It was a shaken and demoralized English column that returned to its northern Irish base at Newry on the evening of May 28, 1595. On May 25, the 1,750-man force, under the command of Marshal Sir Henry Bagenal, had set out to resupply the besieged garrison at Monaghan castle some 20 miles to the west. Nominally, the Irish rebels investing the castle were led by Hugh Roe (or Red Hugh) O’Donnell, but rumor had it that they were actually being commanded by the Anglicized Irish lord on whom the English had counted to assist them against O’Donnell–Hugh O’Neill, the second Earl of Tyrone.

As early as February 16, O’Neill was reported to have aided the rebel followers of his bastard brother, Art MacBaron, in their successful storming of the English fort at the Blackwater River northwest of Newry. Bagenal’s suspicions about O’Neill were confirmed on May 25 when O’Neill rode up with a small troop of horsemen and began surveying the English camp at Ballymoyer, where Bagenal’s men were resting for the evening. Sir Edward York rode out of camp to parley with him, then returned to report that O’Neill had stated that by 10 the next morning, ‘it should be seen whether the Queen or they should be masters of the field and owners of Ulster.’

The English resumed their march toward Monaghan on the morning of May 26, but at Crossdall, just four miles from their destination, their vanguard came under attack by a large Irish force. Expecting the Irish to attack the rearmost division of his column, Bagenal had stayed at the back. Consequently, the officers in the vanguard did not know what to do until Captain Richard Cuney, commanding one of the two Staffordshire companies present, engaged the enemy with 150 musketeers and pikemen. In previous rebellions, such a show of force would have sufficed to scatter any Irish assault, but this time the 300 musket-armed Irishmen who lined up against the English were equally proficient in the use of their weapons. The Irish did not press their advantage, however, and Bagenal was able push on to Monaghan’s garrison, which he provided with supplies and a company of fresh troops.

When Bagenal’s force marched back to Newry on May 27, O’Neill ambushed it at Clontibret, near the border of Monaghan and Armagh counties. During the next seven or eight hours, the English were engaged in a running fight over 14 miles, but they ultimately managed to break out of the trap. Bagenal reported that the expedition had cost him a total of 43 men dead and 139 wounded, including Captain Cuney. Hugh O’Neill’s open defiance against the English at Clontibret escalated the rebellion in the province of Ulster into what the Irish would call the Nine Years’ War, a conflict that would engulf all of Ireland and affect its political and social structure to the present day.

Although England had long claimed Ireland for its own, actual control at the end of the 15th century was limited to the ‘Pale,’ an area not more than 20 miles in diameter around the city of Dublin in the eastern province of Leinster. For the English, only anarchy and barbarism lay beyond the Pale (thus the origin of the phrase). The majority of Ireland consisted of a patchwork of lordships ruled by a collection of Gaelic-Irish and Anglo-Irish dynasties, the latter being descendants of the original 12th-century Anglo-Norman invaders who had adopted Gaelic culture. Although they paid lip service to the government in Dublin and to the crown, the lords collected their own taxes, maintained their own courts of law and waged private wars with their own armies.

That state of affairs was not tolerated after 1485, when the Tudors ascended the English throne and sought unchallenged control over the British Isles. England’s adoption of Protestantism under King Henry VIII caused further alienation with the Gaelic-Irish and Anglo-Irish, who remained Catholic. The loss of England’s continental possessions after the Hundred Years’ War, combined with the discovery of America, shifted English attention westward, renewing interest in the acquisition of land in Ireland as well as the New World. English landlords made little distinction between native Irish and native Americans–both were regarded as’savages’ and a threat to be eliminated, either by being ‘civilized’ with English culture and Protestant religion, or by destruction. Both approaches were resisted by the Irish lords.

In Ulster, the Lord of Tyrone, Shane O’Neill, declared his open defiance of the English in 1561. In order to compete with the growing might of the government forces, Shane expanded the privilege of military service to include the peasantry, whom he equipped with firearms. It was not the English, however, but Hugh O’Donnell, a rival lord of neighboring Tyrconnell, who toppled Shane at the Battle of Farsetmore on May 8, 1567. Shane was subsequently killed on June 2 by the MacDonalds of Antrim, with whom he had hoped to find sanctuary, and his pickled head was delivered to the English viceroy, Sir Henry Sidney, in Dublin.

In Munster and the western province of Connacht, the Anglo-Irish Geraldine League declared their opposition to the government in 1569. Fighting continued until 1583, resulting in the devastation of most of southern Ireland. Hugh O’Neill served with the English army during those campaigns.

