the Nine Years' War.{{Cite journal|author-link=Micheline Kerney Walsh|last=Walsh |first=Micheline |url=http://archive.org/details/the-anonymous-spaniard-of-the-flight-of-the-earls |title=The Anonymous Spaniard of the Flight of the Earls |date=1957b|journal=The Irish Sword|volume=3|issue=11|pages=88–90}} Tyrone also helped stranded nobleman Don Antonio Manrique escape Ulster.{{Sfn|Morgan|1993|p=106}} Ultimately about a dozen Spaniards remained in Ireland.{{Cite news |last=Morgan |first=Hiram |author-link=Hiram Morgan |date=14 April 2015 |title=A race against time to save Spanish Armada wrecks before they are lost forever |url=https://www.irishtimes.com/opinion/a-race-against-time-to-save-spanish-armada-wrecks-before-they-are-lost-forever-1.2174364 |access-date=26 May 2024 |newspaper=The Irish Times |language=en}} Despite their desire to return home, Philip II of Spain believed they would be of better use as interpreters and emissaries for Tyrone. 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.{{sfn|Morgan|2013|p=5}}

{{CSS image crop|Image=Hugh Roe O'Donnell, depiction in stained-glass window by Richard King.webp|bSize=450|cWidth=180|cHeight=290|oTop=90|oLeft=116|Description=Hugh Roe O'Donnell of Tyrconnell was a major ally to Tyrone in the Nine Years' War.|Align=left}}

Tyrone further developed his alliance with the O'Donnell clan—by 1587 his daughter Rose was betrothed to tanist Hugh Roe O'Donnell,{{sfnm|1a1=Walsh|1y=1930|1p=|2a1=Morgan|2y=1993|2pp=96, 124, 128|1pp=36–38}} which outraged Turlough.{{Sfn|McGinty|2013a|p=18}} 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. Lord Deputy Perrot ordered young O'Donnell's kidnapping in 1587 in hopes of destroying this alliance. O'Donnell was imprisoned in Dublin Castle, along with two MacShanes, Art and Henry. Tyrone lobbied for O'Donnell's release,{{Harvnb|Morgan|2009}}, 2nd–3rd paragraph. describing the ordeal as "the most prejudice that might happen unto me".{{Harvnb|Walsh|1930|pp=36–37}}; {{harvnb|Morgan|2014}}, 7th paragraph.

The O'Donnell clan's military power was key to Tyrone ambitions to overthrow Turlough.{{Sfnm|1a1=McGettigan|1y=2005|1pp=52–53, 122|2a1=McGinty|2y=2013a|2p=26}} In summer 1590, Conn MacShane O'Neill alleged that Tyrone "did lay down a plot and practised the escape of Hugh Roe" from prison.{{Sfn|Morgan|1993|p=132}} O'Donnell made a failed prison break attempt in January 1591.{{Sfnm|1a1=Walsh|1y=1922|1p=360|2a1=Morgan|2y=2009|2ps=, 4th paragraph.}} The same month, Tyrone's wife Siobhán (Hugh Roe's elder half-sister) died.{{sfnm|1a1=Walsh|1y=1930|1p=26|2a1=Casway|2y=2016|2p=72}} Around January 1592, Tyrone successfully aided O'Donnell's (and ironically, the MacShanes') escape.{{Sfnm|1a1=McGettigan|1y=2005|1p=50|2a1=Morgan|2y=2009|2ps=, 4th paragraph.}} Tyrone had bribed officials—most likely Lord Deputy FitzWilliam—to aid in O'Donnell's escape.{{Sfn|Morgan|1993|pp=132–133}} 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{{sfn|Webb|1878|pp=391–392}} and was inaugurated as O'Donnell clan chief in April 1592.{{sfn|Walsh|1939|p=237}} 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.{{sfn|McGettigan|2005|pp=50–51}} Henry was later reincarcerated by Tyrone in Ulster.{{Cite web |last=McNally |first=Frank |date=14 January 2017 |title=Hardship for Art's Sake – An Irishman's Diary about the Art O'Neill Challenge |url=https://www.irishtimes.com/opinion/hardship-for-art-s-sake-an-irishman-s-diary-about-the-art-o-neill-challenge-1.2936402 |access-date=2025-04-12 |website=The Irish Times |language=en}}

In the north, Tyrone also had to contend with his "grievous enemy" Nicholas Bagenal, the Marshal of Her Majesty's Irish Army.{{sfnm|1a1=Morgan|1y=2014|1ps=, 4th paragraph|2a1=Casway|2y=2016|2p=72}} Around 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". On 24 October 1590, his son Henry Bagenal succeeded him as Marshal.{{Sfn|Pollard|1885|p=96}}File:SirNicholasBagenal.png's children—marrying Mabel but becoming "arch-enemy" to Henry.]]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.{{Sfn|O'Neill|2017|p=26}} Tyrone, who had owned part of MacMahon's lands under brehon law, was passed over in favour of Henry Bagenal.{{harvnb|Morgan|2014}}, 9th paragraph. Furthermore, Tyrone's authority was directly challenged when Henry was named chief commissioner of Ulster on 18 May 1591.{{Sfnm|1a1=Pollard|1y=1885|1p=96|1ps=: date of Bagenal's appointment|2a1=O'Neill|2y=2017|2p=27|2ps=: appointment was a challenge to Tyrone's authority.}}

Soon afterwards, Tyrone began to woo Mabel, Henry's younger sister.{{Sfn|Pollard|1885|p=96}} This was only months after the similarly-timed deaths of Nicholas Bagenal (February) and Tyrone's late wife Siobhán (January).{{sfnm|1a1=Casway|1y=2016|1p=72|1ps=: Siobhán died in January 1591|2a1=Hawkins|2y=2009|2ps=, 2nd paragraph: Nicholas Bagenal died in February 1591.}} 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.{{harvnb|Clarke|Barry|O'Byrne|2009}}, 2nd paragraph; {{harvnb|Casway|2016|p=72}}. After a dinner at Turvey, the Earl distracted Barnewall while his ally William Warren escorted Mabel to Warren's house in Drumcondra.{{Sfn|Bagenal|1925|p=53}} 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.{{sfnm|1a1=Meehan|1y=1868|1p=414|2a1=Bagenal|2y=1925|2pp=53–54}} 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.{{sfnm|1a1=Bagenal|1y=1925|2a1=Casway|2y=2016|2p=72|3a1=Clarke|3y=2009|1pp=53–54|3a2=Barry|3a3=O'Byrne|3ps=, 2nd paragraph.}}

Jerrold Casway notes that this "whirlwind courtship" is unlike Tyrone's other marriages, which otherwise always had political motives.{{sfn|Casway|2016|p=73}} It is possible Tyrone's judgment was impaired by his feelings.{{harvnb|Clarke|Barry|O'Byrne|2009}}, 2nd paragraph.{{Cite journal |date=1900 |title=The Spaniards in Ireland |url=https://www.jstor.org/stable/20545048 |journal=All Ireland Review |volume=1 |issue=47 |pages=2 |issn=2009-2415 |jstor=20545048}} Mabel was young and attractive, and clearly enamoured by the attention she received from Tyrone.{{sfn|Casway|2016|p=72}} She has been dubbed the "Helen of the Elizabethan Wars", a sobriquet that historians decry as being overly simplistic.{{sfnm|1a1=Morgan|1y=1993|2a1=Newmann|2y=1993|1p=10}} Historians also believe that Tyrone would have recognised the advantages of marrying into the powerful Bagenal family.{{sfnm|3a1=Clarke|3a2=Barry|3a3=O'Byrne|3y=2009|3ps=, 2nd paragraph.|1a1=Morgan|1y=1993|1pp=79, 216|2a1=Canny|2y=2001|2p=81}} The marriage was his attempt to merge the Bagenals' interests with his own{{Sfn|Canny|2001|p=81}} and to neutralise Henry Bagenal's growing power.{{sfn|Morgan|1993|pp=79, 216}}

Bagenal was outraged at the marriage. He refused to pay his sister's dowry,{{sfnm|1a1=Walsh|1y=1930|1pp=16, 18–19|2a1=Pollard|2y=1885|2p=96}} even two years after the marriage,{{sfn|Newmann|1993}} and also had Tyrone's previous divorce investigated, though it was found to be valid.{{harvnb|Morgan|2014}}, 9th paragraph: Bagenal had Tyrone's divorce investigated; {{harvnb|Walsh|1930|p=16}}: Tyrone's divorce was found to be valid. Because of this dramatic episode and their roles as opposing commanders during the Nine Years' War, Bagenal and Tyrone have been called "arch-enemies",{{sfn|Gibson|2013|p=16}} "nemeses"{{sfn|McGinty|2013a|p=22}} and "arch-rivals".{{sfn|O'Neill|2016|p=44}}

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.

File:2052 O'Neill 1574.jpg in the State Papers|left]]

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.{{sfnm|1a1=Morgan|1y=2014|1ps=, 6th paragraph|2a1=O'Neill|2y=2017|2p=23}}

Tyrone's constant disputes with Turlough were fomented by the English with a view to weakening the clan. 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.{{harvnb|Morgan|2014}}, 6th–7th paragraph.

In January 1590, Tyrone organised the execution of his MacShane cousin Hugh Gavelagh,{{sfnm|1a1=Morgan|1y=1993|1pp=75, 107|2a1=O'Hart|2y=1892|2p=722}} who had exposed to FitzWilliam that the Earl was making treasonous dealings with the Spanish.{{sfnm|1a1=Morgan|1y=1993|1pp=73–74|2a1=O'Sullivan Beare|2y=2008|2p=65}} When the MacShanes refused to submit to Tyrone in exchange for Gavelagh's life, Tyrone had Gavelagh hanged at Dungannon by public executioners.{{efn|At the time, it was reputed that Tyrone had hanged Gavelagh over a tree with his bare hands.{{sfn|Morgan|1993|p=75}}{{Cite journal |date=April 1864 |title=ORIGINAL LETTER FROM HUGH O'NEILL RELATING TO THE EXECUTION OF HUGH NA GAVELAGH |url=https://www.proquest.com/openview/831fe93edd8f6e00/1?pq-origsite=gscholar&cbl=3130 |journal=Duffy's Hibernian Magazine: A Monthly Journal of Legends, Tales, and Stories, Irish Antiquities, Biography, Science, and Art |location=London |volume=5 |issue=28 |pages=265–269}} William Parnell states that, because the local population were sympathetic to the MacShanes, no-one from Tír Eoghain was willing to execute Gavelagh.{{Cite book|last=Parnell |first=William |year=1807 |url=https://archive.org/details/historicalapolog00parn|title=An Historical Apology for the Irish Catholics |publisher=H. Fitzpatrick|page=54|edition=2nd|others=Digitized by the Internet Archive in 2014}} 17th-century writer Philip O'Sullivan Beare stated that Tyrone had "a Meath-man acting as executioner" for this same reason.{{sfn|O'Sullivan Beare|2008|p=65}} 19th-century historian John O'Hart stated that Gavelagh was hanged by Loughlin MacMurtogh and his brother, both natives of Fermanagh.{{sfn|O'Hart|1892|p=722}} 20th-century historian Robert Dunlop stated that "if [Tyrone] did not, as was asserted, hang [Gavelagh] with his own hands on a thorn tree, he procured a hangman from Cavan to execute him."{{sfn|Dunlop|1895|p=189}}}} Tyrone proceeded to London where he sufficiently defended himself against England's Privy Council by alleging that Gavelagh was guilty of various crimes.{{Sfn|Walsh|1996|p=20}} Tyrone was placed under house arrest but released by letters of commendation from FitzWilliam and the Dublin government.{{harvnb|Morgan|2014}}, 8th paragraph.

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.{{sfn|Brady|2009b|ps=, 8th paragraph.}} The Earl had effectively become the ruler of Tír Eoghain.{{sfn|McGinty|2013a|p=28}}

By late 1592, the Crown's advances into Gaelic territory, as well as the recent executions of chieftains MacMahon (1590) and Brian O'Rourke (1591) had created a fierce resentment in the Gaelic nobility and Irish Catholic clergy.{{harvnb|McGettigan|2005|pp=51–52, 59|ps=}}; {{harvnb|McGinty|2013a|pp=24–25|ps=}}; {{harvnb|Morgan|2013|p=5|ps=}}. In early April 1593, English captain Humphrey Willis was appointed by FitzWilliam as Sheriff of Fermanagh;{{sfnm|1a1=Morgan|1y=1993|1p=143|2a1=Barry|2y=2009|2ps=, 2nd paragraph.}} he entered the kingdom with at least 100 men and began pillaging and raiding, to the fury of Fermanagh's chieftain Hugh Maguire.{{sfnm|2a1=O'Neill|2y=2017|2p=99|1a1=O'Neill|1y=2016|1pp=42–44}} Morgan states that this was a blatant move to weaken Tyrone's power by subjugating Maguire.{{Sfn|Morgan|1993|pages=|p=143}}File:Enniskillen Castle - geograph.org.uk - 7045728.jpg.]]

