Your Money or Your Life: 5 Famous Highwaymen Who Lived Fast and Died Young

Illustration of Dick Turpin. WIkipedia

For romanticists and anarchists, highwaymen are the ultimate rebels and outlaws. They had no regard for authority or the law and clearly had no fear of death because the judicial system in that era was a lot harsher than it is today. Men, women and even children were routinely hanged for offenses ranging from burglary to cattle rustling, so highwaymen took their lives in their hands every time they committed a crime.

Those who operated in the ‘classical’ tradition were noble and gallant. Yes, they would steal a person’s valuables, but would exercise chivalry and politeness while doing so. Typically, these individuals would hide in the shadows only to spring forth and hold up stagecoaches before disappearing into the darkness once more. Stories of their tales spread rapidly as newspapers highlighted the crimes and bards composed songs in their honor.

In reality, of course, many of these highwaymen were merely beneficiaries of favorable propaganda. A great number of them were vicious, bloodthirsty creatures with scant regard for human life. These so-called ‘gentlemen of the roads’ usually enjoyed short careers and their lives almost always ended in execution.

Turpin by Adrian Teal. Shakespeares England

1 – Dick Turpin (1705? – 1739)

Richard ‘Dick’ Turpin is arguably the most famous highwayman of all time, but tales of his gallantry are greatly romanticized. Practically every piece of the Turpin legend is a complete fabrication. For example, he did not ride his horse Black Bess from York to London in under 24 hours. The ride in question was completed by another highwayman by the name of Jack Nevison in 1676. It was only at the end of his life while awaiting the hangman’s noose that Turpin exhibited any of the charm he is associated with.

He wasn’t even born in York. Turpin was born in Hempstead, Essex and while we don’t know his date of birth, we do know he was baptized on September 21, 1705. As a young man, Turpin likely followed in his father’s footsteps by becoming a butcher but was apparently guilty of disorderly behavior when serving as an apprentice. Once his apprenticeship was finished, he opened a butcher shop and started stealing sheep and other livestock. When he was caught stealing a pair of oxen, he fled to the countryside.

When he emerged from his hiding place, he tried and failed to become a smuggler. While the legend of Turpin tries to paint him as something of a lone gunman, in reality, he spent much of his career as a member of the Essex Gang. Far from being the polite and gallant thief of lore, Turpin and the gang raided isolated farmhouses and tortured the female inhabitants into giving up their valuables. On one occasion, Turpin forced a woman to sit on an open fire until she revealed the location of her treasure.

By 1735, there was a bounty of £50 on the Essex Gang, an enormous amount of money at the time. Local constables caught two members, but Turpin narrowly escaped. He teamed up with swashbuckling highwayman Tom King and from their lair in a cave in Epping Forest; they stole from anyone who passed by. By 1737, there was a bounty of £100 on Turpin’s head, and when a gamekeeper tracked him down in the forest, Turpin killed the man after an altercation.

Turpin stole a horse from a man called Major who responded by sending out leaflets asking for the thief’s capture. The horse was traced to a pub called the Red Lion, and the police were alerted. King came to collect the horse but was arrested by local constables. Turpin heroically arrived on the scene and shot at the police. Unfortunately, he was a terrible shot, and his bullet hit King! His one-time accomplice died soon after but not before revealing information that forced Turpin to hide once again.

He lived under the fake name John Palmer and lived in Yorkshire where he spent his time stealing livestock to fund a lavish lifestyle. One day, he shot his landlord’s chicken, and when the angry man confronted the outlaw, Turpin threatened to kill him. Turpin was arrested, and tales of his cattle rustling activities came to light. He wrote a letter to his brother asking him to provide evidence as to his good character. Unfortunately for Turpin, his brother was a cheapskate who refused to pay for postage and returned the letter to the Post Office. Turpin’s former schoolmaster saw it and recognized the handwriting.

The schoolmaster rode to York and identified Turpin who was sentenced to death. On April 7, 1739, Turpin went through the streets of York and bowed to those who were to witness his execution. He was hanged, but it was during his final day that he showcased the heroism that eluded him during the rest of his life. His legend grew after his death thanks to the work of Harrison Ainsworth who wrote a book with Turpin as a secondary character. However, his exploits captivated readers, and a myth was born. Incidentally, Turpin is NOT buried in York alongside Black Bess.

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  • Will

    If you didn’t limit yourself to Europe the Australian bushrangers and American road agents make some good options.