Born in New York City, Simpson was educated at The Hill School before attending Harvard University. Simpson was commissioned in the British Army serving as a Captain in the Coldstream Guards during World War I. His father, Ernest Louis Simpson, a British citizen of Jewish background whose original surname was Solomon, co-founded the global shipbroking firm Simpson, Spence & Young, trading since 1880. His mother, Charlotte Woodward Gaines, was American, daughter of a New York City attorney. His elder sister and only sibling, Maud Simpson, married, in 1905, MajorPeter Kerr-SmileyMP. Simpson became a British subject during World War I, shortly after graduating from Harvard and renouncing his United States citizenship. "In his younger years he was described as tall, with blue eyes, blond, curly hair, a neat blond moustache and a fastidious dresser," according to an article in The New York Times.
First marriage
His first wife, whom he married in New York City, on 22 February 1923 and divorced in 1928, was Dorothea Dechert, the former wife of James Flanagan Dechert, a Princeton University alumnus, whom she married in May 1916 and divorced in April 1920. Born Dorothea Webb Parsons, she was a daughter of Arthur Webb Parsons, a lawyer, and his wife, the former Frances Margaret Graves. Dorothea and Ernest Simpson had one child, Audrey C. C. Simpson, who married firstly on 5 October 1945, American journalistMurray Rossant and, secondly on 1 April 1949, New York advertising executive Edmund Hope Driggs III. Audrey Simpson Driggs died at Calgary, Canada on 2 November 2013. Simpson also had a stepdaughter by this marriage, Cynthia Josephine Dechert.
Second marriage
Simpson's second wife was Wallis Warfield Spencer, the Blue Ridge Summit, Pennsylvania-born former wife of Earl Winfield Spencer Jr. and the only child of Teackle Wallis Warfield. They married in London, England, on 21 July 1928, and divorced on 3 May 1937. As his obituary in The New York Times noted, the publicity over his second wife's remarriage to the Duke of Windsor and her subsequent fame thrust him into the role of "the forgotten man". The two remained friends, however, the newspaper noted, with the now Duchess of Windsor sending him flowers when he was in hospital for surgery and Simpson offering advice and clarification when his former wife was working on her memoirs.
Third marriage
His third wife was Mary Raffray, a daughter of Henry Child Kirk, proprietor of the Kirk Silversmith Co. of Baltimore, Maryland and his wife, the former Edith Huntemuller, who dedicated her book Her Garden Was Her Delight to her memory. Mary Simpson's letters, along with her sister's, are held at Harvard University Archives. A girlhood friend of Wallis Simpson's, Mary Kirk was a bridesmaid at her first wedding and introduced her to Ernest Simpson in 1925; she also was the "other woman" with whom Simpson took a hotel suite in Berkshire, in order to give his wife evidence of adultery, so that she could bring divorce proceedings against him. Ernest Simpson and Mary Raffray were married in the Diamond Jubilee ballroom of the Brooklawn Country Club in Fairfield, Connecticut on 19 November 1937, six months after the groom's divorce from Wallis Simpson and three weeks after the bride's divorce from Jacques Raffray, a French aviator, whom Mary had married on 29 July 1918. Mary and Ernest Simpson had one child, Ernest Henry Child Simpson, who was born prematurely on 27 September 1939, and christened at the Guards Chapel, Wellington Barracks, London. In June 1940, the Simpsons sent their infant son to the United States to escape the War including the Blitz. However, a month before Mary's death he returned with her to England. Mary Simpson died of breast cancer on 2 October 1941, at the couple's home in Wiltshire. Their son changed his name legally to Aharon Solomons before being commissioned as an officer in the Israeli Army.
Fourth marriage
Simpson's fourth wife was Avril Leveson-Gower, the former wife of Brigadier-GeneralHugh Nugent Leveson-Gower and Prince George Imeretinsky. She was the younger daughter of Sir John Ashley Mullens, of Manor House, Haslemere, Surrey, by his wife, the former Evelyne Maude Adamson. Simpson and Avril Leveson-Gower were married in London on 12 August 1948. By this marriage Simpson had a stepdaughter, Lucinda Gaye Leveson-Gower. Avril Simpson was killed in a car crash in Mexico.
Death
Simpson died suffering from throat cancer, on 30 November 1958 in London, aged 61.