After Willis' first offensive,{{sfn|Morgan|1993|p=143}} a meeting took place at Enniskillen Castle on 8 May, with O'Donnell, Maguire and Brian Oge O'Rourke present.{{Sfn|O'Neill|2016|p=44}} The Sheriff of Monaghan alleged that Tyrone also attended the meeting.{{sfnm|1a1=Morgan|1y=1993|1p=142|2a1=O'Neill|2y=2017|2p=43}} The noblemen were assembled by Edmund MacGauran, a Catholic Archbishop recently returned from Spain{{Sfn|Walsh|1990|pp=68, 74–76}} with promises that Philip II would support oppressed Irish Catholics if they proved themselves by launching prior military action.{{sfnm|1a1=Morgan|1y=2013|1p=5|2a1=O'Neill|2y=2017|2p=28}} 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.{{Sfn|Walsh|1990|pp=74–76}} Catholic Archbishop James O'Hely was tasked with delivering the confederates' messages—he met with Juan de Idiáquez, the royal secretary.{{Sfn|Morgan|2013|pp=5–6}} Idiáquez's notes to Philip II reveal Tyrone's relationship with the emerging confederacy:{{Quote|text="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."}}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.{{Sfn|O'Neill|2016|pp=43–44}} Tyrone often used his relatives and followers to make war on his behalf{{harvnb|Morgan|2014}}, 11th paragraph. and it is unlikely they would have assisted Maguire without Tyrone's permission.{{Sfn|Morgan|1993|p=145}} 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.{{sfn|Webb|1878|p=324}}{{Sfn|O'Neill|2016|p=44}} This conflict is considered to mark the start of the Nine Years' War.{{sfnm|1a1=Morgan|1y=1993|1p=143|2a1=McGinty|2y=2013b|2p=8|3a1=O'Neill|3y=2017|3p=21}}

Subsequently Maguire launched raids across Connacht. Tyrone's nephews—sons of his brother Art MacBaron—also engaged in campaigns against loyalist clans.{{Sfn|O'Neill|2017|pages=28–29}}

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.{{Sfnm|2a1=O'Neill|2y=2017|2pp=25, 42|1a1=McGettigan|1y=2005|1pp=61, 64}}{{efn|See {{harvnb|McGinty|2013a}} for discussion on Tyrone's position in the confederacy.}} Hiram Morgan represents Tyrone as a master strategist who was complicit in rebellion from the start{{Sfn|O'Neill|2017|p=25}} but feigned loyalty to the Crown for strategic reasons.{{Cite journal |last=Morgan |first=Hiram |date=1 June 2007 |title=Red Hugh O'Donnell and the Nine Years War
Sir Henry Docwra, 1564–1631: Derry's Second Founder |url=https://academic.oup.com/ehr/article-abstract/CXXII/497/823/391282 |journal=The English Historical Review |volume=CXXII |issue=497 |pages=823–824 |doi=10.1093/ehr/cem144 |access-date=20 September 2024|url-access=subscription }} James O'Neill agrees that Tyrone was the chief architect of the rebellion, and states that the conflict in Fermanagh allowed Tyrone to diverted English forces and thus suppress English clients in east Ulster.{{Sfn|O'Neill|2016|p=43}} 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. Nicholas Canny similarly states that Tyrone aspired to be the "queen's man in Ulster", was passed over in favour of Henry Bagenal,{{Sfn|Canny|2001|p=81}} and reluctantly pushed into rebellion to prevent his followers defecting to his brother Cormac MacBaron.{{Sfn|O'Neill|2017|p=25}} 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.{{Sfn|McGinty|2013a|p=40}} 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".{{Sfn|McGettigan|2005|p=17}} McGettigan and Morgan disagree over Tyrone's prominence in the confederacy.{{sfn|Kelly|2004|p=160}}{{sfn|McGettigan|2005|p=60}}

By the beginning of the Nine Years' War, Tyrone had formally allied with O'Donnell and Maguire via their marriages to his daughters.{{Cite podcast |last=Graham |url=https://podcasts.apple.com/ie/podcast/in%C3%ADon-dubh-and-red-hugh-odonnell/id1503109266?i=1000633555284 |title=Iníon Dubh and Red Hugh O'Donnell |website=History Ireland |publisher=History Ireland |host= |access-date=13 April 2024 |time=22:25 |date=28 October 2023 |first=Tommy}} O'Donnell married Tyrone's daughter Rose in December 1592,{{Sfnm|1a1=McGettigan|1y=2005|1pp=54–55|2a1=Casway|2y=2016|2p=71}} and Maguire married Tyrone's daughter Margaret around May 1593.{{sfnm|1a1=Moody|1y=1938|1pp=269-270|1ps=: Maguire's widow was Margaret O'Neill|2a1=Walsh|2y=1930|2p=33|2ps=: Maguire married Tyrone's daughter around May 1593.}} 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".{{sfn|Hamilton|1890|p=182}} 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".{{Sfn|Morgan|1993|pp=172–173}} The English government had their suspicions that Tyrone was plotting against them, but he repeatedly proved his loyalty in battles against Irish uprisings.{{Sfn|O'Neill|2017|p=25}} 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.{{Cite journal |last=García Hernán |first=Enrique |author-link=Enrique García Hernán |date=2004 |editor-last=Morgan |editor-first=Hiram |editor-link=Hiram Morgan |title=Philip II's forgotten armada |url=http://www.irishinspain.es/archivos/philip_eghernan.pdf |journal=The Battle of Kinsale |location=Dublin |publisher=Wordwell Ltd |pages=45–58 |isbn=1-869857-70-4 |access-date=26 May 2024}}

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.{{Sfn|Morgan|1993|p=146}} 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.{{Sfn|Morgan|1993|pages=149–150}}

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.{{Sfn|Morgan|1993|pages=146–148}} When Elizabeth I was later briefed on the proceedings, she concluded that Tyrone should have been arrested.{{Sfn|Morgan|1993|p=152}}

Tyrone met with Maguire in early August—within weeks Maguire launched raids into Monaghan.{{Sfn|O'Neill|2017|p=43}}

Maguire's attacks provoked a large-scale military expedition to be led by Bagenal.{{Sfn|O'Neill|2017|p=29}} Tyrone was able to deflect the past allegations and prove his loyalty to the Crown by agreeing to assist Bagenal.{{Sfnm|1a1=McGinty|1y=2013b|1p=8|2a1=Morgan|2y=2014|2ps=, 10th paragraph.}} On 26 September he joined Bagenal and his army at Enniskillen, but the Earl had brought far fewer troops than he had promised.{{Sfn|O'Neill|2017|p=30}} 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.{{Sfn|O'Neill|2016|p=46}}

Their combined forces moved on Maguire's positions on 10 October in what is known as the Battle of Belleek.{{Sfn|O'Neill|2017|p=30}} O'Donnell was in nearby Ballyshannon when the battle was taking place, but he was ordered by Tyrone not to reinforce Maguire. It was estimated that 300 of Maguire's men were killed.{{Sfn|O'Neill|2016|pp=46–47}} Though Maguire's forces were not directly engaged, FitzWilliam was convinced Maguire's revolt had been stopped.{{Sfn|O'Neill|2017|p=32}} 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.{{Sfn|O'Neill|2017|pp=34–35}} Tyrone protested against Bagenal's accusation by claiming that Bagenal and FitzWilliam were conspiring to rob him of the honour he was due.{{Sfn|Dunlop|1895|p=190}}{{Sfn|Morgan|1993|p=159}}

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.{{Sfn|O'Neill|2017|pp=43–44}} The same month, government commissioners surmised that a confederacy had been established between the Ulster lords, and that Tyrone was the leader.{{Sfnm|1a1=Ó Mearáin|1y=1956|1p=6|2a1=Morgan|2y=2014|2ps=, 10th paragraph.}} Despite pressure from Tyrone to feign neutrality,{{Sfn|McGinty|2013b|p=8}} O'Donnell joined Maguire in besieging Enniskillen Castle in early 1594. This signaled to the government O'Donnell's status as a confederate commander.{{sfn|O'Neill|2017|p=37}} 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".{{Sfn|McGinty|2013b|p=12}} Tyrone was subsequently involved in the Battle of the Ford of the Biscuits, which occurred on 7 August.{{Sfn|O'Neill|2017|pp=38, 44}}

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".{{sfn|Morgan|1993|p=|pp=168–172}}

File:Blackwater Fort.png.]]

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.{{Sfn|O'Neill|2017|p=47}} The evidence against Tyrone became too great to ignore, and the government deemed an immediate attack essential.{{Sfnm|1a1=Dunlop|1y=1895|2a1=Morgan|2y=2005|2p=43|1p=190}} A considerable royal force arrived in Waterford on 19 March, but Tyrone had already managed to invade and burn Louth on 17 February.{{Sfn|O'Neill|2017|pp=47–48}}

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,{{sfn|McGinty|2013a|p=41}} such as his brother Cormac MacBaron.{{sfnm|1a1=O'Neill|1y=2016|1p=43|2a1=O'Neill|2y=2017|2p=25}}

{{Main|Battle of Clontibret}}

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.{{Sfn|O'Neill|2017|pages=49–51}} 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.{{sfnm|1a1=O'Sullivan Beare|1y=2008|1p=87|1ps= : a primary source which recounts the melee|2a1=O'Neill|2y=2017|2p=52|2ps=: secondary source|3a1=McGurk|3y=2007|3p=18|3ps=. McGurk states that Donnell Ballagh O'Cahan was the aforementioned O'Cahan.}}

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. Bagenal recorded 31 killed and 103 wounded,{{Sfn|O'Neill|2017|pages=52–53}} though it is likely casualties were much higher.{{Sfn|Ó Mearáin|1956|p=24}} The Irish victory shocked and demoralised the English and was a severe setback early in the war.{{Sfnm|1a1=Ó Mearáin|1y=1956|1p=26|2a1=Morgan|2y=2014|2ps=, 11th paragraph.}} On 24 June, Tyrone was proclaimed a traitor at Dundalk.{{Sfn|Morgan|1993|p=178}} 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.{{Sfn|Dunlop|1895|pp=190–191}}

Upon Turlough's death, Tyrone travelled to Tullyhogue Fort where he was officially inaugurated as O'Neill clan chief on 15 September.{{harvnb|Morgan|2014}}, 12th paragraph: Turlough's death; {{harvnb|Hamilton|1890|p=394}}: date of Tyrone's inauguration. Tyrone was the last inaugurated chief of the O'Neill clan,{{sfn|Connolly|2007|p=431}} and he appointed Cormac MacBaron as his tanist.{{sfn|Hogan|1931|p=242}} 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."{{Sfn|Dunlop|1895|p=191}}

File:Portrait of Philip II of Spain by Sofonisba Anguissola - 002b.jpg's assistance throughout the Nine Years' War.]]

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.{{Sfn|Morgan|1993|pp=194–195|p=}} 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.{{Sfn|O'Neill|2017|p=55}} 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.{{sfn|Morgan|1993|pp=142–143}}

Tyrone sought to delay the war in order to buy time for the arrival of Spanish troops.{{Sfn|O'Neill|2017|pp=60–61}} 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.{{Sfn|O'Neill|2017|p=56}} The discovery of the confederacy's letters to Spain affected negotiations, but ultimately the government was willing to accept Tyrone's assurances.{{Sfn|Dunlop|1895|p=191}} After much deliberation and negotiation,{{harvnb|Morgan|2014}}, 12th paragraph. a cessation of arms was signed by Tyrone on 27 October.{{Sfn|O'Neill|2017|p=56}} This pardoned certain confederates and give them local autonomy. It also acknowledged a tolerance of Catholicism. The confederacy proved to be unsatisfied with the terms,{{Sfn|Morgan|1993|pp=209–210}} but this policy was a success in that Tyrone managed to defer English attempts on his territory for more than two years.{{Sfn|O'Neill|2017|pp=60–63}}{{Sfn|McNeill|1911|pp=109–110}}

Tyrone's wife Mabel died in December 1595.{{harvnb|Clarke|Barry|O'Byrne|2009}}, 4th paragraph. 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.{{Sfnm|1a1=Walsh|1y=1930|1pp=37–38|2a1=Morgan|2y=2009|2p=|2ps=, 10th paragraph.}} This plan came to naught. Tyrone sent his secretary Henry Hovenden into Tyrconnell to handle the situation,{{Sfn|McGettigan|2005|p=81}} and O'Donnell eventually took Rose back.{{harvnb|Walsh|1939|p=237|ps=. fn. 5}}; {{Harvnb|Morgan|2009}}, 10th paragraph.

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".{{Sfn|Dunlop|1895|p=191}} In April 1596, Philip II anxiously exhorted Tyrone to continue the war with England.{{Sfn|Walsh|1996|p=21}} Tyrone thereafter chose to temporize with the authorities, professing his loyalty to the crown whenever circumstances required.{{Sfn|McNeill|1911|pp=109–110}} A hollow peace was signed on 24 April,{{Sfn|Dunlop|1895|p=191}} and further negotiations to develop a peace treaty were almost complete by May.{{Sfn|O'Neill|2017|p=62}}

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.{{Sfn|Morgan|1993|pp=208–210}} 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.{{Sfn|O'Neill|2017|p=62}}{{Sfn|Morgan|1993|p=212}}

Tyrone declared to Norris that he and O'Donnell had rejected further meetings with the Spanish. To put the matter at rest, he submitted Philip II's letter to Russell 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.{{Sfn|Dunlop|1895|p=191}} 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 McHugh 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.{{Sfn|O'Neill|2017|pp=63–64}} 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.{{Sfn|O'Neill|2017|p=65}}

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.{{Sfn|Dunlop|1895|pp=191–192}} 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.{{Sfn|O'Neill|2017|p=66}} 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.{{Sfn|Dunlop|1895|pp=191–192}} Burgh died from illness in October.{{Sfn|O'Neill|2017|pp=68–69}}

It was anticipated that Tyrone would seize this opportunity to overrun the Pale.{{Sfn|Dunlop|1895|p=192}}{{Sfn|O'Neill|2017|pp=|p=69}} 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.{{Sfn|Dunlop|1895|p=192}} Tyrone presented a document of grievances which listed offences committed by the government against the Irish. 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.{{Sfn|Dunlop|1895|p=192}}

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.{{Sfn|McGettigan|2005|p=|pp=79–80}}

{{Main|Battle of the Yellow Ford}}

File:BattleoftheYellowFord.jpg]]

Tyrone's pardon was granted on 11 April 1598. However the Earl felt that the Crown would eventually supersede his authority in Ulster.{{Sfnm|1a1=Dunlop|1y=1895|1p=192|1ps=. "His pardon passed the great seal on 11 April 1598; but, feeling that the demands of the crown, if yielded to, would completely destroy his authority over his urraghs, he took advantage of the expiration of the truce to besiege the fort on the Blackwater."|2a1=Lennon|2y=2005|2p=298|2ps=. "The Earl of Ormond's hopes that a truce made with O'Neill would lead to the restoration of order in Ulster were dashed with the renewal of hostilities in June..."}} When the truce expired in June, Tyrone resumed hostilities.{{Sfn|O'Neill|2017|p=74}} He besieged the Blackwater fort and threatened to starve out the inhabitants.{{Sfnm|1a1=Dunlop|1y=1895|1p=192|2a1=Morgan|2y=2014|2ps=, 13th paragraph.}} 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. The confederates had prepared ditches in the ground to obstruct the enemy.{{Sfn|Lennon|2005|p=298}} Half of Bagenal's 4,000 men were killed, including Bagenal himself,{{Sfnm|1a1=Morgan|1y=2002|1p=4|2a1=Walsh|2y=1996|2p=23}} who was struck by a bullet after lifting his visor.{{Sfn|O'Neill|2017|p=76}}

