Feagh McHugh O'Byrne and the Ulster Princes:
His Role in their Dublin Castle escapes
by
Darren Mac Eiteagáin
Darren Mac Eiteagáin was awarded an MA by University College Dublin in 1995 for a dissertation on Aodh Dubh Domhnaill Prince of Tír Chonaill, 1505-37.

The late sixteenth century is a crucial period in Irish history. It saw the final struggle of many Gaelic Irish lordships to preserve their independence from English domination, culminating in the conflict now known as the Nine Years war. Some of the most dramatic events of this war were played out in County Wicklow, mostly due to the drive and intelligence of one man - Feagh McHugh O'Byrne. One of the more adventurous episodes of the period involved the escapes to Wicklow of the famous Donegal chieftain, Red Hugh O'Donnell. In tales filled with intrigue and even accusations of murder, Red Hugh and some Ulster companions escaped to Wicklow on two occasions, in January 1591 and January 1592. These exploits have long captured the public imagination, even being made into a film in 1966. In this paper it is proposed to examine the role of Feagh McHugh in the two escapes of Red Hugh O'Donnell, as well as examining the part played by Feagh's wife, Rose O'Toole, and her brother Phelim O'Toole of Castlekevin.

The reasons for Feagh's involvement in the escapes of Red Hugh are bound up with the concepts of Gaelic-Irish independence and the counter-reformation. By early 1592 Gaelic Ireland was in a desperate situation, with most of Gaelic-Irish Leinster, Munster and Connaght having been either invaded, planted or subdued. Some areas such as Laois-Offaly and parts of Connacht were still rebellious and islands of independence still existed in in south Munster, but many chieftainships had been abolished or cowed into submission. Even in the north, by far the largest Gaelic-Irish area on the island, both the great lordships of Tir Eoghain and Tir Chonaill were partitioned amongst various claimants. However, the Gaelic-Irish and mountainous heart of County Wicklow, which was under the control of Feagh McHugh O'Byrne, was also counted as one of the most fiercely independent Gaelic-Irish areas in Ireland. Feagh's position was made all the more unusual by virtue of the close proximity of his lordship to the seat of English authority in Ireland - the Dublin Pale. Because of this O'Donnell fled to Glenmalure when he broke out of prison.

Red Hugh O'Donnell came from the lordship of Tir Chonaill - what is now the modern county of Donegal. He was the eldest son of the second marriage of Hugh O'Donnell, the lord of Tir Chonaill, to the famous Inghean Dubh, the daughter of MacDonnell of Scotland. Even as a very young child Red Hugh was of great importance because of the expectations put upon him by his father's adherents. A prophecy became associated with the O'Donnells that a deliverer called Aodh (Hugh) would be born into the family and that he would drive the English out of Ireland. For whatever reason, even as a child this prophecy became associated with Red Hugh. The contemporary biography of Red Hugh, written by one of his court historians, Lughaidh O'Clery, who later travelled on campaign with Red Hugh's army, gives a good indication of the hopes associated with Red Hugh. He begins his book by writing, "A wondrous family indeed sprang from 0 Domhnaill (Aodh, son of Manus, son of Aodh Og, .etc.). Inynne Dubh, daughter of James Mac Domhnaill, of the race of Colla Uais, was wife of 0 Domhnaill, and she was the mother of those of his children who were illustrious. The names of their male children in the order of birth are Aodh Ruadh, Rury, Manus, and Caffar. As for the first son of these, Red Hugh, he grew and throve in shape and comeliness, sense and eloquence, wisdom and understanding, size and fitness, so that his name and fame spread throughout the five provinces of Eire.” Moreover the fame and renown of the youth were reported to the foreigners of Dublin, and they reflected in their minds that there would not be one like him of the Irish to avenge his wrongs and punish the plundering of his race if he was allowed to reach manhood. Red Hugh's mother, Inghean Dubh, was probably responsible for the spread of this prophecy as she was very ambitious for her eldest son.

