# Dictionary of National Biography, 1885-1900/MacDonnell, Sorley Boy

​MACDONNELL, SORLEY BOY (Carolus Flavus) (1506?–1590), Scoto-Irish chieftain, lord: of the Route and constable of Dunluce Castle, born probably in the castle of Dunanynie, near Ballycastle in co. Antrim, about 1505, was sixth and youngest son of Alexander or Alaster MacDonnell, lord of Isla and Cantyre in Scotland and of the Glynns in Ireland, the great-great-grandson of John Mor MacDonnell, who about 1400 married Margaret Bisset of the Glynns. Sorley Boy's mother was Catherine, daughter of John Marfan MacDonnell, lord of Ardnamurchan.
Apparently during one of the many abortive attempts of thelrish government to expel the Hebridean Scots, Sorlev Boy was taken prisoner and incarcerated in Dublin Castle, but after an imprisonment of about twelve months he was, in September 1552, exchanged for certain prisoners made by his brother James on the occasion of Lord-deputy Sir James Croft's unsuccessful attack on the island of Rathlin. Shortly after his release he retaliated by seizing the constable of Carrickfergus Castle, Walter Floody, whom he compelled to pay a heavy ransom. In 1558, on the death of his brother, Colla, Sorley Boy, who had taken an active part in subjugating the MacQuillins of the Route, was appointed by his brother James to the ​lordship of that district. The MacQuillins, however, resisted his authority, and during the spring of 1559 Sorley Boy was busily engaged in raising troops on the Scottish coast. Early in July he landed at Marketon Bay, and finding the MacQuillins strongly posted at the foot of Glenshesk he attacked them at a place called Beal-a-faula and repulsing them with heavy loss drove them southwards. Several bloody encounters followed, but at Slieve-an-aura the MacQuillins and their allies were completely routed, and the MacDonnells re-established in possession of the Route.
The Scottish settlements along the Antrim coast had long been regarded with disfavour by the Englisn government, but the efforts made to destroy them had so signally failed that Elizabeth was quite ready to listen to certain overtures made to her by Sorley Boy shortly after her accession, to submit to her authority on condition of being confirmed in his possessions, and all the more so, probably, because she saw in the Scots a means of curbing the power of Shane O'Neill. To O'Neill the growth of a strong, independent power in the north-east was naturally as displeasing as it was to Elizabeth, but in the event of a rupture with the crown an alliance with Sorley Boy was a thing not to be despised. As for Sorley Boy there can be no doubt that his interest lay in coming to terms with the government. In 1660, when matters between the government and O'Neill were approaching a crisis, he readily consented to follow the lead of Argyll and his brother James in forming a league against Shane O'Neill, merely stipulating that as a reward for his services ne should receive letters of denization and a grant of all the lands he held as deputy for his brother. Elizabeth and her advisers appear to have regarded his claims as somewnat extravagant, but there was an evident desire on their part to arrive at some satisfactory conclusion (see particularly Cecil's own instructions to Henry Warren in State Papers, Ireland, Eliz. ii. 14). Obstacles, however, arose for which neither side was wholly responsible. As time went on and the situation of affairs altered, the government became less anxious to treat, and the murder of Alaster MacRandal Boy Macdonnell and his brother Gillaspic by Andrew Brereton in March 1563 made Sorley Boy stand on the defensive. A month or two later peace was concluded between the government and Shane O'Neill. The latter, who had been waiting his opportunity to break up the northern confederacy, thought the moment for action had arrived. Veiling his intention under the guise of loyalty, he in August 1 564 announced his determination to expel Sorley Boy and the Scots. His resolution was applauded by government and immediately put into execution. In a battle near Coleraine Sorley Boy was himself wounded and his territory afterwards laid waste with fire and sword. In the spring of the following year, 1566, O'Neill renewed his invasion, and, proceeding northward through the Glynns, destroyed as far as possible every trace of the Scottish settlements. At Ballycastle he encountered the MacDonnells, and in the battle that followed Sorley Boy and James MacDonnell were taken prisoners. A few months later James died in prison, not without suspicion that his end had been purposely hastened by O'Neill. For two years Sorley Boy remained in captivity, but early in 1667 Shane O'Neill, whose situation had become desperate, determined — acting, it is conjectured, on the advice of Sorley Boy — to make a personal appeal for assistance to the Antrim Scots. The MacDonnells had neither forgotten nor forgiven his treatment of their chief, and, without supposing his murder to have been deliberately planned beforehand, it may well have been that his presence in their midst and his arrogant demeanour provoked them beyond endurance.
