Thomas Hopley, aged 41 at the time of the incident, was a schoolmaster in Eastbourne who ran a private boarding school from his home at 22 Grand Parade. He was well educated and from a middle-class family, the son of a Royal Navy surgeon and brother of artist Edward Hopley, author Catherine C. Hopley, and editor John Hopley. His household was fairly well off, and he and his wife kept several servants. He had two children, the first of which had brain damage – "popular rumour" blamed this on "his unconventionally bracing notions of neonatal care". However, Hopley was described by Algernon Charles Swinburne as "a person of high attainments and irreproachable character". He expressed "utopian" educational ideals shared by many Victorian educational theorists. He wrote pamphlets on education topics which included "Lectures on the Education of Man", "Help towards the physical, intellectual and moral elevation of all classes of society", and "Wrongs which cry out for redress" advocating the abolition of child labour.
In October 1859, he was offered £180 a year to teach Reginald Channell Cancellor, a "robust" boy who had been "given up as ineducable". Reginald was the son of John Henry Cancellor (1799–1860), a master of the Court of Common Pleas and a "man of fair position" from Barnes, Surrey. The boy had previously been a student at a private school in St. Leonards and under a private tutor. He was not a good student, with contemporary sources suggesting he "had water on the brain" and describing him as "stolid and stupid". Hopley attributed Cancellor's failure to learn to stubbornness. On 18 April 1860 he asked the boy's father for permission to use "severe corporal punishment" to obtain compliance, with permission granted two days later. Hopley did not possess the cane traditionally used to administer corporal punishment to students, so instead he used a skipping rope and a walking stick.