Born about 1545, Hugh Con O’Neill was the son of Matthew and grandson of Conn O’Neill. After his father was murdered by his uncle Shane O’Neill, Hugh was adopted by Giles Hovenden, an Englishman who farmed the property granted to Conn O’Neill’s sons at Balgriffen, near Dublin. Having been taught the English language and ‘civility’ by his foster parents, Hugh showed a preference for English dress and customs, and came to be regarded as a valuable ally by the officials in Dublin, who rewarded his loyalty by making him Earl of Tyrone. O’Neill, however, preferred the independence of an Irish lord to the limited power of an English puppet. In 1593, to the consternation of the English government in Dublin, Hugh accepted the traditional Gaelic title of The O’Neill from the people of Tyrone.

Sir Henry Bagenal was one of the earliest and most persistent doubters of O’Neill’s loyalty to the crown, so one can imagine his reaction upon learning that his sister, Mabel, had fallen for the Earl of Tyrone’s considerable charm. In August 1591, Mabel suddenly eloped with O’Neill, who had already had two wives–one he had divorced and the other had died. They were wed by Thomas Jones, Bishop of Meath, who later claimed to have performed the ceremony for the sake of the lady’s honor. One historian’s reference to Mabel as ‘the Helen of the Elizabethan wars’ may be excessive, but her brother made no secret of his distaste at being related through her marriage ‘with so traitorous a stock and kindred.’ By the time Mabel died in 1596, relations between Bagenal and O’Neill had developed into a full-fledged blood feud.

The two brothers-in-law had occasion to fight side by side on October 10, 1593, when their combined forces of 200 horse and 1,000 foot encountered 1,200 Irishmen, led by Hugh Maguire, holding a salient south of the Erne near Belleek. Using musketeers to cover their flanks, they mounted a well-coordinated assault across two fords and put Maguire to rout, with 300 Irish and only three Englishmen killed. Among the dozen English wounded was O’Neill, who took a spear in the thigh, but Bagenal tellingly omitted his brother-in-law’s contribution to victory in his report.

O’Neill’s loyalty was again put to the test when his son-in-law, Red Hugh O’Donnell, Lord of Tyrconnell, joined Maguire in the investment of Enniskillen castle in June 1594. Hugh O’Neill’s brother, Cormac MacBaron O’Neill, joined the rebels, along with 100 horsemen and 300 musketeers, but Hugh did not–most likely because he believed that O’Donnell was acting too soon. Nevertheless, on August 7, Maguire and Cormac O’Neill routed an English force that was marching to relieve Enniskillen’s garrison at the Arney Ford, which came to be known as the Ford of the Biscuits because of the English supplies that were scattered about after the fight.

The English ordered O’Neill to lead a punitive expedition against O’Donnell. He complied at a snail’s pace, while clandestinely continuing to build up his forces. As Queen Elizabeth I’s most loyal representative in Ulster, O’Neill had been granted the right to maintain 600 troops, trained by English officers in the most up-to-date military methods, including the use of the pike and matchlock firearms–lightweight calivers and heavier but more accurate muskets. By rotating trained men out of the group and raw recruits into it, O’Neill was able to train far more men than the 600 he had been allowed. With the soldiers organized into companies of 100 and armed with the latest weapons imported from Scotland or Spain–or smuggled from English ports–there was little to distinguish O’Neill’s troops from the English, aside from the bagpipes that accompanied them into battle.

By May 1595, O’Neill had recruited and trained some 1,000 cavalrymen, 1,000 pikemen and 4,000 musketeers, along with other troops armed with the more traditional weapons of sword, javelin, battle-ax and bow. At the Battle of Clontibret he finally declared his commitment to the Irish cause, and in June he was proclaimed a traitor. During the battle, O’Neill employed a strategy that he would soon use with greater success. By laying siege to English outposts beyond the Pale, he would compel the enemy to send relief columns to the isolated forts, and he could then am-bush those soldiers. Such guerrilla tactics were perfectly suited to 16th-century Ireland, a land that was still covered by thick forests and numerous bogs.

O’Neill’s strategy was based on lessons learned from previous Irish rebellions. There were essentially only three routes by land into Ulster–along the east coast through Moyry Pass (beyond which lay the English base at Newry), in the center at Enniskillen and along the west coast at the Ford of Ballyshannon. Mindful of the internecine divisions that had led to Shane O’Neill’s downfall, Hugh employed considerable dip-lomatic skill to form a strong coalition of Irish leaders in Ulster and beyond. O’Neill hoped that by exhausting England’s resolve he could gain a negotiated settlement that would leave his power in Ulster intact.

In the early summer of 1595, the O’Donnells captured Sligo, securing the southwest approach to Ulster. The English garrisoned the ruins of Armagh Cathedral, northwest of Newry. O’Neill tore down his castle at Dungannon, thereby eliminating it as a worthwhile objective for the English, and distributed its contents among Tyrone’s crannogs–small, fortified artificial islands. In June, the English lord deputy of Ireland, Sir William Russell, and Sir John Norris, the new commander in Ulster, led a large force to the Blackwater River but then thought better of trying to cross it. The English failed to subdue southwest Ulster and Connacht and had to accept the loss of Sligo.

