Roy (Reuben) was born on 2 October 1909 in Liverpool to Phillip and Perle (Polly) Isenstein. Roy’s parents were immigrants from Odessa who ran a wood importing and cabinet making business. Phillip predeceased Roy, dying in 1942. Roy had five siblings, Esther, Fanny, Myer and Michael. A younger brother Abraham died when he was eight years old.

Before volunteering for the RAF Roy worked as a clerk and a projectionist at a cinema.

Roy was on board Wellington LN379 which took off from RAF Harwell on a night aircraft delivery flight to Tunis in North Africa. The aircraft experienced engine failure shortly after take off and crashed near Chardstock, Devon.