In early 1720s London highway or street robbery, especially by ‘gangs’, was highly topical; for some decades it had been a cause of much anxiety, and had recently been the target of increasingly harsh legislation. Yet the vast literature that “accompanied and stimulated” that legislation has been described by Robert Shoemaker as deeply ambivalent, swinging between negative images of ruthless brutes and positive images of polite gentlemen highwaymen. In Daniel Defoe’s Colonel Jack (1722) the protagonist’s thieving career follows a rising curve of violence, ‘progressing’ from picking merchants’ pockets and compounding to mugging old gentlemen and ambushing apprentices. Jack and his tutor/companion Will then fall into “quite another Vein of Wickedness” by getting in with a gang of footpads and burglars, a promotion Will promises, will make them “all Gentlemen together”. This essay suggests that we read the robbery episodes in this novel as an attempt to “make sense of” such violent crime and its conflicting cultural representations, especially as they relate to the gentlemanly aspirations which are a dominant motif in this novel.