However, before the time of Red Hugh there had been a dramatic decline in the power of the lords of Tir Chonaill. Red Hugh's grandfather Manus O'Donnell (prince of Tir Chonaill 1537-55) and his earlier ancestors, Black Hugh (prince of Tir Chonaill 1505-37) and Red Hugh 1 (prince of Tir Chonaill 1461-1505) had been great leaders. Called 'princes' by foreign kings, they had conquered Fermanagh and Sligo for the O'Donnells and had diplomatic links with the kings of Scotland and France. However, after 1555 lesser men had ruled the lordship and great violence had broken out amongst various rivals. The famous Shane O'Neill had then terrorised Tir Chonaill until, as the Annals state on one occasion, "there was no one ruling Kinel Connell at this time". Although Red Hugh's father, also called Hugh, who became lord of Tir Chonaill in 1566, was able to defeat Shane O'Neill at the battle of Farsetmore in 1567, he was a weak leader. By 1592 power over Sligo and Fermanagh was long gone, and Red Hugh's father had even lost control of some of the sub-lordships of north Donegal such as Castlefinn and Inis Eoghain. Later in 1596, Red Hugh was even to accuse the English sheriff that was sent to Tir Chonaill in the last years of his father's reign of using his by then ill father as little more than a "thrall or vassal, to be as it were a guide for him in the country".

Red Hugh had also many dangerous rivals within the O'Donnell dynasty to contend with. The most dangerous was Domhnall, a son of Red Hugh's father by a woman other than Inghean Dubh. However, he was killed in battle by Inghean Dubh's Scots in 1590. Red Hugh's other main rival was Aodh Dubh, his granduncle. This Aodh Dubh (Black Hugh) was the son of the prince of Tir Chonaill who died in 1537. He was probably born about 1537 himself and was regarded as "the senior of the race of Dalach (the O'Donnells), son of Murchertach, besides Aodh, son of Maghnus (Red Hugh's father)". He was a well known warrior, being described as 'the last generation of the Gaelic heroes and did not die until 1618. He was powerful about his own lands in the tanaiste's portion of Tir Chonaill which was centred in mid-Donegal. Another great rival was Niall Garbh O'Donnell of Castlefinn who had the best claim to the lordship of Tir Chonaill under English law.

Although Red Hugh's father was ill and a weak leader by traditional O'Donnell standards, the English administration in Dublin castle still got wind of Red Hugh's abilities - even though he was only fifteen. It is evident from English sources that Turlough Luineach O'Neill, the declining ruler of west Tyrone, was responsible for this. He kept the lord deputy, Sir John Perrot, well informed about Red Hugh's progress as he approached the age when he could be a threat to him. O'Clery states that the English and Turlough O'Neill were afraid that Red Hugh would combine with Hugh O'Neill, the earl of Tyrone, who then ruled the eastern half of Tyrone from his seat at Dungannon, Although Hugh O'Neill was then following a pro-English policy, this was only to allow him to build up his strength against Turlough Lineach who was chieftain of the O'Neills at this time. Turlough, who ruled west Tyrone from his castle at Strabane, was a shrewd and wily operator but by the late 1580s was in terminal decline and was already being eclipsed by Hugh O'Neill. In order to outflank Turlough Luineach, Hugh O'Neill had already married Red Hugh's sister Siobhan, firmly cementing an unusual alliance between an O'Neill and an O'Donnell.

In 1587 the English therefore decided to break up the budding alliance between Hugh O'Donnell and Hugh O'Neill. The government sources indicate that the plan was discussed about Michaelmas 1587. To save the expense of a punitive raid it was decided to disguise a Dublin merchant ship as "a ship laden with sacks [Spanish wines], as if he had come out of Spain". The crew's orders were to sell cheaply and capture either Red Hugh or his father. The ship, with a full complement of soldiers and generously provisioned with wine, sailed into Lough Swilly in County Donegal disguised to appear as it were a Spanish merchantman selling wine and beer. Such merchantmen sailing into County Donegal were then nothing unusual. Raiding ships had been putting into Tir Chonaill for centuries, from Spain, France, Brittany and Bristol. They traded fine clothes, wines, weapons and firearms for tallow, herring and salmon. English traders who came to Tir Chonaill invariably treated the O'Donnells with the utmost respect. They even called Hugh O'Donnell the 'king of the fish'. As a result, the people of Lough Swilly had no suspicions about the ship that arrived in the bay, ostensibly to trade.

