The Worst Of History: Dick Turpin

“I spend my cash on looking flash and grabbing your attention” is the opening line of ‘Stand And Deliver’ by Adam & The Ants. In the modern era, the highwayman has been romanticised beyond reality, with these street thugs seen as suave and classy individuals despite their status as criminals. Of these, one of the most famous is Dick Turpin — often portrayed as an honourable countryside anti-hero but in reality a murderous felon who ruined the lives of many.

Life & Crimes Of Dick Turpin

By the mid-1730s, Dick Turpin had become a known name in the criminal underworld, joining the notorious Gregory Gang, an Essex-based conglomerate of tyrants.

Turpin began in the butchers’ trade, illegally selling stolen game and poaching for meat. When suspicions grew, he fled, abandoning his wife and falling deeper into crime with the gang. As author Stephen Basdeo noted in Essex Live, “They certainly did steal from people around Epping Forest but… rarely robbed people on the road. Contrary to popular myth, they rarely stopped stagecoaches. They were pretty cowardly and went for lone travellers.”

It is even thought Turpin killed his partner Matthew King during a botched robbery before escaping the scene.

Brutality Behind The Myth

Turpin’s crimes were barbaric. One notorious incident saw him beat a 70-year-old farmer with a pistol and pour boiling water over his head until he revealed where his money was hidden, while another gang member raped a housemaid. Their takings from the ordeal amounted to just £30.

A famous illustration of Turpin throwing a lady into a fire. (Photo courtesy of History Collection)

At 26, Turpin himself was riddled with smallpox, leaving him disfigured. In May 1737, he shot and killed Thomas Morris, a man attempting to capture him in Epping Forest.

The Gentleman’s Gazette described him as:
“About Thirty, by Trade a Butcher, about 5 Feet 9 Inches high, brown Complexion, very much mark’d with the Small Pox, his Cheek-bones broad, his Face thinner towards the Bottom, his Visage short, pretty upright, and broad about the Shoulders.”

Capture & Execution

Living under the alias John Palmer, Turpin carried on with theft and violence, even shooting animals — then a capital crime. His downfall came when he wrote to his brother-in-law. The postmaster recognised Turpin’s handwriting from his school days and reported him.

Found guilty of horse theft, Turpin was sentenced to hang. On the day of execution, he dressed in new clothes and paid onlookers to attend so he would not face the humiliation of an empty crowd.

He was executed by slow strangulation, his body left on display at the gallows. The New York Times later remarked in 1910 that it was “a source of no little satisfaction to know that the notorious English criminal was properly hanged for his deeds.”

Reinventing Turpin

After his death, Turpin’s legend might have faded into obscurity, but 19th-century literature revived his name. William Harrison Ainsworth’s 1834 novel Rookwood painted Turpin as a sympathetic outlaw, complete with invented stories such as his fabled overnight ride from London to York on his horse, Black Bess.

This romantic reinvention was eagerly picked up by penny dreadfuls and later by poetry, most famously Alfred Noyes’ The Highwayman (1906).

A lively and colourful depiction of Dick Turpin (Photo courtesy of Blackheath and Greenwich History Pod)

Pop Culture & The Highwayman Image

Songs like ‘Whiskey In A Jar’, ‘Stand And Deliver’, Jimmy Webb’s ‘Highwayman’, and traditional folk ballads have cemented the image of highwaymen as glamorous rebels rather than violent criminals. Comedy and pop culture have played their part too — with portrayals ranging from Carry On, Dick to Noel Fielding’s upcoming take on the character.

One of the reasons Dick Turpin and his kind are remembered so fondly is thanks to folk music. Whiskey in the Jar is an old Irish ballad about a highwayman who robs a wealthy official, only to be betrayed by his lover. The song doesn’t name Turpin, but it plays into the same archetype: the dashing rogue living fast and dying young.

Over the centuries, that romanticised idea of the highwayman bled into popular culture. By the time Thin Lizzy electrified the ballad in the 1970s, and Metallica turned it into a heavy metal anthem in the late 1990s, the real brutality of men like Turpin had long been forgotten. Instead, the image stuck: bold, fearless, and oddly sympathetic outlaws — a far cry from the violent truth.

The Reality We Ignore

Turpin’s popularity today largely stems from the fact that he was executed for horse theft — a crime that later came to seem trivial. Yet this sanitises the truth of his brutality. He was not a Robin Hood figure but a violent thug who beat, tortured, and killed.

As History Extra put it:
“The image is a wildly romanticised fallacy but continues to transform brutish killers into ‘gentlemen of the road’.”

And as History Press concluded:
“Now many years on we are far removed from his evil deeds, and so choose to gloss over them in favour of a more palatable version of historic events – for tourism’s and legend’s sake.”

The Worst of History: Series Recap

For now, this marks the end of our Worst of History series. We’ve travelled through centuries of cruelty, disaster, and devastation — from ancient horrors to modern atrocities — highlighting some of the darkest chapters humanity has endured (and sometimes inflicted).

While this may be the stopping point for the moment, here’s everything we’ve covered so far: