The Most Notorious Highwaymen In History

The best-known highwayman is undoubtedly Dick Turpin, who, on his horse Black Bess (Thomas Boulter reportedly named his own horse in honor of Turpin's famous steed), elicited bounty from the wealthy nobles of 18th century England in a crowd-pleasingly swashbuckling manner. But according to Stand and Deliver, Turpin's reputation is only half of the story

The best-known highwayman is undoubtedly Dick Turpin, who, on his horse Black Bess (Thomas Boulter reportedly named his own horse in honor of Turpin's famous steed), elicited bounty from the wealthy nobles of 18th century England in a crowd-pleasingly swashbuckling manner. But according to Stand and Deliver, Turpin's reputation is only half of the story — "it was only at the very end of his life, while waiting to be hanged at York racecourse, that Turpin exhibited any of the swaggering nonchalance, heroism, or derring-do usually attributed to him. Prior to that, both his existence and his criminal ventures had been squalid."

The son of a farmer and innkeeper, Turpin began his criminal career as part of the Essex Gang, named after the county Turpin and his accomplices terrorized, after being caught rustling cattle. The gang, who according to Britannica specialized in deer stealing and smuggling, broke up in 1735, and Turpin headed north to set up as a bogus horse dealer.

He was arrested and hanged for his crimes in 1739 but had an afterlife as a folk hero, thanks in part to "Rookwood," an 1834 poem by William Harrison Ainsworth valorizing the outlaw. Such depictions have romanticized Turpin beyond compare, to the point that his use of brutal violence — and, indeed, murder — has been all but erased from popular memory.

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