The confederacy's success at the battle was the greatest victory by Irish forces against England,{{sfnm|1a1=Morgan|1y=2004|1p=306|2a1=Encyclopedia Britannica|2y=2024}} and it sparked a general revolt throughout the country, particularly the south.{{Sfnm|1a1=McNeill|1y=1911|1p=110|2a1=Dunlop|2y=1895|2p=192}} Tyrone has been criticised for failing to immediately capitalise on his victory,{{Sfnm|1a1=McNeill|1y=1911|1p=110|2a1=Dunlop|2y=1895|2p=192–193|3a1=Morgan|3y=2014|3ps=, 13th paragraph.}} as he let three months elapse before launching a major attack into Munster.{{Sfn|Dunlop|1895|p=192–193}} However, it is possible Tyrone sustained heavy losses from the battle.{{harvnb|Morgan|2014}}, 13th paragraph. One estimate puts Irish losses at the battle of the Yellow Ford at around 200 killed.{{Sfn|O'Neill|2017|p=77}} News of the battle spread across western Europe, prompting Philip II to send a congratulatory letter to the confederates. Unfortunately for Tyrone,{{Sfn|McGettigan|2005|p=85}} Philip II died the following month; he was succeeded by his son Philip III.{{cite EB9|wstitle=Philip II. of Spain|volume=XVIII|last=|first=|author-link=|pages=743–746|short=1}}

{{Main|Essex in Ireland}}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.{{sfn|Hull|1931}} Essex had an existing connection with Ireland and Tyrone, as his father Walter Devereux was one of Tyrone's early allies.{{Sfn|Morgan|2002|p=1}} 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".{{sfn|Hull|1931}}File:Robert Devereux, 2nd Earl of Essex F-000593.jpg, commander of the failed Irish campaign]]

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.{{Sfnm|1a1=Morgan|1y=2002|1pp=8–10|2a1=Morgan|2y=2014|2ps=, 14th paragraph: largest English army ever dispatched to Ireland.|1ps=: Essex arrived in Dublin on 15 April with 17,000 foot and 1,500 horse}} The situation in Ireland was practically unaltered since the battle of the Yellow Ford.{{Sfnm|1a1=Dunlop|1y=1895|1p=193|2a1=McNeill|2y=1911|2p=110}} Despite his resources, Essex's Irish campaign proved to be a failure. He led months of ill-managed operations in the south of Ireland,{{Sfn|Morgan|2002|pp=11–12}} lost hundreds of soldiers to disease, desertion and warfare (particularly the Battle of Curlew Pass),{{Sfn|Morgan|2002|p=15}} and executed every tenth officer for cowardice.{{harvnb|McCormack|2011}}, 6th paragraph. 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.{{Sfnm|1a1=O'Neill|1y=2021|1pp=252–253|1ps=: Catherine at Tyrone's camp|3a1=Casway|3y=2016|3p=69|3ps=: Catherine was Tyrone's fourth wife.|2a1=Walsh|2y=1930|2p=20|2ps=: Catherine's marriage in August 1597}} Towards the end of July, Essex received letters from the queen with peremptory orders to travel northwards and attack Tyrone with all speed.{{Sfnm|1a1=Dunlop|1y=1895|1p=193|2a1=Morgan|2y=2002|2p=16}}

Tyrone skirmished with Essex's forces as they approached the borders of Ulster, but this was nothing like a general engagement.{{Sfn|Dunlop|1895|p=193}} Essex's numbers had dwindled to only 4,500 and Tyrone, whose army far outnumbered Essex's, refused to give battle.{{Sfn|O'Neill|2017|p=94}} Tyrone sent his counsellor Henry O'Hagan to request a parley,{{sfnm|1a1=Falls|1y=1997|1p=244|2a1=Hull|2y=1931}} and Essex stubbornly agreed only after Tyrone had asked three times.{{Sfnm|1a1=Morgan|1y=2002|1p=17|2a1=Hull|2y=1931}}

On 7 September 1599, at the ford of Bellaclinthe on the River Lagan, Tyrone met Essex for a half-hour parley.{{Sfnm|1a1=O'Neill|1y=2017|1p=94|2a1=Falls|2y=1997|2p=245|3a1=Morgan|3y=2002|3pp=17–18}} Tyrone waded his horse into the river whilst Essex stayed on the bank.{{Sfnm|1a1=Falls|1y=1997|2a1=Morgan|2y=2002|3a1=Hull|3y=1931|1p=245|2pp=19–20}} Tyrone doffed his cap, saluting Essex "with a great deal of reverence".{{sfnm|1a1=Hull|1y=1931|2a1=Morgan|2y=2014|2ps=, 14th paragraph.}} 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.{{Sfn|Morgan|2002|p=20}} Essex was not familiar with Tyrone's wily nature and gullibly accepted these proposals.{{Sfnm|2a1=Morgan|2y=2002|2p=22|1a1=Dunlop|1y=1895|1p=193}} Because their parley was conducted privately, out of earshot of their armies,{{sfnm|1a1=Falls|1y=1997|2a1=Morgan|2y=2002|1p=245|2pp=19–20}} Essex was later accused of conspiring with Tyrone to seize the thrones of England and Ireland.{{sfnm|1a1=Hull|1y=1931|2a1=Morgan|2y=2014|2ps=, 14th paragraph.}} These accusations are far-fetched and obviously defamatory.{{Sfnm|1a1=Dunlop|1y=1895|1p=193|2a1=Morgan|2y=2002|2p=20}}

File:Essex-Tyrone-Meeting.jpg

A more formal meeting occurred later that day at the same ford, with six witnesses on each side attending.{{sfnm|1a1=Brewer|1a2=Bullen|1y=1869|1p=324|2a1=Hull|2y=1931|3a1=McCormack|3y=2011|3ps=, 7th paragraph.}}{{Efn|The confederate witnesses were Cormac MacBaron O'Neill, Arthur Roe Magennis, Hugh Maguire, Ever MacCooley MacMahon, Henry Hovenden and Richard Owen. The royalist witnesses were Henry Wriothesley, George Bourchier, Warham St Leger, Henry Danvers and William Constable. The sixth royalist witness was either Edward Wingfield or William Warren.{{sfn|Brewer|Bullen|1869|p=324}}{{sfn|Falls|1997|pp=245–246}}}} 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.{{sfn|Hull|1931}} Elizabeth I was displeased by the favourable conditions allowed to Tyrone and by Essex's treatment of him as an equal.{{Sfnm|1a1=McNeill|1y=1911|1p=110|2a1=Dunlop|2y=1895|2p=193}} 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. Following a failed uprising, Essex was eventually executed for treason on 25 February 1601.{{harvnb|McCormack|2011}}, 9th paragraph.

On 5 November 1599, in a strong position after Essex's failed campaign,{{Sfn|Lennon|2005|p=300}} Tyrone issued a public proclamation declaring a holy war against England.{{Sfn|Morgan|1994|p=2}}{{Harvnb|Morgan|2014}}, 15th paragraph. 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.{{Citation |last=O'Neill |first=Hugh |title=Hugh O'Neill's War aims |date=5 November 1599 |url=https://celt.ucc.ie/published/E590001-003/ |archive-url=https://web.archive.org/web/20210506063650/https://celt.ucc.ie/published/E590001-003/ |archive-date=6 May 2021 |url-status=live |author-link=Hugh O'Neill, Earl of Tyrone}}{{Sfn|Morgan|1994|pp=1–2}} 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.{{Sfn|Morgan|1994|p=5}}

Tyrone's main goal was now to win over Ireland's English-speaking Catholic population (the "Old English").{{sfnm|1a1=Morgan|1y=1994|2a1=Lennon|2y=2005|1pp=1–2|2pp=300–301}} 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.{{sfn|O'Connor|2002|pp=6–8}} He declared that "if [he] had to be king of Ireland without having the catholic religion, [he] would not the same accept".{{Sfnm|1a1=Meehan|1y=1868|1p=33|2a1=Morgan|2y=2014|2ps=, 15th paragraph.}} Tyrone gained a token of encouragement from Pope Clement VIII, who entitled him "Captain General of the Catholic Army in Ireland".{{sfn|McGurk|2001|p=17}} In late 1599 and early 1600, the Earl was in Munster on pilgrimage.{{Sfnm|1a1=O'Connor|1y=2002|1pp=10–11|2a1=Dunlop|2y=1895|2pp=193–194}} He supported the claim of James FitzThomas Fitzgerald (the Súgán Earl) to the Earldom of Desmond,{{harvnb|McNeill|1911|p=110}}; {{harvnb|Morgan|2014}}, 15th paragraph. and recognised Florence MacCarthy as the MacCarthy Mor at Inniscarra.{{Sfnm|1a1=O'Hart|1y=1892|1p=114|2a1=Dunlop|2y=1895|2pp=193–194}} However the Munster expedition ended in failure when in early March,{{Sfn|Dunlop|1895|pp=193–194}} confederacy commander Maguire was shot and killed by English forces whilst on a nearby reconnaissance mission.{{sfn|Barry|2009|ps=, 6th paragraph.}} Maguire's death was a major loss to the confederacy and prompted Tyrone to abruptly return to Ulster.{{Sfn|Lennon|2005|p=301}} 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.{{sfnm|1a1=McGurk|1y=2001|1p=17|2a1=Morgan|2y=2014|2ps=, 15th–16th paragraph.}}

Tyrone stimulated the Irish-Spanish alliance by sending his son Henry to Spain in April 1600.{{harvnb|Morgan|2014}}, 16th paragraph. At this time controversial Jesuit James Archer operated as his representative at the Spanish court.{{Cite journal |last=Woods |first=C. J. |date=October 2009 |title=Archer, James |url=https://www.dib.ie/biography/archer-james-a0196 |url-status=live |journal=Dictionary of Irish Biography |doi=10.3318/dib.000196.v1 |archive-url=https://web.archive.org/web/20240712020155/https://www.dib.ie/biography/archer-james-a0196 |archive-date=12 July 2024 |access-date=6 July 2024|url-access=subscription }} 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.{{Sfn|Dunlop|1895|p=194}}

File:Sir Charles Blount c 1594.jpg, the royal army greatly weakened the confederacy.]]

In February 1600, Charles Blount, 8th Baron Mountjoy, Essex's successor as Lord Deputy, arrived in Ireland.{{Sfnm|1a1=Walsh|1y=1996|1p=30|2a1=O'Neill|2y=2017|2pp=119, 123}} He was a protégé of Essex and similarly a favourite at court.{{Cite journal |last=Hawkins |first=Richard |date=October 2009b |title=Blount, Charles Brooke |url=https://www.dib.ie/biography/blount-charles-brooke-a0747 |journal=Dictionary of Irish Biography |doi=10.3318/dib.000747.v1 |url-access=subscription |archive-url=https://web.archive.org/web/20210803200157/https://www.dib.ie/biography/blount-charles-brooke-a0747 |archive-date=3 August 2021 |access-date=10 March 2025}} Mountjoy posed a major threat to Tyrone as he began immediately revitalising and restoring confidence in the royal army.{{Sfnm|1a1=Lennon|1y=2005|1p=301|2a1=O'Neill|2y=2017|2p=123}} He assigned veteran soldiers Arthur Chichester and George Carew to Ulster and Munster respectively.{{Sfn|Connolly|2007|p=389}}

In May 1600 the English achieved a strategic breakthrough when Henry 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 English. These Irish soldiers, particularly Niall Garve O'Donnell and Arthur O'Neill, emboldened the English troops and allowed Docwra to significantly weaken Tyrone's forces.{{Sfn|O'Neill|2017|p=|pp=130–131}}

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.{{Sfn|McNeill|1911|p=110}}{{sfn|Dunlop|1895|p=194}} Tyrone was in a desperate position. Upset with setbacks, he began drinking heavily and took his frustrations out on his wife Catherine.{{Sfn|Casway|2016|p=73}}

{{Main|4th Spanish Armada|Siege of Kinsale}}

As 1601 began, Philip III was focused on dispatching an expedition to Ireland in order to improve his position in the Anglo-Spanish War.{{Sfn|Lennon|2005|p=302}} In October 1601, the long-awaited aid from Spain appeared in the form of an army under Spanish commander Juan del Águila, which occupied the town of Kinsale in the extreme south of the country.{{Sfnm|1a1=McNeill|1y=1911|1p=110|2a1=McGurk|2y=2001|2pp=16–17}} 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.{{sfn|McGurk|2001|pp=16–17}} Mountjoy rushed to contain the Spanish, 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. They gained little support en route. Tyrone's army united with O'Donnell's at Bandon on 15 December.{{sfn|McGurk|2001|pp=17–18}}File:Kinsale-1601-02.jpg]]The Irish presence at Kinsale trapped the English between the confederates and the Spaniards.{{sfnm|1a1=McGurk|1y=2001|1p=18|2a1=Morgan|2y=2014|2ps=, 17th paragraph.}} 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.{{sfn|Dunlop|1895|p=194}} 17th-century 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.{{sfn|McGinty|2013b|p=11}} Morgan claims it was the pressure from the beleaguered Spaniards that wore down Tyrone, and that the Earl also had his reputation on the line.{{harvnb|Morgan|2014}}, 17th paragraph. In any case, Tyrone uncharacteristically yielded to the Spanish officers and resolved to make an immediate joint attack.{{sfn|Dunlop|1895|p=194}}{{sfn|McGurk|2001|p=18}}

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.{{sfn|McGurk|2001|pp=18–20}} 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. He was strongly in favour of another attempt but was unable to persuade his surviving soldiers. O'Donnell was in a state of nervous breakdown.{{sfn|McGettigan|2005|pp=108–109}} The defeat at Kinsale was a fatal blow to the confederacy{{sfn|O'Neill|2017|p=169}} and destroyed any chance of winning the war. In the haste to leave Munster, 140 of Tyrone's men drowned while passing the Blackwater.{{sfn|McGettigan|2005|p=109}} According to Carew, a troop of women could have beaten Tyrone's army on its homeward march.{{sfn|Dunlop|1895|p=194}}

{{Main|Treaty of Mellifont}}

Tyrone reluctantly allowed O'Donnell to travel to Spain to seek further military assistance from Philip III.{{Sfn|McGettigan|2005|p=109}} 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.{{Sfn|McNeill|1911|p=110}} The Crown's army swept the country.{{sfn|O'Neill|2017|pp=169–175}} The English forces began to close in on Tyrone—Mountjoy from the south, and Dowcra and Chichester from the north.{{Sfn|Lennon|2005|p=303}} Mountjoy destroyed the traditional O'Neill inauguration stone at Tullyhogue.{{sfn|O'Neill|2017|p=175}} 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.{{sfn|Lennon|2005|p=303}}

