Arthur J. Raffles, fictional ‘cracksman’ by night and England cricketing star by day, burst onto the literary scene in 1898. Created by Ernest William Hornung, brother-in-law of Sherlock Holmes’ author Sir Arthur Conan Doyle, Raffles was Holmes’ antithesis: the fun-loving master thief. Embodying the ‘pleasure culture’ surrounding the burglar, Raffles’ physical attractiveness and athleticism blurred the lines between moral virtue and romantic allure. As the original novels were continually remade in theatre and film and their characters reincarnated in those media, newspapers began to label real burglars ‘Raffles’. This chapter examines how, where criminality was concerned, distinguishing between fact and fiction presented unnecessary (and unheeded) complications to commercial success. Espying an opportunity, ex-criminals appropriated this sympathetic ‘Raffles’ title for themselves, using the idea of ‘real-life Raffles’ to fashion glamorous celebrity personae through lucrative autobiographical writings. The character became an international phenomenon, beloved by audiences across Europe and America who flocked to see his exploits at the cinema and continually identified the burglar as an English ‘hero’, akin to Robin Hood. Yet Raffles was no philanthropist. Keeping the jewels for himself and glorifying in escaping capture by police, Raffles was a figure of danger for many contemporaries, who identified the longevity of his success as a harbinger of popular unrest caused by economic depression that might seduce generations of young people into a life of crime. The chapter historicizes how cultural responses to romanticized versions of burglary were conditioned by critiques of poverty and the habits of the wealthy.