He travelled to Scotland in early 1591 seeking assistance from King James VI, however, he was to become the first man extradited within Britain on allegations of crimes committed in Ireland and was sentenced to death in London in November 1591.
[1] He assumed leadership of his Irish clan in the mid-1560s having assassinated his elder brothers, but his territory of west Bréifne on the border of Ulster soon came under the administration of the newly created Presidency of Connacht.
[citation needed] A decade later, Sir Edward Waterhouse thought of him as, "being somewhat learned but of an insolent and proud nature and no further obedient than is constrained by her Majesty's forces".
It was suspected his actions were induced by an involvement with the Old English family of the Dillons in adjacent Meath, who were engaged in an effort to spread their influence and possessions in the northern midlands, rather than by outright collusion in the rebel Geraldine cause.
A further factor was almost certainly the August 1579 torture and execution of his son, Franciscan Friar Conn Ó Ruairc, by Tudor Army troops outside the city walls of Kilmallock under orders from Sir William Drury.
Both Friar Conn and his companion in death, Bishop Pádraig Ó hÉilí, were Beatified in 1992 by Pope John Paul II, along with 15 other Irish Catholic Martyrs.
Ó Ruairc immediately complained of harassment by the new president in the spring and summer of that year, and in September Bingham was ordered by his superior in Dublin Castle to temporise and refrain from making expeditions into Bréifne.
He was thus due to receive a regrant of his lands by knight-service in return for a chief horse and an engraved gold token to be presented to the lord deputy each year at midsummer.
Thus, in the spring of 1590, Bingham's forces occupied west Breifne and O'Rourke fled; later that year the adjacent territory of Monaghan was seized by the crown after the execution at law of the resident lord, Hugh Roe MacMahon.
In consultation with the English ambassador Robert Bowes, King James VI denied him an audience, and Queen Elizabeth (relying on the Treaty of Berwick (1586)) made a strong request for the delivery of O'Rourke into her custody.
[4] The matter was put to the Scottish Privy Council, which readily ordered – in the face of some objections – the arrest and delivery to English crown forces of the rebel Irish lord.
Meanwhile, articles had been framed at Dublin against O'Rourke with the reluctant aid of Bingham (curiously, he complained of being bullied into his testimony), and there was also an indictment laid by a jury in Sligo.
These matters were transferred to England, where the grand jury of Middlesex found evidence of various offences of treason, the most substantial of which concerned the assistance given to Armada survivors, the attempt to raise mercenaries in Scotland, and various armed raids made by O'Rourke into counties Sligo and Roscommon.
There was one further charge that related to an odd incident in 1589, when a representation of the Queen (whether a wood carving or painting is not known) was said to have been tied to a horse's tail at O'Rourke's command and dragged in the mud.
The defendant was asked how he wished to be tried and answered that he would submit to trial by jury if he were given a week to examine the evidence, then allowed a good legal advocate, and only if the Queen herself sat in judgment.
In response, he was abused by O'Rourke with jibes over his uncertain faith and credit and dismissed as a man of depraved life who had broken his vow by abjuring the rule of the Franciscans.
What is remarkable is the combination used in his downfall: first, the campaign conducted under Fitzwilliam to bring pressure to bear on the borders of Ulster; and then the co-operation of the Scots king with the English, resulting in the first extradition within Britain and a trial for treason committed "beyond the seas".