Hugh Dubh O Neill, The Irish Man Who Beat Oliver Cromwell Three Times

Over 400 years ago Oliver Cromwell and his New Model Army invaded Ireland and butchered their way across the countryside leaving hundreds of thousands of Irish men,women, and children, killed, wounded and destitute. You would be forgiven for believing that the Irish put up a feeble resistance against the might of Cromwells marauding forces, led like lambs to the slaughter against the all conquering English Army, but you would be wrong. In the resistance that stood against Cromwells barbaric savagery one man stood out, a colossus by the name of Hugh Dubh O Neill.
O Neill not only defeated Cromwell at the siege of Clonmel he humiliated him. Here was England’s supposedly unbeatable military genius having rings run around him not only on the battlefield but off it too.Cromwell had rode into Clonmel expecting an encore to what he would have deemed a successful campaign in Ireland but what he hadn’t bargained for was that the town was going to be defended by a group of battle hard-ended Ulstermen led by the wily, intelligent, and fox like Hugh Dubh.
When the dust had settled O Neill killed almost 3,000 of Cromwell’s finest Soldiers, roughly 25% of the New Model Army! To put this in context, up until that point the most casualties the self proclaimed Lord Protector of England had suffered was 400 killed during the early stages of the English Civil War. It was a monumental reversal for a man who up until that point was deemed virtually invincible. But O Neill wasn’t finished yet as he then went on to further humiliate Cromwell by performing a virtual Houdini by evading capture and then vanishing into the Tipperary air like a ghost in the night.  
But on the day and weeks leading up to the battle victory looked anything but assured for Hugh Dubh O Neill. In fact, to the casual observer it looked like O Neill was facing certain defeat. Outnumbered by nearly 8 to 1 and with his food and supplies dwindling to extinction things looked bleak for the Spanish born Irishman. Coming up against an opponent with more men, more arms, more ammunition, more food, and more money. In many ways O Neill was the quintessential no hoper, but in spite of the odds being stacked against him Hubh Dubh was in no mood to give up and remained determined to level Cromwell with a bloody nose that he wouldn’t be forgetting any time soon.  
On the other hand, Oliver Cromwells The New Model Army would have rode onto the outskirts of Clonmel with all the assuredness and confidence that only a string of victories could bring. Fresh from the military triumph of Kilkenny Cromwell’s soldiers would have been cocksure of certain victory.  The easy capture of Clonmel would have been seen as virtual a formality. The cherry on top of the cake of Cromwell’s successful subjugation of Ireland.
Cromwell’s plan was simple, if Hugh Dubh didn’t surrender and bow down before him then he would bombard the town with artillery and then he would breach the walls and then deliver whatever justice he deemed fit. But what Cromwell hadn’t bargained for was that he coming up against a formidable military strategist who had the wherewithal to outwit the best of opponents.
At this stage The Lord Protector would have had scant information in relation to Hugh Dubh and he certainly wouldn’t have viewed him as being any kind of meaningful threat but time would soon change Cromwell’s mind.  
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So on the 27th of April 1650 Oliver Cromwell and 9,000 troops from his seemingly invincible New Model Army arrived outside the walls of Clonmel. His forces buoyant after having enjoyed a long run of success.
A partial blockade had been in place outside of Clonmel since the Winter Offensive, and this blockade had the effect of weakening the supplies that where inside the town. From Hugh Dubhs perspective, further setbacks came in the shape of the plague that had the effect of leaving many defenders and civilians dead or seriously ill. O Neill received some reinforcements from random groups of solders who had fled in the wake of Cromwells massacres in Drogheda and Wexford.  
O Neill’s troops where bolstered by soldiers from Cashel and Kilkenny who had fled after Cromwell captured both towns. These reinforcements would have increased the men under his command to around 1,500 but more does not always mean quality as Hugh Dubh was to soon find out.
One of these new soldiers, Colonel Edmund Fennell, had agreed for a sum of money and a full pardon for taking up arms against the Parliamentarians, to open the gates at midnight on the North side of Clonmel and let 500 of the besieging force to gain entry. But O Neill was as untrusting as he was cunning, and when he inspected Fennels guard on the North Gate his intuition told him that treachery was afloat.
O Neill trusted his instincts and took instant action by ordering that Fennels troops be relieved from the gate and replaced with a reliable guard of Ulster Troops. At the appointed time of midnight the North Gate was opened, but instead of the receiving safe passage into the confinements of the city the New Model Army was instead met with a ferocious volley of fire from the Ulstermen, a volley that killed up to 500 of Cromwells soldiers. Hugh Dubh O Neill had dramatically drawn first blood.  
Not to be deterred by the early setback, Cromwell put his men to work by ensuring that his standard guns where safely in place. But the English Commander was a dealt a blow when he realised that these guns wouldn’t have the power to make the breach in the walls that he needed. This fact became apparent after he bombarded the northern side of the walls with his field guns but the cannon balls had a limited impact and failed to make any serious headway. In spite of this, when any kind of gap was made in the wall, The Lord Protector ordered his men to attack but these advances where soon repulsed by O Neills Pikemen and Muskets.
