To supplement his income and help pay for his legal training, Druitt worked as an assistant schoolmaster at George Valentine's boarding school, 9 Eliot Place, Blackheath, London, from 1880. The school had a long and distinguished history; Benjamin Disraeli had been a pupil there in the 1810s, and boys from the school had been playmates of a younger son of Queen Victoria, Prince Arthur, Duke of Connaught, who as a boy in the 1860s had lived nearby at Greenwich Park. Druitt's post came with accommodation in Eliot Place, and the long school holidays gave him time to study the law and to pursue his interest in cricket.