At the time Red Hugh was staying with his foster-father, MacSweeney Doe, a powerful chieftain in north-west Donegal. However, he had decided to visit the neighbouring chieftain Mac Sweeney Fanad. It was at the harbour of MacSweeney Fanad's main castle, Rathmullen, that the English ship was anchored. When the English spies discovered that Red Hugh had come to the castle they cleverly refused to issue any more drink, saying that supplies were exhausted but that if the nobles of the territory would like some more, they could come aboard and be given some of the crew's supply. Again it must be remembered that Red Hugh was only fifteen and that the Irish of Tir Chonaill usually had nothing to fear from merchant men. O'Clery states that Red Hugh had none of his advisers with him, only a band of young followers. In the event Red Hugh went aboard and was wined and dined until, as O'Clery put it, they were all "merry and cheerful". At this point their weapons were taken away and Red Hugh and his companions were locked in a secure cabin from which they were unable to escape. O'Clery and the Annalists state that news of Red Hugh's capture spread through the local area like wildfire and that Red Hugh's foster father, Eoghan Og MacSweeney, galloped over to offer any other hostages in exchange. However, as O'Clery put it, "This did not avail him, for there was not in the province of Ulster a hostage whom they would take in his place, since it was solely to look for him they had come". In the end the English ship simply weighed anchor and sailed away, leaving behind a furious populace who had no boats at hand to pursue the kidnappers.

Red Hugh was brought to Dublin and imprisoned in a secure compartment in Dublin castle where he was held for three years and three months. It is here that Feagh McHugh and his sons and his second wife, Rose O'Toole, and her brother Phelim O'Toole of Castlekevin enters the story. The State Papers of 1588 show that when Red Hugh had been imprisoned for about a year, his fellow prisoners included Redmond and Brian, two sons of Feagh McHugh, as well as Hugh O'Toole, another of Feagh's pledges. Some of Red Hugh's people were also held in the castle at this time and these included Domhnall Gorm MacSweeney, Eoghan O'Gallagher and an Eoghan MacSweeney, probably also taken by the English merchant ship. It is not known if Red Hugh befriended Redmond and Brian but O'Clery states that the captives spent their days and nights telling each other of the various wrongs and injustices inflicted on their families by the English. O'Clery also states that to Red Hugh: "It was anguish and sickness of mind and great pain to him to be as he was, and it was not on his own account but because of the unfortunate straits in which his friends and kinsmen, his chieftains and leaders, his clerics and holy ecclesiastics, his poets and learned men, his subjects and whole people were, owing to their expulsion and banishment to other territories throughout Eire".

Red Hugh's father pleaded unsuccessfully with the authorities in Dublin to release his captive son. On one occasion he even offered to trade thirty Spaniards he had rescued from an Armada wreck. However, Red Hugh came to realise he would have to rely on himself to effect his freedom. O'Clery states that Red Hugh was "always meditating and searching how to find a way of escape". However, in a great escape from Dublin castle in 1589 the unfortunate Red Hugh was left behind. In May of that year twenty-two prisoners from Tir Chonaill, Fermanagh, Wicklow and the Pale broke out of the castle. These included Feagh's sons, Redmond and Brian, along with some O'Tooles. Ten were soon recaptured but twelve, who probably fled south to Feagh McHugh in Glenmalure, guided by Redmond and Brian, eluded the pursuers. Significantly, amongst the successful escapees to Glenmalure were two of Red Hugh's men, Eoghan O'Gallagher and Domnall Gorm McSweeney. On this occasion Red Hugh could not escape because every night he was put into a very secure cell and not allowed out until the following morning. However, as O'Clery put it, "there is no watch of which advantage may not be taken at last."

While held in the castle Red Hugh was visited by a number of Gaelic-Irish nobles who befriended him and gave him gifts of money, clothes and food. These included some of his own people who were probably hiding in Glenmalure, Fergus O'Farrell of Annally (now the modern county of Longford) and Phelim O'Toole of Castlekevin in central Wicklow. Phelim was a brother of Feagh's second wife Rose O'Toole, and governed the O'Toole lordship of Fir Tire, centred on Castlekevin, during the minority of his nephew Feagh O'Toole. The boy Feagh (anglicised Luke) was destined to achieve fame later as a colonel of the Confederate Catholics in the 1640s. These nobles visited Red Hugh on the gamble that he would assist them later if he ever escaped and became lord of Tir Chonaill. Certainly Red Hugh later assisted Fergus O'Farrell's branch of the O'Farrell dynasty in a great raid in 1595. In all probability Phelim O'Toole was sent by Feagh McHugh and his wife Rose. Feagh could not afford to be seen personally visiting Red Hugh; his brother-in-law would, however, be deemed a satisfactory emissary. The astute and highly intelligent Feagh was in all likelihood already allied to Hugh O'Neill, earl of Tyrone. O'Neill, Red Hugh's own brother-in-law, needed his release as early as possible and so was laying the groundwork for his escape. It would seem probable that a decision had been made that if Red Hugh succeeded in breaking out he should head south either to Feagh in Glenmalure or Phelim in Castlekevin rather than expose himself to greater danger by trying to go back directly to Tir Chonaill. In all these plans Feagh had to look to his own position and balance what needed to be done to help Hugh O'Neill and the O'Donnells with the fact that the English in Dublin were much nearer to him than to his allies in Ulster.

