16 Highway Robbers So Bad They Made it Into the History Books

16 Highway Robbers So Bad They Made it Into the History Books

Natasha sheldon - December 17, 2018

Highwaymen were the robbers of the road, audacious mounted thieves who famously waylaid their victims with the cry “stand and deliver.” Most people have heard of famous highway robbers such as the infamous Dick Turpin. However, many other highway robbers remain relatively unknown. These little-known highwaymen- and women spanned many time periods and countries. Their lives, while relatively obscure, were often audacious and violent. They could also be comic- and even sad. Here are sixteen of the strangest, funniest, bloodiest and most tragic tales of lesser-known highway robbers.

16 Highway Robbers So Bad They Made it Into the History Books
Portrait of Mary Frith (Moll Cutpurse) Wellcome Collection gallery (2018-04-01): https://wellcomecollection.org/works/ma2yxpfh CC-BY-4.0

16. Mary Frith: aka “Moll Cutpurse”- Who reputedly took up Highway Robbery in her Fifties

Mary Frith or Moll Cutpurse was a thief, crossdresser, and ardent royalist who took to the road in her late fifties to rob: “Roundheads, or rebels, that fomented the Civil War against King Charles I.” Moll turned to a life of crime in her teens when in 1600 she was indicted for stealing 2s 11d. She earned her name ‘cutpurse’ when she moved on to stealing purses from passers-by and was burnt “in the hand” four times for theft. Later in life, Moll fenced stolen goods- and was a madame. Such was Moll’s success from crime; she was able to buy an upmarket townhouse and employ three maids.

When the English Civil War broke out, legend says Moll took to the road to avenge the wrongs done to Charles I- aided by the fact that she already routinely dressed and behaved like a man, drinking, smoking, and fighting. The authorities reputedly arrested her after she robbed the Roundhead General Fairfax of“Two hundred and fifty jacobuses on Hounslow Heath”-but not before she shot Fairfax in the arm and killed two of his servant’s horses. However, Moll escaped the noose by paying a £2000 bribe and completing a stint in Bedlam, which she left in 1644.

16 Highway Robbers So Bad They Made it Into the History Books
“Engraving of Captain James Hind.” Source: National Portrait Gallery. Wikimedia Commons. Public Domain.

15. Captain James Hind: The Royalist who robbed Cromwell.

Moll Cutpurse was not the only person to take to highway robbery as a way of supporting Charles I. During the 1650s, the antics of Captain James Hind appeared in at least 16 printed pamphlets as he took to the road, robbing roundheads linked to the death of Charles II. Amongst his victims was Hugh Peters, the Puritan preacher who had advocated Charles’s death and even prayed at his execution- and Oliver Cromwell himself. The Lord Protector was on his way to London with a guard of seven men when Hind and his partner Thomas Allen accosted them. The soldiers took Allen during the scuffle, but Hind escaped.

Despite having such prominent roundheads at his mercy, Hind did not kill any of them. Indeed, the Newgate Calendar noted that “never was highwayman more careful than Hind to avoid bloodshed.” In 1651, he abandoned robbery to join the royalist army of King Charles II in Scotland where he became a Captain. However, after Parliament’s forces once again defeated the Royalists at Worcester; a friend betrayed Hind. On September 24, 1652, he was hung, then drawn and quartered for treason. Hind stood resolute in the face of his awful death, expressing no remorse and plenty of pleasure for the fact that, for a time at least, he had the Roundheads at his mercy.

16 Highway Robbers So Bad They Made it Into the History Books
Bill Henderson / Nevison’s Plaque, Nevison’s Leap, Ferrybridge Road, Pontefract. / CC BY-SA 2.0

14 “Swift Nick” Nevison: The Highwayman who escaped jail by Faking the Plague.

William “Swift Nick” Nevison earned the name ‘Swift Nick” after making a 200-mile dash from Kent to York in record time so he could establish an alibi for a robbery he had committed. In 1661, after robbing a wealthy grazier of a small fortune, he retired from the road and returned to his home in Pomfret, Yorkshire to make up with his father. However, after the old man died and the money ran out, Swift Nick returned to his old ways- until he was captured during a robbery in Leicestershire and sentenced to hang.

