Your Money or Your Life: 5 Famous Highwaymen Who Lived Fast and Died Young

Your Money or Your Life: 5 Famous Highwaymen Who Lived Fast and Died Young

Patrick Lynch - April 9, 2017

For romanticists and anarchists, highwaymen are the ultimate rebels and outlaws. They had no regard for authority or the law and clearly had no fear of death because the judicial system in that era was a lot harsher than it is today. Men, women and even children were routinely hanged for offenses ranging from burglary to cattle rustling, so highwaymen took their lives in their hands every time they committed a crime.

Those who operated in the ‘classical’ tradition were noble and gallant. Yes, they would steal a person’s valuables, but would exercise chivalry and politeness while doing so. Typically, these individuals would hide in the shadows only to spring forth and hold up stagecoaches before disappearing into the darkness once more. Stories of their tales spread rapidly as newspapers highlighted the crimes and bards composed songs in their honor.

In reality, of course, many of these highwaymen were merely beneficiaries of favorable propaganda. A great number of them were vicious, bloodthirsty creatures with scant regard for human life. These so-called ‘gentlemen of the roads’ usually enjoyed short careers and their lives almost always ended in execution.

Your Money or Your Life: 5 Famous Highwaymen Who Lived Fast and Died Young
Turpin by Adrian Teal. Shakespeares England

1 – Dick Turpin (1705? – 1739)

Richard ‘Dick’ Turpin is arguably the most famous highwayman of all time, but tales of his gallantry are greatly romanticized. Practically every piece of the Turpin legend is a complete fabrication. For example, he did not ride his horse Black Bess from York to London in under 24 hours. The ride in question was completed by another highwayman by the name of Jack Nevison in 1676. It was only at the end of his life while awaiting the hangman’s noose that Turpin exhibited any of the charm he is associated with.

He wasn’t even born in York. Turpin was born in Hempstead, Essex and while we don’t know his date of birth, we do know he was baptized on September 21, 1705. As a young man, Turpin likely followed in his father’s footsteps by becoming a butcher but was apparently guilty of disorderly behavior when serving as an apprentice. Once his apprenticeship was finished, he opened a butcher shop and started stealing sheep and other livestock. When he was caught stealing a pair of oxen, he fled to the countryside.

When he emerged from his hiding place, he tried and failed to become a smuggler. While the legend of Turpin tries to paint him as something of a lone gunman, in reality, he spent much of his career as a member of the Essex Gang. Far from being the polite and gallant thief of lore, Turpin and the gang raided isolated farmhouses and tortured the female inhabitants into giving up their valuables. On one occasion, Turpin forced a woman to sit on an open fire until she revealed the location of her treasure.

By 1735, there was a bounty of £50 on the Essex Gang, an enormous amount of money at the time. Local constables caught two members, but Turpin narrowly escaped. He teamed up with swashbuckling highwayman Tom King and from their lair in a cave in Epping Forest; they stole from anyone who passed by. By 1737, there was a bounty of £100 on Turpin’s head, and when a gamekeeper tracked him down in the forest, Turpin killed the man after an altercation.

Turpin stole a horse from a man called Major who responded by sending out leaflets asking for the thief’s capture. The horse was traced to a pub called the Red Lion, and the police were alerted. King came to collect the horse but was arrested by local constables. Turpin heroically arrived on the scene and shot at the police. Unfortunately, he was a terrible shot, and his bullet hit King! His one-time accomplice died soon after but not before revealing information that forced Turpin to hide once again.

He lived under the fake name John Palmer and lived in Yorkshire where he spent his time stealing livestock to fund a lavish lifestyle. One day, he shot his landlord’s chicken, and when the angry man confronted the outlaw, Turpin threatened to kill him. Turpin was arrested, and tales of his cattle rustling activities came to light. He wrote a letter to his brother asking him to provide evidence as to his good character. Unfortunately for Turpin, his brother was a cheapskate who refused to pay for postage and returned the letter to the Post Office. Turpin’s former schoolmaster saw it and recognized the handwriting.

The schoolmaster rode to York and identified Turpin who was sentenced to death. On April 7, 1739, Turpin went through the streets of York and bowed to those who were to witness his execution. He was hanged, but it was during his final day that he showcased the heroism that eluded him during the rest of his life. His legend grew after his death thanks to the work of Harrison Ainsworth who wrote a book with Turpin as a secondary character. However, his exploits captivated readers, and a myth was born. Incidentally, Turpin is NOT buried in York alongside Black Bess.

