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The Battle of Deputy’s Pass

The Battle of Deputy’s Pass is fought in County Wicklow on May 29, 1599, during the Nine Years’ War in Ireland. A Gaelic Irish force under Felim McFiach O’Byrne ambushes an English army of about 500, under Sir Henry Harington, which is marching from Rathdrum to Wicklow. The English army is routed and loses about 250 men.

The O’Byrnes had been allied to Hugh O’Neill, Earl of Tyrone, since the outbreak of the Nine Years’ War in 1593. Fiach McHugh O’Byrne had worked together with O’Neill, so much that he is described as the earl’s “right arm in Leinster.” However, when Fiach is killed in 1597, the power of the O’Byrnes seems to wane. When Robert Devereux, 2nd Earl of Essex, is appointed Lord Lieutenant of Ireland in 1599, he orders Harrington into County Wicklow to deal with the O’Byrnes and their allies, the O’Tooles.

Harrington’s force consists of five foot companies, but four of them are inexperienced levies recently raised in England. The only experienced foot company is that of Captain Loftus, whose men are mostly Irish. The companies are organised into a regiment under the command of Sir Alexander Radcliffe. To this is added fifty horsemen commanded by Captain Charles Montague. Harrington wants to take his troops out to scout the Irish fortifications on the ford of the Avonmore River at Rathdrum, and possibly to give his raw troops some experience in fieldcraft. His first attempt to view the Irish position on May 28 fails. Harrington returns to his camp about a mile from the ford. A second effort to view the Irish fortifications is made on May 28, but this is turned back due to poor weather. Harrington orders the men to march back to Wicklow town.

The English army stretches out in a column. In the lead is the van, then the baggage, followed by the battle and then the rear. Captain Atherton, the Sergeant Major of the army, has little doubt that the weight of any Irish attack will fall on the rear of the column. Thus, the horse (cavalry) is placed at the rear. The army has marched little over a mile before the Irish shot (musketeers and caliver-men) begin skirmishing with the rear of Harrington’s force. The Irish try to take a ford to block the advance, but the English secure the crossing, with the shot of the English rear skirmishing with the Irish, allowing the rest of the army to pass unhindered.

The march continues two miles to another ford, with the rear continuing to hold O’Byrne’s Irish shot at bay. Again, the English shot secures the crossing, as Irish fire slackens, possibly due to a shortage of gunpowder. Harrington places 40–50 shot behind an earthen bank on the left flank of the column on the far side of the ford. The Irish bring up a stand of pikemen, but their attack is limited to the English left, as the right of the column is shielded by thick gorse bushes. Atherton gathers 60–80 men to counter-attack the Irish pike. The English shot behind the bank is to hold their fire until Atherton attacks, but instead prematurely fires a single volley at the Irish pike then abandons their position. Without the support from their shot, Atherton’s men refuse to charge the Irish, then withdraw to the main body of the English column.

Atherton finds that the English shot have fled the column, abandoning the main stand of English pike. Now exposed to Irish gunfire, the English pike become disordered as they press to make the river crossing. Exploiting the English confusion, the Irish pike charges into the English rear, killing many without resistance. Montague’s English cavalry charges to support the panicking infantry, but the Irish pike square opens, allowing the horse to pass through. The Irish pike spear the English horse as they pass, including Montague who is wounded by a pike thrust into his side. Despite their officer’s best efforts, the English soldiers’ resistance collapses. The rout continues with the Irish slaughtering Harrington’s men to within one and a half miles of Wicklow town. All the English companies lose their colours, except for Captain Loftus, but they are later recovered by the English horse. After the battle, Radcliffe estimates the English army has lost 250 men killed, missing or deserted.

The first English reports suggest that they lost the battle due to the inexperience of most of their troops. Harrington at first blames the English pikemen for refusing to fight, but at the court-martial in July, Harrington, supported by two of his officers (Captains Linley and Mallory) blames Captain Loftus and his Lieutenant Walsh. This is convenient, as Loftus had died from his wounds and could not refute their accusations. Their version is supported by a map drawn of the battle, possibly by Montague (Harrington’s nephew). Loftus and Walsh are found guilty by the court-martial. Loftus is already dead, but Walsh is executed by firing squad. Mallory and Linley are not found guilty, but they are cashiered, losing command of their foot companies. The men in Loftus’ company are sentenced to death but this is commuted to decimation by drawing lots. Even by Elizabethan standards this is deemed overly harsh. Though Harrington is not charged with misconduct, he is never given command of a force this size again.


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The Battle of Curlew Pass

The Battle of Curlew Pass is fought on August 15, 1599, during the campaign of the Earl of Essex in the Nine Years’ War, between an English force under Sir Conyers Clifford and a rebel Irish force led by Hugh Roe O’Donnell. The English are ambushed and routed while marching through a pass in the Curlew Mountains, near the town of Boyle, in northwestern Ireland. The English forces suffer heavy casualties. Losses by allied Irish forces are not recorded but are probably minimal.