Nevison was kept chained under close guard at Leicester jail. He suddenly fell ill, and his friends summoned a doctor who diagnosed a ‘pestilential fever”. Nevison moved to a private cell and jailers gave him a wide birth, while the doctor was left to nurse him back to health for the gallows. However, Nevison grew worse and died- and the jailers were only too happy to let the doctor take the body, which was covered with plague sores. However, not long afterward, Swift Nick was back on the road. Some initially believed him to be a ghost- until they realized Swift Nick’s illness had been nothing more than a cunning plan to escape.


16 Highway Robbers So Bad They Made it Into the History Books
The Magpie on the Gallows by Pieter Brueghel the Elder, 1568. Wikimedia Commons. Public Domain

13. Joan Philips: The Female Half of a Seventeenth Century “Bonnie and Clyde”

Joan Philips was the daughter of a respectable Northamptonshire farmer, who could have had any man she pleased. However, Joan rejected them all in favor of petty thief Edward Bracey. Bracey had initially been after Joan’s dowry and planned to abandon her once he got hold of the cash. However, he soon discovered that Joan was more than his match. The couple robbed Joans father and made off with the loot for their happily ever after a life of crime. They never married but lived and worked together, robbing on the highway until they brought an inn in Bristol with their ill-gotten gains.

After a year, the Braceys were back robbing the highway. In 1685, their luck finally ran out. Joan was captured during the robbery of a stagecoach, and shortly afterward, William died of a pistol shot while resisting arrest. Joan meanwhile was tried at Nottingham and sentenced to hang. Legend says Joan Philips met her end down Wilford Lane, close to the place she fell. However, it could be this seventeenth century Bonniemay not have existed at all. For historians can find little evidence of Joan Philips the highway woman and certainly no mention of her hanging down Wilford Lane or anywhere else.

16 Highway Robbers So Bad They Made it Into the History Books
Des voleurs attaquant des voyageurs dans une gorge de Montagnes by Philip James de Loutherbourg. Picture by Ji-Elle. Wikimedia Commons. Creative Commons Attribution-Share Alike 3.0 Unported license.

12. Jocelin Harwood: The Highwayman who was so wicked, his fellow thieves betrayed him to the law.

Jocelin Harwood nearly lost his life on his very first highway robbery when his victims shot the horse from under him. However, the setback left Harwood undeterred, and for the next few years, he enjoyed an unremarkable highway career. In 1692, when he was just twenty-three, Harwood learned of a Shropshire gentleman, Sir Nehemiah Burroughs, who had a fortune worth of plate in his house. So, with two accomplices, Harwood decided to try his hand at burglary. The gang tied up the servants and Sir Nehemiah and his wife. Then, Harwood made his way to the room of the Burroughs’s daughters.

As Harwood was tying the young ladies up, one of them was foolish enough to ask Harwood to be gentle. In return, she promised not to identify Harwood if he was arrested. “Shall you so? “said Harwood, “I’ll take care then to prevent your doing any mischief. “He then proceeded to murder both girls, “cut[ing] them both in pieces.” Then, he returned to the bedroom of Sir Nehemiah and his wife and killed them too. According to the Newgate Calendar, Harwood’s accomplices were horrified and quickly hatched a plot to expose Harwood ” to justice.” So they overcame Harwood, tied him up and left him with a piece of incriminating evidence. Harwood hung while his accomplices made it to safety with the loot.

16 Highway Robbers So Bad They Made it Into the History Books
The Robber Punished by Sebastiaen Vrancx. Wikimedia Commons. Public Domain.

11. Tom Rowland: The Highwayman who committed Robbery Disguised as a woman.

Tom Rowland robbed the roads of England for an impressive eighteen years. However, what made his robberies notable was that he carried them out in full female costume- even riding side-saddle. Indeed, Rowland only ever switched to ride a stride if he needed to make an unusually swift get away. Rowland was finally caught in 1699 when he was apprehended robbing a person on Hounslow Heath of £1200 worth of bone lace. The court condemned Rowland to death and his execution scheduled for October 24, 1699.

