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Dick Turpin by Steve Jobson

Dandy or thug? Myth-making and the highwayman

Essay | 12 minute read
Violent, notorious, pockmarked, murdering highwayman: who was Dick Turpin and why has his myth endured?

‘I’m the dandy highwayman who you’re too scared to mention,’ cantillates a lustily swash and buckled Adam Ant in the video to 1981’s ‘Stand and Deliver’. And very dandy he is too: gold-trimmed tricorn; red bows fluttering discreetly at the end of unfettered obsidian locks; the trademark faux-native stripe of ivory white across every New Romantic teenager’s most coveted cheekbones. A stage coach is robbed, the passengers relieved of their prudery; Ant grins, fondles the tip of his flintlock pistol and stabs his tightly black-leather clad hips wham bam into the chorus.

Is there an antonym (pun intended) for turning in your grave? What do the deceased do if history has not only forgiven their sins, but gifted them a rather pleasing makeover and rebrand into the bargain?

‘Richard Turpin, a butcher by trade, [is] a tall fresh coloured man, very much marked with the small pox,’ according to a 1735 deposition by John Wheeler, youngest member of the infamous Gregory Gang and the first to crumble under questioning. The gang terrorised Essex properties in the early 1730s, but all were eventually caught, and hanged or deported; Dick Turpin, with his slippery knack for hegira, evaded capture until 1739. Wheeler offers brief but telling physical descriptions of Turpin’s associates, but this testimony is the only information we have about the likeness of one of the most notorious criminals in England’s history.

Derek Barlow, in his essential and exhaustive history, Dick Turpin and the Gregory Gang, tackles this enigma in an appendix, concluding that ‘Turpin was neither drawn, nor sketched, nor painted, during his lifetime’. Of a nineteenth-century engraving falsely purporting to be a portrait first printed in the Tyburn Chronicle of 1742, he allows some interesting creative conjecture:

‘With regard to what in any event must surely be a flattering likeness, the portrait does contain elements of Turpin’s general description which makes one look twice and perhaps wonder … And with another look it is not too difficult to imagine the stippling about the face to be smallpox scars, and the curl of the lower lip to be a reflection of Turpin’s own mean nature.’

Hardly a heartthrob: Turpin was calamitously pockmarked. Given that we know little about him from the historical record outside of his crimes (violent burglary, physical assault, murder), it is tempting, as Barlow does, to make his ugliness a dramatic cypher for his ‘mean’ character. Perhaps the experience of surviving smallpox as a child, and the disfigurement that resulted, contributed to Turpin’s aggressively antisocial relationship with the world. Was he more than just the irredeemable mindless thug of Barlow’s account? Have the last three centuries actually distilled his character, revealing to us the misunderstood dandy within? Well, no. History has been kind, but not honest.

Turpin owes a debt of gratitude to William Harrison Ainsworth’s nineteenth-century romantic novel Rookwood, which rescued his fading legend from the murk of obscurity and thrust it front-and-centre back into the public imagination. Ainsworth’s Turpin is a handsome rogue, a sort of Han Solo of the home counties, whose preoccupations are romantic conquest and feats of gallantry (it was Ainsworth who created the myth of Turpin’s 200-mile overnight ride to York on the equally fictitious but magnificent Black Bess).

The real Richard Turpin was born in Essex in 1705, to a publican of modest means. He was literate, having been taught to read and write by an older boy, James Smith, and entered an apprenticeship as a butcher in his early teens. He either failed in his trade or was seduced by the lure of a more insouciant living, because by the early 1730s he had taken up with venison poachers in Epping Forest. A generous King’s ransom rapidly made the crime of deer-stealing prohibitively risky; Turpin instead embarked on a new, gin-fuelled career as a housebreaker with a loose assemblage of career criminals, led by the unsavoury Gregory brothers. A string of particularly unpleasant burglaries follows. In one, Turpin strips an elderly man of his breeches, pulls him around by the nose and thrashes his bare legs and buttocks; in another, Samuel, the oldest and nastiest Gregory, drags a maid upstairs and rapes her at gunpoint.

Dick Turpin, circa 1754 (Photo by Universal History Archive/Getty Images)

At the height of their infamy, when most of the country would have been aware of the gang’s prolific brutality, the callow informant Wheeler rats on his entourage. Samuel Gregory ends up rotting in a gibbet in Edgware, after being publically executed at Tyburn. He is defiant to the end, behaving in a ‘bold, impudent, senseless manner, talking during the prayers to the people in the cart [and] looking about him at the mob’ according to assizes in the National Archives. He meets his end with equanimity, as is perhaps to be expected from an individual that modern mental health professionals would probably label a sociopath. Details from the assizes of his final moments are chilling:

‘Gregory … showed he had no regard for religion, and as little sense of the crimes he had been guilty of; and what was still more extraordinary, it appeared, that his obstinacy did not proceed from a mad despair, or from being always intoxicated with strong liquors; for when he was carried to the gallows he appeared to be quite sober, and more tranquil than is usually observed in persons just going to submit to fate.’

Turpin escapes, probably to Holland for a year, before returning to England and a new life as a highwayman. Within months there is a bounty on his head; in 1737, Turpin is surprised by a keeper near his hideout in Epping Forest and commits his only murder, setting in motion a series of events which ends with his capture and execution in York in April 1739.

In 1737, two years before Turpin’s death, a man called Richard Bayes was landlord at a Leytonstone pub, The Green Man, which still stands today. The theft of a patron’s horse outside the establishment evidently sparked his interest in Turpin’s criminal career, as Bayes was the author of the highwayman’s first biography, published hurriedly after Turpin’s execution in 1739. He writes:

‘Richard Turpin … was son of John Turpin of Hempstead in Essex, who put him to school to one Smith as a writing master; from thence he was placed apprentice to a butcher in Whitechapel, where he served his time; he was frequently guilty of misdemeanours, and behaved in a loose disorderly manner.’

In this remarkable truncation of childhood, as Bayes greedily races to expose the flaws in Turpin’s adolescent personality, there is a lot we can unpack for dramatic source material if we are looking to piece together the narrative of Turpin’s life. John Turpin’s concern for his son’s education and betterment are rewarded later with imprisonment, after he is caught in a possession of a stolen horse, a gift from his son after months of estrangement. ‘Perhaps by now his father had realised that he could not believe his son in anything but accepted the story as being easier than the lie,’ speculates Barlow. ‘And in September 1738, when he himself was charged with stealing the horse left with him by his son, he may have found it less painful to say that he had bought the horse, rather than that he had accepted it as evidence of that son having put his life of crime behind him.’

A Victorian highwayman, from The life of the late John Mylton by Charles Apperley, or Nimrod. Original artwork drawn and etched by Henry Alken (Photo by Hulton Archive/Getty Images)

When we look at the bare bones of these relationships in situ, we are bound to overreach when looking for motivation and motive – so much of human history is of course unknowable. Nonetheless, I think it is important to engage in these creative speculative leaps in order to breathe empathy back into the stories of people who are dead on the historical page but were once very much alive. Turpin’s life is full of these painful moments, where we wince at the cruelty of his own selfishness or the extraordinary coincidences that appear, in retrospect, to foreshadow his inevitable demise.

James Smith, a friend of the Turpin family, taught Turpin to ‘make letters’ when he was about eleven or twelve years old, according to his recorded testimony at Turpin’s trial. Years later, when Turpin, operating under the alias of John Palmer, is in York Castle awaiting trial for horse-theft in the East Riding of Yorkshire, he writes to his family in Hempstead asking for assistance. By now, Turpin is the most wanted man in the country, after a string of highway robberies and his one cowardly murder. He has fled to the relative obscurity of East Riding and has been apprehended for the repeated theft of livestock. In a twist of fate that seems hand-delivered by some malevolent, theatrical daemon of irony, Smith is present in the post office after the letter is returned unopened by Turpin’s exasperated brother-in-law. Smith recognises the handwriting he himself taught Turpin to indite, and his student’s fate is sealed.

Barlow’s analysis of these circumstances is doggedly forensic, and he even goes as far as intimating that Smith wrote the letter himself, after being made aware of a man in York Castle who matched Turpin’s description. Regardless, Smith subsequently makes the trip to York to identify John Palmer as Richard Turpin. It is hard not to feel a shiver of sympathy for Turpin when we imagine Smith appearing at his cell door. Regardless, this is the unhappy life of an ugly man, punctuated no doubt by brief peaks of adrenalin-driven abandon amidst the troughs of self-hatred and aimless thuggery. Dead at 34, with not a great deal to be proud of. Yet somehow Turpin ends up, two and a half centuries later, at the sharp end of a number one pop record, countless film adaptations, and a successful TV drama series that ran for four seasons between 1979 and 1982, with a cheekily handsome Richard O’Sullivan in the lead role. Again, in the series, it is the Rookwood re-imagining of Turpin that endures, as O’Sullivan rides a glossy Black Bess from one benevolent caper to the next, escaping the gallows (hooray!) at the very last moment.