The first escape of Red Hugh appears to have been entirely his own doing. The only help received by him from the outside came from one of his own people who was staying in Glenmalure. Red Hugh's escape appears to have caught Phelim O'Toole and Feagh McHugh by surprise; they were probably not informed that the escape plan had of necessity to be kept secret. In early January 1591 Red Hugh chose a number of companions from his fellow prisoners and took his opportunity to escape. The Annals name one, Art Kavanagh, described as a -certain famous hero of the Lagenians, of the race of Cathaoir Mor". O'Sullivan Beare names another two, Domhnall McSweeney Gorm and Hugh O'Gallagher, though that writer appears to have confused this escape with the larger one of 1589. Dublin castle was then surrounded by a deep water-filled moat, crossed only by a wooden bridge, guarded inside and out by a party of English soldiers. However, late December and early January is a festive and very cold time of year and Red Hugh noticed that the guards outside the castle gate on the wooden bridge had withdrawn indoors. What Red Hugh and his companions decided to do was just before they were locked into their secure cells at night to go to the room above the door of the castle and climb on to the wooden bridge outside using ropes. Showing a meticulous cast of mind, Red Hugh had previously noticed that there were two iron rings on the castle door. He had accordingly equipped himself with a piece of wood the thickness of a fist, and ramming it through the iron rings firmly locked the door from the outside. Red Hugh's ally on the outside then ran to meet them at the opposite end of the bridge. He had brought two swords with him, concealed under his cloak. These were given to Red Hugh who, in turn, gave one to Art Kavanagh who courageously covered their flight through the streets of Dublin.

The escape of the prisoners was not discovered for some time and by then the fugitives had got clear of the city altogether, the gates having been left open. When the castle guards discovered their charges had fled, they tried to follow in pursuit but were unable to open the door because of the wooden bolt Red Hugh had inserted in the iron rings. The guards were reduced to shouting across to a row of houses on the far side of the moat until they were heard. Eventually some people realised what had happened and came and released the bolt. A great mob of people then set out in pursuit of Red Hugh but he was long gone.

A great deal of interest and speculation has arisen as to the precise escape route followed by Red Hugh. The point of origin - Dublin castle, and the ultimate destination - the wooded hills about Castlekevin, are known but the other particulars of the escape route are perforce conjecture. O'Clery and the Annals state that Red Hugh and his companions leaped over many walls and fences outside Dublin and that they then fled over the numerous roads and paths of Sliabh Rua. O'Clery states that "fear did not allow them go by the usual roads”. In modern times Sliabh Rua has become associated with Three Rock Mountain. However, the Gaelic Irish sources indicate that Sliabh Rua is intended to mean the entire mountain range between the Gaelic Irish of central Wicklow and the Pale. O'Clery described it as "long and very wide; it was the boundary between the province of Leinster and the English of Dublin". Father Walsh, the best authority on the life of Red Hugh, completely discounts Three Rock Mountain as being the escape route. He notes that it is almost 1,500 ft high, and instead favours Gleann na Smol as the route of flight. This seems more plausible as it would have taken the escapees down by way of Lough Bray and the Sally Gap to the valley of the Avonmore and Annamoe which he states was "a natural and not, in those days, easily discovered route to the home of the O'Tooles of Castlekevin”.

In any case Red Hugh and his companions fled all night until in exhaustion they slept in the middle of a dense wood, still in great fear of being caught by pursuers. The confinement for over three years in a prison was, however, beginning to take its toll on Red Hugh. Because his shoes were old and unused to the wet they fell apart at the seams and his feet soon became badly cut by furze bushes and briars. He began to fall behind his fellow escapees until they abandoned him and continued on their own. O'Clery states that they left Red Hugh "in great sorrow and affliction [but] left him their blessing", and that he was then left alone with "a small party" of his people. This would suggest that he had been met somewhere on the way by more of his people from Glenmalure. At this stage Red Hugh decided to make contact with Phelim O'Toole, "a friend of Aodh [Hugh] before this time". While he hid in a wood, Red Hugh sent one of his men down to Castlekevin to seek help from O'Toole. All the Gaelic Irish sources agree that Phelim was very glad to hear of the successful escape of Red Hugh and that he wanted to help him. But this is where Phelim's problems began. Phelim was not the chieftain of the Castlekevin O'Tooles but only acting so during the minority of his nephew Feagh O'Toole, and because of this situation most of the other O'Tooles of Castlekevin refused to allow him assist Red Hugh. Don Philip O'Sullivan Beare wrote that Phelim O'Toole desired to aid O'Donnell "though he would imperil his property and get into difficulties". However, O'Sullivan also states that Rose O'Toole, Phelim's sister and Feagh McHugh's wife, happened to be in Castlekevin at the time and came up with a strategy, which if it had worked would have saved both Red Hugh and Phelim from their dilemmas.