English forces destroyed crops and livestock in Ulster in 1601–1602,{{Sfn|O'Neill|2017|pp=169–175}} 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,{{harvnb|Clavin|2009}}, 4th paragraph. which drastically weakened the Earl's power.{{Sfn|Walsh|1996|p=48}} In June 1602 Tyrone destroyed his capital at Dungannon and retreated into the woods of Glenconkeyne.{{Sfn|O'Neill|2017|pp=169–175}} Despite O'Donnell's petitioning to Philip III, the promised Spanish fleet was repeatedly delayed due to a lack of resources.{{sfnm|1a1=Walsh|1y=1996|1p=32|2a1=McGettigan|2y=2005|2p=114}} O'Donnell died in Simancas of a sudden illness on 30 August.{{Sfn|Morgan|2009|ps=, 13th paragraph.}} The Spanish government subsequently abandoned plans to support the confederacy and instead sought a peace treaty with England.{{Sfn|Ekin|2015|p=317}}File:TyroneSubmitstoMountjoy.png

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.{{Sfn|O'Neill|2017|pp=191–192}} 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.{{sfn|McGurk|2007|p=20}} The royal army's use of scorched earth tactics led to famine across 1602–1603,{{Sfn|Lennon|2005|p=303}} with conditions so extreme that the local population were reduced to cannibalism. 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.{{Sfn|O'Neill|2017|p=192}}

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.{{Sfn|O'Neill|2017|p=192}} Early in 1603, Mountjoy opened negotiations with Tyrone.{{Sfnm|1a1=McNeill|1y=1911|1p=110|1ps=. states that Elizabeth instructed Mountjoy to open negotiations.|2a1=Lennon|2y=2005|2p=303|2ps=. states that Mountjoy opened negotiations himself against Elizabeth's wishes.}} 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.{{Sfnm|1a1=Lennon|1y=2005|1pp=303–304|2a1=O'Neill|2y=2017|2p=192}} 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. These were particularly generous terms.{{sfnm|1a1=McGurk|1y=2007|1p=18|2a1=O'Neill|2y=2017|2p=192}} On 8 April Tyrone renewed his submission before Mountjoy and the council in Dublin.{{Sfn|Dunlop|1895|pp=194–195}} This was where Tyrone heard of the queen's death;{{Sfn|O'Neill|2017|p=192}} he apparently wept with frustration. After Tyrone's submission, the remaining confederates followed suit. This marked the end of the Nine Years' War.{{Sfn|O'Neill|2017|p=193}}

In summer 1603, Tyrone sailed to England with Mountjoy and Rory O'Donnell (Hugh Roe O'Donnell's younger brother) to meet Elizabeth's successor James I.{{harvnb|Walsh|1996|p=37|ps=: In summer 1603 Tyrone and O'Donnell's younger brother Rory travelled to London to meet the king}}; {{harvnb|O'Neill|2017|p=193|ps=: In the summer, Tyrone travelled to England with Mountjoy to meet the king.}} Fynes Moryson recorded that, as Tyrone traveled through Wales on his way to London, widows of British soldiers hurled "dirt and stones at the Earl... and [reviled] him with bitter words".{{Sfn|Smith|1996|p=18}} Tyrone and Rory arrived at London on 4 June{{Sfn|Dunlop|1895|p=195}} and presented themselves at Hampton Court.{{Sfn|McNeill|1911|p=110}} Many English courtiers were greatly incensed at the gracious reception accorded by the king to these notable rebels. 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".{{Sfnm|1a1=Dunlop|1y=1895|1p=195|2a1=O'Neill|2y=2017|2p=193}} Tyrone even went hunting with the new king.{{Sfn|O'Neill|2017|p=193}}

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.{{harvnb|McNeill|1911|p=110}}; {{harvnb|Morgan|2014}}, 18th paragraph. He was also bold enough to request the lord presidency of Ulster, but was only allowed lieutenancy of Tyrone and Armagh.{{harvnb|Morgan|2014}}, 18th paragraph. Rory was created 1st Earl of Tyrconnell.{{Harvnb|O'Byrne|2009d}}, 3rd paragraph. 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.{{Sfn|O'Neill|2017|p=193}}

File:ArthurChichester BaronChichesterOfBelfast Belfast Harbour Commissioners.jpg's antagonism towards Tyrone was a contributing factor to the latter's flight.]]

Tyrone returned to Ireland at the end of August 1603{{Sfn|Dunlop|1895|p=195}} and began rebuilding his estates, an easy task under the reserved government of George Carey, who had replaced Mountjoy as Lord Deputy.{{Sfn|O'Neill|2017|p=193}} As part of the Treaty of Mellifont, Tyrone was given authority over O'Cahan,{{Sfn|Lennon|2005|p=304}} whom he retained animosity towards due to his desertion during the war.{{sfn|McGurk|2007|p=|pp=17–19}} 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.{{Sfn|Dunlop|1895|p=195}} 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.{{sfn|McGurk|2007|pp=18–19}}

Arthur Chichester became Lord Deputy in February 1605.{{Cite book |last=Healy |first=Timothy Michael |author-link=Tim Healy (politician) |url=https://archive.org/details/stolenwaterspage00healuoft |title=Stolen waters: a page in the conquest of Ulster |publisher=Longmans, Green, and Co. |year=1913 |location=London |pages=377}} 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.{{Sfn|O'Neill|2017|pp=193–194}} Chichester was also antagonistic to Tyrone, forcing him to attend Protestant services and accusing him of plotting with Spain. It became clear to Tyrone that the restoration of his earldom meant little.{{sfn|McGurk|2007|p=18}} 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.{{sfnm|1a1=Casway|1y=2016|1pp=73–74|2a1=O'Neill|2y=2017|2p=194}}

Tyrone lost his support from the council when Mountjoy died in April 1606.{{Sfnm|1a1=Smith|1y=1996|1p=20|2a1=McGurk|2y=2007|2p=19|3a1=O'Neill|3y=2017|3p=194}} 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.{{sfnm|1a1=Dunlop|1y=1895|1p=195|2a1=Smith|2y=1996|2p=19}} 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.{{sfn|McGurk|2007|p=19}} 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,{{sfnm|1a1=McGurk|1y=2007|1p=19|2a1=Morgan|2y=2014|2ps=, 19th paragraph.}} who he was apparently never actually divorced from.{{sfnm|2a1=McGurk|2y=2007|2p=19|1a1=Walsh|1y=1930|1p=38}} 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."{{Sfn|Walsh|1930|p=38}} In March 1607 O'Cahan repudiated his marriage to Rose{{sfn|Clavin|2009|ps=, 5th paragraph.}} and before the end of the year he had married another woman.{{Sfn|Walsh|1929|p=570}} Tyrone had asked for Rose's dowry back,{{Sfnm|1a1=Walsh|1y=1929|1p=570|2a1=McGurk|2y=2007|2p=19}} but O'Cahan retained it.{{Sfn|Walsh|1930|p=38}} It is clear that government officials were harnessing O'Cahan's hostility to orchestrate Tyrone's undoing.{{Sfn|McGurk|2007|p=19}}

File:Rory O'Donnell, Earl of Tyrconnell.png, Hugh Roe O'Donnell's younger brother.]]

Tensions between Tyrone and the English government escalated. Tyrone's continued correspondence with Spain broke his promises made at Mellifont.{{sfn|McGurk|2007|p=20}} In 1607, the Earl of Tyrconnell accidentally exposed a plot to seize Dublin Castle, hopefully with Tyrone's involvement, during a conversation with Richard Nugent, Lord Delvin.{{Sfn|Bagwell|1895|p=445}}

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.{{Sfn|Dunlop|1895|p=195}} 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.{{sfn|McGurk|2007|p=19}} 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.{{Sfn|Dunlop|1895|p=195}}{{cite DNB|wstitle=O'Cahan, Donnell Ballagh|volume=41|last=Pollard|first=Albert|author-link=Albert Pollard|pages=344-345|year=|short=}} Tyrone was ordered to present himself in London at the beginning of Michaelmas term (late September).{{Sfn|Walsh|1996|p=55}}

By September, Tyrconnell's supposed plot was known to the government. 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.{{sfn|Walsh|1996|p=55}} Historians are undecided on whether this plot actually existed and if the government intended to arrest Tyrone.{{harvnb|McGurk|2007|p=20|ps=. "On whether there was a government plot against O'Neill's life the historical jury is still out".}}; {{harvnb|Smith|1996|pp=17–20|ps=. "Their allegation that there was an official plot against O'Neill is still in question. However they were certainly wrong in claiming that O'Neill

was innocent of plotting himself..."}}; {{harvnb|Bagwell|1895|p=445|ps=. "So far as Tyrconnel was concerned there can be no doubt that he had been in correspondence with Spain, but it must remain uncertain whether there was any conspiracy."}} The exact cause of Tyrone's flight is a matter of controversy among historians,{{harvnb|Bagwell|1895|p=445|ps=. "The immediate cause of their sudden departure may be doubtful, but not the real causes."}}; {{harvnb|Smith|1996|pp=17–20|ps=. "One of the most argued over events in the career of Hugh O'Neill, second Earl of Tyrone, is his departure from Ireland..."}}; {{harvnb|Walsh|1996|p=9|ps=. "The factors which induced O Neill to leave Ireland in 1607 have always been a matter of controversy among historians."}}; {{harvnb|McGurk|2007|ps=. "O'Neill's decision to leave Ireland has puzzled contemporaries and successive generations of historians..."|p=18}}; {{harvnb|Morgan|2014|ps=, 19th paragraph. "There is no satisfactory explanation for the panicked flight of Hugh O'Neill..."}} though he certainly believed that his arrest was imminent.{{Sfn|Walsh|1996|pp=9–10}} 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.{{Sfnm|1a1=Walsh|1y=1996|2a1=Hegarty|2y=2010|2p=9|1pp=55–58}} Tyrconnell already planned to leave the country and flee to Spain, and he convinced Tyrone to come with him. Tyrone was at Slane with Chichester when news of the vessel's arrival reached him.{{Sfnm|1a1=Walsh|1y=1996|1p=59|2a1=Hegarty|2y=2010|2p=9}} He seemed to have come to an immediate snap decision.{{Harvnb|Morgan|2014}}, 19th paragraph. Attorney-General Davies recollected that Tyrone left Slane in an unusually solemn manner, farewelling every servant and child in the house.{{Sfn|Hegarty|2010|p=9}}

{{Main|Flight of the Earls}}

File:Flight-of-the-Earls-Engraving.jpg

"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 A Coruña in Spain. Accompanying them were their wives, families and retainers, numbering about ninety-nine persons.{{sfn|McGurk|2007|p=16}} The Flight is seen to symbolically mark the collapse of Gaelic Irish society.{{Cite journal |last=Ó Ciardha |first=Éamonn |date=August 2007 |title=Cáit ar ghabhadar Gaoidhil? [Where will the Irish go?] |url= |url-status=dead |journal=History Ireland |volume=15 |issue=4 |pages=5–6 |jstor=27725645}} 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".{{Sfn|Casway|2016|pp=74–75}}

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.{{sfn|Walsh|1996|pp=64–65}} Despite the earls' petitioning, Philip III would not allow the refugees to enter Spain for fear of violating the 1604 Anglo-Spanish peace treaty.{{sfn|Walsh|1996|pp=68–71}} Spain was on the verge of bankruptcy and could not afford another war with England.{{sfn|McGurk|2007|pp=20–21}} 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 and the women in a coach) left Leuven to travel southwards.{{sfn|Walsh|1996|pp=73–74}} The nobles left their younger children behind in Leuven under the care of Irish Franciscans at St Anthony's College.{{Sfn|Casway|2016|p=75}}

File:Flight of Earls (1607).svg to Rome]]

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.{{Harvnb|Walsh|1996|pp=7, 79}}; {{harvnb|O'Byrne|2009d}}, 4th paragraph. The journey to Rome was recorded in great detail by writer Tadhg Ó Cianáin.{{Cite book |last=Ó Cianáin |first=Tadhg |author-link=Tadhg Ó Cianáin |url=https://celt.ucc.ie/published/T100070.html |title=The Flight of the Earls |publisher=CELT: Corpus of Electronic Texts Edition |year=2005 |translator-last=Walsh |translator-first=Paul |orig-date=1608 |archive-url=https://web.archive.org/web/20240418101936/https://celt.ucc.ie/published/T100070.html |archive-date=18 April 2024 |url-status=live}}{{Sfn|Hegarty|2010|p=|pp=10–11}} In November 1607 the flight was proclaimed as treasonous by James I.{{Citation |title=A Proclamation touching the Earles of Tyrone and Tyrconnell |date=15 November 1607 |url=https://celt.ucc.ie/published/E600001-002/text001.html |archive-url=https://web.archive.org/web/20181231230742/https://celt.ucc.ie/published/E600001-002/text001.html |archive-date=31 December 2018 |url-status=live |place=London |publisher=Robert Barker}}{{sfn|Walsh|1996|p=71}} A bill of attainder was passed against Tyrone by the Parliament of Ireland on 28 October 1614.{{sfn|Cokayne|1896|p=450}}

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.{{Sfn|Dunlop|1895|pp=195–196}} The earls were displeased with the small size of their pension.{{Sfn|Walsh|1996|p=80}} Compared to Tyrone's arrangements in Ireland, this was a miserly lifestyle.{{harvnb|Casway|2003|p=62}}. "[Tyrone's wife Catherine] found neither the climate, nor the separation from her children, nor her diminished lifestyle acceptable." Catherine became highly distressed by the Roman climate and her separation from her children, though Tyrone forbade her from relocating to Leuven.{{Sfn|Casway|2016|p=75}} 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.{{Sfn|Ó Fearghail|2009|p=47}} In July 1608 Tyrconnell died of a fever,{{harvnb|O'Byrne|2009d}}, 4th paragraph. and by 1610, Tyrone's eldest sons Hugh and Henry had also died.{{Sfn|Walsh|1996|p=11}} Tyrone continued to petition Philip III for his assistance, pleading him to "liberate [Catholic Ireland] from heresy and tyranny",{{sfn|Casway|2011|p=111}} but had no success.{{Sfn|Walsh|1996|p=11}}

Tyrone quickly became disillusioned with his exile and yearned to return to his position in Ireland.{{Sfnm|1a1=Canny|1y=2001|1pp=418–419|2a1=Ó Fearghail|2y=2009|2p=47}} For the rest of his life, he did not give up the possibility of returning to Ireland.{{Sfnm|1a1=Walsh|1y=1996|1p=11|2a1=Morgan|2y=2014|2ps=, 21st paragraph.}} 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.{{Harvnb|Morgan|2014}}, 21st paragraph. 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".{{Sfn|Walsh|1996|p=11}} 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".{{harvnb|Walsh|1957a|p=13}}. fn. 3.