In April 1599, Robert Devereux, 2nd Earl of Essex, lands in Ireland with over 17,000 troops and cavalry to put down the rebellion of Hugh O’Neill and Red Hugh O’Donnell, which has spread from Ulster to all Ireland. To this end, he supports an Irish enemy of O’Donnell’s, Sir Donogh O’Connor (O’Connor Sligo), encouraging him to repossess those territories of his in Sligo that O’Donnell has occupied. Sligo Town is an excellent advance base, with Ballyshannon 20 miles to the northeast commanding an important river-ford at the principal western passage into O’Donnell’s country in Ulster. English military advisers have long urged the government councils in Dublin and London to capture these strategic points. O’Connor’s brother-in-law, Tibbot ne Long Bourke, is appointed joint-commander with an English captain of a force sailing from Galway, and O’Connor is expected to receive them in Sligo. However, O’Donnell quickly besieges O’Connor at Collooney Castle with over 2,000 men in an effort to starve him out, and Essex is put on the back foot. Essex has no option but to support the besieged O’Connor, one of the few Gaelic chieftains the Crown can rely upon for support. He orders the experienced Sir Conyers Clifford, who is based in Athlone, to relieve the castle with 1,500 English infantry and 200 cavalry. It is hoped that the operation would also distract the chief rebel, O’Neill, and afford the crown an opportunity to march into his Ulster territory across its southeastern border.

O’Donnell leaves 300 men at Collooney Castle under his cousin, Niall Garbh O’Donnell, and sends another 600 to Sligo town to prevent the landing of English reinforcements under Tibbot ne Long Bourke. He then marches to Dunavaragh with 1,500 of his men, where he is joined by additional forces under local chieftains Conor MacDermott and Brian Óg na Samhthach Ó Ruairc. The Irish then carefully prepare an ambush site in the Curlew Mountains, along the English line of march. O’Donnell has trees felled and placed along the road to impede their progress. When he gets word of the English passing through Boyle, O’Donnell positions his men. Musketeers, archers and javelin men are placed in the woods alongside the road to harass the English. The main body of Irish infantry, armed with pikes and axes, are placed out of sight behind the ridge of the mountain.

In hot harvest weather, Clifford’s force marches from Athlone through Roscommon, Tulsk and Boyle. At 4:00 PM on August 15, they reach the foot of the Curlew Mountains, which have to be crossed before Sligo can be approached. The expedition is poorly supplied, and Clifford’s men are tired and hungry, and probably in no fit state to continue. But Clifford has received false intelligence that the pass is undefended, and he therefore chooses to seize the opportunity and march across, promising his troops plenty of beef in the evening. This means that his men miss out on the rest that had been planned for them in Boyle, whereas the Irish are well fed and prepared.

The English come under gunfire, arrow and javelin attack as soon as they reach the first of O’Donnell’s barricades, between Boyle and Ballinafad. The barricade is immediately abandoned by the Irish but as the English moved past and proceed up the hill they sustain further casualties. The road consists of “stones of six or seven foot broad, lying above ground, with plashes of bog between them,” and is lined with woodland on one side. The further the English advance, the more intensive the rebels’ fire becomes, and some English soldiers begin to lose their nerve and slip away. Eventually, there is a firefight, lasting about 90 minutes, at the end of which the English vanguard has run out of gunpowder. The commander of the vanguard, Alexander Radcliffe, can no longer control his troops. They wheel about in a panic and collide with the main column, which breaks and flees. The commander leads a charge with his remaining pikemen but is shot dead. With the English ranks in disarray, the main body of Irish infantry, which has concealed itself on the reverse slope of the hill, closes in and fights hand to hand. Clifford tries to regain control over his men, but appears overcome by his circumstances. He manages to rally himself and is killed by a pike-thrust as he rushes the enemy. The English are routed, but the situation is prevented from becoming a complete disaster for them when the commander of the horse, Sir Griffin Markham, charges uphill and temporarily drives the rebels back.

Though the actions of the English cavalry allows many of their foot soldiers to escape, Clifford’s men are pursued as far as the town of Boyle, where they find shelter in Boyle Abbey. About 500 English are killed in the battle. Irish losses are not recorded, but are probably small, having been firing from prepared positions and then routing a disorganised and demoralised enemy.

Clifford’s head is cut off and delivered to O’Donnell, who has remained nearby but without taking part in the fight. While the head is brought to Collooney Castle to intimidate its defenders, the trunk is carried by MacDermott to the monastery of Lough Key, where he hopes to use it to ransom his own prisoners. At last, the trunk is given a decent burial in the monastery.

O’Connor Sligo surrenders the castle shortly afterwards and reluctantly joins with the rebels. After the victory, there is a noticeable increase in the rate of desertion by Irish troops from the ranks of Essex’s army, and the earl orders that the surviving troops be divided up as fit only to hold walls.

The battle is a classic Gaelic Irish ambush, similar to the Battle of Glenmalure in 1580 or the Battle of the Yellow Ford in 1598. According to the Annals of the Four Masters, the victory is put down to the intercession of the Blessed Mary, rather than to arms. But Clifford had been overconfident, a trait in him that Essex once warned against, and it is clear that English military commanders are choosing to learn the hard way about the increased effectiveness of Irish rebel forces. Queen Elizabeth I‘s principal secretary, Sir Robert Cecil, rates this defeat (and the simultaneous defeat of Sir Henry Harrington in the Battle of Deputy’s Pass in County Wicklow) as the two heaviest blows ever suffered by the English in Ireland, and seeks to lay the blame indirectly on Essex. It leaves O’Donnell and O’Neill free from any threat from the Connacht side, and renders a land-based attack through Armagh highly improbable, a factor that weighs with Essex as he marches northward later in the year and enters a truce with O’Neill.

In August 1602, the Curlew Pass is the scene of the last victory won by the rebels during the war, when a panicking English force is again routed and suffers significant losses. This time the rebels are led by Rory O’Donnell who commands 400 musketeers.

Today the battlefield at Curlew Pass is overlooked by an impressionistic sculpture by Maurice Harron called “The Gaelic Chieftain”, unveiled in 1999.