As Christmas of 1588 approached De Cuellar was becoming unsettled at Rosclogher. Having refused MacClancy’s offer of marriage to a sister his request for a guide to bring him to the north coast where he might find a boat to take him to Scotland was declined. De Cuellar started to become uneasy around MacClancy fearing, perhaps, hidden purpose behind his friendship towards the Spaniards. He heard rumours of MacClancy’s intention to forcibly detain him and the other Spaniards whom he wanted to remain as his personal guard. Had he heard of the plots for a rebellion. One of MacClany’s sons told him he wouldn’t allow them to leave until further aid arrived from Spain. Through the Winter rumours were rife of the impending arrival next Spring of an army from Spain under William Stanley which would signal a general uprising in the west. In any future uprising the Spaniards would undoubtedly see action. They had already proved their mettle defending Rosclogher against The Lord Depty’s men. How did the Spaniards feel about forming the personal bodyguard of a Gaelic warlord? MacClancy was prepared to imprison the Spaniards in order to prevent them leaving. Knowing of MacClancy’s intentions De Cuellar met with four of his companions to discuss their predicament. They seem to have been informed of the escape route to Scotland other survivors had taken through the north. They were aware that Spaniards were receiving help from chieftains on the north coast and felt that, if they could make it to the north coast, then there were good odds on them finding transport to take them to Scotland. The five resolved leave Roclogher secretly at the earliest opportunity. Before dawn ten days after Christmas, on January 4th 1589 De Cuellar and his four companions stole quietly away from the shores of Lough Melvin in darkness.
It is interesting that De Cuellar decided to leave Rosclogher ten days after Christmas. It makes a curious coincidence in the discrepancy between the two forms calendars which was in use at this time. On Friday 15th October 1582 the Gregorian calendar, which is used today, was introduced by the Papacy. It was a modified and more accurate version of the older Julian calendar which, it was calculated, was no longer synchronized with the seasons. When the Gregorian calendar was adopted ten days were dropped (5th to 15th October, 1582) to bring the modified calendar back into alignment with the seasons. Catholic nations adopted the new calendar. However during this era of Reformation, Counter Reformation and religious wars Protestant states refused to introduce it to their realms. The result was that across Europe two calendars were in use each ten days apart. In Ireland the rebel Catholic chieftains adopted the Gregorian calendar in defiance of the English administration which retained the old style. Spies watching Brian O’Rourke noted that he had disloyally ‘kept his Christmas according to the Pope's computation. That winter Tadhg MacClancy with his Spanish contingent celebrated Christmas ten days before their Protestant counterparts. De Cuellar and his companions set out on their trek on what was Christmas day according to the Old style calendar.
Leaving Rosclogher the first major obstacle confronting the Spaniards was the river Erne. It is a wide, deep river with only three convenient crossing points, Ballyshannon, Belleek and Enniskillen. The closest of these to Rosclogher was Belleek, a twelve mile walk from the southern shore of Lough Melvin. The chief of the O’Gallaghers, Owen MacTool resided here. An important figure in southern Donegal he was loyal to the crown and had aided Fitzwilliam in his attempt to take Rosclogher. But after escorting the Lord Deputy to Donegal castle he had then been taken prisoner. He remained with Fitzwilliam through his circuit of Ulster and, on his return to the capital, was imprisoned in Dublin castle as a surety for the payment of crown rents by his Hugh Dubh O’Donnell. He was kept there until 1594. A group of English captains were then set loose in Donegal. Captains Connell and Bowen were given charge of Donegal and ran amok. If an English garrison had been placed at Belleek the Spaniards may have hoped they would be inside celebrating Christmas while they slipped quietly across the river nearby. The twelve days of Christmas may have been a good time for the small group to attempt the dangerous journey through the north.
Tadhg MacClancy when refusing to supply a guide for De Cuellar to reach the north coast gave as his reason that the roads were unsafe. While this may simply have been a convenient excuse to detain the Spaniard it was, nevertheless, true. Since the arrival of the Armada the English garrison in Ireland had been doubled. Bands of soldiers were still active in the north looking out for renegade survivors. In western Ulster existing tensions amongst some of the principal families in the north had been heightened by the events surrounding the Armada. Recriminations and accusations began to fly almost as soon as the Girona departed from Killybegs on its ill-fated journey around the north coast. The lord of Tirconnel, Hugh MacManus O’Donnell had shown himself to be very weak during the Armada crisis. The imprisonment of his son, Hugh Roe, in Dublin castle affected him greatly. He had sided with the Government and did nothing to aid the Spaniards while many others had put themselves at great risk by aiding the Armada survivors. Fitzwilliam created further tensions in the region during his expedition to the northwest when he apprehended Eoghan MacTool O’Gallagher and Sean Og O’Doherty. The act was seen as treacherous as O’Gallagher and O’Doherty were loyal to the government. The bickering between Turlough O’Neill and O’Donnell became hostile. Threats were issued against O’Donnell. In a Letter to the Privy council Lord Deputy Fitzwilliam wrote of the disgust O’Neill felt for O’Donnell’s betrayal of the Spaniards ‘Tyrone hath bitterly reproved O'Donnell, saying he and his posterity may seek a dwelling in another country for having betrayed the Spaniards their only refuge. O’Neill lent his support to the O’Donnells of Castlefinn in their attempt to depose the vulnerable chieftain and claim the Lordship of Tirconnell for themselves.