File:San Pietro in Montorio Grab Hugh O'Neill.jpg, Prince Hugh O'Neill, skeleton"|left|250x250px]]It has been alleged that Tyrone became blind in his last years,{{sfnm|1a1=Dunlop|1y=1895|1p=196|2y=1896|2p=450|2a1=Cokayne|3a1=O'Hart|3p=725|3y=1892}} but this is probably propaganda spread by Chichester. Tyrone remained in good health throughout 1615 but he became seriously ill in January 1616.{{Sfn|Walsh|1996|pp=129–131}} He died in Rome on 20 July.{{sfnm|1a1=McNeill|2a1=Hogan|1y=1911|2y=1931|2p=242|3a1=Morgan|3y=2014|3ps=, 21st paragraph.|1p=110}}

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."{{Sfn|Walsh|1996|p=|pp=132–133}}

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.{{sfnm|1a1=Walsh|1y=1996|1p=133|2a1=FitzPatrick|2y=2007|2pp=47–49}} 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".{{Cite journal |last=FitzPatrick |first=Elizabeth |date=2017 |title=The Exilic Burial Place of a Gaelic Irish Community at San Pietro in Montorio, Rome |url= |journal=Papers of the British School at Rome |volume=85 |pages=205–239 |issn=0068-2462 |jstor=26578329}} This explains the brevity of the inscription on Tyrone's tomb.{{Sfn|FitzPatrick|2007|pp=47–48}} Allegedly, his bones were moved seven years after burial, and his hands were found to be perfectly intact.{{Sfn|Morgan|2016}} The original tombstone was lost in 1849 during the Risorgimento. In 1989 Tomás Ó Fiaich laid a new marble plaque with the same inscription.{{cite web |title=News 2005 |url=http://www.rsai.ie/index.cfm?action=obj.display&obj_id=133 |url-status=dead |archive-url=https://web.archive.org/web/20110927165828/http://www.rsai.ie/index.cfm?action=obj.display&obj_id=133 |archive-date=27 September 2011 |website=Royal Society of Antiquaries of Ireland |at=11 April 2005}}{{sfn|FitzPatrick|2007|pp=48–49}}

Upon news of Tyrone's death, the court poets of Ireland engaged in the contention of the bards.{{Cite book |last= |first= |url=https://archive.org/details/iomarbhghnabhf20mckeuoft |title=Iomarbhágh na bhfileadh: The contention of the bards |publisher=Simpkin, Marshall, Hamilton, Kent & Co. |others=Irish Texts Society. Digitized by the Internet Archive in 2008 with funding from the Microsoft Corporation |year=1918 |editor-last=McKenna |editor-first=Lambert |editor-link=Lambert McKenna |location=London |pages=136–137}}{{Cite news |last=McNally |first=Frank |date=27 May 2016 |title=All chieftains great and small – An Irishman's Diary about Hugh O'Neill (and some of his followers) |url=https://www.irishtimes.com/opinion/all-chieftains-great-and-small-an-irishman-s-diary-about-hugh-o-neill-and-some-of-his-followers-1.2662157 |url-status=live |archive-url=https://web.archive.org/web/20240827074125/https://www.irishtimes.com/opinion/all-chieftains-great-and-small-an-irishman-s-diary-about-hugh-o-neill-and-some-of-his-followers-1.2662157 |archive-date=27 August 2024 |access-date=27 August 2024 |newspaper=The Irish Times |language=en}} His presence in Europe was a constant source of concern for the English, and his death came as a welcome relief.{{Cite web |last=Rafferty |first=Pat John |title=Reactions and reports on the death of the Great O'Neill |url=http://www.irishidentity.com/stories/greatoneill.htm |archive-url=https://web.archive.org/web/20240511132443/http://www.irishidentity.com/stories/greatoneill.htm |archive-date=11 May 2024 |access-date=11 May 2024 |website=Irish Identity}} The Annals of the Four Masters, compiled in 1636,{{Cite book |last1= |first1= |url=https://archive.org/details/annalsofkingdomo01ocle/page/n13/mode/2up?q=1636 |title=Annals of the kingdom of Ireland, by the Four Masters, from the earliest period to the year 1616|date=1856 |publisher=Hodges, Smith and Co. |others= |editor-last=O'Donovan |editor-first=John |editor-link=John O'Donovan (scholar) |edition=2 |volume=I |location=Dublin |page=xi}} 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". Conversely, because Tyrone had deserted his people in 1607, his own generation expressed little admiration for him.{{Sfn|Canny|2022|p=49}}

Historian James MacGeoghegan rehabilitated Tyrone's image in the seventeenth century.{{sfn|Canny|2022|p=50}} 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.{{sfnm|1a1=Canny|1y=2022|1pp=30, 50|2a1=McGinty|2y=2013a|2p=14}} Mitchel also credited Tyrone with the development of modern Irish nationalism and the concept of the first independent Irish state.{{sfnm|1a1=McGinty|1y=2013a|1pp=14–15|2a1=Morgan|2y=2016}} 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,{{sfn|Power|2010|p=382}} whose traditional Celtic upbringing, sensational prison break saga and tragic early death made him a Gaelic Irish martyr and national hero.{{sfnm|1a1=Kelly|1y=2004|1p=160|2a1=Mitchell|2y=2024|2p=76}}

Seán Ó Faoláin's biography The Great O'Neill (1942) is the most influential modern work on Tyrone.{{Harvnb|Morgan|2014}}, 22nd paragraph. It attracted a large readership but is today considered inaccurate and overdramatised.{{Sfn|Canny|2022|p=26}}{{Citation |last=Morgan |first=Hiram |title=O'Faoláin's Great O'Neill |date=25 February 2000 |url=https://celt.ucc.ie/OFaolain.pdf |archive-url=https://web.archive.org/web/20240917092603/https://celt.ucc.ie/OFaolain.pdf |archive-date=17 September 2024}} 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. The Great O'Neill was so popular that it was used by Brian Friel as the basis for his 1988 play Making History, which focuses on Tyrone reckoning with his legacy post-Flight.

Hiram Morgan's book Tyrone's Rebellion (1993), which focuses on Tyrone's life up to 1596,{{Sfn|O'Neill|2017|p=15}} restored the Earl to the status he was formerly afforded by contemporary English commentators.{{sfn|Power|2010|p=382}} Tyrone now overshadows O'Donnell in most modern depictions of the Nine Years' War.{{sfn|Kelly|2004|p=160}} Morgan judges Tyrone more harshly than Ó Faoláin, and compared to other historians, he portrays Tyrone as loyal to the confederacy from the beginning.{{Sfn|O'Neill|2017|p=25}}{{Cite AV media |url=https://www.youtube.com/watch?v=y_-pO0nmuhk |title=The Nine Years war (RTÉ Cork Project and UCC) |date=24 May 2024 |last=Irish Medieval History |time=1:12 |access-date=12 October 2024 |via=YouTube}} Generally speaking, contemporary historians see Tyrone as a more compelling figure than O'Donnell.{{sfn|Kelly|2004|p=160}} They also recognise Tyrone's self-serving reasons for entering the war{{Sfnm|1a1=O'Connor|1y=2002|1pp=3–4|2a1=Morgan|2y=2014|2ps=, 23rd paragraph.}} and blame Tyrone for expediting Gaelic Ireland's decline.{{Cite web |last=Neary |first=Marina J. |date=2010 |title=Hugh O'Neill: a Provocateur of Fate |url=http://bewilderingstories.com/issue413/oneill.html |url-status=live |archive-url=https://web.archive.org/web/20111013064049/http://bewilderingstories.com/issue413/oneill.html |archive-date=13 October 2011 |access-date=16 February 2024 |website=Bewildering Stories}}

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. In his day, he was one of the richest lords in Ireland.{{Sfn|O'Neill|2017|p=219}}

Tyrone introduced a "military revolution" to Ireland with his use of firepower and field fortifications in Irish warfare.{{Sfn|Morgan|2016}} His revenue allowed him to purchase muskets, pikes and ammunition from Britain. Firearms were the primary weapon in Tyrone's army.{{Sfn|O'Neill|2017|pp=52–53}} 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.{{Sfn|O'Neill|2017|pp=44–45}}{{Sfn|Walsh|1996|p=21}} Across late 1594 and early 1595, he bought £8,000 worth of gunpowder, lead and firearms from Scotland.{{Sfn|O'Neill|2017|pp=44–45}}File:Pamphlet.jpg, an infantry formation often used by Tyrone's forces]]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, including pike and shot.{{sfn|O'Neill|2017|pp=52–53}} Many of his soldiers were being trained by veterans returned from the Spanish army. Tyrone also had several Spanish and English military advisors in his pay, the Spanish ones having been sent by Philip II.

Tyrone's forces were very poor at siege warfare, as evident by their many failures to capture the occupied Blackwater fort. Tyrone had not been formally trained in regular warfare, hence why most of his successful battles were fought guerilla-style.{{Sfn|Morgan|1993|pp=217–218}} Nevertheless with only small forces he was able to defeat the best English generals sent by Elizabeth I and exhaust her resources.{{Sfn|Walsh|1996|p=15}} 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".{{sfn|Canny|2022|p=50}} Henry IV of France declared Tyrone to be one of the best generals of his time.{{Sfnm|1a1=Walsh|1y=1996|1p=15|2a1=Morgan|2y=2016}}

Wartime propaganda depicted Tyrone as a "Catholic crusader", though many of his contemporaries had their doubts regarding the sincerity of his religious convictions.{{Sfn|O'Connor|2002|p=1}} It is generally believed that his preoccupations were political rather than religious.{{Sfn|Morgan|1993|p=214}} 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".{{harvnb|Morgan|2014}}, 14th paragraph.

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.{{Sfn|Morgan|1993|p=214}} In fact, his background gave him the advantage of having allies from both British and Irish backgrounds.{{sfnm|1a1=Morgan|1y=2014|1ps=, 4th paragraph|2a1=Ricketts|2y=2020|2p=8}}

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.{{sfnm|1a1=Morgan|1y=1993|2a1=O'Connor|2y=2002|2p=2|1p=215}} Tyrone's 1591 marriage ceremony was performed by a Protestant bishop, because Tyrone wanted the marriage recognised under English law.{{sfnm|1a1=Meehan|1y=1868|1p=414|2a1=Bagenal|2y=1925|2pp=53–54}} Mabel later converted to Catholicism.{{harvnb|Clarke|Barry|O'Byrne|2009}}, 4th paragraph; {{harvnb|Casway|2016|p=72}}. Tyrone celebrated Easter 1584 per the Pope's new Gregorian calendar.{{sfnm|1a1=O'Connor|1y=2002|2a1=Morgan|2y=1994|2p=5|1p=2}}

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.{{Sfn|Morgan|1994|pp=2–3}} In fact, during 1596 peace negotiations the religious nature of his demands came as a surprise to the Dublin government;{{Sfn|O'Connor|2002|p=7}} though he was willing to drop his demand for liberty of conscience.{{Sfn|Morgan|1993|p=204}} His wartime appeals to Spain typically highlighted the persecution Ireland suffered as a fellow Catholic nation.{{Sfnm|1a1=O'Connor|1y=2002|1pp=3–4|2a1=Morgan|2y=2013|2p=5}}

Historians Nicholas Canny and Thomas O'Connor believe that Tyrone underwent a genuine religious conversion in the late 1590s.{{Sfn|Canny|2022|p=49}}{{Sfn|O'Connor|2002|p=8}} 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.{{Sfn|O'Connor|2002|pp=7–8, 13}} In the same year Tyrone went on pilgrimage to Holycross in Munster.{{Sfn|O'Connor|2002|pp=10–11}} 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.{{Sfn|O'Connor|2002|pp=6–7}} 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.{{Sfn|Ricketts|2020|pp=7–8}} During his exile, Tyrone interacted with the Pope and partook in traditional pilgrimages,{{Sfn|Ó Fearghail|2009|p=47}} but his religious views were apparently less dogmatic. This hints that Lombard may have exaggerated Tyrone's devoutness.{{Sfn|Canny|2022|pp=49–50}} Ultimately, Tyrone left no personal record of his faith.{{Sfn|O'Connor|2002|p=2}}

File:Hugh O'Neill from La spada d'Orione.png

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.{{Sfn|Morgan|1993|p=217}} 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".{{sfn|Morgan|2004|p=305}} 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.{{Harvnb|Morgan|2014}}, 4th paragraph.{{Sfn|O'Neill|2017|p=22}} 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.{{sfnm|1a1=Hogan|1y=1931|1p=242|1ps=. "...despite his English upbringing [Tyrone] identified his fortunes with those of the traditional order as completely as many of his predecessors, who were unable to speak a word of English, and knew as little about English life as they did about French or Italian."|2a1=MacCaffrey|2y=1992|2ps=. "The new earl stood out among the Gaelic lords as virtually the only one who was fully conversant with English custom and culture."|3a1=Canny|3y=2022|3pp=30–31|3ps=. "He marvelled how 'the grandson of the Dundalk blacksmith', who was also seemingly an autodidact, was equally 'at home in the halls of Greenwich as Dungannon'..."}}

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'".{{Sfn|Meehan|1868|p=288}} Tyrone was also a skilled negotiator; he typically played the "good cop" to O'Donnell's "bad cop" during meetings with the government.{{Harvnb|Morgan|2014}}, 23rd paragraph. O'Donnell was more aggressive and militaristic whereas Tyrone favoured negotiation with their enemies.{{sfn|McGinty|2013b|p=13}} He avoided impulsive decisions 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.{{Cite book |last=D'Alton |first=Edward Alfred |url=https://archive.org/details/historyofireland03dalt |title=History of Ireland: from the earliest times to the present day |publisher=The Gresham Publishing Company |volume=Half-volume III |location=London |publication-date=1913 |pages=129–130}} The 20th-century historian John McGurk described O'Neill as having the "rare gift of patience and the ability to inspire loyalty among erstwhile feuding chieftains".{{Sfn|McGurk|1997|p=9}}

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.{{Sfn|Morgan|1993|pp=217–218}} 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.{{harvnb|Morgan|2014}}, 23rd paragraph. "He miscalculated his own and Ireland's importance in great power politics, becoming a pawn when he committed himself to Spanish intervention during the war and then sacrificing his position by fleeing in the mistaken hope of their benevolence."; {{harvnb|Morgan|2016}}. "O'Neill's real failure was his inability to win over the Catholic old English of Dublin, the Pale and other Irish towns." 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. 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.{{Sfn|Canny|2022|p=49}} Like his chieftain predecessors, Tyrone spent his life focused primarily on the pursuit and retention of power.

