[1] He grew up in Upper Clapton and Woodford Green, he then attended the City of London School[2] and trained as an English teacher at Trent Park College of Education, now part of Middlesex University.
Diamond wrote a regular column for the Saturday edition of The Times from 1992 onwards called "Something for the Weekend", and worked as a presenter on BBC radio and television.
In 1999, he was shortlisted for the Samuel Johnson Prize for his book C: Because Cowards Get Cancer Too.... A BBC documentary was filmed for Inside Story which followed him through treatment, and showed his frustration with his speech difficulties following throat, and later tongue, surgery.
Diamond's second book, Snake Oil and Other Preoccupations, was edited by his brother-in-law Dominic Lawson, editor of The Sunday Telegraph, and published posthumously (with a foreword by Richard Dawkins).
[3] It contained the six chapters of his "uncomplimentary look at the world of complementary medicine" which he had completed before his death, and some of his columns from The Times and The Jewish Chronicle.