Henry Singleton (1682–1759) was an Irish politician and judge, who is remembered now mainly for his friendship with Jonathan Swift, and for his notable acts of charity during the Great Irish Famine of 1740-1, in which between 300,000 and 500,000 people (possibly 20% of the overall population) died. Singleton House, his impressive townhouse in Drogheda, no longer exists.

He held the Mastership until his death, despite ever-increasing health problems which left him in "a melancholy condition". He died unmarried in 1759 and was buried in St. Peter's Church of Ireland, Drogheda, where his nephew Sydenham Singleton erected an impressive monument in his memory, sculpted by John Hickey.^[9] His law library is now held by Columbia University.^[10]

His will contains a long list of bequests to his surviving sisters, and to his numerous nephews and nieces. The principal beneficiary was his niece Mary, daughter of his brother the Rev. Rowland Singleton, vicar of Termonfeckin, and his wife Elizabeth Graham, and sister of Charity Singleton Cope (1707-1779), who married Sir William Yorke as her second husband. Mary married Philip Tisdall, Attorney General for Ireland from 1760 to 1777, who was a dominant figure in the Irish Government for many years. Tisdall hoped to succeed Singleton as Master of the Rolls, but was passed over. Mary ("la belle Marie") was a noted beauty: she and Philip were both painted by the celebrated Swiss painter Angelica Kauffman.^[11]

In 1731 he built an impressive residence named Singleton House at Laurence Street, Drogheda.^[12] It has been described as a three-storey mansion of red brick, with seven bay windows and magnificent oak-panelled interiors. It became derelict in the 20th century, and was demolished (illegally) in 1989.^[13]

In Dublin, he lived at Belvedere House, Drumcondra, which he rented from his friend and political connections colleague Marmaduke Coghill, and which he extensively improved. He also owned property in County Cavan^[3]

Despite a rather haughty manner, which led to his nickname "the Prime Serjeant Grand", and is borne out by the portrait of him by Michael Ford in his judicial robes,^[14] Singleton was loved and respected by those who knew him well. He enjoyed the friendship of Jonathan Swift who called him "the first of the worthiest" and appointed him his executor.^[15] William Yorke, his successor as Chief Justice, and husband of his niece Charity, even while nudging him towards retirement, had nothing but praise for Singleton both as a man and a judge. Another influential friend was the politician and judge Robert Lindsay, who married Henry's sister Elizabeth, and was also a friend of Swift. George Stone, the powerful Archbishop of Armagh, also had high regard for him. The best tribute to his character is his noble behaviour during the Great Famine of 1740-41 when he donated much of his personal fortune to the relief of the poor of Drogheda, one of the towns worst affected by the famine, and adjourned the Court of Common Pleas, so that he could return home and supervise the relief works.^[16]