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

{{Quote|text="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".{{sfn|Morgan|1993|p=3}}}}

In his late teens, he married a daughter of Brian McPhelim O'Neill of Clandeboye{{Sfn|Casway|2016|p=70}}—possibly named Katherine{{Sfn|Canny|2004|p=839}} or Feodora.{{sfn|Gibson|2013|ps=. "Hugh O'Neill [d.1616] m Feodora O'Neill"}} 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.{{Sfn|Casway|2016|pp=70–71}} Thus, the children of this marriage were considered illegitimate by English society.{{Sfnm|1a1=Walsh|1y=1930|1pp=29–30|2a1=Casway|2y=2016|2p=71}} Tyrone's first wife later married Niall MacBrian Faghartach O'Neill.{{Sfnm|3a1=Walsh|3y=1930|3p=17|1a1=Dunlop|1y=1895|1p=196|4a1=Casway|4y=2016|4p=78|2a1=Cokayne|2y=1896|2p=450|2ps=. fn. b.|4ps=. fn. 5.}}

Their children include:

• A daughter who married Ross McMahon{{Sfn|Casway|2016|p=71}} shortly before February 1579. Towards the end of 1579, her father intended to remarry her to Philip O'Relieghe.{{Sfn|Walsh|1930|p=33}} After the execution of her father-in-law Hugh Roe MacMahon in 1590,{{Sfn|McGettigan|2005|p=51}} Tyrone was denied the dowry he was owed from the marriage.{{Sfnm|1a1=Walsh|1y=1930|1p=33|2a1=McGinty|2y=2013a|2pp=24–25}}
• Conn{{Sfn|Casway|2016|p=71}} (died December 1601),{{Sfn|Walsh|1930|pp=29–30}} known as Conn Mac An Iarla,{{Sfnm|2a1=O'Neill|2p=37|2y=2017|1pp=69–70|1y=1993|1a1=Morgan}} 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.{{Sfn|Walsh|1930|pp=29–30}}

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

• Rose{{efn|Morgan presumes that Rose's mother was Tyrone's first wife.{{sfn|Morgan|1993|p=96}} Casway and Morwenna Donnelly confirm that this is possible.{{sfn|Casway|2016|p=78}}{{Cite journal |last=Donnelly |first=Morwenna |date=1986 |title=Red Hugh and Rose O'Neill |journal=Donegal Annual |issue=38 |pages=46–51}} McGettigan believes Rose's mother was Brian McPhelim's daughter, whom he describes as a concubine of Tyrone.{{sfn|McGettigan|2005|pp=55, 70}} In 1606, Rose was described by loyalist Niall Garve O'Donnell as illegitimate,{{sfn|Walsh|1930|p=37}} though all of the children of Tyrone's annulled first marriage were considered illegitimate by English society.{{Sfnm|1a1=Walsh|1y=1930|1pp=29–30|2a1=Casway|2y=2016|2p=71}}}} ({{fl.}} 1587 – 1607), who was betrothed to Hugh Roe O'Donnell by 1587.{{sfnm|1a1=Walsh|1y=1930|1pp=36–38|2a1=Morgan|2y=1993|2pp=96, 124, 128}} They married in December 1592{{Sfnm|1a1=McGettigan|1y=2005|1pp=54–55|2a1=Casway|2y=2016|2p=71}} and separated in 1595.{{Harvnb|Morgan|2009}}, 10th paragraph. Despite reconciling in April 1597, by the following year they had divorced,{{harvnb|Walsh|1939|p=237|ps=. fn. 5.}} putting Tyrone's partnership with O'Donnell under strain.{{Sfn|McGinty|2013a|pp=43–44}} 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{{harvnb|Clavin|2009}}, 2nd & 5th paragraph. and remarried to another woman.{{Sfn|Walsh|1929|p=570}}
• A daughter who married her first cousin Henry McArt O'Neill, son of Art MacBaron O'Neill{{Sfn|Walsh|1930|p=44}}

Hugh married Siobhán O'Donnell (died January 1591) in June 1574,{{Sfn|Walsh|1930|pp=17–18, 26}} beginning his enduring alliance with the O'Donnells of Tyrconnell.{{sfn|Morgan|1993|p=135}} The 1st Earl of Essex announced the marriage on 14 June 1574.{{Sfn|Walsh|1930|p=17}}

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.{{Sfn|Morgan|1993|p=93}} In February 1579 it was reported that Hugh and Turlough "knit up such a league of friendship",{{Sfn|McGinty|2013a|p=19}} with Tyrone accompanying Turlough on various hostings. However this alliance (and the engagement) was soon called off.{{Sfn|Morgan|1993|p=93}} Hugh was bought off by a government commission{{sfn|Morgan|2005|p=42}} who convinced Hugh that Turlough would probably die soon enough due to his age and ill health.{{sfn|Dunlop|1895|p=188}} 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.{{Sfn|McGinty|2013a|p=19}}

They had two sons and multiple daughters:

• Margaret ({{fl.}} 1598) who married Richard Butler, 3rd Viscount Mountgarret{{Sfnm|1a1=Dunlop|1y=1895|1p=196|1ps=. "[Siobhán gave birth to] two other daughters—one married to Magennis, and the other to Richard Butler, viscount Mountgarret."|2a1=Walsh|2y=1930|2pp=35–36|2ps=. "Margaret. This daughter was the wife of Richard Butler, son and heir of Edmund Butler, second Viscount Mountgarret."}} shortly before 8 October 1596{{Cite book|url=https://archive.org/details/isbn_0198613598/mode/2up |title=Oxford Dictionary of National Biography: in association with the British Academy: from the earliest times to the year 2000|date=2004 |publisher=Oxford University Press |others=Internet Archive |isbn=978-0-19-861411-1 |editor-last=Matthew |editor-first=Henry Colin Gray |volume=9 |pages=196 |quote=Shortly before 8 October 1596, he married Margaret O'Neill, daughter of Hugh O'Neill, earl of Tyrone, with whom he had three sons and six daughters|editor-last2=Harrison |editor-first2=Brian}}—possibly in October 1595.{{Cite journal |last=Edwards |first=David |date=October 2009 |title=Butler, Richard |url=https://www.dib.ie/biography/butler-richard-a1283 |url-status=live |journal=Dictionary of Irish Biography |doi=10.3318/dib.001283.v1 |archive-url=https://web.archive.org/web/20240407163436/https://www.dib.ie/biography/butler-richard-a1283 |archive-date=7 April 2024 |access-date=18 September 2024|url-access=subscription }}
• Sarah ({{fl.}} 1595–1602),{{Efn|Sarah's death date has alternately been given as 1639, 26 April 1640, or sometime after 31 March 1642.{{sfn|Walsh|1930|p=39}}}} who married Arthur Roe Magennis, 1st Viscount Iveagh{{Sfnm|1a1=Dunlop|1y=1895|1p=196|1ps=. "[Siobhán gave birth to] two other daughters—one married to Magennis..."|2a1=Walsh|2y=1930|2pp=38–39|2ps=. "Sorcha, or Sarah. The daughter of O Neill so named, married Sir Arthur Magennis..."|3a1=Casway|3y=2016|3ps=, p. 71. "[Siobhán] gave birth two surviving sons, Hugh and Henry, and possibly three daughters, Alice, Sarah and Mary."; p. 78. fn. 9. "...Sarah (Sorcha) was Sir Arthur Magennis' wife."}} in 1590.{{sfnm|1a1=Walsh|1y=1930|1p=38|1ps=. "Sarah was married some time prior to March 4, 1595..."|2a1=Guinness|2y=1932|2p=97|2ps=. "[Sir Arthur Magennis] married, in 1590, Sarah, daughter of Hugh O'Neill, Earl of Tyrone."}} Through Sarah, Tyrone is an ancestor to the Anglo-Irish Wellesley family.{{Cite news |last=Humphrys |first=Mark |date=21 May 2011 |title=The Queen's Irish ancestors |url=https://www.irishtimes.com/opinion/letters/the-queen-s-irish-ancestors-1.578269 |url-status=live |archive-url=https://web.archive.org/web/20150926133225/https://www.irishtimes.com/opinion/letters/the-queen-s-irish-ancestors-1.578269 |archive-date=26 September 2015 |access-date=18 September 2024 |newspaper=The Irish Times |language=en}}{{Cite web |last=Humphrys |first=Mark |title=The Queen's Irish ancestry |url=https://humphrysfamilytree.com/talk.queen.html |url-status=live |archive-url=https://web.archive.org/web/20240918075739/https://humphrysfamilytree.com/talk.queen.html |archive-date=18 September 2024 |access-date=18 September 2024 |website=humphrysfamilytree.com}}
• Mary ({{fl.}} 1608), who married Brian McHugh Og MacMahon.{{Sfnm|2a1=Casway|2y=2016|2ps=, p. 71. "[Siobhán] gave birth two surviving sons, Hugh and Henry, and possibly three daughters, Alice, Sarah and Mary."; p. 78. fn. 9. "...Mary wedded Hugh MacMahon..."|1a1=Walsh|1y=1930|1p=40|1ps=. "Mary. This was the name of the wife of Brian mac Hugh Og Mac Mahon..."}} According to historian George Hill, Mary is the same woman who married Ross McMahon.{{Sfn|Walsh|1930|p=33}}{{Cite book |last=Hill |first=George |url=https://archive.org/details/historicalaccoun00hill_0/page/40/mode/2up |title=An historical account of the plantation in Ulster at the commencement of the seventeenth century, 1608-1620 |publisher=McCaw, Stevenson and Orr |location=Belfast |publication-date=1877 |pages=41 |postscript=. fn. 40.}}
• Alice{{Sfn|Cokayne|1910|p=174}} (1583{{Sfn|Hill|1873|p=222}} – {{circa|1665}}{{Cite book|page=359 |last=Ohlmeyer |author-link=Jane Ohlmeyer |first=Jane H |date=2001 |orig-year=1993 |title=Civil War and Restoration in the Three Stuart Kingdoms: The Career of Randal MacDonnell, Marquis of Antrim |publisher=Four Courts Press |location=Dublin |isbn=978-0521419789 |url=https://books.google.com/books?id=YFciAQAAIAAJ}}) who married Randal MacDonnell, 1st Earl of Antrim in 1604.{{Sfnm|1a1=Casway|1y=2016|1pp=71, 78|2a1=Cokayne|2y=1910|2p=174|3a1=Hill|3y=1873|3p=222}} She was younger than her sisters Sarah and Mary, and older than her brother Hugh.{{Sfn|Hill|1873|p=222}}
• Hugh, 4th Baron Dungannon ({{circa|1585}} – September 1609); he died in Rome and was buried in San Pietro in Montorio on 24 September.{{Sfnm|1a1=Casway|1y=2016|1ps=: Dungannon died in Rome in September 1609|3a1=Walsh|3y=1930|3p=30|3ps=. "According to the epitaph over his tomb in the church of San Pietro in Montorio in Rome, he was then in his twenty-fourth year."|2a1=Walsh|2y=1996|2p=95|2ps=: Dungannon was buried on 24 September 1609|1pp=71–72}}
• Henry ({{circa|1586}} – 25 August 1610); he became colonel of the first Irish regiment in the Spanish army.{{Sfnm|2a1=Morgan|2y=2013|2pp=9–10|1pp=7–9|1y=1957a|1a1=Walsh|2ps=: colonel of the first Irish regiment.|1ps=: birth and death dates}}

Tyrone was betrothed to Mabel Bagenal ({{circa|1571}} – December 1595) in July 1591. They married on 3 August 1591 and had no offspring together.{{harvnb|Clarke|Barry|O'Byrne|2009}}, 1st–4th paragraph.

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". Casway believes that despite the romantic circumstances of their courtship, the marriage "probably ran its course" and Tyrone would have continued with his concubines.{{sfn|Casway|2016|pp=72–73}} 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".{{sfn|Dunlop|1895|pp=189–190}}{{Cite book |last=Salter |first=Richard |url=http://archive.org/details/elizabethiherrei0000salt |title=Elizabeth I and her reign |date=1988 |publisher=Macmillan Education |others=Digitized by the Internet Archive in 2022 with funding from Kahle/Austin Foundation |isbn=978-0-333-42381-3 |location=Basingstoke |pages=108}} Mabel died in December 1595, aged 24 years old.

Tyrone married Catherine Magennis (died March 1619) around August 1597.{{Sfnm|2a1=Casway|2y=2016|1y=1930|1a1=Walsh|1p=20|2p=77|2ps=: died March 1619|1ps=: married around August 1597}} He jilted the daughter of Angus MacDonald, 8th of Dunnyveg, to marry Catherine instead.{{Cite journal |last=O'Byrne |first=Emmett |author-link=Emmett O'Byrne |date=October 2009 |title=MacDonnell (Nic Dhomhnaill), Fiona (Fionnghuala) ('Iníon Dubh') |url=https://www.dib.ie/biography/macdonnell-nic-dhomhnaill-fiona-fionnghuala-inion-dubh-a6337 |url-status=live |journal=Dictionary of Irish Biography |doi=10.3318/dib.006337.v1 |archive-url=https://web.archive.org/web/20240418131718/https://www.dib.ie/biography/macdonnell-nic-dhomhnaill-fiona-fionnghuala-inion-dubh-a6337 |archive-date=18 April 2024|url-access=subscription }} It was a political marriage intended to bring the previously neutral Magennis family into the confederacy.{{Sfn|Casway|2016|p=73}} 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".{{Sfn|Casway|2016|pp=73–74}} Catherine reluctantly accompanied Tyrone on his flight. His will did not sufficiently provide for her, and she died penniless in Naples.{{sfnm|1a1=Casway|1y=2003|1pp=63–64|2a1=Casway|2y=2016|2pp=73–77}} 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.{{Sfn|Walsh|1957a|pp=10–21}}
• Conn Ruadh ({{circa|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.{{Sfnm|1a1=Dunlop|1y=1895|1p=196|2a1=Walsh|2y=1930|2pp=31–32|3a1=Casway|3y=2003|3p=61|2ps=: known as Conn Ruadh or Conn na Creige, born circa 1602, committed to the Tower on 12 August 1622|3ps=: left behind at the time of the Flight.|1ps=: educated at Eton as a Protestant}}
• Brian ({{circa|1604}} – 16 August 1617), who was found hanged in his room in Brussels with his hands tied behind his back, possibly assassinated.{{Sfnm|1a1=Walsh|1y=1930|1pp=9, 31|2a1=McGurk|2y=2007|2p=16|1ps=: Assassinated aged thirteen on 16 August 1617|2ps=: found hanged in his room in Brussels}}

