The O’Byrne’s had been a consistent source of trouble for the English in Ireland.
Frequently raiding into the Pale and other English controlled or English friendly areas from their lands in Wicklow, the O’Byrne’s were a clan that had an almost inherent ability to irritate and threaten the English position. Their forts and castles in the Wicklow Mountains and forests made them almost impossible to root out without great loss, allowing them numerous safe havens from which to strike out at Dublin and the surrounding region before retreating back in the face of English strength. Ever since the Norman invasion, when the O’Byrne’s were first consolidating their hold over Wicklow, this had been the pattern, a cycle of raid, demands, pardons, and raids again.
The O’Byrne’s were one of many Gaelic clans and families in South Leinster willing to tow the line with the English when it suited them, “rebelling” when it didn’t. I use quote marks to illustrate that it wasn’t really “rebellion”, since the O’Byrne’s never had strong ties of allegiance to the English beyond empty formulas, easily broken when the time was deemed advantageous.
1580 was another one of those times. The leader of the O’Byrne’s then was Fiach McHugh. Now in his mid-forties, he had spent his whole life taking shots at the English and Dublin, leading raids, fermenting unhappiness, aiding rebels in neighbouring areas. Becoming head of his clan in 1579, he was determined to make a bigger statement against the English then he previously had.
The Tudors had not been entirely stand-offish in regards Wicklow. A low grade counter-insurgency campaign had been fought there, exemplified by small garrisons scattered throughout the area, with local commanders given a great deal of leeway in how they were allowed to go about their business. But ultimately these efforts were piecemeal and ineffective, and did little to curtail the threat of the O’Byrne’s.
But it was provocation all the same. The vicious actions of these English garrisons, not unlike those of the English campaigning in Desmond, were stirring up great resentment, and not just from the O’Byrne’s. Aside from that, Fiach would surely have seen enticing advantages in throwing his lot in with the Desmond rebels. Rumours were awash at the time that substantial reinforcements were coming from Spain and the Papal States, forces that would turn the tide decisively against the English. In such an endeavour, Fiach would be well placed to take advantage, being situated so close to the heartland of the Tudor administration. Fiach may have seen himself as a later day Art MacMurragh, the warlord who could dominate all of Leinster and drive the English before him.
But in order to do that, he would need more men then he had at his own personal command. The O’Byrne’s might have been good raiders, but they lacked the manpower to put full armies in the field. Help on that score came from James Eustace.
Eustace was the Viscount of Baltinglass, in the south-west of Wicklow. A member of the “Old English” community – the descendents of the original Norman settlers, those who had become “more Irish than the Irish themselves” – he was a staunch Catholic and was angered by the discrimination of the Protestant reformation and the marginalisation of his level of Irish society by the Tudors. The “New English”, the more recent settlers, were receiving better treatment and better positions in the Pale government than the “Old English”, who now identified themselves more strongly with their Gaelic neighbours than their cross-sea ruler.
For all those reasons, Eustace threw his lot in with Fiach when it came to rebellion, probably hoping, like James Fitzmaurice had for Desmond, that defeating the English in Ireland would be enough to see the discrimination rolled back and the return of more power to the Old English gentry. Eustace brought more men and material to Fiach’s side, overlooking previous disputes between the two. More Gaelic clans, like the Kavanagh’s and the O’Toole’s also joined this new army.
This unlikely coalition had chosen their time of rising very carefully, seeing in the Desmond rebellion an opportunity to strike a huge blow against the English. John of Desmond, his forces in a rather grave position with Munster, immediately rode to Laois when this rebellion began in order to meet with Fiach and perhaps co-ordinate their forces.
This was a truly fateful meeting, the scattered nature of Irish resistance to English rule being one of its key weaknesses. If a proper policy of combined operations could be worked out, perhaps with the Geraldines tying down substantial English manpower in Desmond while this Leinster coalition struck at the Pale with force, then serious things could be achieved, and all with the prospect of support from outside Ireland.
But, it was not to be. Aside from some joint raids and ambushes in Laois and the Barrow Valley region, there was limited cooperation between the Geraldine and Leinster rebels. Perhaps plans were simply too hard to work out, or chains of command could not be agreed. Either way, while the two rebellions helped each other indirectly (and indeed, the Leinster one could not have existed without the Desmond uprising), there was to be no great combined offensive against the English from Munster and Leinster. That being said, the fighting that took place in Leinster is still generally considered part of the Desmond rebellions.
In the summer of 1580, with the position of rebellion that Fiach and Eustace were engaging on very clear, the O’Byrne clan went on a campaign of burning and destruction in County Carlow. Such actions brought the attention of the Pale in a large way, terrified that they could face such a damaging rebellion so close to home. While Desmond was not exactly distant, the Geraldines were never in a position where they could have legitimately threatened Dublin. Fiach O’Byrne was.
