HUGH O'NEILL (c. 1540-1616), and earl (known as the great earl) of Tyrone, was the second son of Matthew, reputed illegiti mate son of Conn, ist earl of Tyrone. 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 re turned 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 158o, and assisted Sir John Perrot against the Scots of Ulster in 1584. In the following year he attended 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, but after Hugh's inauguration as the O'Neill on Turlough's resig nation in 1593, he was supreme in the north. 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 ordered to Ireland to subdue him in 1595, but Tyrone took the Blackwater fort and Sligo castle before Norris was prepared ; he was there upon 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 com munications with Philip II. of Spain, their letters to whom were intercepted by the viceroy, Sir William Russell. They presented themselves as champions of the Catholic religion, claiming re ligious and political liberty for the Irish. In April 1596 Tyrone received promises of help from Spain. He temporized success fully for more than two years, making professions of loyalty which deceived Sir John Norris and the earl of Ormonde. In 1598 a formal pardon was granted to Tyrone by Elizabeth. Within two months he was again in the field, and on Aug. he destroyed an English force under Bagnal at the Yellow ford on the Blackwater. 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 the Geraldine clansmen—discontent broke into flame. But Tyrone procrastinated. Eight months after the battle of the Yellow ford, the earl of Essex landed in Ireland. He met Tyrone
at a ford on the Lagan on Sept. 7, 1599, when a truce was arranged; but Elizabeth objected to the conditions allowed to the O'Neill and to Essex's treatment of him as an equal. 'Tyrone then issued a manifesto to the Catholics of Ireland summoning them to join his standard. After an inconclusive campaign in Munster in January 160o, he returned to Donegal, where he received supplies from Spain and a token of encouragement from Pope Clement VIII. In May of the same year armies under Sir Henry Docwra and Mountjoy compelled 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 John D'Aquila. The attack failed. O'Donnell went to Spain, where he died and Tyrone with a shattered force went to the north, where he renewed his temporizing policy. Early in 1603 Elizabeth instructed Mountjoy to open negotiations; and in April, Tyrone, in ignorance of Elizabeth's death, made his submission. In Dublin 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. James confirmed Tyrone in his title and estates, but new disputes arose on 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), Tyrone resolved to fly from the country.
"The flight of the earls," one of the most celebrated episodes in Irish history, occurred on Sept. 14, 1607, when Tyrone and Tyrconnel embarked at midnight at Rathn'iullen on Lough Swilly, with their wives, families and retainers, numbering 99 and sailed for Spain. Driven by contrary winds to take shelter in the Seine, the refugees passed the winter in the Netherlands, and in 1608 went to Rome, where they were 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 July 20, 1616. He was four times married, and had a large number both of legitimate and illegitimate children.