Clan chief
Upon Elizabeth's accession in 1559 Sorley Boy had submitted to her authority under Thomas Radclyffe, 3rd Earl of Sussex, then Lord-Lieutenant of Ireland, and in return was confirmed in his Irish possessions.
In 1562 Shane O'Neill paid his celebrated visit to London, where he obtained recognition by Elizabeth of his claims as head of the O'Neills. But in 1563, Sussex mounted a campaign against O'Neill, in which Sorley Boy played his part. Sussex retired in frustration, and O'Neill entered into a sustained offensive against the MacDonnells, ostensibly in the interests of ridding the English of Scottish interference in Ireland: he defeated Sorley Boy near Coleraine in the summer of 1564, laying waste his territory; in 1565 he invaded the Glynns, destroying all Scottish settlements there, and at the Battle of Glentasie he won a decisive victory, in which James MacDonnell and Sorley Boy were taken prisoner and Dunluce Castle fell into O'Neill's hands.
James died soon afterwards, but Sorley Boy remained O'Neill's captive until 1567, during which period he seems to have won his captor's confidence. After his unexpected defeat by the O'Donnells in the battle of Farsetmore, O'Neill turned to the MacDonnells for assistance and attended a feast laid on by them at Cushendun, bringing with him out of captivity Sorley Boy and his late brother's widow, Agnes, to secure an alliance with the Scots. In an event which seems to have had the approbation of the lord deputy of Ireland, Henry Sidney, O'Neill was stabbed and murdered by his hosts. Sorley Boy visited Scotland immediately and returned to Marketon Bay with 600 redshanks, in whose presence he swore never to leave Ireland.
In 1569, an alliance between the O'Neills and MacDonnells was secured upon the marriage on Rathlin Island of Shane's successor, Turlough Lynagh O'Neill, to the widow Agnes. Sorley Boy spent the next few years striving to frustrate the schemes of Sir Thomas Smith, and later of the Earl of Essex, for colonising Ulster with English settlers. (See Plantations of Ireland for details). He was willing to come to terms with the government provided his claims to the lands were allowed, but Essex determined to reduce him to unconditional submission. After a retreat into Scotland, Sorley Boy returned and made an unsuccessful attempt on the crown garrison at Carrickfergus. In time, he did come to terms with Smith, who supported his claims to title in the Route on condition that he take up the reformed religion. In 1573, letters of denization were addressed to Sorley Boy from the crown, but Essex frustrated these with the renewal of his plantation scheme; still, Sorley Boy managed to hold his position, when Essex failed in his negotiation with the Scottish regent and the Earl of Argyll of a withdrawal of the Scots from Ulster.
Essex then switched tack, having struck a deal with Turlough Lynagh, and defeated Sorley Boy around Castle Toome, where the Bann flows out of Lough Neagh. Essex had to withdraw to Carrickfergus for lack of provisions, but he then ordered a follow-up operation, with the intention of driving the Scots from Ulster. Under the commands of John Norris and Francis Drake an amphibious strike force proceeded by sea from Carrickfergus to Rathlin Island, where Sorley Boy's children and valuables, together with the families of his principal retainers, had been lodged for safety; and while the chieftain was himself at Ballycastle, within sight of the island, its garrison along with civilians hiding on it were massacred by Norris' troops. Sorley Boy retaliated with a successful raid on Carrickfergus, in which the garrison broke before a highland charge, and managed to partly re-establish his power in the Glynns and the Route.
In 1583, taking advantage of Sorley's perceived weakness through the absence of a significant number of MacDonnell warriors, who had been hired by Turlough Lynagh for a campaign in the west, the Mac Quillans made their last great attempt to decisively defeat the MacDonnells and recover the Route. In alliance with Sir Hugh MacPhelim Bacagh O'Neill of Edenduffcarrick (Shane's Castle, Randalstown) and accompanied by two companies of English musketeers 'sent from the pale' and commanded by the newly appointed Senechel of Clandeboye, Captain Chatterton, the Mac Quillans launched a devastating raid on the northern glens. Sorley assembled a small force which threatened the main camp of the raiders sited on a broad ridge near Slieve na Orra. The cavalry and heavy infantry of the raiders were tricked into charging the small, apparently vulnerable, MacDonnell host across what they believed to be sound ground but what was in fact a deep bog, where they were incapacitated and decisively defeated by the MacDonnells. Hugh Mac Phelim and Chatterton fled, but were hunted down and killed near the summit of Orra while Rory Oge MacQuillan sought refuge on a crannog at Loughgile, where he was killed by a pursuer. This action is called the battle of Slieve-an-aura and has been inaccurately dated to 1559 by a number of sources, following Rev. George Hill's history, The MacDonnells of Antrim. The accurate date has been preserved in the State Papers for Ireland.
On surveying the results, Lord Deputy Sidney agreed to a ceasefire, although he supported the claims of the MacQuillans to the Route, and of Sorley Boy's nephews (sons of the widow Agnes) to possession of the Glens – a typical Campbell manoeuvre, effected through their alliance with Turlough Lynagh. At the same time, Sidney forwarded to London Sorley Boy's petition for title, although it sat there without response for years. With fortitude, the MacDonnells managed to strengthen their position through an alliance with Turlough Lynagh, and by a formidable immigration of followers from the Scottish Isles following their decisive victory at Aura.
