James Keating

He was born in Bree, County Wexford. Little seems to be known of his early life. He joined the Order of Knights Hospitallers, rose rapidly through its ranks and in 1461 became Prior of the Order's Irish house at Kilmainham.

Soon after his appointment as Prior, he committed a crime which might well have ended his career and even his life. At Pentecost 1462 Sir Robert Dowdall, the Chief Justice of the Irish Common Pleas, came on a pilgrimage to Kilmainham. Keating attacked him with a sword and appears to have had every intention of killing him. The motive for the attack is unknown, although crimes of violence, even among the ruling class were not uncommon in that era: twenty years earlier another senior Irish judge, Chief Baron James Cornwalsh, had been murdered.

Keating was arrested and arraigned for trial before Parliament on a number of charges including atttempted murder, but the charges were dropped on condition that he pay Dowdall 100 marks in damages (although it seems that he never actually did so). He probably owed his immunity from punishment was to the influence of the powerful Anglo-Irish magnate Thomas FitzGerald, 7th Earl of Kildare, who acted as Keating's patron. For the next few years he seems to have run the Order smoothly enough. He was later accused of bankrupting the Irish house: in his defence he pointed out that his superiors in Rhodes in 1467 had increased the annual payment due to them from Ireland from £40 to £70 without consultation or any regard to the Irish house's ability to pay, and he was hard put to find the extra money.

As Prior of Kilmainham he was entitled to sit in the Parliament of Ireland and on the Privy Council and was expected to play a key role in Irish politics. During the Wars of the Roses, the dynastic struggle between rival branches of the English Royal family, Keating in common with almost all the Anglo-Irish nobility favoured the House of York over the rival House of Lancaster. The victory of York over Lancaster in the year Keating became Prior should therefore have increased his standing. However he was in temporary disgrace when in 1467 King Edward IV sent the notoriously ruthless John Tiptoft, 1st Earl of Worcester (nicknamed "The Butcher of England") to be Lord Lieutenant of Ireland. Worcester held a Parliament at Drogheda where he proceeded to deal with those whom he regarded as his enemies, including the Earl of Kildare, who fled abroad, and Keating, who was imprisoned.

Lord Grey

His fortunes improved after the House of Lancaster, which had briefly regained the throne in 1470-1, was finally crushed at the Battle of Tewkesbury. Among the defeated Lancastrians who were executed for treason after Tewkesbury was Sir John Langstrother, Prior of the English Hospitallers. Keating by contrast was commended by the victorious Yorkists for his loyalty. In 1478 however he clashed again with the English Crown when King Edward, to strengthen his authority, sent Lord Grey of Codnor to be Lord Lieutenant. The Anglo-Irish nobles, led by Gerald FitzGerald, 8th Earl of Kildare and his father-in-law Baron Portlester, simply refused to recognize his authority:Keating who had assumed the role of Constable of Dublin Castle, apparently by force, played a key role in these events by refusing Lord Grey entry to the Castle. After a few months of deadlock, the King yielded and Grey returned to England. leaving Keating and his allies triumphant.

Marmaduke Lumley

The next threat to his position came from his own superiors in Rhodes, who were outraged by his refusal to give any assistance to the beleaguered Order against the Ottoman Empire during the Siege of Rhodes (1480). In 1482 he was removed from office and replaced by an English member of the Order, Marmaduke Lumley, who obtained Papal approval for his election.Keating however was not a man to submit lightly to such a decision, and when Lumley landed at Clontarf, Dublin, Keating led a large force which captured and imprisoned him, and later put him in chains. Both the Papal Legate, Octavio de Palatio, and the Archbishop of Dublin, John Walton, expressed their outrage and demanded Lumley's release. In 1484 they sent a troop of soldiers to free him, but Keating, who was a trained soldier like all his Order, easily defeated it. Lumley died in prison soon after. Keating was excommunicated for his actions, but true to his character, simply ignored the excommunication.

Lambert Simnel in Ireland

The downfall of the House of York at the Battle of Bosworth in 1485, and the establishment of the Tudor dynasty under King Henry VII was unwelcome news to the pro-Yorkist Anglo-Irish nobility, led by the Earl of Kildare and his father-in-law Lord Portlester, and their resistance to the House of Tudor led to Keating's ultimate ruin. In 1487 Kildare, Portlester, Keating and their allies made the mistake of supporting the claims of the pretender Lambert Simnel, who claimed to be Edward Plantagenet, 17th Earl of Warwick, the rightful heir of the House of York. Simnel was an imposter, but was said to strongly resemble the real Warwick, who was a prisoner in the Tower of London. Simnel was crowned in Dublin and invaded England with a large army, only to be crushed at the Battle of Stoke Field.

Henry VII was remarkably merciful in victory: Simnel became a royal servant and almost all of the Anglo-Irish nobility received a royal pardon. The one notable exception was Keating, whose record of violence, and defiance both of the Crown and his own superiors evidently made it impossible for the King to trust him. The Crown chose to regard him as the "prime instigator" of the rebellion, although historians usually give that role to the Earl of Kildare. Despite repeated pleas he was refused a pardon and deprived of office once more. Showing all his old stubbornness he refused to leave Kilmainham, but was finally ejected in 1491. He died in poverty soon afterwards.