The Brit History Fiver – Five Famous Highwaymen (and Women)

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August 24, 2020 By John Rabon Leave a Comment
Stand and deliver!  The famous words of the highwayman, who robbed wealthy people as they traveled, once inspired fear in those traveling along British roads for nearly 200 years.   Interestingly, some of them began life or were wealthy nobles themselves, turning to crime after falling on hard times or simply for the thrill.  Some even built up celebrity followings thanks to their notoriety or the use of their ill-gotten gains to support their communities.  We have identified five of who we believe are the most famous and important British highwaymen below and if you think there’s someone we missed, let us know in the comments.
John Rann
Also known as Sixteen Stringed Jack, John Rann was one of the first highwaymen to achieve a sort of celebrity.  Rann began a life of crime thanks to living well beyond his means, and his nickname came from the colorful ribbons he wore around his knees, supposedly representing every time he had been acquitted for robbery.  He often managed to elude justice due to a lack of evidence or witnesses failing to identify him, but was finally convicted and hanged in 1774.  It’s said that part of his popularity came from his charismatic nature and it was said he even entertained the crowd and the hangman on his way to the gallows.
Jack Sheppard
Jack Sheppard was practically born into a life of crime.  Growing up in Spitalfields, which was notorious for robbers, prostitutes, and highwaymen, Sheppard quickly fell into crime at the age of 20 thanks to a life of drinking a whoring.  His legitimate career as a carpenter suffered, and he turned to highway robbery as a means to support himself.  Sheppard is most famous for his numerous escapes from prison.  Sheppard escaped from St. Anne’s Roundhouse and Newgate twice before being hanged at Tyburn in 1724.  There had allegedly been a plan to rescue him from this fate by his friends, who had hoped to revive him as it was sometimes possible to survive the hanging, but the crowd surged forward and pulled on his legs to grant him a quick death and spare him suffering.
Katherine Ferrers

While there were cases of nobles turning to crime after losing their fortunes, rarer were the nobles who robbed while they were still rich.  Katherine Ferrers, in addition to being a noblewoman, was, according to legend, one of the few women to engage in highway robbery.  Allegedly, Lady Ferrers would wine and dine guests at her home and then retreat to bed as they were leaving, only to change her clothes to rob the same guests as they rode home.  Also known as “The Wicked Lady”, she died at the age of twenty-six, allegedly as the result of one of her marks firing on her during a robbery.
Humphrey Kynaston
One of the earliest operating highwaymen on this list, Sir Humphrey Kynaston as another noble who resorted to crime after squandering his family fortune.  He lived and operated primarily in Shropshire at the turn of the 16th Century and had the distinction of never having been caught by authorities.  He was partially aided by the locals to whom he would give some of goods that he had stolen, thus ensuring their willingness to protect him.  The local sheriff also reportedly attempted to stop him by removing planks from a bridge, but Sir Humphrey and his horse Beezlebub simply leapt over them.
Dick Turpin
Perhaps the most notorious highwayman of all, Dick Turpin operated in the 18th Century and entered crime as part of a gang of deer thieves in the 1730s.  He then became part of the Essex Gang that made its living by robbing wealthy homes, but after the authorities broke up the robbers, he turned to being a highwayman.  Turpin was arrested in 1738 for horse theft and hanged in 1739.  While he was certainly legendary within his own time, his later fame was due to the romanticized accounts of his crimes from Victorian author William Harrison Ainsworth, who transformed Turpin from a robber and murderer into a gentleman thief.

About John RabonThe Hitchhiker’s Guide has this to say about John Rabon: When not pretending to travel in time and space, eating bananas, and claiming that things are “fantastic”, John lives in North Carolina. There he works and writes, eagerly awaiting the next episodes of Doctor Who and Top Gear. He also enjoys good movies, good craft beer, and fighting dragons. Lots of dragons.Reader Interactions

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