Rose was Feagh's second wife and a generation younger than him. Either because of her beauty or intellect, most probably both, she had a great hold over Feagh. One poet in the Leabhar Branach describes her as "a blazing meteor, wine of grape, flower of women... She glows with the fire of youth. She is the life and death of heroes." Folklore which survived for centuries in Glenmalure also retained a folk memory of her, one nineteenth century source stating: "that there once lived there a powerful lady named Rosha, who had only to put on her red mantle to fill the whole district with fire and blood. The English feared Rose and her qualities, one English observer referring to her as "The ace of hartes in wickedness". Rose's power was also greatly enhanced by the fact that her two sisters, Una and Catherine, were married to Feagh's two sons, Phelim and Redmond, while another sister Siobhan was married to Eamonn mac Shane Óg O'Byrne, Feagh's step-brother. It is unclear when Rose married Feagh McHugh, but it may have been much earlier than 1584. A marriage contract between the two existed until the nineteenth century but has since been lost.

By now the O'Tooles of Castlekevin who had disagreed with Phelim had found out which wood Red Hugh was hiding in and had set out to track him down. As a result Rose advised that Phelim should capture Red Hugh himself, first of all for O'Donnell's safety. It was then that Feagh McHugh came into play. Rose suggested that Phelim should pretend to take Red Hugh back to the English in Dublin but that he should be ambushed on the way by Feagh McHugh who would then take O'Donnell back with him to the safety of Glenmalure. From both English and Irish sources it is clear that Phelim O'Toole was a staunch adherent of Feagh McHugh and accordingly would have willingly co-operated in the interception. Rose gambled that her husband would get away with this, he being too powerful for the English to touch without incurring considerable expense and the deployment of a large number of troops. On the other hand her brother Phelim was in a vulnerable position, a column of troops under one of the Carews having already been despatched south from Dublin. In the event the plan almost worked. Phelim found Red Hugh before the other pursuers and waited for Feagh McHugh to arrive with his men. Nature, however, intervened. According to O'Sullivan Beare, very heavy rain began to fall and the Avonmore became deeply flooded, preventing Feagh's troop from fording the river. In this connection it has to be realised that rivers in Ireland in the sixteenth century were much wider and deeper than today; sources even refer to travellers needing boats to ford the Vartry between Ashford and Rathnew. In the end, Feagh having failed to arrive, Phelim O'Toole felt he had no option but to return Red Hugh to Dublin where, O'Clery states, "the Council were delighted there at”.

At this point it is perhaps appropriate to deal with a matter of confusion which has arisen about the first escape of Red Hugh. This is the question of the two Phelim O'Tooles. In 1591 there were two prominent persons of that name in Wicklow. One was Phelim O'Toole of Castlekevin, the brother of Rose O'Toole whom we have just discussed. The other was Phelim O'Toole of Powerscourt, who married Feagh McHugh's sister Isabella in 1578. Although the most prominent O'Tooles of their time, neither Phelim of Castlekevin nor Phelim of Powerscourt were chieftains of their branches of the O'Tooles. As already noted, Phelim of Castlekevin was administering Fir Tire during the minority of his nephew. Similarly Phelim of Powerscourt ruled Fir Cualann although his nephew Art was the legal heir. References to these latter two occur prominently in the English State Papers, mainly arising out of the dispute between Phelim of Powerscourt and his nephew Art over control of the lordship. On one occasion Art even offered to fight Phelim, with one hand tied behind his back, for control over the lordship, although Art states that Phelim declined to accept the challenge. Although Phelim O'Toole of Castlekevin is mentioned in the Irish sources and records such as the fiants, his complete absence from the more accessible English records has misled many historians, most notably John O'Donovan who went to great lengths to prove that Red Hugh fled to Powerscourt and not to Castlekevin.