To the government, however, Sorley Boy was almost as objectionable as Shane Neill, and various schemes were set on foot to compel him to abandon his Irish possessions. But Sorley Boy, who since the death of Shane had been occupied in strengthening his connection in Scotland, landed at Marketon Bay on 27 Nov. at the head of six or seven hundred redshanks, in whose presence he swore never to leave Ireland with his good-will. The news of his landing spread considerable consternation through official circles, but though Elizabeth issued peremptory orders for his expulsion, no attempt was made to execute them, and Sorley Boy, who consistently aimed at conciliation, after again urging the legal recognition of his claims, returned to Scotland, where he appears to have taken a personal part in a conflict between the Clan Donnell and MacLeans. During the year there were continual rumours of a combination between him and Turlough Luineach O'Neill, but though he was probably present at the marriage of Turlough and the widow of his brother James in Rathlin Island in the autumn of 1569, it was not till February 1571, when the air was full of the colonisation schemes of Sir Thomas Smith and others, that he deemed his presence in Ireland necessary. Leaving his son Donnell with three hundred Scots to guard the Glynns, he returned to ​Scotland to raise fresh troops. In February 1572 he made a sudden attack on Carrickfergus, but was repulsed by the garrison, and himself wounded. He had naturally felt apprehensive at the announcement of Smith's intention, but finding the latter after a time willing to come to terms with him, he again preferred a petition to be recognised as the legal owner of the territory he claimed. In forwarding his petition Smith suggested that if it was granted it would be advisable to persuade Sorley Boy to adopt the reformed religion. On 14 April 1573 letters patent of denization were addressed to him, but the determination of the Earl of Essex to resume Smith's project seems to have had the effect of frustrating them. Nevertheless, the arrival of the Earl of Essex in the summer of that year, notwithstanding his efforts to smooth the way by negotiating with the regent of Scotland and the Earl of Argyll for the revocation of the Scots, did not materially affect the situation. For finding Sir Brian MacPhelim O'Neill [q. v.], on whose submission he had laid considerable store, but a fickle ally, he in November turned his attention to Sorley Boy, who had recently renewed his offer of submission. Nothing, however, came of the matter, and in July 1575 Essex, having managed to come to some sort of terms with Turlough Luineach, made a determined effort to subdue Sorley Boy. Somewhere in the neighbourhood of Castle Toome he inflicted a sharp defeat upon him, but provisions running short he returned to Carrickfergus, where he deputed Captain John Norris [q. v.] to proceed by sea against Rathlin Island, where Sorley Boy had 'put most of his plate, most of his children, and the children of most part of his gentlemen with their wives,' for the sake of safety. Norris carried out his instructions to the letter, and Sorley Boy, who from the mainland saw the massacre of all those that were nearest and dearest to him, went almost frantic with despair. Notwithstanding his terrible loss, Sorley Boy in the beginning of September swooped down on Carrickfergus and carried off all the townsmen's cattle, defeating the garrison who tried to rescue them. A month later Sir Henry Sidney found the Glynns and Route in the possession of Sorley Boy, 'the country full or corn and cattle, and the Scots very haughty and proud by reason of the late victories he hath had.' Sorley Boy was, however, willing to treat on the old terms, and Sidney having agreed to a cessation of hostilities, undertook to forward his petition, though personally in favour of restoring the MacQuillins to the Route, and of supporting the claims of James MacDonnell's sons to the Glynns. The privy council, to whom he referred the question, declined to move in the matter, and things were allowed to drift back into their old position. The same policy of inaction was pursued by Sidney's immediate successors, and notwithstanding the efforts of the MacQuillins to recover the Route, Sorley Boy, by fresh arrivals from Scotland and by his alliances with Turlough Luineach, became yearly more powerful. So great indeed was the influx of Scots at this time, that, according to Sir Nicholas Malby [q. v.], Ulster threatened to become a second Scotland.
