In 1884 Henry was described by the deputy governor of Portland Prison as “…the point where the gentleman ends and the habitual criminal begins”. The habitual criminal was, in mid-Victorian England, conceived as a member of the criminal classes, who were described as atavistic primitives in the Darwinian sense, indolent but armed with animal cunning. A gentleman offender like Henry challenged these assumptions. This paper examines the case of Henry, an educated man from a prosperous and well-connected family who faced charges of fraud, forgery, theft and bigamy, and who was in the divorce courts three times. Henry was sentenced to penal servitude three times, serving ten years in gaol. His case will be used to test theories of class and gender, and of crime and punishment in Victorian England. The paper explores how Henry, a serial exploiter of women, avoided conviction for some frauds, but was less successful with others, and analyses his attempts while in gaol to cling on to his social status.