While Red Hugh suffered under tighter security than applied to most of the other prisoners during his first period in Dublin castle, on being returned there his treatment was even harsher. The Gaelic Irish sources state that when he was secured in the Bermingharn tower, iron chains were put on him. The English sources confirm this, adding further that the chief jailer checked the chains twice every twenty-four hours?' O'Clery states that after the capture of Red Hugh "There came a great gloom over the Irish, and certainly the failure of the escape was a set-back for the plans of Hugh O'Neill. It is now that suits under O'Neill's name for the release of Red Hugh occur in the English State Papers?' It appears that also at this time O'Neill began to bribe English officials in an attempt to secure the second escape of Red Hugh. As O'Clery put it, "Aodh O'Neill had many friends too among the English themselves, for he gave them large presents and stipends of gold and silver for supporting him and speaking on his behalf in the Council." For a Gaelic Irish leader, Hugh O'Neill was very well connected at court and in the English Pale and it seems that his efforts at bribery soon began to bear fruit. Queen Elizabeth was later to write that "O'Donnell escaped by practice of money bestowed on somebody". It is unclear if Feagh McHugh played any role in this, other than being told to be prepared should Red Hugh escape to Wicklow again.

Almost a year after the first escape, on the night of 'Christmas of the Star', that is the twelfth day-January 6th, Red Hugh O'Donnell escaped from Dublin castle for the second time. Some confusion has arisen about this date but it is clearly stated in O'Clery's account. The second escape was much better planned than the first. According to Philip O'Sullivan Beare, Red Hugh planned his escape with Henry and Art O'Neill, two sons of Shane O'Neill, who were imprisoned with him. Red Hugh had also help from a friend on the outside, a certain Edward Eustace who was trusted by Feagh McHugh as well. Eustace secretly visited Red Hugh disguised as a horseboy. According to O'Sullivan Beare, Feagh had promised "a guide who would conduct him to his house in Glenmalure and that he would send him thence safely into Ulster". Eustace also promised to have four horses waiting for Red Hugh when he escaped. A file and I a very long silk rope' were smuggled in to Red Hugh on this occasion and Red Hugh and his companions were much better prepared for the rough terrain, having thick, padded shoes bound by thongs which stretched up their legs.

Red Hugh's two fellow escapees on this occasion were a strange choice as they were the sons of Shane O'Neill - no friend of the O'Donnells. Shane O'Neill had captured Red Hugh's uncle who had been lord of Tir Chonaill, and confined him for years on a crannog prison in Tir Eoghain. Shane then terrorised Donegal for eight years until Red Hugh's father finally defeated him, leaving O'Neill to flee to the MacDonnells of Antrim who promptly assassinated him. Shane's sons had been dispersed all over Ulster as prisoners and refugees, where Hugh O'Neill, Red Hugh's ally, hunted them down and had them either imprisoned or killed. Art and Henry had ended up in Dublin castle, but the most successful of Shane's sons, Hugh Geimhleach, managed to escape to Scotland. Quite an able individual, he returned to Ulster in 1589 with nine Scottish galleys fully manned with mercenaries. However, he was hunted down by Hugh O'Neill who executed him in the same year, saying that Hugh Geimhleach would have done the same to him given half a chance. It would seem probable that Red Hugh was confined in the same cell as the two O'Neills and was obliged to take them with him when escaping.

As in 1591, Red Hugh used his own judgement and waited for the right opportunity. According to the English State Papers, in early January 1592 the chief jailer, John Maplesden, was lying on his death bed. He had been ill for six months and died two days after Red Hugh's second escape. Because of Maplesden's illness, his chief assistant became lax in the performance of his duties and neglected to guard Red Hugh as closely as he should have done. It is here that the hand of Hugh O'Neill may have been involved. O'Neill may have engineered the situation to maintain Maplesden in his position though unable to perform his duties - effectively tantamount to not having a chief jailer at all.

The escape bid began when Red Hugh cut the fastenings of his own and his two companions' chains with the smuggled file. However, almost immediately his plans began to go awry. The three used the silk rope to slide down a privy and into the moat surrounding the castle. However, after carefully sliding down the rope first Henry O'Neill disappeared into the night, and made his own way to Ulster. He did not even wait for his brother. O'Clery states that Henry was the eldest of the party, Red Hugh then being about nineteen. O'Clery also commented that Red Hugh was very angry that Henry had deserted them. In all probability, Henry did not trust Feagh McHugh on account of his being an ally of Hugh O'Neill. However, from what we know of the admirable character of Red Hugh it is likely that he would have done everything possible to protect his friends had they remained loyal and helped him.

