The news of the Spaniards’ arrival had been speedily conveyed to the Ulster chieftains. Their disappointment at the smallness of the succour so long waited for, and at the ill selection of a landing place, must have been extreme. They knew, however, that this was their last chance, and they prepared to march southwards in all haste. Hugh Ruadh called together the sub-chiefs who still adhered to him, and, when all were assembled with their forces at Ballymote, he started on his long journey, at the head of about three thousand men.
It was November, and the task before O’Donnell, of marching troops for a distance amounting to more than two-thirds of the length of Ireland at such a season, was no easy one. However, the clansmen were hardy, inured to brave all conditions of weather and to travel long distances on foot. They pushed on over the Curlew Hills into Roscommon, and proceeded through Co. Galway to Shannon Harbour, where they were ferried over the great river. They went on south, through the King’s Co, and on to the barony of Ikerrin in Tipperary. Here, at Drumsaileach, near Roscrea, they halted awhile to await O’Neill.
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In 1565 Sydney came again as Deputy, and endeavoured to negotiate with Shane with a view to a permanent peace, but he found him more exacting in his demands, and haughtier in speech, than ever. ” For the Queen, I confess she is my sovereign lady, yet I never made peace with her but by her own asking,” he said. ” My ancestors were Kings of Ulster. Ulster was theirs and shall be mine. . . . With this sword I won (the lands), and with this sword I shall keep them.” Sydney at once renewed the war, and marched northward into Tir Owen. Very little except cattle spoils was gained. Finally, Sydney returned homeward, and, more candid than Sussex, did not even pretend to have achieved any notable success.
Still, Shane’s position was a perilous one. Many of his neighbours were jealous of him, and his policy had ever been rather to crush than to conciliate those who opposed him. He now invaded the O’Donnell territory, and Hugh, the newly-elected O’Donnell chief, defeated his army with great slaughter at Farsetmore near Letterkenny. Shane and a small band of soldiers with difficulty crossed the Swilly and escaped.
Shane was now anxious to be gone as speedily as possible, but certain of the English ministers were inclined to detain him. The agreement made, they said, was that he should return home safely, but when was not specified. Without violation of the words of the safe conduct, he might be forced to remain in England for any length of time they chose. It might well have happened that they should have taken advantage of this quibble, and that Shane should have seen his native land no more, but for the news that came from Ireland in spring. Ulster, it was declared, was in as bad a state of disorder as ever it had been, and young Brian, “the Earl of Tyrone,” as the English called him, had been murdered by the followers of Turlough Lynnach O’Neill, a cousin of his. Things being in this state, it seemed best to send Shane back, and so in May he was sent.
Before leaving London, however, he had been required to sign certain conditions. Afterwards, he declared that, of his own free will, he never would have consented to them, and so did not hold himself bound to observe what he had subscribed. Yet the conditions seem far from dishonourable or derogatory to him. They place him in the position of a tributory prince ; confirming his authority over his sub-chiefs, and making him independent of the Deputy, except for the obligation of attending his ” hostings.” Shane did not linger in Dublin, which he reached on May 26th (1562). As fast as a fleet horse could carry him, he sped back to his native Ulster.