Russell was only too glad when the Irish agreed to a truce in southeast Ulster, which lasted until the summer of 1597. During that time, however, the English were alarmed to learn that a priest named Piers O’Cullen of Clogher had sailed to Spain, bearing a letter dated September 19 and signed by O’Neill and O’Donnell. The letter beseeched the Spanish king to send 2,000 to 3,000 men, along with arms and money, to Ireland ‘to restore the faith of the [Catholic] Church and so secure you a kingdom.’ By seeking aid from England’s principal rival, the Irish coalition was raising the stakes of the war.

Russell led a lightning raid into Wicklow in the spring of 1597 and returned with the head of Feagh McHugh O’Byrne, a prominent rebel leader. In May, however, Russell was replaced as deputy by Thomas Lord Burgh, who proposed a somewhat grandiose plan in which his forces would converge with those of Sir Conyers Clifford, the governor of Connacht, deep inside Ulster at Lough Foyle. Marching swiftly from Newry, Burgh’s 3,500-man column reached the Blackwater and overran an earthwork on the north bank on July 14. O’Neill’s main forces blocked any further English advance, and Burgh settled on building a new Blackwater fort to replace one that O’Neill had destroyed in 1595.

Meanwhile, Clifford and about 1,200 troops had retaken Sligo, forced their way across the Erne River and reached Ashroe Abbey on July 30. Three miles away lay Ballyshannon Castle, but before Clifford could assault it, he learned on August 1 that Burgh, contrary to his original plan to meet Clifford at Lough Foyle, was retiring to Newry. Furthermore, Cormac O’Neill was leading 1,000 Irishmen to relieve O’Donnell while Hugh Maguire and Brian O’Rourke were crossing the Erne to cut off the English. Clifford prudently retired, but not without enduring a reprise of the running battle of Clontibret, in which his column moved eight miles in six hours, fighting all the way. The English gunpowder ran out, but Clifford’s pikemen managed to fend off attacks from both sides and reach Connacht on August 2. In a chivalrous salute to their opponents, the Irish dubbed the part of the Erne that Clifford’s men crossed Casan-na-gCuradh–the Ford of Heroes.

Burgh’s success had been strictly temporary, but he held high hopes that the resurrected Blackwater fort, with its 150-man garrison under the command of Welsh Captain Thomas Williams, would be the linchpin of ultimate victory. On October 2, O’Neill’s men assaulted the earthworks with scaling ladders, only to be repulsed by the defenders, whose arsenal included two robinets (light field guns) and two arquebuses-à-croc. Then on October 13 Burgh died of the ‘Irish ague’ (typhus), as had so many of England’s troops stationed in Ireland. O’Neill, who later admitted to Williams that he had lost 400 men in his attempts to storm the fort, made no further assaults but kept it under a close blockade. The garrison had to fight to obtain firewood or water from the surrounding area, and by November its supplies of beef and biscuit were running dangerously short.

After Burgh’s death, command of the English forces fell to Thomas Butler, Earl of Ormonde. Believing that time was on his side, O’Neill negotiated another truce, during which Ormonde expressed regret that ‘the scurvey fort at Blackwater’ had ever been built. Isolated and requiring an army for its maintenance, the outpost that the late Lord Burgh had conceived as ‘an eyesore in the heart of Tyrone’s country’ was proving to be only an expensive liability.

As the truce reached its end in June 1598, Queen Elizabeth’s Irish Council considered abandoning the fort but was concerned that the consequent loss of face would encourage O’Neill, who reportedly was preparing to threaten the Pale itself. On August 2, 1,400 reinforcements landed in Dublin, and Bagenal offered to command any column that was sent to the Blackwater. After debating the matter, the government decided in favor of a relief expedition.

Bagenal was an experienced, courageous soldier who had considerable knowledge of the area. His principal weakness, already demonstrated at Clontibret, was a tendency to let his divisions become too widely separated and thus lose overall control, which Ormonde later stated was a danger ‘whereof I often warned the Marshal to take special care before he went hence.’

Bagenal’s relief force amounted to a large army for the time and place in which it was mustered–3,901 foot soldiers, as well as 320 horse, who were ‘old’ (experienced) troops. About a quarter of his 40 infantry companies had seen combat, including four that had campaigned in Picardy before arriving at Waterford in March. As many as half of his men were Irish–indeed, roughly three-quarters of the queen’s troops in Ireland in June 1598 were said to be Irish. The rest were levies or conscripts from the English shires, and some 1,500 were recruits who had landed late in July, only partly trained and poorly disciplined. The force had four cannons, the largest of which was a saker, smaller than a 6-pounder.

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