He belonged to an Anglo-Irish family which had long been settled at Moyglare, County Meath He was a cousin of Sir Walter Delahide, who married Janet FitzEustace, an aunt of Gerald FitzGerald, 9th Earl of Kildare. The FitzGerald family had been almost all-powerful in Irish politics since the 1470s, but the ruling class eventually split into pro-Kildare and anti-Kildare factions. Given their close family ties, it was natural for Richard to look to the Earl of Kildare to advance his career. Though little is known of his legal practice, it was almost certainly on Kildare's nomination that he was appointed Chief Justice of the Common Pleas in 1514; he held that office for 20 years, though he was threatened with removal in 1529. He was also made Chancellor of the Irish Exchequer in 1533.
Silken Thomas Rebellion
The Geraldine connection proved disastrous for Delahide when, on the false report of his father's death, the 9th Earl of Kildare's son and heir Thomas, nicknamed "Silken Thomas" rebelled against Henry VIII. The judge pleaded that he was completely loyal to the Crown, but apart from his own ties to the FitzGerald family, the main supporters, if not instigators, of the rebellion were the Delahides of Moyclare. The "most false disloyal traitor" James Delahide, described as Thomas FitzGerald's "principal counsellor in all his doings" was the son of Richard's cousin Walter, and James' parents and brothers were also said to be involved in the rebellion. Inevitably, Richard was removed from office both as Chief Justice and Chancellor of the Exchequer.
Later career
Judging by his letters to Thomas Cromwell, Delahide seemed less concerned at the risk being prosecuted for treason than with the loss of his public offices. Elrington Ball quotes his abject letter to Cromwell in 1534 in which Delahide denied that he had ever slandered Cromwell : in good faith I never spoke nor thought to speak any such thoughts...I know it well ye be of our Sovereign Lord's Privy Council and as high in his favour as any man. He greatly resented the loss of the office of Chancellor of the Exchequer to Thomas Cusack but grudgingly conceded: I would have been contented that he should have enjoyed the same accordingly though it had rightfully been mine own. Delahide's main concern was to be restored to the office of Chief Justice : he wrote that there is labours made for mine office of Justiceship wherein I have truly to the best of my little power served the King's Grace by the space of 20 years trusting that there shall be no good cause proved why his Grace should move me from the same. Delahide's pleas were partly successful: although he was not restored to office as Chief Justice, in 1537 he was made Chief Baron, and held that office until his death in 1540.
Personal life
He married Jenet Plunket, daughter of Christopher Plunkett and granddaughter of his predecessor as Chief Justice of the Irish Common Pleas, Sir Thomas Plunket; they had at least one son, George. Richard lived partly at Loughshinny and partly at the Castle of the Ward. His widow and son were still living at the Ward in 1542 but soon afterwards it came into possession of Lord Howth.
