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Updated: May 4, 2025
In 1498, he took Dungannon and Omagh, "with great guns," from the insurgents against the authority of his grandson, Turlogh O'Neil, and restored them to Turlogh; the next year he visited O'Donnell, and brought his son Henry to be fostered among the kindly Irish of Tyrconnell. In the year 1500 he also placed the Castle of Kinnaird in the custody of Turlogh O'Neil.
In the year 1002, we find him at Ballysadare, in Sligo, challenging their obedience; in 1004, we find him at Armagh "offering twenty ounces of gold on Patrick's altar," staying a week there and receiving hostages; in 1005, he marched through Connaught, crossed the river Erne at Ballyshannon, proceeded through Tyrconnell and Tyrowen, crossed the Bann into Antrim, and returned through Down and Dundalk, "about Lammas," to Tara.
Tyrconnell was known to meditate the repeal of the Act of Settlement; the general rumour of a Protestant massacre fixed for the 9th of December, originated no one knew how, was spread about no one knew by whom.
In this most important battle no O'Donnell is found fighting with King Brian, though immediately afterwards we find Donnell Oge of Tyrconnell endeavouring to subjugate Tyrone, and active afterwards in the aid of his cousins, the grandsons of Cathal Crovdearg, in Connaught.
O'Donnell rendezvoused at Ballymote, from which he set out, at the head of 2,500 men, of Tyrconnell and Connaught, on the 2nd day of November. O'Neil, with McDonnell of Antrim, McGennis of Down, McMahon of Monaghan, and others, his suffragans, marched at the head of between 3,000 and 4,000 men, through West-Meath towards Ormond.
Ireland offers but little field for anyone's ambition. Since King James came to the throne, and especially since Tyrconnell became governor, things have been a little more favourable for us; and I have hopes, yet, that justice will be done to the Catholic population of this unhappy country.
Accordingly, the Protestant troops, under Colonel Lundy, entered the town, and Lord Mountjoy assumed the governorship. Tyrconnell soon perceived that he had made a mistake in sending Mountjoy to Derry, for instead of overawing the inhabitants, his regiment had, in fact, become a part of the rebel garrison.
This we have seen in a previous chapter, and Sir John Davies has been obliged to confess its truth, admitting the difference between a tributary and a subject nation. A glance shows us the importance of the almost unanimous outcry of the clansmen of Tyrone, Tyrconnell, and of other parts of Ireland.
In the third and fourth years of Henry, Hugh O'Donnell, lord of Tyrconnell, passing through England, on a pilgrimage to Rome, was entertained with great honour at Windsor and Greenwich for four months each time. He returned to Ulster deeply impressed with the magnificence of the young monarch and the resources of his kingdom.
Tyrconnell, Berwick, Sir Richard Nagle, who had succeeded the Earl of Melfort as chief secretary for King James, all ranked before him at the board, and when Saint Ruth arrived to take command-in-chief, he might fairly have complained that he was deprived of the chief reward to which he had looked forward.
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