Red Hugh was the second to slide down the rope and was followed by Art O'Neill. Art, however, dislodged a stone which struck him heavily and he fell badly injured into the moat. This was an unfortunate occurrence as the fugitives' heavy clothes were left tied in bundles inside the castle and there was no way now of retrieving them. Red Hugh rescued Art and after swimming to the opposite bank met their trusted guide Edward Eustace. According to O'Sullivan Beare, Red Hugh also met with a guide sent by Feagh McHugh. However, that writer appears to have misidentified Eustace as the number of fugitives only added up to three, not four. Eustace's plans had also gone awry. Unknown to him, a friend had taken the four horses he had hidden for three days. He had, however, kept the escape plans a secret and agreed to guide Red Hugh to Glenmalure on foot.

Although the route of the second escape is also unknown, it is probable that it was much further west than the previous escape, taking Red Hugh again up Gleann na Smol, but then west of the Avonmore, between Duff mountain and Tonelagee. This is made more likely by the fact that as a Eustace, Edward would have been more familiar with west Wicklow than more eastern areas. In fact his family could have been connected with Ballyeustace near Greenan. At first the three fugitives walked towards the gates of the city, mingling with the people of Dublin. O'Clery states that no one paid any attention to them and that they managed to get outside the city gates before they were closed. They then had to scale the actual Pale palisade itself, described as a "thick rampart ... [a] strong, huge palisade which was outside the city, until they came to the slopes of Sliabh Rua". It was now that Red Hugh needed to show his strength of character. The prisoners were soaked to the skin after swimming the castle moat but had left their heavy clothes inside the castle. It was now the depths of winter and they were in the Wicklow mountains with little to protect themselves against the harsh weather. Art O'Neill, in addition to having being injured by the dislodged stone in the castle privy, had grown fat in prison and was very unfit. O'Clery commented that "his gait was feeble and slow, for he was corpulent, thick-thighed, and he had been a long time closely confined in the prison."" As a result he became weak. However, rather than abandoning him, Red Hugh put Art between himself and Edward Eustace and together the two of them carried Art through the snow of the Wicklow mountains.

Eventually, after many miles through woods and rough terrain, Red Hugh and Eustace could carry O'Neill no further. By now the three fugitives were on the north-western slopes of Table Mountain, in a wood to the south of Granabeg. O'Clery states that they were "under the shelter of a lofty cliff in the high moorland". In desperation, Red Hugh sent Eustace down into Glenmalure to get help from Feagh McHugh. Feagh was then in Ballinacor, sheltering from the dreadful night when Eustace managed to reach him. He was told by Eustace "that they would not be overtaken alive if he did not go their assistance immediately". According to O'Clery, Feagh immediately sent a party of trusted people back up to Table Mountain with Eustace, bearing food, ale and beer for the fugitives. O'Sullivan Beare differs somewhat with this, stating that "Feagh left no stone unturned to supply them with food, but was long prevented by those who observed his smallest act and movement as that of a suspected man. At last on the third night he sent food by four soldiers." (Again, O'Clery's account has the appearance of being the more accurate.) All Irish sources agree that at this stage Feagh's only interest was in rescuing the escaped prisoners, and that this included Art O'Neill - even if Feagh had been aware of the implications of Art being one of Shane O'Neill's sons.

When Feagh McHugh's rescue party reached Red Hugh and Art O'Neill, according to the Annals they found that "Alas! Unhappy and miserable was their condition... Their bodies were covered over with white-bordered shrouds of hailstones freezing around them on every side, and their light clothes and fine threaded shirts too adhered to their skin; and their large shoes and leather tongs on their shins and feet; so that covered as they were with snow, it did not appear to the men who had arrived that they were human beings at all, for they found no life in their members, but just as if they were dead. The Annals go on to state that "They were raised by them from their bed, and they requested of them to take some of the meat and drink; but this they were not able to avail themselves of, for every drink they took they rejected again on the instant; so that Art at length died, and was buried in that place. As to Hugh, after some time he retained the beer; and, after drinking it, his energies were restored, except the use of his two feet, for they were dead members, without feeling, swollen and blistered by the frost and snow. The men carried him to the valley which we have mentioned, and he was placed in a sequestered house, in a solitary part of a dense wood, where he remained under care until a messenger came privately from his brother-in-law, the Earl O'Neill, to inquire after him". O'Sullivan Beare states that Red Hugh ate some leaves on the third day of his wait and that this saved him, Art refusing to take any. There was some speculation in Highland Scottish circles supporting the sons of Shane O'Neill against Hugh O'Neill and Red Hugh O'Donnell that Feagh McHugh's men murdered Art O'Neill that night on Table Mountain. However, the sole reference to this is a letter from Art's cousin, Lachlan MacLean, in the Scottish State Papers where he states that his kinsman was killed. Both Irish accounts, however, clearly state that Feagh did everything in his power to save the two fugitives. There is no hint in the English sources either of any foul deeds; one would not expect any omission here had there been the slightest whiff of suspicion. In one letter the Lord Deputy, William Fitzwilliam, noted that "The younger of Shane O'Neill's sons, Art Oge O'Neill, for aught that 1 can learn is dead."" O'Sullivan Beare states that Red Hugh was so upset at Art's decline that at first he too refused to eat or drink. It is unlikely therefore that he would have permitted Feagh's men to kill Art, although O'Sullivan does say that Art was removed from Red Hugh's sight.