Because of his success on the road, Harwood was able to pay for good, private quarters while in prison. On the morning of his execution, the Newgate Calendar noted with some disgust that his money even brought him a few hours ‘entertainment’ with a prostitute. Some have suggested that Rowland only dressed as a woman to hide his identity-which could well have worked as it certainly explains his long career. However, the sheer impracticality of female clothing suggests this isn’t the whole story. Could it be that Rowland dressed as a woman because he enjoyed it?


16 Highway Robbers So Bad They Made it Into the History Books
“The permanent gallows at Tyburn.” c 1680. The National Archives. Wikimedia Commons. Public Domain

10. John Smith: The Unsuccessful Highwayman who only lasted one week.

Twenty-three-year-old wigmaker John Smith had tastes that far outstripped his income. So, on October 29, 1704, Smith and an accomplice decided to earn some extra cash through part-time highway robbery. Firstly they needed a horse. So they staked out the road close to the Tyburn gallows while they waited for a likely mount. The location spooked Smith who suddenly had a premonition that Tyburn was the place he would end his days. However, his companion talked him round and the pair soon successfully ‘acquired’ a grey mare from a Mr. William Birch.

So began a successful week of robberies for Smith. Then, on November 6, a passing gentleman and his servant interrupted Smith mid-robbery. They drove Smith into the woods- and set up the hue and cry. Soon, seven or eight local people had flush out the beleaguered Smith and captured him at gunpoint. The mob searched Smith and found the stolen goods upon his person. On December 20, 1704, Smiths premonition came true when he hung at Tyburn. However, before his death, he blamed his downfall not on his inexperience- but his horse. The mare, was a ‘jade,’ Smith complained, too worn out and broken to be of much use to a would be highwayman.


16 Highway Robbers So Bad They Made it Into the History Books
Asalto al coche by Francisco Goya. c. 1786. Wikimedia Commons. Public Domain.

9. Jack Ovet, the Lovelorn Highwayman of Nottinghamshire

Cobbler Jack Ovet had aspirations to be a gentleman highwayman. So he gave up shoemaking and took to the road instead. Ovets career was reasonably successful if unremarkable-until the day he robbed the Worcester stagecoach. On board were several young ladies who Ovet robbed with characteristic courtesy. However, one of his victims captivated him and stole his heart. “Your charms have softened my temper, and I am no more the man I was.” Ovet reputedly told her as he purloined her valuables. However, Ovet vowed that he would pay the lady back- if she would give him her address!

Remarkably, the lady complied. A week later she received a letter from Ovet – not to return her money but to propose! “Though I lately had the cruelty to rob you of twenty guineas, yet you committed a greater robbery at the same time in robbing me of my heart.” declared Ovet. He asked his ladylove to send him her answer. The lady, however, was not seduced-and more than a little annoyed that Ovet had not returned her money. She declined Ovets proposal- and told him she looked forward to his death on the gallows. The heartbroken highwayman was captured not long afterward, and on May 5, 1708, his ladylove got her wish.

16 Highway Robbers So Bad They Made it Into the History Books
Juraj Jánošík (1688-1713), a Slovak Carpathian Highwaymen – detail of a statue in the Smetana Park in Hořice, Jičín District, the Czech Republic. Sculptor: Franta Úprka. Picture Credit: Jirka23. Wikimedia Commons Creative Commons Attribution-Share Alike 3.0 Unported, 2.5 Generic, 2.0 Generic and 1.0 Generic license.

8. Juraj Jánošík: The Slovakian Robin Hood

Late seventeenth, early eighteenth century Slovakia was a place of great social instability and injustice. As a result, some people became outlaws- from necessity or choice. Juraj Janosik was one of them. The son of peasant farmers, Janosik was serving as a prison guard when, he met the man who changed his life, Tomas Uhorcik, the leader of a notorious gang of outlaws. Janosik and Uhorcik struck up an unlikely friendship and when they met again several years later, Uhorcik having escaped prison and Janosik having resigned from the army, they banded together to undertake their first raid, stealing a cargo of canvas from a wagon.

