Although Tyrone went to Dublin and denied being a party to the revolt, he knew the die was cast and, early in 1595, he sent his brother Art to besiege the English garrison of Portmore on the Blackwater. On May 27, at Clontibret, The ÓNeill himself ambushed Sir Henry Bagenel’s army, who were returning from re-supplying the English garrison in Monaghan, killing 31 English and wounding 109. Bagenel was astonished at ÓNeill’s skill. Only a cavalry charge on ÓNeill himself averted complete annihilation of the English. Sligo and Cavan soon fell to the Gael, allowing the conflict to spread to Connacht and Leinster. Hugh ÓNeill was proclaimed traitor by the English in June and The Nine Years’ War had begun.

        One Irish leader who joined Tyrone was James FitzGerald, nephew of the murdered 15th Earl of Desmond. In 1598, ÓNeill named him an earl. He came to be known as the “Sugan Earl” (Earl of Straw) and was a distinguished leader in Munster, in spite of his title, until he was finally captured May 29, 1601. The Gaelic leaders knew that Ireland, disunited as she was, needed assistance to prevail. Most of the assistance which reached them was from the “buannachan” (Scottish - hired soldiers billeted on the people at will) from Scotland, in spite of the failure of Angus of Dun Naibhig to break the English blockade, but the Scots who did reach Ireland had no cannon. In September, 1595, ÓNeill and ÓDonnell wrote a joint letter to Philip II, asking his assistance to deliver Ireland from the yoke of the heretic. They subsequently sent several appeals to Pope Clement VIII and, after Philip II’s death, to Philip III, appealing to them on the basis that it was a religious war. Although the replies were gracious and encouraging, the assistance promised was delayed from year to year. Catholic Ireland, insignificant to the great powers, never had effective support from the church or from continental Catholic regimes. Pope Clement VIII sent ÓNeill only a “phoenix feather” (peacock crown) and his blessing.

        The revolt spread all over Ireland anyway, and chiefs and Anglo-Irish nobles from every province joined ÓNeill and ÓDonnell, although the most important, the Earl of Kildare and the Earl of Ormonde, remained loyal to the English throughout the war. It should be noted here that Kildare was no longer a FitzGerald and the gallóglaigh of the MacDonnells of Leinster was no longer in existence, having apparently disbanded at the conclusion of their service in 1579. The betrayal of Sligo Castle into ÓDonnell’s hands gave him hegemony in the west, but several of the Gaelic chiefs and the Anglo-Irish nobles changed sides more than once. Apparently, few other than ÓNeill and ÓDonnell recognized the struggle as a national war for independence.

        Philip II of Spain raised his third armada in 1597, in the last attempt of his life to defeat his royal cousin, Elizabeth. Ruler of a vast empire including Spain, Portugal, half of Italy, the Netherlands and the West Indies, Philip knew only frustration. He had already dispatched a powerful fleet to Ireland, although it had been shattered in the Bay of Biscay in a storm, with the loss of twenty ships. Ironically, an English fleet, commanded by the current Earl of Essex, Robert Devereux, and sent to attack Philip’s present buildup, had just been crushed in a similar Biscay storm. As Essex repaired the damage, Philip was distracted from further support to Ireland by the prospect of another English attack on Spain.

        Hugh Buidhe MacDonnell of Leinster’s second son, Alexander, enlisted in a company of the Clanrickard Burkes, probably the MacDonnell Gallóglaigh Of Mayo. But his commander MacWilliam (not a MacDonnell), would not fight and Alexander was compelled to surrender to the English on February 11, 1597, giving his son Marcus as hostage to his good faith. Fergus, who would later become 6th of Leinster, sued for peace on behalf of all MacWilliam’s men in County Mayo, including Ab MacDonnell.

