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Culture: Two British Highwaymen Who Stole More Than Just Business Letters


You’d imagine that the words “Stand and deliver!” would be uttered from the mouth of a thoroughly gallant, exuberantly handsome and well-groomed gentleman, whilst sitting on horseback, pistol in hand, eyes hidden behind a mask, and smiling broadly, while relieving carriage passengers of their belongings.

But, really, the truth of the matter is far from this image, and these men (occasionally women) were in-the-main simplistic criminals with little to no other talents for which to earn them a daily crust.

Lady Katherine Ferrers


1634 – 1660

Our Lady Katherine Ferrers married at a young age of either 12 or 14, according to accounts. Her husband, Sir Thomas Fanshaw, was merely 16. The couple resided at the Ferrers’ home in Hertfordshire, and it’s been widely portrayed that our Lady Katherine was a bit on the loopy side – insane.

Little did her husband know it, but Lady Katherine was focused on robbing his dinner guests, once they’d left the confines of his rather stately home. Thus, amicable hostess by evening, she would then retire to her chambers whilst their guests left. Next, she would quickly trade over her fanciful dress for black pants, mask, and dark cloak of a highwayman.

She’d mount up on her black horse, and off she’d go into the dark of the night to rob those very same individuals she’d been dining with just half an hour beforehand. And it was not merely the contents of 10 business envelopes she was intent on.

One night, while she was out partaking in her secondary occupation, she met with a farmer by the name of Ralph Chaplin. As it happens, his nighttime pastime was of a similar ilk to our lady Katherine’s. They teamed together for a while, but after a time, he was caught by the law, as it was then, and unceremoniously hanged by the roadside.

Katherine’s career was relatively successful, however, one night, when she was out preying on the unsuspecting, a wagon passenger shot her. She managed to return to her family estate before she passed away at the age of 26.

As it happens, upon her death, it was not merely the mysterious nighttime robberies that ceased, but cows were no longer being shot dead as they stood in their fields, and the fires that had regularly been breaking out also ceased. Further, no other innocent parties were shot and killed on their own property by an unseen, mysterious assailant.

None of the crimes were directly connected to Katherine, though the locals believed it was she who was responsible. She was buried at St. Mary’s Church in Ware, England, on June 13, 1660.

Dick Turpin

1705 – 1739

Mr. Turpin is undoubtedly one of, if not the best known of Britain’s and Europe’s highwaymen. And yet, he’s arguably the worst example of the concept of what a gentlemanly highwayman was supposed to be.

Dick Turpin was born in Essex in 1705. He could have followed in his father’s footsteps as a butcher, but apparently, he wasn’t cut out for the work. Thus, instead, he opted to join a local gang, and began to raid houses in and around the London area. The gang stole whatever they could, and then destroyed what remained.

Turpin was one of the final gang members to be caught. He’d moved on from stealing from homes to holding up carriages that were on their way either to or from London.

As you’d perhaps expect, many of the tales surrounding Turpin are pure fantasy. He was said to be dashingly handsome; his horse was said to be beautiful and unceasingly devoted to him. And so forth.

But the truth of the matter is that Turpin was nothing but a cold-hearted murderer, who was frequently privy to egotistical boasting, and this is what finally led to his downfall.

Once he’d been trialed and executed for his crimes in 1739, Turpin gained fame as a gentleman highway robber through an 1834 publication of a book called Rockwood. Nevertheless, perhaps a bit more fitting to his life was the fate of his corpse.

On the very same night that he was buried, his body was dug up by grave robbers, who then proceeded to sell the corpse to a local doctor for dissection, as was relatively common practice of the time. His body was discovered and reburied, and the doctor, or surgeon, if you will, was fined.


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Robert D. Cobb
Founder, Publisher and CEO of INSCMagazine. Works have appeared and featured in places such as Forbes, Huffington Post, ESPN and NBC Sports to name a few. Follow me on Twitter at @RobCobb_INSC, email me at [email protected]

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