In truth, we find him in 1739 at York Castle, manacled to the wall of a dingy stone cell. The gaol is now a museum, with Turpin’s original accommodation preserved. Here his life had shrunk from the respective pastoral or hedonistic freedoms of Hempstead, London and East Riding to the merciless encroaching walls of incarceration and regret. After his conviction, he is led to his death to the gallows in the city on a cold crisp April morning. How keenly Turpin’s poor choices must have stung as he was carted through delighted crowds to the place of execution; as he looked up at the three-legged mare, the last horse he would ever ride, through a haze of noise and gin. We’ll never know how he really felt; we peddle the fantasy. It’s a well-worn road in British myth-making. But let’s put these criminals back on trial.

In the dock: the two Kray twins biopics. Peter Medak’s 1990 hyper-stylised music video of a film, with Spandau Ballet’s Kemp brothers pouting their way around East London in slick spray-on suits, reinvents the sixties London gangland brothers as priapic fashion icons; Brian Helgeland’s 2015 Legend, with Tom Hardy playing both roles, pushes back at the narcissism, with Hardy’s face heavy in prosthetics as Ronnie Kray and doubling down on Ronnie’s nasality for comic effect.

Both films bristle with a manufactured and choreographed machismo: the Kemps brawl with their enemies in dimly lit snooker halls and conjure hidden swords from umbrellas in the cloak room; Reggie-Hardy pours himself a slow pint of Guinness in the pub (‘Look at that. Full of iron, that is’) while his tooled-up enemies close in, Ronnie-Hardy lurking unseen behind them, hammer in hand. Both are stagey scenes of bubblegum violence, either startlingly bloodless (Legend) or cocksure gruesome (The Krays). None of it rings true.

Does it matter? Watch both scenes on YouTube, and then finish the troika with a clip of the real twins from a grainy black and white television interview. At one point, Ronnie is asked about London clubland’s reputation for being ‘very tough’ (a more bullish modern-day interviewer might have chosen the less timidly euphemistic ‘vicious and unpoliceable’). Ronnie is soft-spoken, like his brother; they are as well-groomed and polite and butter-wouldn’t-melt as naughty schoolboys seeking re-assimilation in a morning assembly. ‘Well I think most clubs are very respectable,’ deadpans Ronnie. ‘I don’t think there’s any trouble at all in them.’ Then silence, like the measured beat of a stand-up comedian.

‘Except occasionally.’ As menacing as these two must have been in the flesh, they are duller than accountants in a TV studio. Yet drama has shied away from portraying them without irony or vainglory, from showing violence and its victims as they are – the sickening and sad truth of it all, the fear and panic and misery. Ditto train robber Ronnie Biggs, ditto any of the (albeit gripping) adaptations of the lives of serial killers like John Christie or Fred West, ditto burglar, murderer and highwayman Richard Turpin. Perhaps we lose an opportunity here, to force ourselves to empathize with the grimy banality of crime; to say, as all of Shakespeare (via John Bradford) so emphatically does, ‘There but for the Grace of God go I.’

Turpin’s headstone, in St George’s churchyard, Yorkshire (Photo by RDImages/Epics/Getty Images)

It’s not easy to sympathise with a life of self-interested parasitism, but we can surely afford a scintilla of pity for a man who, according to Barlow, fights unsuccessfully to hide his terror from the crowd as he climbs the ladder to the gallows:

‘[Turpin] appears to have been assured, he bowed, and when his leg trembled he stamped it down, then, with bravado, he looked about the crowd and eventually threw himself off the ladder … All things considered, drunk or not, he made a brave enough exit for a man who had no choice in the matter.’

Writers of drama can give a voice back to these infamous dead; we can let them speak again, as flawed and ordinary human beings, rather than as glamorous and totemic outliers headed for anthemic self-destruction. The music commentator Tom Ewing writes that ‘on “Stand and Deliver” [Adam Ant] pitches the costume drama just right – a riot of colour and a tiny hint of danger. Seeing the video I knew this record was more of an Event than anything I’d heard before.’ Pop is one thing, film and television are another, but we are liable to make pop idols of our historic villains when we ignore their warts, their pockmarks, their terrible decisions, their scarred and blemished legacies.

‘I seem to have walked a double path most of my life,’ Reggie Kray once wrote. ‘Perhaps an extra step in one of those directions might have seen me celebrated rather than notorious.’

Alastair Hagger is writing a four-part television screenplay, The Notorious Turpin: The Butcher, The Rake, The Highwayman and The Thief, as part of his PhD practice as research at the University of West London