        In September, 1601, Philip III of Spain sent 4,000 well equipped Spanish troops under Don Juan d’Aquila to aid ÓNeill, after promising a much larger force. Rather than sailing to Ulster, the Spaniard, using very poor judgment, landed at Kinsale, in an area in the south that was firmly in control of the English and was immediately besieged by Mountjoy. Elizabeth saw this invasion as the most formidable challenge to her authority that had yet arisen and gave Blount 20,000 men to deal with it. It was more than six weeks before ÓNeill and ÓDonnell could march the length of Ireland with 6,500 Irish troops to relieve their allies. Their army included Randal Arranagh and 400 of the MacDonnells of Antrim, as well as a Spanish contingent of 150 who had landed at Bearhaven. It was the largest native Irish force ever assembled. ÓDonnell marched his force south, evading George Carew, who blocked his way at Cashel, by a brilliant flanking maneuvre over the Slievefelim Mountains. He and ÓNeill fought through the English lines to join d’Aquila on December 24, 1601, but their troops were exhausted by the effort. Outnumbered two to one, when the English initiated the battle on Christmas Day, the Irish were routed.

        Thereafter, one Irish stronghold after another fell to the Sasunnaich and the fragile Irish alliance disintegrated. Red Hugh ÓDonnell fled to Spain, as did John Desmond, brother of the Sugan Earl, and ÓNeill retreated to Dungannon in Tyrone. An English force under Lord Mountjoy invaded Tyrone and destroyed the crowning stone of the ÓNeills at Tullaghogue. After living for more than a year as a fugitive, Hugh surrendered to Mountjoy at Mellifont on March 28, 1603. Elizabeth had died four days earlier, but Ireland was conquered and disarmed.

        Red Hugh ÓDonnell, age twenty-eight, was poisoned by English agents of Mountjoy, probably lead by a James Blake of Galway, at Simancas in France. Even though ÓNeill signed a treaty with Elizabeth, as soon as she died March 24, 1603, James Stuart, her successor, conspired with his Secretary of State, Lord Howth and a jealous Donal ÓCahan, to falsely accuse ÓNeill and the other northern chiefs of corresponding with the King of Spain in a plot to seize Dublin Castle and begin a new rebellion. ÓNeill, Rory ÓDonnell, Red Hugh’s brother and successor, and ninety-seven trusted friends had no choice but to flee into exile. They boarded a French ship at Rathmullan in Lough Swilly on September 4, 1607, never to return. This “Imeacht na n’ Iarlai” (Flight of the Earls), left all of Ireland undefended and England had complete control for the first time. The consensus, commemorated with the words “Now stolen is the soul from Eire’s breast,” is that this marked the end of Gaelic civilization in Ireland. Using feudal precedent, James I, new King of England, seized their lands on the pretext that they were forfeited to the crown for treason. His officials argued that the recent rebellion showed that the continued existence of Catholic landowners in Ireland was a threat to the very security of England.

        The Earl of Tyrone went into exile with every intention of returning to Ireland. The centerpiece of Gaelic hopes was the Irish regiment stationed in Spanish Flanders, commanded by one of ÓNeills sons. Officered by the best of Ireland’s youth, including Captain Sorley MacDonnell of Antrim who sponsored "The Annals Of The Four Masters," it was believed that, if brought to Ireland, it was a superior force to any in Ulster. Tyrone desperately attempted to reach Flanders and enlist the services of the regiment. But the Spanish, now at peace with England and intending the Irish Regiment for their own use, prevented him. ÓNeill visited several of the courts of Europe, eventually settling in Rome, where he finally received his only aid from the pope, a pension. English agents surrounded him until his death in 1616. Their reports mention that, in the evenings, ÓNeill’s face would glow, he would strike the table and say, “They will yet have a good day in Ireland!” He was buried with royal honors in the Franciscan Church of San Pietro di Montorio on Janiculum Hill, next to the remains of Hugh Ruaidh, who had been interred there eight years previously. One of ÓNeill’s sons died before him; and another, Brian, page to the Archdukes of Brussels, was murdered by English agents. This was the last attempt for Ireland’s independence until the Twentieth Century. But as poetic justice, the last of the Tudors was dead as well.