When Uhorcik left to marry, Janosik was in sole charge of their gang. He instigated a change in direction, turning the gangs attention from modest carters to robbing wealthy merchants and aristocrats. Janosik also shared his loot with local people, who showed their gratitude by hiding the band from the law. However, in 1711, Janosiks career ended abruptly when soldiers captured him during a visit with Uhorcik. On March 17, 1713, aged just 25, Juraj Janosik was hung from a hook in the Slovak town of Liptovsky Mikulas. The Slovak people immortalizing him as a national hero because of his generosity- and his stand against authority.

16 Highway Robbers So Bad They Made it Into the History Books
Seascape with Sailors Sheltering from a Rainstorm by Bonaventura Peeters, the Elder. Wikimedia Commons. Public Domain

7. Jack Blewitt: The Soldier, Sailor, and Slave who become a Highway Robber.

Jack Blewitt never enjoyed much luck. He converted to Catholicism in an attempt to gain promotion in the army of King James II- only for the Protestant William of Orange to oust the Catholic King. Next Jack tried his luck at sea. He joined a slaver bound for Nigeria and was sent ashore to trade leftover copper bars with the locals- only to be overcome and enslaved himself. Blewitt spent the next 14 months passing from master to master until his final owner ransomed him to an English ship. Finally, back in England, penniless and without prospects, Blewitt decided to turn to highway robbery.

Blewitt stole a horse-only only to realize it was useless to him without pistols. So he took his mount to Smithfield market, intending to sell it and steal another later. However, the horse’s original owner spotted the creature, and before the day was out, Jack Blewit found himself in Newgate Prison. For a time his luck turned, and a sympathetic judge spared him. Once out of prison, Jack took to highway robbery once more. However, Jack Blewits meager luck finally ran out in 1713 after he killed a farmer’s daughter for £14. Blood splatters on his coat identified Blewit as the murderer, and he hung in the town of Hereford.

16 Highway Robbers So Bad They Made it Into the History Books
Photograph of St Eunan’s Cathedral, Raphoe, Co. Donegal, Ireland. Picture Credit: JohnArmagh. Wikimedia Commons. Creative Commons Attribution-Share Alike 3.0 Unported license.

6. Philip Twysden: The Bishop turned Highwayman.

Philip Twysden was a member of a respectable Kent dynasty and the Bishop of Raphoe in Ireland. In 1752, he died mysteriously after being taken ill on Hounslow Heath. His family gave out the story that Bishop Twysden had died of an inflammation of the bowels. However, a rumor began to spread that the bishop had died of a pistol shot, acquired when he was out robbing passers-by on Hounslow Heath. According to nineteenth-century English writer and politician, Grantley Berkeley, Bishop Twysden was “found suspiciously out at night on Hounslow Heath and was most unquestionably shot through the body,” by none other than one of his own brother’s dinner guests, returning home!

Understandably, the Twysden family wanted to hush up such a shameful death. But why would a bishop be driven to highway robbery in the first place? Money troubles are the explanation given by Ronald and Christopher Hatton. The Twysden family fortunes were already on the wane because of the spendthrift habits of the bishop’s grandfather. The bishop’s father had attempted to mend the family fortunes. However, it was not enough to help Philip Twysden who, not long before his ignominious death, had been declared bankrupt after spending the family’s savings in London. Perhaps, like so many others, Bishop Philip Twysden saw highway robbery as a solution to his money troubles.

16 Highway Robbers So Bad They Made it Into the History Books
The execution of Robespierre and his supporters by guillotine. Wikimedia Commons. Public Domain

5. Nicolas Jacques Pelletier: The French Highwayman who was the first person executed by Guillotine.

In November 1791, Frenchman Nicolas Jacques Pelletier committed his last crime, a highway robbery in Paris. Pelletier and his gang waylaid a traveler along the Rue Bourbon-Villeneuve and robbed and murdered him. The crime was public, and locals quickly raised the hue and cry was quickly raised. Pelletier’s accomplices escaped. However, Pelletier was captured, tried and condemned to die – a sentence that was ratified by three separate courts. Pelletier’s punishment was due to be carried out on December 31, 1791. However, it was delayed because the newly appointed National Assembly was looking for a quick, clean method of execution applicable to rich and poor alike.

