The criminal most romanticized by the early press is the highwayman. A mounted robber, the highwayman steals personal property while riding a horse. Throughout the eighteenth-century, he enjoyed the reputation of a gentlemanly thief, reflecting his skillful use of a horse and firearms and his need to bravely confront his victims. Engaging, quite literally, in highway robbery, the highwayman would stop private carriages and public stagecoaches and demand money, watches, and jewelry from the travelers; he would also stop foot travelers bringing goods and money into and out of London. Travelers expected to be robbed and thus practiced a bit of counter-deception; they often carried two purses: a small one to give to the highwayman and a large one in which to hide their real riches. The highwayman's folk hero status resulted from a belief that he stole from the rich in order to, Robin Hood-like, benefit the poor. In addition, as historian Peter Linebaugh emphasizes, he “represented personal independence and power, a figure apparently who was neither an oppressor…nor limited to a life of service” and trade.
The highwayman haunted the roadways radiating out from London. As London grew, so did its commerce with surrounding communities—and so did the opportunities for stealing from travelers on these vital trade routes. The highwayman practices a type of crime that captures the development of modern London: a city of growth, mobililty, trade, and economic interdependency.
Highwaymen had their exploits recorded in short pamphlets and in longer collections of stories about famous criminals, such as Alexander Smith's A Compleat History of the Lives and Robberies of the most Notorious Highway-men, Foot-pads, Shop-lifts, and Cheats… (1714). Smith recorded the criminal lives of highwaymen such as Captain James Hind (executed 1652), William Davis, known as the “Golden Farmer” (executed 1689), and James Whitney (executed 1694). John Gay’s immensely successful mock-opera, The Beggar’s Opera (1728), features a highwayman, Macheath, who is not only cunningly smart, but attractive enough to win the affections of every woman in the play.