His mother, Marsali (née Seal),[3] was a schoolmistress who married John Montgomery after her first husband, Roger de Winton Kelsall Winlaw, died in 1942 on active service in the Royal Air Force.
[1] After leaving school, he worked for three years as an articled law clerk, before gaining a place at Cambridge University to read history.
Often retold was the story of his having eaten the largest breakfast ever served at The Connaught hotel in 1972; the head waiter reported to his table that the previous record holder had been King Farouk I of Egypt.
[1][2] After leaving school at Harrow, Massingberd discarded initial plans to attend the University of Cambridge, instead choosing to work as a law clerk.
"[14] He termed the late maverick Dead Sea Scrolls academician John Allegro, who later argued for Judeo-Christian cultism regarding mushrooms and sexual intercourse, the "Liberace of biblical scholarship.
Following his editorship tenure, obituaries in not only The Daily Telegraph but in many other British publications, such as The Times of London, took on the dryly impish character for which his writings had become famous.
[2] After his resignation, Massingberd continued to write, authoring book reviews for The Daily Telegraph as well as several theatrical works.
When one of his theatre pieces, Love and Art, was produced at the Wallace Collection in 2005, Massingberd played one of the roles on stage.