The precise location of Art's death was unknown to historians until 1929 when a writer for the Irish Independent visited Granabeg under Table Mountain. He wrote "We met and spoke to an inhabitant of a place called Granabeg near Ballyknockan. We elicited during the conversation that there is oral tradition in the neighbourhood that Art O'Neill is buried on the mountain south of the road between that place and Glenmalure. One can see on the side of the mountain above, a hollow like a large hole surrounded by a lofty cliff. That hollow is called 'Art's Grave'. There is a path going past it and in summer, even to this day, the sheep are driven along that path to Glenmalure. Liam Price agreed with this discovery, noting that the place traditionally called Art's Grave was ', situated to the south-east of Granabeg, towards Glenmalure, in the townland of Oakwood, near the boundary between it and Knocknadroose". Today a cross marks the general spot. It is unlikely that Art's Lough, much further to the south-east, has any association with Art O'Neill.

During the course of his stay in the 'sequestered' cabin in Glenmalure, Red Hugh was treated for frostbite by Feagh's doctors. Because his toes had been so badly affected Red Hugh was unable to walk and had to be lifted on and off horseback. Eventually he had to have his two big toes amputated to the "second joint", as he later wrote himself. While recuperating in Glenmalure, Red Hugh received many gifts, including fine horses, from Feagh. The government's reluctance to attack Feagh there ensured Red Hugh's safety from re-capture. Instead of dispatching a force directly against Feagh they placed guards on all the shallow fords of the Liffey as well as along the border with O'Neill's lands in Tyrone. Red Hugh remained in Glenmalure under Feagh's protection until Turlough Buidhe O'Hagan, one of Hugh O'Neill's most trusted men, arrived to guide Red Hugh back to Ulster. In one final gesture Feagh sent a troop of horse to guard Red Hugh until he had crossed a difficult ford on the Liffey close to Dublin. Phelim O'Toole accompanied Red Hugh on this journey, making his peace with O'Donnell and they both pledged friendship and amity with each other.

After a dangerous journey Red Hugh succeeded in returning to Tir Chonaill where he quickly expelled the English sheriff, was elected O'Donnell, and succeeded in uniting his lordship which had been split for almost three decades. He then helped Hugh O'Neill to overthrow Turlough Luineach O'Neill, and with O'Neill and Hugh Maguire began to form the confederacy which fought the Nine Years war and almost succeeded in securing independence for many of the Gaelic Irish areas of Ireland. In all of this Feagh McHugh played a crucial role. Without his help in 1592 Red Hugh would have frozen to death on the slopes of Table Mountain. At some risk to his own position, Feagh sheltered Red Hugh and then succeeded in spiriting him away to Ulster. Feagh's motivation in all of this is an interesting question. His links with Hugh O'Neill are of great importance. By the leadership he displayed in resisting English advancement in Leinster, and his family's attachment to and indeed investment in Gaelic-Irish culture, evidenced by their patronage of the Leabhar Branach and the Mac Eochaidh family of poets, Feagh demonstrated a sense of identity which could be termed 'nationalism'. The roles of his wife Rose and her brother, Phelim O'Toole of Castlekevin, in the escape of 1591 are also of considerable importance. It is clear that they desired to help Red Hugh and wanted his escape to succeed. However, they were caught in an exposed position and had to make what they thought of as the right decision at the time. In this, if Feagh McHugh had managed to ford the Avonmore, Red Hugh's first escape attempt might have been a success. His imprisonment with Brian and Redmond McFeagh is also interesting, and it is this link which may have provided the inspiration for Red Hugh's eventual escape to Glenmalure.