So, while Pelletier spent three months anticipating his execution, surgeon Antoine Louison oversaw the construction of the first guillotine in Strasburg. The official executioner, Sanson then tested the machine, using live animals before moving onto human corpses. On March 23, 1792, the National Assembly signed off the guillotine and on April 25, 1792, Pelletier became its first victim. A large crowd had assembled, curious to see what manner of death the ominous contraption set up on the scaffold could inflict. Sadly, it was less spectacular than they hoped. Pelletier was quickly despatched, immediately rousing several disappointed members of the crowd to call out “Give me back my wooden gallows,”

16 Highway Robbers So Bad They Made it Into the History Books
Dick Turpin. Wikimedia Commons. Public Domain

4. George Davenport: The Leicestershire Highwayman who cheated the Hangman.

When frame knitter George Davenport turned to a life of crime, he preferred to remain in his home county of Leicestershire rather than head for the bright lights of London. After cutting his teeth on fraud and deserting from 40 army regiments, Davenport joined the army properly and fought in the American war of Independence. However, once his army career was over, he returned home to Wigston and took to the roads of Leicestershire. Here, Davenport became something of a local hero as he was known to prey only on the wealthy and, like Robin Hood, shared some of his ill-gotten gains with the local poor.

No one would betray George Davenport- although Davenport himself often courted capture. One evening, he was drinking in an inn when he saw a poster offering a reward for his arrest. “I am George Davenport, catch me if you can” he announced to the astounded drinkers, hightailing it off the premises before anyone could follow. In August 1797, Davenport was finally captured and sentenced to hang at Red Hill Gallows. However, he had to have the last laugh. Hangmen could claim any of the possessions of the executed criminal found “outside the shroud”. So, to cheat the hangman of his due, Davenport went to his death wearing his shroud over his clothing.

16 Highway Robbers So Bad They Made it Into the History Books
Robert Snooks’ gravestone, Boxmoor, Hertfordshire, UK. Picture Credit: Rob Farrow. Wikimedia Commons. Creative Commons Attribution-Share Alike 2.0 Generic license.

3. Robert Snooks: The Last Person in England Hanged for Highway Robbery

By the early nineteenth century, highway robbery began to die. However, some still tried their luck on the road- probably because if caught, offenders were more likely to be transported than hung. The last man executed for highway robbery was James Robber or RobertSnook, who met his end on March 11, 1802, on desolate Boxmoor Common in Hertfordshire. On May 10, 1801, Snook stole six leather bags of letters and bank and promissory notes from the mail coach. Theft of the post was a serious offense because it threatened the commercial interests to the country.” Sothe Postmaster General added a £200 reward to the standard £100 offered by the Parliament for the apprehension of highwaymen.

It was a broken saddle girth left behind at the scene of the crime that several people had seen Snook trying to mend earlier that day, that identified Snook as the thief. He was captured during another robbery, and convicted because he used one of the stolen banknotes to purchase some cloth. Snook was sentenced to hang. He met his end bravely. While taking his final drink at a local pub, he joked with spectators hurrying to see him die “Its no good hurrying-they can’t start the fun until I get there.”

16 Highway Robbers So Bad They Made it Into the History Books
Picture of a highwayman. Wikimedia Commons. Public Domain.

2. Michael Martin aka Captain Lightfoot, The Last New England Highwayman

In 1816, twenty-year-old Michael Martin of Conahy, County Kilkenny had a chance encounter that changed his life. Martin met a man he thought was an Anglican vicar in a pub. The pair got drunk together and the vicarcoaxed Martins life story from him. The next morning, the vicar revealed himself to be none other than John Doherty, aka Captain Thunderbolt, Ireland’s most famous highwayman. Doherty was impressed by Martin’s exploits and his apparent resourcefulness and offered to take the young man under his wing. So Martin adopted the name “Captain Lightfoot” and took to the road with Doherty.