Tyrone was known to have various concubines.{{Sfnm|1a1=Casway|1y=2016|1pp=69, 73|2a1=Ricketts|2y=2020|2p=7}} He had many illegitimate children or children of unknown maternal origin:

• Margaret O'Neill ({{fl.}} 1593–1612), who married Hugh Maguire around May 1593{{sfnm|1a1=Moody|1y=1938|1pp=269-270|1ps=: Maguire's widow was Margaret O'Neill|2a1=Walsh|2y=1930|2p=33|2ps=: Maguire married Tyrone's daughter around May 1593.}}
• Catherine O'Neill ({{fl.}} 1602), who married Henry Oge O'Neill{{Sfnm|1a1=Walsh|1y=1930|1pp=35, 65–67|2a1=Casway|2y=1984|2p=273}} and had a son, Turlough McHenry O'Neill.{{Sfn|Casway|1984|p=273}} Her husband and son both died in 1608 fighting against O'Doherty's rebellion.{{Sfn|Walsh|1930|p=|pp=65–66}}
• A daughter, who married Donnell Oneyle{{Sfn|Walsh|1930|p=46}}
• Bridget ({{fl.}} 1615) who was with Tyrone in Rome before his death.{{Sfn|Walsh|1930|pp=44–45}} She presumably took part in the Flight.{{Sfn|Walsh|1996|p=74}}
• A daughter ({{fl.}} 1610) who married Brian Art Roe McEny{{Sfn|Walsh|1930|p=45}}

File:HughO'Neill Alleged Portrait.jpg

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.{{Cite news |date=18 February 2016 |title=Priest penetrates Vatican secrecy in quest for lost portrait of Irish rebel leader Hugh O'Neill |url=https://www.midulstermail.co.uk/news/priest-penetrates-vatican-secrecy-in-quest-for-lost-portrait-of-irish-rebel-leader-hugh-o-neill-1-7222314 |url-status=dead |archive-url=https://web.archive.org/web/20180617215909/https://www.midulstermail.co.uk/news/priest-penetrates-vatican-secrecy-in-quest-for-lost-portrait-of-irish-rebel-leader-hugh-o-neill-1-7222314 |archive-date=17 June 2018 |access-date=17 June 2018 |publisher=Mid-Ulster Mail}}{{Cite book |last=O'Donnell |first=Francis Martin |author-link=Francis Martin O'Donnell |url=https://www.academia.edu/43816384 |title=What did they really look like? An Iconography of the O'Donnells of Tyrconnell: myth, allegory, prejudice, and evidence |date=2020 |publisher=Tyrconnell-Fyngal Publishing |pages=5–9}} According to historian Benedict Fearon, Tyrone allegedly sat for a portrait during his last years in Rome.{{Sfn|Hegarty|2010|p=18}}

An illustration of Tyrone appears in Primo Demaschino's La Spada d'Orione, published in Rome in 1680.{{sfnm|1a1=Morgan|1y=2005|1p=40|2a1=Morgan|2y=2016}} Tyrone's likeness in this illustration was based on the Vatican fresco.{{Sfn|Morgan|2016}} 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.{{Cite book |last=South Kensington Museum |url=https://books.google.com/books?id=p8IrAAAAYAAJ&q=%22Exhibition+of+National+Portraits%22 |title=Catalogue of the First Special Exhibition of National Portraits Ending with the Reign of King James the Second, on Loan to the South Kensington Museum. April 1866 |date=January 1866 |publisher=Strangeways and Walden |pages=65 |language=en}}{{Sfn|Dunlop|1895|p=196}}{{Cite wikisource|title=Page:Notes and Queries - Series 9 - Volume 3.djvu/177}} The old age portrait was presumably the La Spada d'Orione illustration.

By the 1990s, the armoured portrait was in the possession of Lord Dunsany. This reputed nineteenth-century portrait, from an original in the Vatican,{{harvnb|Morgan|1993}}. Back cover. "Reputed portrait of Hugh O'Neill, Earl of Tyrone, from an original in the Vatican, courtesy of Lord Dunsany".{{sfn|Morgan|1995|p=13}} was based on Tyrone's likeness from the La Spada d'Orione illustration.{{sfn|Morgan|2005|p=40}} William Holl the Younger produced an engraving of Tyrone based on this portrait.{{harvnb|Morgan|2014}}. "...engraving by William Holl (d. 1871)". 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.{{Sfn|Ekin|2015|p=|pp=223–224}}

The Ulster Museum owns two portraits of Tyrone—both were painted in the 19th century.{{Cite web |title=Hugh O'Neill (c.1540–1616), 2nd Earl of Tyrone {{!}} Art UK |url=https://artuk.org/discover/artworks/hugh-oneill-c-15401616-2nd-earl-of-tyrone-122979 |url-status=live |archive-url=https://web.archive.org/web/20240606011906/https://artuk.org/discover/artworks/hugh-oneill-c-15401616-2nd-earl-of-tyrone-122979 |archive-date=6 June 2024 |access-date=6 June 2024 |website=artuk.org |language=en}}{{Cite web |title=Hugh O'Neill (c.1540–1616), 2nd Earl of Tyrone {{!}} Art UK |url=https://artuk.org/discover/artworks/hugh-oneill-c-15401616-2nd-earl-of-tyrone-122978 |url-status=live |archive-url=https://web.archive.org/web/20240606011857/https://artuk.org/discover/artworks/hugh-oneill-c-15401616-2nd-earl-of-tyrone-122978 |archive-date=6 June 2024 |access-date=6 June 2024 |website=artuk.org |language=en}}

• 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.{{Cite book |url=https://archive.org/details/in.ernet.dli.2015.75098 |title=The Golden Treasury of Scottish Poetry |publisher=The Macmillan Company |year=1941 |editor-last=MacDiarmid |editor-first=Hugh |editor-link=Hugh MacDiarmid |pages=63–65}}
• 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.{{Cite web |title=Flint and Mirror |url=https://us.macmillan.com/books/9781250817525/flintandmirror |url-status=live |archive-url=https://web.archive.org/web/20240516224611/https://us.macmillan.com/books/9781250817525/flintandmirror |archive-date=16 May 2024 |access-date=17 May 2024 |website=Macmillan Publishers}}

• Hugh O'Neill was played by Alan Hale Sr. in The Private Lives of Elizabeth and Essex (1939).{{sfn|Klossner|2002|p=306}}
• 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.{{Cite web |title=Fighting Prince of Donegal, The (film) |url=https://d23.com/a-to-z/fighting-prince-of-donegal-the-film/ |url-status=live |archive-url=https://web.archive.org/web/20240517012232/https://d23.com/a-to-z/fighting-prince-of-donegal-the-film/ |archive-date=17 May 2024 |access-date=17 May 2024 |website=D23 |language=en-US}}{{Cite web |title=The Fighting Prince of Donegal |url=https://movies.disney.com/the-fighting-prince-of-donegal |url-status=dead |archive-url=https://web.archive.org/web/20180512020936/http://movies.disney.com/the-fighting-prince-of-donegal |archive-date=12 May 2018 |website=Disney Movies}}{{sfn|Klossner|2002|p=139}}
• 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.{{Cite journal |last=Morgan |first=Hiram |author-link=Hiram Morgan |date=June 2021 |title=Elizabeth R |url=https://www.historyireland.com/elizabeth-r/ |url-status=live |journal=History Ireland |volume=29 |issue=3 |archive-url=https://web.archive.org/web/20240516224612/https://www.historyireland.com/elizabeth-r/ |archive-date=16 May 2024}}
• The BBC Northern Ireland documentary programme You Thought You Knew - The Plantation depicts several events from Tyrone's life via re-enactment.{{Cite web |title=BBC One - You Thought You Knew - Episode guide |url=https://www.bbc.co.uk/programmes/p008dnp0/episodes/guide |access-date=24 August 2024 |website=BBC |language=en-GB}}{{Cite web |title=BBC One - You Thought You Knew, Series 1, The Plantation - Clips |url=https://www.bbc.co.uk/programmes/p008dv7s/clips |access-date=24 August 2024 |website=BBC |language=en-GB}}
• In 2021, it was reported that writer Jack Armstrong was developing a television drama, titled The O'Neill, centered on Tyrone.{{Cite web |last=Hopewell |first=John |date=13 September 2021 |title='Game of Thrones' Aidan Gillen, 'Barbarians' Stephen Saint Leger Board Gaelic Epic 'The O'Neill' (EXCLUSIVE) |url=https://variety.com/2021/tv/global/aidan-gillen-stephen-saint-leger-the-oneill-1235062220/ |url-status=live |archive-url=https://web.archive.org/web/20210916194837/https://variety.com/2021/tv/global/aidan-gillen-stephen-saint-leger-the-oneill-1235062220/ |archive-date=16 September 2021 |access-date=19 May 2024 |website=Variety |language=en-US}}

• 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.{{Cite journal |last=Campbell |first=Patrick J. |date=1989 |title=Brian Friel's 'Making History' |url=https://www.jstor.org/stable/29742391 |journal=Seanchas Ardmhacha: Journal of the Armagh Diocesan Historical Society |volume=13 |issue=2 |pages=291–293 |jstor=29742391 |issn=0488-0196}} Stephen Rea played Tyrone in Making History's original production.{{Cite journal|pages=62–63 |last=Morgan |first=Hiram |author-link=Hiram Morgan |date=August 2007 |title=Theatre Eye: Playing the earl: Brian Friel's Making History|jstor=27725661|url=https://www.historyireland.com/theatre-eye-playing-the-earl-brian-friels-making-history/ |url-status=live |journal=History Ireland |volume=15 |issue=4}} Denis Conway played Tyrone in a 2007 production to mark the 400th anniversary of the Flight of the Earls.
• Running Beast, a 2007 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.{{Cite web |date=29 August 2007 |title=Running Best takes flight |url=https://www.independent.ie/regionals/sligo/lifestyle/running-best-takes-flight/27555533.html |url-status=live |archive-url=https://web.archive.org/web/20240517012232/https://www.independent.ie/regionals/sligo/lifestyle/running-best-takes-flight/27555533.html |archive-date=17 May 2024 |access-date=17 May 2024 |website=Irish Independent |language=en}}{{Cite web |title=Running Beast |url=https://www.centreculturelirlandais.com/en/whats-on/exhibitions-events/running-beast |url-status=live |archive-url=https://web.archive.org/web/20240517012233/https://www.centreculturelirlandais.com/en/whats-on/exhibitions-events/running-beast |archive-date=17 May 2024 |access-date=17 May 2024 |website=Centre Culturel Irlandais |language=en-IE}}{{Cite journal |last=O'Flaherty |first=Eamon |date=December 2008 |title=Theatre Eye |url=https://www.historyireland.com/theatre-eye-6/ |url-status=live |journal=History Ireland |volume=16 |issue=6 |archive-url=https://web.archive.org/web/20240301111752/https://www.historyireland.com/theatre-eye-6/ |archive-date=1 March 2024}}

{{Notelist}}

{{Reflist}}

{{Refbegin|30em}}

• {{Cite book |last=Bagenal |first=Philip H. |url=https://archive.org/details/vicissitudesofan00bage |title=Vicissitudes of an Anglo-Irish Family 1530-1800: A Story of Irish Romance and Tragedy |publisher=Clement Ingleby, At the Sign of the Boar's Head |year=1925 |location=London |others=Digitized by the Internet Archive in 2018}}
• {{cite DNB|wstitle=O'Donnell, Rory|volume=41|last=Bagwell|first=Richard|author-link=Richard Bagwell|pages=444-447}}
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• {{Cite journal |last=Brady |first=Ciaran |date=October 2009a |title=O'Neill, Shane (Seaán) |url=https://www.dib.ie/biography/oneill-shane-seaan-a6966 |url-status=live |journal=Dictionary of Irish Biography |doi=10.3318/dib.006966.v1 |archive-url=https://web.archive.org/web/20240513110036/https://www.dib.ie/biography/oneill-shane-seaan-a6966 |archive-date=13 May 2024 |access-date=26 June 2024 |url-access=subscription}}
• {{Cite journal |last=Brady |first=Ciaran |date=October 2009b |title=O'Neill, Turlough Luineach |url=https://www.dib.ie/biography/oneill-turlough-luineach-a6967 |url-status=live |journal=Dictionary of Irish Biography |doi=10.3318/dib.006967.v1 |archive-url=https://web.archive.org/web/20240222003717/https://www.dib.ie/biography/oneill-turlough-luineach-a6967 |archive-date=22 February 2024 |access-date=12 August 2024 |url-access=subscription}}
• {{Cite book |last=Brady |first=Ciaran |date=2015 |orig-date=1st pub. 1996 |title=Shane O'Neill |edition=New |publisher=University College Dublin Press for the Historical Association of Ireland |location=Dublin |isbn=978-1-91082005-6 |url=https://archive.org/details/shaneoneill0000brad/}}
• {{cite book |editor1-last=Brewer |editor1-first=J. S. |editor2-last=Bullen |editor2-first=W. |title=Calendar of Carew Manuscripts in the Lambeth Library. Vol III: 1599-1600 |others=(6 vols, 1867–73) |place=London |publisher=Longman & Co., et al. |year=1869 |url=https://archive.org/details/calendarofcarewm03lambiala}}
• {{Cite book |last=Canny |first=Nicholas |date=2001 |title=Making Ireland British 1580–1650 |publisher=Oxford University Press |location=Oxford |isbn=0-19-820091-9 |url=https://archive.org/details/makingirelandbri00cann/ |url-access=registration |author-link=Nicholas Canny}}
• {{Cite encyclopedia |last=Canny |first=Nicholas |editor1-last=Matthew |editor1-first=Colin |editor1-link=Colin Matthew |editor2-last=Harrison |editor2-first=Brian |editor2-link=Brian Harrison (historian) |date=2004 |title=O'Neill, Hugh [Aodh O'Neill], second earl of Tyrone (1583–1616) |encyclopedia=Oxford Dictionary of National Biography |volume=41 |publisher=Oxford University Press |location=New York |pages=837–845 |isbn=0-19-861391-1 |url=https://archive.org/details/isbn_0198613911/page/837/ |url-access=registration}}
• {{Cite journal |last=Canny |first=Nicholas |date=7 June 2022 |title=Hugh O'Neill in Irish historical discourse, c.1550–2021 |journal=Irish Historical Studies |language=en |volume=46 |issue=169 |pages=25–51 |doi=10.1017/ihs.2022.2 |issn=0021-1214 |doi-access=free}}
• {{cite book |last=Casway |first=Jerrold |date=1984 |title=Owen Roe O'Neill and the Struggle for Catholic Ireland |url=https://archive.org/details/owenroeoneillstr0000casw |publisher=University of Pennsylvania Press |others=Digitized by the Internet Archive in 2022 with funding from Kahle/Austin Foundation |isbn=0-8122-7895-X |location=Philadelphia}}
• {{Cite journal |last=Casway |first=Jerrold |date=2003 |title=Heroines or Victims? The Women of the Flight of the Earls |url=https://www.jstor.org/stable/20557855 |journal=New Hibernia Review / Iris Éireannach Nua |volume=7 |issue=1 |pages=56–74 |issn=1092-3977 |jstor=20557855}}
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• {{Cite journal |last=Smith |first=Murray |date=1996 |title=Flight of the Earls?: Changing Views on O'Neill's Departure from Ireland |journal=History Ireland |volume=4 |issue=1 |jstor=27724309 |pages=17–20}}
• {{Cite journal |last=Walsh |first=Paul |author-link=Paul Walsh (priest) |date=1922 |title=Hugh Roe O'Donnell's Sisters |url=https://archive.org/details/s5p1irishecclesi19dubluoft |journal=The Irish Ecclesiastical Record |location=Dublin |volume=XIX |pages=358–364}}
• {{Cite journal |last=Walsh |first=Paul |date=1929 |title=The Book of O'Donnell's Daughter |url=https://archive.org/details/irishecclesiasti33dubl/page/564/mode/2up |journal=The Irish Ecclesiastical Record |pages=561–575 |location=Dublin |volume=XXXIII}}
• {{Cite book |url=https://archive.org/details/g-004983 |title=The Will and Family of Hugh O'Neill, Earl of Tyrone [with an Appendix of Genealogies] |year=1930 |editor-last=Walsh |editor-first=Paul |location=Dublin |publisher=Sign of the Three Candles}}
• {{Cite journal |last=Walsh |first=Paul |date=1939 |title=Historical Criticism of the Life of Hugh Roe O'Donnell |url=https://www.jstor.org/stable/30005953 |journal=Irish Historical Studies |volume=1 |issue=3 |pages=229–250 |issn=0021-1214 |jstor=30005953}}
• {{Cite book |last=Walsh |first=Micheline |author-link=Micheline Kerney Walsh |url=https://archive.org/details/g-004964 |title=The O'Neills in Spain |date=April 1957a}}
• {{Cite journal |last=Walsh |first=Micheline Kerney |date=1990 |title=Archbishop Magauran and His Return to Ireland, October 1592 |url=https://www.jstor.org/stable/29742439 |journal=Seanchas Ardmhacha: Journal of the Armagh Diocesan Historical Society |volume=14 |issue=1 |pages=68–79 |doi=10.2307/29742439 |issn=0488-0196 |jstor=29742439 |url-access=subscription}}
• {{Cite book |last=Walsh |first=Micheline Kerney |url=https://archive.org/details/exileofirelandhu0000wals |title=An exile of Ireland, Hugh O'Neill, Prince of Ulster |date=1996 |publisher=Four Courts Press |isbn=978-1-85182-234-8 |location=Dublin}}
• {{Cite book |last=Webb |first=Alfred |author-link=Alfred Webb |url=https://archive.org/details/compendiumofiris00webb |title=A Compendium of Irish Biography |date=1878 |publisher=M. H. Gill & Son |postscript=. "Maguire, Hugh". pp. 324–325. "O'Donnell, Hugh Roe". pp. 391–393.}}

