He succeeded his brother, Brian, when the latter was murdered by Turlough in 1562, as baron of Dungannon. He was brought up in London, but returned to Ireland in 1567 after the death of Shane, under the protection of Sir Henry Sidney. He served with the English against Desmond in Munster in 1580, and assisted Sir John Perrot against the Scots of Ulster in 1584. In the following year he was allowed to attend parliament as [Earl of Tyrone], though Conn's title had been for life only, and had not been assumed by Brian Hugh's constant disputes with Turlough were fomented by the English with a view to weakening the power of the O'Neills, but after Hugh's inauguration as the O'Neill on Turlough's resignation in 1593, he was left without a rival in the north.
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. Having roused the ire of Sir Henry Bagnal (or Bagenal) by eloping with his sister in 1591, he afterwards assisted him in defeating Hugh Maguire at Belleek in 1593; and then again went into opposition and sought aid from Spain and Scotland. Sir John Norris was accordingly ordered to Ireland with a considerable force to subdue him in 1595, but Tyrone succeeded in taking the Blackwater Fort and Sligo Castle before Norris was prepared; and he was thereupon proclaimed a traitor of Dundalk.
In spite of the traditional enmity between the O'Neills and the O'Donnells, Tyrone allied himself with Hugh Roe O'Donnell, nephew of Shane's former enemy Calvagh O'Donnell, and the two chieftains opened communications with Philip II of Spain, their letters to whom were intercepted by the viceroy, Sir William Russell. They put themselves forward as the champions of the Catholic religion, claiming liberty of conscience as well as political liberty for the native inhabitants of Ireland. In April 1596 Tyrone received promises of help from Spain. This increased his anxiety to temporize, which he did with signal success for more than two years, making from time to time as circumstances required, professions of loyalty which deceived Sir John Norris and the earl of Ormonde.
In 1598 a cessation of hostilities was arranged, and a formal pardon granted to Tyrone by Elizabeth. Within two months he was again in the field, and on August 14 he destroyed an English force under Bagnal at the Yellow Ford on the Black-water. If the earl had known how to profit by this victory, he might now have successfully withstood the English power in Ireland; for in every part of Ireland--and especially in the south, where James Fitzthomas Fitzgerald with O'Neill's support was asserting his claim to the earldom of Desmond at the head of a formidable army of Geraldine clansmen--discontent broke into flame. But Tyrone, who possessed but little generalship, procrastinated until the golden opportunity was lost.
Eight months after the battle of the Yellow Ford, the earl of Essex landed in Ireland to find that Tyrone had done nothing in the interval to improve his position. Acting on the queen's explicit instructions, Essex, after some ill-managed operations, had a meeting with Tyrone at a ford on the Lagan on th 7th of September 1599, when a truce was arranged; but Elizabeth was displeased by the favourable conditions allowed to the O'Neill and by Essex's treatment of him as an equal, Tyrone continued to concert measures with the Irish leaders in Munster, and issued a manifesto to the Catholics of Ireland summoning them to join his standard; protesting that the interests of religion were his first care. After an inconclusive campaign in Munster in January 1600, he returned in haste to Donegal, where he received supplies from Spain and a token of encouragement from Pope Clement VIII. In May of the same year Sir Henry Docwra, at the head of a considerable army, took up a position at Derry, while Mountjoy marched from Westmeath to Newry to support him, compelling O'Neill to retire to Armagh, a large reward having been offered for his capture alive or dead.
The appearance of a Spanish force at Kinsale drew Mountjoy to Munster in 1601; Tyrone followed him, and at Bandon joined forces with O'Donnell and with the Spaniards under Don Juan d'Aquila. The attack of these allies on the English completely failed. O'Donnell went to Spain, where he died soon afterwards, and Tyrone with a shattered force made his way once more to the north, where he renewed his policy of ostensibly seeking pardon while warily evading his enemies. Early in 1603 Elizabeth instructed Mountjoy to open negotiations with the rebellious chieftains; and in April, Tyrone, in ignorance of Elizabeth's death, made his submission to Mountjoy.
In Dublin, whither he proceeded with Mountjoy, he heard of the accession of King James, at whose court he presented himself in June accompanied by Rory O'Donnell, who had become chief of the O'Donnells after the departure of his brother Hugh Roe. The English courtiers were greatly incensed at the gracious reception accorded to these notable rebels by King James; but although Tyrone was confirmed in his title and estates, he had no sooner returned to Ireland than he again engaged in dispute with the government concerning his rights over certain of his feudatories, of whom Donnal O'Cahan was the most important. This dispute dragged on till 1607, when Tyrone arranged to go to London to submit the matter to the king. Warned, however, that his arrest was imminent, and possibly persuaded by Rory O'Donnell (created earl of Tyrconnel in 1603), whose relations with Spain had endangered his own safety, Tyrone resolved to fly from the country.
"The flight of the earls," one of the most celebrated episodes in Irish history, occurred on September 14, 1607, when Tyrone and Tyrconnel embarked at midnight at Rathmullen on Lough Swilly, with their wives, families and retainers, numbering ninety-nine persons, and sailed for Spain. Driven by contrary winds to take shelter in the Seine, the refugees passed the winter in the Netherlands, and in April 1608 proceeded to Rome, where they were welcomed and hospitably entertained by Pope Paul V, and where Tyrconnel died the same year. In 1613 Tyrone was outlawed and attainted by the Irish parliament, and he died in Rome on the 20th of July 1616. He was four times married, and had a large number both of legitimate and illegitimate children.
{| border="2" align="center"
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|width="30%" align="center"|Preceded by:
Conn O'Neill
|width="40%" align="center"|Earl of Tyrone
|width="30%" align="center"|Followed by:
Henry Hugh O'Neill
|}
Reference
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