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Jerry Abershawe depicted in a cigarette card from the 1920s

Stand and deliver! Britain's most famous highwaymen and women

Image: Jerry Abershawe's cigarette card as part of Lambert & Butler pirates and highwaymen series from the 1920s | Public Domain

The pages of British history are packed full of the exploits of convicted criminals - from murderers and pirates to gangsters and robbers. In fact, some of these felonious figures even became folk heroes, such as Robin Hood and Dick Turpin. Hood and Turpin were highwaymen - thieves who specialised in robbing travellers.

Known as the ‘gentleman of the road’, in the 17th and 18th centuries highwaymen were considered to be at the top of the social hierarchy of criminals, with footpads (muggers) below them and pickpockets being the lowest of the low.

Here we look at seven of the most famous British men and women ever to demand, ‘Your money or your life!’ from their victims.

1. Humphrey Kynaston (d. 1534)

Born in Shropshire to a noble family and brought up in a castle, Kynaston has gone down in history as something of a Robin Hood figure.

But he wasn’t known as ‘Wild Humphrey’ for nothing. Said to be a hellraiser, the volatile young gent soon landed himself in hot water when he was convicted of murder and outlawed in 1491.

From his new home and base, a cave deep in the Shropshire countryside, he spent the next three decades robbing the rich and giving to the poor (reputedly). It was said, too, that if Humphrey saw two carts on the road, one with three horses and the other with one, he’d take it upon himself to make sure they left with two horses each.

Local authorities tried many times to snare him, but Humphrey and his horse, Beelzebub, always got away. After being pardoned by the king in around 1518, it is said that he died peacefully about sixteen years later.

2. Katherine Ferrers (1634-1660)

Though born into a wealthy family, Hertfordshire noblewoman Katherine Ferrers, immortalised in film and literature as the ‘Wicked Lady’, supposedly fell on hard times after her marriage and was obliged to take up highway robbery. According to legend, the filching Lady Ferrers held up countless road users in Hertfordshire, particularly around Nomansland Common, just north of St Albans, where a pub now bears her moniker.

Said to slip in and out of her mansion at night by a secret staircase, Ferrers was also reputed to have slain a constable.

On Nomansland Common in June 1660 the villainous Kate carried out her last stick up – but it went wrong, and she was shot, haring off into the night on her horse, mortally wounded. Her body was found by her servants the next day.

3. John Nevison (1648 - 1684)

Seventeenth-century mounted mugger John Nevison’s fame has endured so much that in 2009, a blue plaque was erected at the site of his arrest in Wakefield.

Born near Doncaster and operating out of Newark, Nottinghamshire in the 1670s and 1680s, Nevison was a prolific and successful highwayman. Said to be a gentleman thief who never used violence and only robbed the rich, he was known to have run protection rackets and just before he was hanged, he confessed to killing a constable.

Nevison was once admitted into a band of countryside rogues, who initiated him by reciting their code of conduct and ceremoniously pouring a pint of ale on his head while he was knelt down. The gang then married him to one of their number, a seventeen-year-old girl. The wedding consisted of them lying on the ground with a freshly-decapitated chicken between them, saying their vows, then spending their wedding night in a barn.

During the night, Nevison snuck off and went to London, but soon got fed up with the noise and hubbub of the capital and returned to Yorkshire, where he was captured while having a pint in a pub near Wakefield.

4. Jane Voss (d. 1684)

Born in London, Jane Voss ran away from home as a teenager and joined a gang of travelling thieves in Surrey. After this pupillage in pilfering, Jane moved west and became well-known as a pistol-wielding highwaywoman, riding around robbing travellers with her boyfriend as a Stuart-era Bonnie and Clyde.

In the years before her death, Voss acted as a sort of consultant to London thieves, such was her recognised expertise in the art of pinching. She is alleged to have assisted such infamous fences as Thomas Sadler, who lifted the Lord Chancellor’s mace in 1677.

The story of Jane’s life is - though factually dubious - dramatic and exciting, such as the time when she escaped from prison in Wiltshire, leaving her lover to take the rap and be sent to the gallows. In fact, a contemporary account of Voss’s life claims that as many as eighteen ‘reputed husbands or friends’ of Jane’s ended up dying in the hangman’s noose.

Voss had previously served over twelve different spells in Newgate prison before her final stint at the infamous jail, from where she was taken on the morning of 19th December 1684 to Tyburn and executed for the theft of a silver tankard.

5. William Spiggot (1691/2 – 1721)

One of the most ruthless and fearsome of all highwaymen was surely Hereford-born William Spiggot, the scourge of southern England’s coaching routes in the early 18th century. For upwards of twelve years, Spiggot led a gang of ruffians, forcing coach passengers to depart with their possessions at pistol point.

In January 1721, the famous thief-taker Jonathan Wild arrested Spiggot and his gang at a tavern. During the melee Spiggot fired off a round, shooting the pub’s landlord in the shoulder.

While languishing in Newgate Prison before his execution, Spiggot reportedly confessed to committing ‘about a hundred’ robberies.

Spiggot is famous for being ‘pressed to plead’ at Newgate prison. In this court-ordered ordeal, he was tied to the hard prison floor and then had around 183 kilograms of lead weights placed onto his chest. The pain was too much to bear and he agreed to plead, was convicted, and died by the rope at Tyburn on 11th February 1721.

6. Dick Turpin (1705 - 1739)

Hands down (or should that be hands up?) the most famous British highwayman is Dick Turpin, born Richard Turpin in his father’s pub in the village of Hempstead, Essex.

A prolific thief from a young age, Turpin’s infamous career as a highwayman started in about 1735. Operating out of Epping Forest, he was known for holding up, often with violence and terror, mail coaches and stagecoaches.

Turpin’s celebrated twelve-hour, 200-mile ride from London to York on his horse, Black Bess, in order to establish an alibi, almost certainly never happened, but has endured as part of Turpin folklore.

In 1737, Turpin murdered a man in Epping Forest who had tried to detain him. He fled to Yorkshire and went by the alias John Palmer. Finding himself incarcerated in York Prison, he wrote to his brother asking for a character reference. Famously, the letter was seen by Turpin’s old schoolmaster, who alerted the authorities to the true identity of John Palmer. Turpin was hanged in York in April 1739.

7. Jerry Abershawe (1773 - 1795)

Jerry Abershawe was known as ‘The Laughing Highwayman’ and was even reported to have been chuckling away while being driven to his execution. Abershawe plied his illegal trade near his hometown of Kingston upon Thames, on the roads running southwest out of London.

Considered one of the last true highwaymen, Abershawe was described as a handsome, dashing young man, but he was also a feared criminal with a reputation for brutality.

In one famous incident, the notorious criminal called a doctor out to his headquarters - the Bald-Faced Stag Inn - in the middle of the night. The poorly highwayman suggested the physician be escorted home by one of his men, for his protection. The brave medic, unaware of the identity of his patient, declared that he wasn’t afraid of bumping into anyone, even the notorious Jerry Abershawe.

In London in January 1795, Abershawe shot two men who had been sent to arrest him, killing one and injuring the other. Abershawe was strung up on Kennington Common in August 1795 and his dead body was then gibbeted (hung in chains on a gallows) at Putney Common.