{{Refend}}

{{Refbegin}}

• {{Cite AFM}}
• {{Cite book |title=Calendar of State Papers: Carew MSS |series=6 vols |location=London |year=1867–1873}}
• {{Cite book |title=Calendar of State Papers relating to Ireland |location=London}}
• [http://www.ucc.ie/celt/published/E590001-003 Hugh O'Neill, War aims], in {{Cite book |title=Calendar of State Papers relating to Ireland, 1599–1600 |location=London |year=1899 |pages=[https://archive.org/details/calendarireland08greauoft/page/279 279]–81 |url=https://archive.org/details/calendarireland08greauoft}}
• {{Cite book |title=Life of Aodh O'Neill, Prince of Ulster |last=Mitchel |first=John |publisher=James Duffy |year=1845 |location=Dublin |url=https://archive.org/details/lifeandtimesaod01mitcgoog/page/n7/mode/2up |author-link=John Mitchel}}
• {{Cite book |last=Stafford |first=Thomas |author-link=Thomas Stafford (MP) |editor-last=O'Grady |editor-first=Standish |date=1896 |orig-date=1st pub. 1633 |title=Pacata Hibernia |volume=I |publisher=Downey and Co. |location=London |oclc=1050247906 |url=https://archive.org/details/pacatahiberniaor01staf_0/ |ref=none}} – 1600 to 1601
• {{Cite book |last=Stafford |first=Thomas |author-link=Thomas Stafford (MP) |editor-last=O'Grady |editor-first=Standish |date=1896 |orig-date=1st pub. 1633 |title=Pacata Hibernia |volume=II |publisher=Downey and Co. |location=London |oclc=4313009 |url=https://archive.org/details/pacatahiberniao01totngoog |ref=none}} – 1601 to 1602

• {{Cite journal |last=Canny |first=Nicholas P. |date=1970 |title=Hugh O'Neill, Earl of Tyrone, and the Changing Face of Gaelic Ulster |url=https://www.jstor.org/stable/20495951 |journal=Studia Hibernica |issue=10 |pages=7–35 |doi=10.3828/sh.1970.10.1 |jstor=20495951 |issn=0081-6477 |url-access=subscription}}
• {{cite book |first=Nicholas P. |last=Canny |title=The Elizabethan Conquest of Ireland: A Pattern Established, 1565–76 |location=London |year=1976 |isbn=0-85527-034-9 |url=https://archive.org/details/elizabethanconqu0000cann}}
• {{Cite book |last=Ellis |first=Steven G. |date=2014 |title=Ireland in the Age of the Tudors, 1447–1603 |edition=2nd |publisher=Routledge |location=Abingdon |isbn=978-1-317-90143-3 |url=https://books.google.com/books?id=CXPXAwAAQBAJ}}
• {{cite book |last=FitzSimons |first=Fiona |year=2001 |chapter=Fosterage and Gossipred in Late Medieval Ireland: Some new evidence |editor-first1=Patrick J. |editor-last1=Duffy |editor-first2=David |editor-last2=Edwards |editor-first3=Elizabeth |editor-last3=FitzPatrick |title=Gaelic Ireland c. 1250-1650 |pages=138–152 |location=Dublin}}
• {{Cite book |last=Hayes-McCoy |first=Gerard Anthony |author-link=Gerard Anthony Hayes-McCoy |date=1990 |orig-date=1st pub. 1969 |title=Irish Battles: A Military History of Ireland |publisher=The Appletree Press |location=Belfast |isbn=0-86281-250-X |url=https://archive.org/details/irishbattlesmili0000haye/ |url-access=registration |ref=none}}
• {{Cite book |last=Henry |first=Gráinne |editor-last=Mac Cuarta |editor-first=Brian |date=1997 |title=Ulster 1641: Aspects of the rising |chapter=Ulster Exiles in Europe, 1605–1641 |pages=37–60 |publisher=The Institute of Irish Studies. Queen's University of Belfast |location=Belfast |isbn=978-0-85389-591-6 |url=https://books.google.com/books?id=iLJaAAAAYAAJ}}
• {{Cite book |url=https://books.google.com/books?id=nHasAgAAQBAJ&pg=PA517 |title=Tudor England: An Encyclopedia |publisher=Garland Publishing |year=2001 |isbn=978-1-136-74530-0 |editor-last=Kinney |editor-first=Arthur F. |pages=517–518 |editor-last2=Swain |editor-first2=David W.}}
• {{Cite book |last=Jefferies |first=Henry A. |editor1-last=Dillon |editor1-first=Charles |editor2-last=Jefferies |editor2-first=Henry A. |editor3-last=Nolan |editor3-first=William |date=2000 |title=Tyrone: History & Society |chapter=Hugh O'Neill, earl of Tyrone, c. 1550–1616 |pages=181–232 |publisher=Geography Publications |location=Dublin |isbn=978-0-906602-71-3 |url=https://books.google.com/books?id=W5EiAQAAIAAJ |ref=none}}
• {{Cite book |last=McCavitt |first=John |url=https://books.google.com/books?id=jGqCAAAAIAAJ |title=The Flight of the Earls |date=2002 |publisher=Gill & MacMillan |isbn=978-0-7171-3047-4 |location=Dublin}}
• {{Cite journal |last=Morgan |first=Hiram |date=1993b |title=Hugh O'Neill and the Nine Years War in Tudor Ireland |url=https://www.jstor.org/stable/2639514 |journal=The Historical Journal |volume=36 |issue=1 |pages=21–37 |issn=0018-246X |jstor=2639514}}
• {{cite journal |last=Morgan |year=1997 |url=https://celt.ucc.ie/Ceasefire.pdf |journal=Dúiche Néill: Journal of the O¹Neill Country Historical Society |title=The 1597 Ceasefire Documents}}
• {{Cite journal |last=Morgan |first=Hiram |date=2014b |title=The deputy's defence: Sir William Fitzwilliam's Apology on the outbreak of the Nine Years War in Ireland |url=https://www.jstor.org/stable/10.3318/priac.2014.114.01 |journal=Proceedings of the Royal Irish Academy: Archaeology, Culture, History, Literature |volume=114C |pages=181–214 |doi=10.3318/priac.2014.114.01 |issn=0035-8991 |url-access=subscription}}
• {{Cite journal |last=Morgan |first=Hiram |date=2016b |title=The Long Shadow of Seán Ó Faoláin's Great O'Neill |url=https://www.academia.edu/37774350/THE_LONG_SHADOW_OF_SE%C3%81N_OFAOL%C3%81INS_GREAT_ONEILL |journal=Dúiche Néill: Journal of the O'Neill Country Historical Society |volume=XXIII |pages=19–26}}
• {{Cite journal |last=McGurk |first=John |date=1997 |title=The Battle of the Yellow Ford, August 1598 |journal=Dúiche Néill: Journal of the O'Neill Country Historical Society |volume=11 |pages=34–55 |ref=none}}
• {{Cite book |last=Mitchel |first=John |author-link=John Mitchel |url=https://archive.org/details/lifetimesofaodho00mitcuoft/lifetimesofaodho00mitcuoft/page/n9/mode/2up?q=red+hugh+o%5C'donnell |title=The life and times of Aodh O'Neill, Prince of Ulster |date= |publisher=P. M. Haverty |others=Digitized by the Internet Archive in 2007 |location=New York |publication-date=1868}}
• {{Cite book |url=https://archive.org/details/newhistoryofirel0000unse |title=A new history of Ireland |date=1976 |publisher=Clarendon Press |others=Digitized by the Internet Archive in 2022 with Funding from Kahle/Austin Foundation |isbn=0-19-821739-0 |editor-last=Moody |editor-first=T. W. |volume=III |location=Oxford |pages=193 |editor-last2=Martin |editor-first2=F. X. |editor-last3=Byrne |editor-first3=F. J.}}
• {{Cite book |last=O'Faolain |first=Sean |author-link=Seán Ó Faoláin |date=1942 |title=The Great O'Neill: A biography of Hugh O'Neill, Earl of Tyrone, 1550–1616 |publisher=Duell, Sloan and Pierce |location=New York |oclc=1379073 |url=https://archive.org/details/greatoneill0000unse/ |url-access=registration}}
• {{Cite journal |last=Sheridan |first=James |date=2021 |title=The aftermath of the death of Shane O'Neill in Tyrone and the rise of Turlough Luineach O'Neill (1567–72) |url=https://www.jstor.org/stable/48747417 |journal=Seanchas Ardmhacha: Journal of the Armagh Diocesan Historical Society |volume=27 |issue=2 |pages=82–111 |doi=10.2307/48747417 |issn=0488-0196}}
• {{Cite book |last=Silke |first=John J. |date=1970 |title=Kinsale: The Spanish Intervention in Ireland at the End of the Elizabethan Wars |publisher=Liverpool University Press |location=Liverpool |isbn=9780853230908 |url=https://archive.org/details/kinsalespanishin0000silk/ |ref=none}}
• {{Cite book |last=Strachey |first=Lytton |author-link=Lytton Strachey |date=1930 |orig-date=1st pub. 1928 |title=Elizabeth and Essex: A Tragic History |publisher=Chatto & Windus |location=London |oclc=1037867845 |url=https://archive.org/details/in.ernet.dli.2015.175886/}}
• {{Cite journal |title=The Ulster Journal of Archaeology |url=https://www.jstor.org/stable/community.29825421 |journal=The Ulster Journal of Archaeology |jstor=community.29825421}}
• {{cite journal |last=Walsh |first=Micheline |year=1974 |title=The Will of John O'Neill, Third Earl of Tyrone |url=https://www.jstor.org/stable/29740847 |journal=Seanchas Ardmhacha: Journal of the Armagh Diocesan Historical Society |volume=7 |issue=2 |pages=320–325 |doi=10.2307/29740847 |jstor=29740847 |url-access=subscription}}

{{Refend}}{{S-start}}

{{S-hou|Ó Néill}}

{{S-reg}}

{{S-bef|

| before = Turlough Luineach O'Neill

}}

{{S-ttl

| title = Ó Néill

| years = 1595–1616

}}

{{S-non

| reason = Dormant

}}

{{S-reg|ie}}

{{S-bef

| before = Conn Bacagh O'Neill

}}

{{S-ttl

| title = Earl of Tyrone

| years = 1587–1613

}}

{{S-non

| reason = Forfeit
(Successor Shane O'Neill recognised by Spain)

}}

{{S-bef

| before = Brian O'Neill

}}

{{S-ttl

| title = Baron Dungannon

| years = 1562–1587

}}

{{s-aft

| after = Hugh O'Neill

}}

{{S-end}}

{{Ó Néill}}

{{Flight of the Earls}}

{{Authority control}}

{{DEFAULTSORT:Hugh Oneill, 2nd Earl Of}}

Category:1550s births

Category:1616 deaths

Category:16th-century Irish nobility

Category:17th-century Irish nobility

Category:Burials at San Pietro in Montorio

Tyrone, Hugh O'Neill, 2nd Earl of

Category:Flight of the Earls

Category:Irish chiefs of the name

Category:Irish emigrants to Italy

Category:Irish rebels

ONeill

Category:O'Neill dynasty

Category:Immigrants to the Papal States

Category:People of Elizabethan Ireland

Category:People of the Nine Years' War (Ireland)

Category:People of the Second Desmond Rebellion