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Strapped for time and with one eye on going back to England Cromwell was in no mood to try and starve Clonmel into submission so he decided in putting his heavier siege guns in place.  But this was going to prove no easy task as most of the guns weighed some 6,000 pounds and they would also have to be hauled overland using hundreds of Oxen.  
Inside the garrison Hugh Dubh worked on keeping the morale of men high. O Neill would have realised that his badly outnumbered and out-gunned forces stood little chance against the marauding New Model Army but in spite of the seemingly impossible odds O Neill was in no mood to capitulate.  
Outnumbered, out-gunned, out-manned, and out fed O Neill set to work in defending Clonmel against the inevitable onslaught. He busied himself by organizing raids against the besiegers. Determined to use every last inch to his advantage O Neill launched his attacks under cover of darkness, harrying and disrupting the enemy force.
The ambushes and guerilla tactics would have had the effect of delaying Cromwell’s preparations for battle, and more importantly, would have begun to chip away at the seemingly Invincible Cromwellian morale, sowing seeds of doubt where previously none existed.  And on one occasion, Irish forces launched a surprise attack through a weakened section of defences and killed nearly 40 English Soldiers before retreating back into the relative safety of Clonmel.
Eventually Cromwell got his heavy guns in place and strategically placed them two hundred yards away form the North Gate of the town. This area was chosen for a number of reasons, but chiefly because behind the walls lay the widest street in the town and this would allow the Parliamentary forces to storm inside any breach and hopefully, from Cromwell’s perspective, quickly capture the town. But Hugh Dubh was no mans fool and would have realised that this was going to be the most likely place for any assault to take place and so he set about preparing for the attack.
One eyes witness described how O Neill, ‘set all men and maids to work, townsmen and soldiers….to draw dunghills, mortar, stones, and timber, and made a long lane a mans height and about eighty yards length, on both sides up from the breach, with a foot bank at the back of it; and caused (to be) place(d) engines on both sides of the same, and two guns at the end of it invisible opposite to the breach, and so ordered all things against a storm.’
In spite of Hugh Dubh’s best preparations hell was about to be unleashed on Clonmel. So on the 16th of May 1650 Cromwell ordered his heavy siege guns to open fire. The sheer destructive power of the guns must have been a sight to witness and after only one day of intense firing a breach had been secured through the walls that stood in the way.  With the defences of Clonmel seemingly crumbling Cromwell immediately prepared to launch an assault upon the town the very next morning.
 His plan was simple, to pour masses of infantry into the breach and to push back the defenders inside. Once his soldiers had secured entry they would then open the gates and this would allow Cromwell’s Calvary, led by Cromwell himself, entry into the town where they would enjoy a triumphant coup de grace to their successful campaign in Ireland. Seeing the breach in the walls many of the soldiers of the New Model Army must have already been tasting victory. Their thoughts probably flitting back to their families and enjoying food and drink as they regaled tales of their ‘heroism’ against the barbarous Irish. At this stage, for all intensive purposes the conquest of Clonmel was simply a process of dotting the I’s and crossing the T’s.
The cunning O Neill like a master chess player had anticipated where a breach was going to be blown and once the hole was blown he used all the experience he had gathered fighting in the fields of Flanders and further a field to deadly use. He quickly set his men to building another fortification behind the breach but this was no ordinary fortification it was one built into the shape of a V with the tip of the V pointing directly at the Parliamentarian Army.
 The fortification was made of earth and was lined at the top with wood and more importantly it was lined with masses of muskets. At the very tip there were two cannon pointing out which where loaded to the brim with chain shot. At this stage what Cromwell and the New Model Army didn’t know was that O Neill had created the perfect killing ground. The wily battle hardened veteran was slowly luring Oliver Cromwell into a trap.
The next morning when dawn broke the New Model army advanced towards the hole in the wall and nearly straight away masses of men became trapped in between the breach in the wall and the newly built fortifications. Hugh Dubh ordered his men to open fire and rained down musket and cannon fire upon the helpless Cromwellian soldiers. The red hot chain shot cut threw the Cromwell’s Troops like a knife through butter. But Hugh Dubh wasn’t finished yet as he then proceeded to rain down large logs hanging from some kind of booby trap device which inflicted further casualties on the parliamentarians.
After a long and bloody slaughter some remnants of the bloodied, battered, and brusied New Model Army where able to retreat and limp back to relative safety. Hundreds of their comrades lay dead and dieing on the ground many of them moaning from the agony of their wounds.Cromwell had been waiting in anticipation for the North Gate to open but when he saw the bloodied stragglers coming back from the breach in the walls he realised that things had gone disastrously wrong.  
