Although the Crown hoped to mold him into a puppet ruler sympathetic to the English government, by the 1570s he had built a strong network of both British and Irish contacts which he utilised for his pursuit of political power.

[15] Sidney granted Hugh territory in Oneilland, intending to keep Turlough from crossing south past the River Blackwater, thus creating further discord within the O'Neill family.

[52] 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.

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.

[34][85] Around 1589 Nicholas Bagenal described Tyrone as "as so allied by kindred in blood and affinity as also by marriages and fosters and other friendships as if he should be ill-disposed might hap put the crown of England to more charges than the purchase of Ulster should be worth".

[111] Tyrone reputedly hanged Gavelagh over a tree with his bare hands[112]—though other sources claim the executioner was from Meath or Cavan, given Tír Eoghain's population were sympathetic to the MacShanes.

[41] Nicholas Canny similarly states that Tyrone aspired to be the "queen's man in Ulster", was passed over in favour of Henry Bagenal,[102] and reluctantly pushed into rebellion to prevent his followers defecting to his brother Cormac MacBaron.

[169] 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,[41][170] such as his brother Cormac MacBaron.

[34][116] 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.

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.

[201] 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.

[214] 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".

[217] The confederates felt the English threat had weakened enough that they could safely travel with their wives—Tyrone's fourth wife Catherine Magennis,[218] whom he had married circa 1597,[219] was present at his camp in June 1599 during her first pregnancy.

[249] However the Munster expedition ended in failure[250] when in early March,[251] confederacy commander Maguire was shot and killed by English forces whilst on a nearby reconnaissance mission.

[252] 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.

[253] 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.

[260] In October 1601, the long-awaited aid from Spain appeared in the form of an army under Spanish commander Don Juan del Águila, which occupied the town of Kinsale in the extreme south of the country.

[264] Contemporary writers Lughaidh Ó Cléirigh and Philip O'Sullivan Beare claim that O'Donnell naively urged Tyrone to attack, but not all modern historians believe these accounts are accurate.

[284] Tyrone returned to Ireland at the end of August[275] and began rebuilding his estates, an easy task under the reserved government of Sir George Carey, who had replaced Mountjoy as Lord Deputy.

[277] In 1607, the 1st Earl of Tyrconnell accidentally exposed a plot to seize Dublin Castle, hopefully with Tyrone's involvement, during a conversation with Richard Nugent, Lord Delvin.

[301][302] 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.

[1] The pope granted Tyrone a monthly pension of a hundred crowns, and a house (on Borgo Vecchio) rent-free, together with an allowance of bread and wine for ten persons.

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

[328] 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".

[336] 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.

[359] 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".

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.

[34][362] 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.

Painted circa 1610, the fresco depicts his attendance at the 1608 canonization of Frances of Rome by Pope Paul V. He stands next to the 1st Earl of Tyrconnell, sometimes mistaken for the Spanish ambassador.

[431] According to Des Ekin, this common image of Tyrone as a stocky armoured figure with cropped hair and a bushy black beard is "almost certainly a Victorian fantasy".