 After gaining three O-levels, he was expelled at 16 for being a "disruptive influence" after several misdemeanours.After short periods working in the City and in public relations, Dempster joined the "Daily Express" in 1963 and remained at the title until 1971.Here he was a contributor to the 'William Hickey' column, and used his contacts to gain stories about the aristocracy and other public figures.