In the mid 1890s Oscar Wilde was imprisoned for a homosexual relationship with the son of the Duke of Queensberry. Within weeks there were rumours that conditions within British prisons were so severe that the poet and playwright was showing signs of mental illness. Concerns over Wilde's health helped generate substantial interest in how British penal policy was conducted and contributed to a growing momentum for prison reform.

This essay relates Oscar Wilde's experiences to the modernisation of the British prison system. It shows how the issues raised by his imprisonment overlapped with those discussed by the Gladstone Report of April 1895. More importantly, the essay also highlights the little-known critique of the prison system which Wilde published after his release. As he put it: 'Ordinary cruelty is simply stupidity..... Wherever these is centralisation there is stupidity. What is inhuman in modern life is officialism. Authority is as destructive to those who exercise it as to those on whom it is exercised.' In other words, the article shows how Wilde started to develop a discussion of the potential failings of modern bureacracies which more frequently is associated with theorists such as Arendt and Baumann.