Such was the situation of affairs in August 1584, when Sir John Perrot [q. v.], alarmed by rumours of fresh arrivals, determined to make a strenuous effort to expel Sorley Boy. Mustering what forces he could, he proceeded northwards ; but the news of his preparations had already alarmed Sorley Boy, who, after making hasty arrangements for the safety of his followers, slipped across to Scotland, where he had soon collected four thousand Islesmen, with whose assistance he determined to make a resolute effort to recover his position in Ulster. Perrot, who had reaped little honour from his elaborate expedition, seems to have connived at a scheme for Sorley Boy's assassination, which, however, proved unsuccessful (State Papers, Ireland, Eliz. cxii. 90, ii.) In January 1585 Sorley Boy arrived at Cushindun with what forces he could muster, just in time to save his nephew, Donnell Gorme, who was vainly trying to hold his own against Sir W. Stanley and Sir H. Bagenal, from destruction. But the situation offered little prospect of success, and having obtained an interview with Captain Carleil, he offered to submit on the conditions offered him ten years before by Sir Henry Sidney. But Perrot, who had determined to expel him, declined to listen to any terms, and so, hunted from one stronghold to another, Sorley Boy was at last glad to escape to Scotland. A few months later the MacDonnells, notwithstanding the threats fulminated against them by James VI (Hamilton Papers, ii. 682), were back again in considerable numbers in the Glynns, and a small body of them having succeeded in recapturing Dunluce Castle, Perrot reluctantly consented to treat with Sorley Boy. The latter was at first unwilling to go to Dublin, but the execution of his eldest son, Alaster, broke his resolution, and in June 1586 he presented himself before the lord deputy. Prostrating himself before a picture of Queen Elizabeth, and kissing 'the pantofle of the same' (Cal. State Papers, Ireland, iv. 85), he ​admitted that he had no legal right in Ulster, expressed his sorrow for his past contumacy, and promised faithfully to abide by such conditions as were imposed upon him. An official, it is said (Hill, MacDonnell of Antrim, p. 187), brutally showed him his son's head over the castle gate, to which he proudly replied, 'My son hath many heads.' On 18 June indentures were signed (Cal. Careio MSS. ii. 427), whereby he received letters of denization, together with a grant by knight's service, the yearly payment of fifty beeves, twelve horsemen, and forty footmen to every hosting, to himself, and the issue male of his body, of all the land between the Bann and the Bush, embracing the greater part of the Route, the constableship of Dunluce Castle, and such land to the east as was not included in a grant to his nephew Angus. From this time forward he gave no trouble to the state, though his name figures in a list of 'doubtful persons' drawn up by Sir William Fitzwilliam [q. v.] in 1689. He died at Dunanynie Castle early in 1690, and was buried in the older vault in the abbey of Bunnamairge. It is traditionally stated that when his son Randal built the new vault in 1621 he transferred his father's remains thither, but no trace of his coffin is now to be found.
By his wife Mary, daughter of Con O'Neill, first earl of Tyrone, who died in 1682, Sorley Boy had, among other children, Alaster, who was killed, as noted above, in 1686; Donnell, who is said to have been slain by Turlough Luineach O'Neill; Sir James, who succeeded his father, and died suddenly at Dunluce on 13 April 1601; Sir Randal, first earl of Antrim (d. 1636) [q. v.]; Angus, and Ludar or Lother, who was implicated in the 1614 conspiracy. Of his daughters, one is said to have been married to the chief of the Macnaghtens in Scotland; another to MacQuillin of the Route; a third to Cormack O'Neill, brother of Hugh, earl of Tyrone; a fourth to Magennis, lord of Iveagh, and a fifth to Shane MacBrian MacPhelim O'Neill of Clandeboye (see MacFirbis's pedigree in Hill, MacDormells of Antrim, App. i. and the pedigree in Harl. MS. 1426, f. 188).
From information received by Sir W. Fitzwilliam in October 1688 (Cal. State Papers, Ireland, iv. 63, 64), it appears that Sorley Boy, who was then about eighty-three years of age, married in that month a daughter of Turlough Luineach O'Neill.
[Lodge's Peerage, ed. Archdall, vol. i.; Hill's Macdonnells of Antrim; State Papers in Rolls Office, London; Hamilton's Cal. of Irish State Papers, vols, i-iv.; Cal. of Carew MSS. vols. i-ii.; Morrin's Cal. of Patent Rolls, Eliz.; Cat. of Fiants, Eliz.; Collins's Sydney Papers; Devereux's Lives of the Earls of Essex; Kilkenny Archæol. Journal, 1885, pp. 133-48; D. Gregory's Western Highlands; Spottiswoode Miscellany, ii. 361; Bagwell's Ireland under the Tudors; Ulster Journal of Archæology, vols. v. viii.; Annals of the Four Masters, ed. O'Donovan, vi. 1895; Hist. MSS. Comm. 3rd Rep. p. 48.]
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