Soldiers who only a few hours previously would have been cocksure of victory now refused to follow Cromwell’s orders and launch another attack on the city. For the first time in Cromwell’s long military career he was staring defeat in the face.   
Only a few hours previously he was contemplating a triumphant entry into Clonmel now he had to deal with the first serious setback of his military career. But the Lord Protector of England wasn’t about to give up just yet. He tried to rise the spirits of his troops and cajole them into launching another attack but his men, having witnessed the horror that was rained down upon their comrades only a few minutes previously refused.
Instead it was decided that the best option was to get his cavalry to dismount from their horses and launch a second assault upon the fortifications. It was hoped by Cromwell and his advisers that the better quality armour and the fresher and stronger cavalry would make the crucial difference.
At about 3pm Colonel Sankey and Colonel Culme led a column of dismounted cavalry right back into the inferno. Initially the cavalrymen forced the defenders at the outside perimeter back into the breach but they soon encountered the same problem as their predecessors with masses of musket and chain shot raining down on top of them.
 A fierce battle ensued with each side vying for control. O Neill’s troops fought with ferocity and used every kind of conceivable weapon they could get their hands on, including pitchforks and other makeshift weapons. Colonel Culme and many of the other senior officers where cut down in the early exchanges.  The vicious battle continued for nearly three hours with the roar of cannon, musket shot, and the crys of the dieing filling the Tipperary air. Eventually as the casualty rate increased the attackers where once more forced to retreat.
Cromwell refusing to give up hope and ordered his men to stay in the breach to try and prevent O Neills men from repairing the damage but his exhausted soldiers once more refused to follow his orders. This must have been particularly frustrating for a Commander who was used to getting his own way and instilling iron discipline upon his men. An eye witness described the events, ‘Neither the threats of the General nor the bloody swords of inferior officers was sufficient enough to keep them from turning tail to the assault.’ Another observer described the heroism of O Neill’s Soldiers,“There never was seen so hot a storm of so long continuance and so gallantly defended, neither in England or Ireland.”
But at the greatest moment of his career Hugh Dubh O Neill had to face reality. Out of arms and ammunition he had shot his bolt. He had to retreat, otherwise it was only a matter of time before his virtually unarmed and helpless soldiers would have faced certain annihilation at the hands of the vengeful New Model Army. But the Irishman wasn’t finished with Oliver Cromwell yet, because like a Scorpio he had one last sting in the tail awaiting England’s Lord Protector.
O Neill approached the Mayor of the Town Mayor White and told him that he planned to escape and that he should approach Cromwell and ask him for generous terms of surrender but not to ask for these terms until his army had escaped. Under cover of darkness Hugh Dubh led the remnants of his army and the camp followers across the River Suir and away to safety.
Once White was sure that Hugh Dubh and his army had escaped he sent a message to Cromwell asking for terms of surrender. Oliver couldn’t believe his luck and readily offered generous terms in an attempt to end the bloody debacle.  Believing that he was on the verge of capturing the finest Irish Army in the field the English Commander would have been been salivating at the thoughts of turning a sorry defeat into victory.
When both Cromwell and White had signed the articles of surrender Cromwell asked White how O Neill had reacted to the surrender and when he informed him that he didn’t know as O Neill and his army had left the night before, Cromwell was apoplectic with rage. ‘You knave have you served me so, and did not tell me so before.’ The Lord Mayor replied,“If his excellency had of asked me then I should you have told him.”
He asked the Mayor who was this Dubh O Neill and when the Mayor responded that he was an overseas soldier born in Spain, Cromwell snarled, “God damn you and your oversea. By god I will follow this Hugh Dubh wherever he goes.” Cromwell immediately ordered his Cavalry to pursue O Neill. But O Neill having stolen a march on Cromwell managed to safely secure the safety of the majority of his soldiers.
For obvious reasons, Cromwell would have been very reluctant to discuss the actual attrition rate at Clonmel least it damage his stellar reputation amongst his supporters in England and elsewhere.
The number of actual dead has been disputed with some people reckoning on the lower end of the scale that Cromwell lost around 1,500 men, and with other figures suggesting nearly 3,000 having perished.
Whatever the truth of the matter, one thing is for sure, the defeat at Clonmel was an astonishing reversal for Cromwell. Losing in a single engagement more men than he had lost since the New Model Army took to the field ten years previous. Previous to Clonmel the highest rate of casualties that Cromwell had suffered was when 400 killed at the Battle of Naseby.
An eyewitness said that Cromwell was ‘as much vexed as ever he was since he put on a helmet against the King, for such a repulse he did not usually meet with.’
Another observer at the time paid glowing tribute to Hugh Dubh O Neill and his men, ‘The stoutest enemy that ever was found by our army in Ireland, and it is in my opinion, and very many more, that there was never so hot a storm of so long a continuance, and so gallantly defended, neither in England nor in Ireland.’