However, after three years there was nowhere left to hide. In 1819, the pair separated, and Martin boarded a ship for a new life in America. Martin tried to turn over a new leaf. However, when he found himself in debt, Captain Lightfoot returned to the road. Lightfoot’s enjoyed many American adventures, including escaping with his life from twenty Native American braves after he robbed their chief. He even reset his own dislocated his shoulder in a barn using his cravat and suspender while fleeing a mob after his final robbery in Medway. However, on this occasion, he was caught and in December 1821 became the last man to hang for highway robbery in New England.

16 Highway Robbers So Bad They Made it Into the History Books
Wood engraving of Australian bushranger Dan Morgan by Samuel Calvert, 1864. Wikimedia Commons. Public Domain.

1. ‘Mad’ Dan Morgan: The Unstable Australian Bushranger who held up landlords and helped their employees.

“Bushrangers” were the highway robbers of the Australian outback and Mad Dan Morgan was one of the most notorious. In 1860, Morgan absconding from a ticket of leave after being released early from a twelve-year sentence for highway robbery. He headed into the bush and began work as a station hand. However, Morgan just couldn’t stick at honest work. In August 1860, he stole a horse from his employers and escaped into western New South Wales where he began his criminal career in earnest, robbing bush stations and coaches.

By 1864, Morgan had a £1000 price on his head for the murders of Henry Baylis, a police magistrate, police Sergeant, David Maginnity and overseer John Mclean. However, Morgans victims were usually exploitative landowners. Morgan delighted in forcing them to make amends to their workers. However, he was also erratic and unstable, and just as likely to kill his victims on a whim as he was to toy with them. It was this behavior that earned him the name “Mad Dan”. Mad Dans reign of terror ended in 1865 when he was shot from behind while fleeing a botched robbery at the Peechelba Station near Wangaratta, Victoria. After his death, ghoulish souvenir hunters harvested his characteristic long black locks and beard.


Where Do We Get This Stuff? Here are our Sources:

Juraj Jánošík, Legendary Slovak Thief Turned Hero, Lucia F, Slavorum

Juraj Janosik, Dr.Jana Kurucárová, tikzilina.eu

1652: Captian James Hind, Royalist Highwaymen, Headsman, Executed today, September 24, 2008

The Newgate Calendar, Vol 1, Ed. Donal Ó Danachair, Ex-Classics project, 2009

The Newgate Calendar: Comprising Interesting Memoirs of the Most Notorious Characters Who Have Been Convicted of Outrages on the Laws of England Since the Commencement of the Eighteenth Century; with Occasional Anecdotes and Observations, Speeches, Confessions, and Last Exclamations of Sufferers, Volume2, Andrew Knapp and William Baldwin, J Robins and Company, 1825

The Annual register, Longmans, Green, 1800

The Little Book of Leicestershire, Natasha Sheldon, The History Press, 2017

Joan Philips, Highwaywoman, West Bridgeford and District Local History Society.

Watling Street: Travels Through Britain and Its Ever-Present Past, John Higgs, Hachette UK, 2017

Notes on the Family of Twysden and Twisden, By Ronald G. Hatton, C.B.E., D.Sc., F.R.S., and the Rev. Christopher H. Hatton, O.S.B., Archaeologia Cantiana Vol. 58 – 1945 page 46. Kent Archaeological Society.

Highwaymen: capture and punishment, The Gazette: Official Public Record.

Nicolas Jacques Pelletier, Wikipedia.

The Guillotine’s First Cut, Christopher Klein, History, April 25, 2012

Robert Snooks, Wikimedia Commons.

Snook’s Grave, Boxmoor Common, Hertfordshire, Paul Grantham, The Granthams, February 17, 2004

Thunderbolt and Lightfoot, the highwaymen who raised hell in New England, Eoin Butler, The Irish Times, January 28, 2017

Lightfoot and Thunderbolt – The Last New England Highwaymen, The New England Historical Society.

Morgan, Daniel (Dan) (1830-1865), John McQuilton, Australian Dictionary of Biography, 2005

Morgan the Bushranger, The Argus. Melbourne. 14 April 1865. p. 6. via National Library of Australia, 2012

Mary Frith, 17th-Century London’s Smoking, Thieving, Foul-Mouthed “Roaring Girl”, Mental Floss, October 31, 2018