Bourke was inaugurated in Kilmaine by Hugh Roe O'Donnell in December 1595 during the Nine Years' War to consolidate control of Mayo for the rebel Irish Alliance.
The struggle for dominance over the MacWilliam Lordship, which corresponds to modern-day County Mayo, was intense and the control of the region frequently changed hands.
[2] It is also suspected that John Burke, who was made commander of the Connacht forces during the Irish Confederate Wars in 1642, was also a son of Kittagh's, having been born in County Mayo yet spending "30 years in the service of Spain".
This was an English policy under which Risdeárd Bourke was recognized as the rightful lord of the MacWilliam territories, making his eldest son the automatic heir.
Following his escape, Kittagh was declared an outlaw, his castles at Cloonagashel, Castlebar, and Belleek were seized, and small English garrisons were stationed in them.
[6] In the early stages of the Nine Years' War from 1593 to 1595 the nobles of Connacht were largely sympathetic to the cause of the Ulster lords O'Donnell and O'Neill, and detested the presence of the Binghams (Richard and his brothers George and John) in their province.
The veteran soldiers who were already there were not given enough supplies and ammunition to retake lost territory, or even engage the rebels at all in most cases, and the new arrivals were so unskilled in the use of their weapons that their captains were forced to give them to the Irish shots in their pay.
[8] Sir Geoffrey Fenton temporarily relieved Bingham of his command and asked the Connacht rebels to meet him in Galway to agree a peace.
Ultimately, in a highly untraditional and heavily guarded assembly, O'Donnell publicly endorsed Kittagh, anointing him with the MacWilliam title, to the surprise of many.
The Mayor of Galway, Oliver Oge French, expressed distrust toward O'Donnell due to the widespread destruction he had caused since the war began.
In retaliation, on the night of January 17, 1596, Kittagh and O'Donnell executed a surprise attack on Galway, burning several houses on the city's outskirts and killing six people before being driven off by cannon fire.
The rebels then retreated to Mayo, burning every village en route and warning the non-rebellious Galway inhabitants of harsher treatment by the Spaniards compared to what they had inflicted on Athenry.
While his Ulster allies had retreated from the province, Kittagh intended to remain throughout the winter "through the strength of the bogs and the woods" as he knew Clifford did not have adequate manpower or supplies to push him out of Mayo.
Safe in the knowledge that Clifford couldn't venture far into the county, they were ill-prepared for a surprise attack by Tibbot na Long, in which they lost 40 of their men (including Kittagh's brother Thomas) along with the remainder of their supplies, forcing them to retreat once again to Ulster.
[16] By the end of October 1597 Kittagh was once again in exile and all of his approximately 1,000 followers in Mayo who had risen up to join the rebellion had now applied to Clifford for protection from the rebels, chiefly O’Donnell, whom they feared might return.
[citation needed] A truce was signed between the Irish alliance and the Dublin government, in effect from January to June 1598, during which time O’Neill negotiated with the English.
This was firmly rejected as Elizabeth had not been beaten to the point where she would be willing to disband her government's administration in Mayo and restore an abolished chieftainship, particularly to someone who was much loathed by his kinsmen and currently living in exile in Tyrconnell.
Relative calm returned to Connacht for the duration of the truce, but following the Irish alliance's decisive victory over the English forces at Yellow Ford on 14 August, the spectre of Kittagh once again loomed over Mayo.
[17] Clifford was evidently correct in this regard as, following O’Donnell and Kittagh's return in mid-September, he noted "On the first day of MacWilliam's coming with O'Donnell's whole force.
The McDonagh’s betrayed the English and took possession of Ballymote Castle, and offered to sell it back to Clifford before handing it over to O’Donnell intact in exchange for £400 and 300 cows.
In July, he was given £1500 by the English government, which forbade its administrators in Ireland from diverting from him, and was tasked with rebuilding the castle at Sligo, a town which was presently occupied by the pro-English O’Conors.
Tibbot na Long sailed from Galway with military stores, provisions and building supplies and anchored in Sligo Bay awaiting Clifford, who was traveling north from Tulsk.
The only thing that prevented complete catastrophe was an uphill cavalry charge led by Sir Griffin Markham, which stalled O'Rourke's men long enough to allow the routed soldiers to escape.
It was here that O’Donnell proposed to O’Flaherty that Tibbot na Long, who possessed 3 three large galleys capable of carrying 300 men each, turn on the English ships accompanying him and seize them.
[20] O’Donnell arranged a peace treaty between the warring factions of the Mac William Íochtar clan in December 1599, which was primarily a truce between the two Tibbots.
Throughout 1600 the English made stunning gains across Ireland, primarily due to Baron Mountjoy's scorched earth policy, which led to widespread famine across the country rendering it difficult for the Irish Alliance to hold onto the land they had taken.
There are numerous examples of this, but the so-called masterstroke of the war came when Niall Garbh betrayed the alliance and allowed 4,000 English soldiers led by Henry Docwra to land at Lough Foyle, gutting the once impenetrable core of the rebellion, Tyrone and Tyrconnell.
[21] Conscious of the changing tide of the war, Kittagh traveled to Galway city in June 1600 to meet with the notorious assassin James Blake (alias Captain Blackcaddell, the man who would later attempt to poison O'Donnell in Spain in 1602) to propose a plan of betrayal which was to be passed on by Blake to Captain Thomas Lee, whose eagerness to advance politically saw him engaged in widespread machinations throughout Ireland.
He would then kill and/or capture the rebel commanders and bring them or their bodies to Killybegs castle on Donegal's west coast, which he planned to purchase from Chief MacSweeny, his brother-in-law, for approximately £1,000.
While marching back to his home of Tirawley, Kittagh encountered the forces of his rival claimant and a fierce battle ensued during which Richard was killed.