This trouble coincided with the arrival of a new Lord Deputy in Ireland. Arthur Grey, the Baron Grey de Wilton, who was a veteran of the fighting in France a few decades before that had seen the last English presence in that country eliminated. Arriving that summer with fresh troops from England, Grey was determined to make an impact as soon as possible. With sufficient forces engaging the Geraldines in Desmond for the moment, his eye became fixed to the south.
Within a very short time of arriving in his new position, Grey was on the march with 3’000 of his men, along with additional forces supplied by Gerald, the Earl of Kildare, a figure who was nominally loyal to the English crown yet is frequently absent in accounts of actually fighting the rebels of the time.
Grey headed west into Kildare, and then turned east and south, marching straight into the heart of the Wicklow Mountains. All sources mention local commanders advising him against this course of action. While the weather in August was probably acceptable for campaigning, the terrain was not. Aside from the mountains, the area was covered in forest and bogs (and largely still is today) and Grey was inexperienced in the workings and tactical realties of Irish warfare. Like so many before him, he had a big army, but no real idea how to use it effectively against a Gaelic foe.
Perhaps Grey simply wanted to make as much of an impression as soon as he could. Perhaps he was arrogant and ill-judged the situation. Maybe he just got unlucky. Whatever it was, he was leading his army into a disaster. Fiach, on hearing of the approach of this large force, did the usual Irish thing and retreated. Large set-piece battles were not his style, and he must not have valued the chances of his own troops against the well-armed English. Fiach and Eustace had their fair share of guns and projectile weaponry (they probably had the service of some gallowglass looking to fight back against the English), but most of their army was still lightly armoured Irish “kern” fighters, likely to get slaughtered by English musketry in a straight up encounter. Instead, Fiach took the bulk of his force and settled in at one of his families main forts at Ballinacor in the Glenmalure Valley, around 20 km east of modern day Wicklow Town. Presumably he thought that Grey would simply exhaust himself out in the business of trying to catch Fiach in such difficult land, and would turn back to the Pale before too long.
This was not what Grey did. On the 25th of August, he arrived near Ballinacor, having forced his army through the Wicklow Mountains from the north. Looking down the Glenmalure Valley, he decided to send half of his army forward in battle array, seeking to flush his enemies out of their fort before riding them down with his cavalry contingent. This plan went into effect despite the disagreement of many other officers, but Grey was not to be dissuaded.
Fiach had been well-warned of the enemy approach, and had decided to take full advantage of the rare opportunity he had been presented with. The 1500 or so English were probably marching down what is now the Wicklow Way, not too far from Glendalough, with high, rocky, forested hills on either side of them.
When this advance force had gone far enough, Fiach sprang his trap. His men, behind the cover that the hills offered, opened up with a blistering fire from both sides, probably arrows as well as gunpowder weapons. The surprise was immense and the effect disastrous. The English fired back but the Irish were too well entrenched for it to be effective, too high up in the hills to be reached on foot. After a period of sniping where the English suffered horribly, discipline and morale began to snap. At this point, the kerns burst forward with their light arms and smashed into the disintegrating English lines. The rout was total. A huge proportion of the English in the valley, perhaps as many as 800, were killed in the disorganised retreat that followed, leaving behind much of their arms and other equipment. Fiach pursued them all the way out of the valley, before he was checked by the English cavalry.
A presumably stunned Grey was forced to turn around and take what was left of his army back to the Pale, feeling the brunt of continued guerrilla attack from Fiach’s men all the way. It was hard to put any kind of positive spin on what had happened: it was the worst English defeat in Ireland in years, generations even. In a fight against the Irish, one has to look back almost as far as the confrontations between Richard II and Art MacMurragh in 1399 for something comparable in terms of lost prestige or Dysert O’Dea in 1318 to find something comparable in terms of lost men.
But that being said, neither Fiach O’Byrne nor James Eustace were able to make much use of the victory. Their contribution to the rest of the Desmond Rebellion would be much more small-scale, the raids, ambushes and guerrilla war they were used to, though the English would prove very reluctant to head out south again. Fiach was even able to penetrate as far as the Dublin suburbs, but ultimately he had reached the highpoint of his revolt at Glenmalure. There would be no more large scale engagements in Leinster, though the victory at Glenmalure temporarily had must of the country in “a scene of strife and dissension” according to the Four Masters. Repression against the Old English skyrocketed in the aftermath, with this branch of Irish life now seen by the English as much an enemy as the Irish.
Glenmalure is a very rare example of a total victory by an Irish army against an English one. It was a result, almost entirely, of Grey’s incompetence and inexperience when it came to fighting in Irish terrain. Fiach may have been painted as some kind of marital genius in the aftermath, but it was not hard to defeat an English army that had blundered so spectacularly, marching straight into such an ambush-friendly environment.
In an interesting tidbit, though the battle certainly took place in Wicklow, it became the inspiration for the county song of Carlow, “Follow me up to Carlow”, apparently after some orders from Fiach during the fight.
Grey had little time to stay at home and lick his wounds. Within a month of his defeat, the long-awaited reinforcements from the Papacy arrived in Desmond. The rebellion was rapidly reaching its decisive point.
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