Sydney was born on 10 July 1922 in Marylebone, London to Samuel and Amelia nee Woolf and had one brother named Emmanuel David. Sydney attended St Marylebone Grammar School from 1931-1936 and St Paul’s School in London where he obtained colours for cricket, rugby and boxing. Before he was 18 he joined the Hove Home Guard and then volunteered for the RAF. In 1939, the family lived together with his mother Amelia’s family in Hove, Sussex and Benjamin was listed as working as a traveller for the fur industry.

Sydney was trained in California and received his wings in 1942. He was then based in Malta with 1435 Squadron and on the 12 July 1943 he was providing air support for the invasion of Sicily in Spitfire EN287. He was shot down in combat with Me.109s near Augusta two days after his 21st birthday. His body was recovered and he was buried in Sicily.