Singleton, Henry (1682–1759), politician and judge, was fourth son of Edward Singleton of Drogheda, Co. Louth, MP in the Irish house of commons, and Catherine Singleton (née Newtown). He was educated at Mr Ellis Walker's school in Drogheda, before entering TCD (1698) and graduating with a BA (1703). He entered the Inner Temple (1702) and was called to the Irish bar (1707). Listed as recorder of Drogheda in 1708, he took one of the two parliamentary seats for the town in the 1713 election, replacing his father, who had died since the last parliamentary session. He continued to represent the town until 1740.
Singleton was initially regarded as tory, and numbered Jonathan Swift (qv) and Bishop George Berkeley (qv) among his friends. His toryism, like that of Marmaduke Coghill (qv), his close friend and political ally since 1724, was motivated by support for the interests of the Church of Ireland against dissent, rather than attachment to the house of Stuart. Like other Hanoverian tories, he became a supporter of William Conolly (qv) after 1715. He used his professional skills as a lawyer to advance his political career, becoming a trusted parliamentary lieutenant of the speaker, who described him as ‘now very hearty with our friends’ in 1726 (Conolly to Delafaye, 25 Feb. 1726, TNA, SP/63/387/77). Cautious and conservative in manner, he was appointed prime serjeant in 1726. He was considered as a possible speaker of the house of commons in 1733, on the death of Sir Ralph Gore (qv), but his tory past prevented his ascent to the chair, which went instead to Henry Boyle (qv), leader of the Munster faction once dominated by Alan Brodrick (qv). This marked the end of the dominance of Conolly and his successors, and marked the end of Singleton's active political career. In 1739 he hoped to be appointed lord chancellor when that office fell vacant, but he was again disappointed. Instead he became chief justice of the common pleas (1740).
He brought ‘learning and judgement to the bench’ where he presided for twelve years, until his retirement in 1752 (Kelly, 25). However, during the money bill dispute in the early 1750s he was persuaded to take office again to shore up the Castle party against Speaker Boyle, and was appointed master of the rolls when Thomas Carter (qv), a leading member of the opposition or ‘speaker's party’, was dismissed from that office. The appointment caused some surprise as the duke of Newcastle considered that ‘the late chief justice Singleton (tho’ in every respect a most able and deserving man) is thought to be rather worn out in business, and it is late for him to begin to conduct affairs in the house of commons’ (Falkiner, 541) – from which he had automatically resigned on his appointment to the bench in 1740. In May 1754 Archbishop George Stone (qv) was forced to admit that ‘Mr Singleton will never be able to take an active part in business, but it is certain that the office of master of the rolls could not rest with so much dignity in other hands’ (ibid.). Singleton appears to have had a stroke shortly after his appointment, as on 7 September 1753 Archbishop Stone wrote to Lord George Sackville (qv) that ‘he has wasted very much since you saw him, and when he speaks is with difficulty to be understood’, and on 12 April 1754: ‘he is a melancholy object and I think can hold out but a very short time’ (Falkiner, 745). However, he survived until 1759, dying on 9 November 1759.
Singleton had a residence in Jervis St., Dublin, and also Belvedere House, Drumcondra, handily situated on the road to Drogheda, which he rented from Marmaduke Coghill. Singleton was responsible for developing the house and grounds, and for naming it Belvedere. Much of this work took place after 1750, when Singleton took the advice of William Bristow, chief commissioner of the revenue and amateur architect, regarding the improvement of his estate. Bristow's additions to the house, including the addition of what Mrs Delany called ‘an absurd room’ did not meet with universal approval, but certainly Singleton on his death left behind ‘an attractive if architecturally problematical villa located in a maturing larger and more regular demesne than that which he had rented thirty-five years previously’ (Kelly, 27). It now forms part of St Patrick's College, Drumcondra. He also had a house in Drogheda; which later became Drogheda grammar school before being demolished illegally in 1989. In 1754 he bought the estate of Shercock, Co. Cavan. Singleton never married; his establishment at Belvedere was overseen by his sister Patience. He was buried in St Peter's church, Drogheda, where his nephew Sydenham Singleton erected a very elaborate monument in his memory in 1789. There is an engraving by J. Brooks in the NGI. His legal library was acquired by Columbia University Library, New York, in 1937, and includes a notebook of cases heard in the years 1716–34.