Through 1588 and 1589 Donegal was falling into turmoil. Hugh Gallagher, a son-in-law of Calvagh O’Donnell of Castlefinn led the opposition to the ruling O’Donnells. Ineen Dubh had him murdered by her Scots bodyguards at Mongavlin crannog. Donnell MacHugh, who had been appointed Sheriff of Donegal by Fitzwilliam, together with the O’Gallaghers, made an attack on Conn O’Donnell of Castlefinn, chief of the rival branch. Preys were taken and Calvagh Og, a son of Conn’s, was killed. In the aftermath of Fitzwilliams expedition Hugh McHugh Dubh O’Donnell seized Belleek castle. O’Donnell himself with a large band crossed the river Finn to raid Turlough Luineach’s lands. It was reported that O’Neill ‘with the assistance of Capt. Merryman and some English soldiers followed him, and not only rescued the prey but also killed some of O'Donnell’s chief leaders and people’. O’Neill and the Castlefinn O’Donnells then combined and retaliated. They attacked the O’Gallagher territories of Tirhugh between Belleek and Donegal town. After a hard fought battle in which the Gallaghers and the MacSweeneys were defeated O’Neill’s men came away enriched with spoils. Leaders of the MacSweeney Banagh sept began attacking each other for control of their territory. Meanwhile the English Captain Connell, who had gained the confidence of Hugh O’Donnell, took the Lord prisoner. While he would later be rescued the Lordship of Tirconnel was becoming riven with animosity and dissension. The chaotic mess made it too dangerous for Ineen Dubh, the formidable wife of O’Donnell, to remain at Donegal. She fled temporarily, to her kin, the MacDonalds of the Isles, burning the castle and hall to prevent an English garrison being installed there.
De Cuellar doesn’t describe the route he took to the north coast. It is unlikely that the group journeyed through Donegal as it was becoming too dangerous and, in any case, it was known that Spaniards trying to make their way home were leaving from the north Antrim coast. Francisco merely says that they ‘went journeying through mountains and deserted places, with great hardship’ before arriving at Dunluce after twenty days on the road. It is about one hundred miles from Rosclogher to Dunluce. The Spaniards were making this journey when the days were at their shortest and during the coldest time of the year but even so, they must have covered more than five miles each day. There is no indication from De Cuellar’s account of any assistance being given to the Spaniards though they had to find food and shelter somewhere on the journey. Places where they could have expected to find shelter were at Strabane, with Turlough Luineach O’Neill, Dungiven with the O’Kanes or even Dungannon where Hugh O’Neill, the Earl of Tyrone, resided. Had they stayed with these chieftains De Cuellar would presumably have mentioned this. So to guess from his brief description of the route and his subsequent experiences it seems the De Cuellar followed a route across the Sperrin mountains through central Ulster to the coast finding some shelter along the way but not with any of the principal lords of the province.
The Spaniards reached Dunluce around January 24th. This was the territory of the MacDonnell clan, a Scots gallowglass family from the Western Isles who, under the warrior Sorley Buidhe MacDonnell, had established themselves along the north coast of Antrim known as ‘The Route’. The Girona was wrecked in this district, not far from the Giants causeway on October 28th with terrible loss of life. Alonso De Leyva and almost 1,300 men went down after the ship’s rudder failed causing the ship to drift onto rocks where she broke up. Nine men were pulled alive from the water and given shelter by the MacDonnells. They also recovered numerous barrels of wine, valuables and two cannons which were dragged to Dunluce and mounted on the castle wall. Five of these survivors accompanied Sorley Boy when he travelled to Strabane to seek the hand of Turlough Luineach O’Neill’s daughter in marriage. They and thirty two survivors from the massacre of Alonso De Luzon’s force at Illagh were given aid by Sorley Boy who under pressure from Fitzwilliam defiantly refused to hand over the survivors. They were subsequently transported to Islay, the island stronghold of the MacDonnells across the North channel. From there they were brought to the Scottish mainland at Ayr where the townspeople were hospitable. The Spaniards were even given new shoes to help them on their way out of town. At Edinburgh the King, James VI, ordered accommodation to be provided for them. Before Christmas transport and letters of safe conduct had been arranged and they embarked for France, arriving in Le Havre on December 26th.
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