Your Money or Your Life: 5 Famous Highwaymen Who Lived Fast and Died Young
Janosik by excharny. DeviantArt

2 – Juri Janosik (1688 – 1713)

Also known as the Carpathian Robin Hood, Janosik was a famous Slovak highwayman. Like many other outlaws, tales of his deeds are almost certainly exaggerated as he became the main character of many poems, films and novels in Slovakia and Poland. According to legend, he stole money from rich nobles and gave it to the poor; just like fictional British outlaw Robin Hood.

Janosik was born in Terchova, the Kingdom of Hungary (modern-day Slovakia) in 1688. He clearly had a rebellious streak from a young age because he fought with Kuruc insurgents when he was just 15 years of age. After the Kuruc lost at the Battle of Trencin in 1708, Janosik joined the Habsburg army. Two years later, he helped a man named Tomas Uhorcik escape when he worked as a prison guard and together, the two men formed a highwayman group. Janosik became a leader when Uhorcik left, and it appears as if there is some truth to the group’s exploits.

Janosik seemingly told his men to treat their victims with respect; they were chivalrous to those they stole from and were not responsible for any deaths. On one occasion, the group accidentally injured a priest during a robbery and tended to his wounds. There is even a suggestion that the group did share a portion of their ill-gotten gains with the poorer elements of society. Other sources disagree with the notion of a ‘gentlemanly group of outlaws’ and suggest the group were violent and often murdered soldiers. Janosik supposedly killed rivals within the clan and is portrayed by some as a cruel individual.

Whatever the reality, the group’s antics made them a prime target for authorities and in 1712, Janosik was caught, arrested and detained at the Mansion of Hrachov but oddly enough, he was released soon afterward. There is an account which says the gang killed a priest, but details are not clear. As a result, a manhunt took place, and Janosik met up with his old comrade Uhorcik who ran a pub under an assumed name.

In the spring of 1713, the authorities finally caught up with him, and Janosik was tried, found guilty and executed. While some historians say he was hanged, other sources suggest the Outlaw suffered a cruel fate. He was stabbed with a hook and left dangling on the gallows until he bled to death. Janosik only gained fame in the 1830s when he was depicted as a romantic hero. Since the early 20th century, the life and death of Janosik have become the stuff of legend, and it is routinely depicted in books and on the big screen.

Your Money or Your Life: 5 Famous Highwaymen Who Lived Fast and Died Young
Romanticized account of a Duval holdup. Outlaws and Highwaymen

3 – Claude Duval (1643 -1670)

Unlike robbers such as Dick Turpin, Duval was the gallant highwayman of lore. As always, his deeds are certainly embellished, but there is evidence to suggest that he was the genuine article when it came to ‘gentleman thieves.’ Duval was born in Normandy, France in 1643 and he moved to Paris aged 14 to work as a domestic servant. A few years later, he worked as a stable boy for English Royalists and eventually moved to England after Charles II was restored to the throne. His first job in England was as a footman to the Duke of Richmond.

What drove him into a life of crime is unclear but soon after arriving in England, he began his career as a highwayman. He typically stole from stagecoaches that traveled between Highgate and Islington and unlike most robbers of the day, Duval acquitted himself well and became famed for his polite manner when relieving people of their valuables and for his fashionable clothing.

According to legend, he did not physically injure any of his victims although he reportedly tied the Master of the Buckhounds to a tree and stole 50 guineas. One of the most famous tales involving Duval related to an occasion when he stopped a stagecoach containing a nobleman and his wife. The lady played a tune on her flageolet as a means of showing the thief that she wasn’t frightened. Apparently, Duval told the lady that he admired her musical ability and suggested that she could dance just as well. Then she exited the carriage and danced with the robber. One version of the story says Duval only took £100 when the couple had £400. Another version states that he demanded £400 for the dance.

Like every other highwayman of the time, Duval was a wanted man, and he wisely fled to France to avoid capture. However, he only stayed away from England for a few months and was apparently arrested in a London tavern soon after his return. According to the historical record, Sir William Morton sentenced him to death on January 17, 1670, after finding him guilty of perpetrating six robberies. Despite appeals for clemency, Duval was hanged at Tyburn four days later, and his body was buried beneath the church of St Paul’s in Covent Garden. Tales of his exploits have inspired many legends, and his ghost is said to haunt the Holt Hotel in Oxfordshire.

Your Money or Your Life: 5 Famous Highwaymen Who Lived Fast and Died Young
Death of Pelletier. View Suggestions

4 – Nicolas-Jacques Pelletier (1756 – 1792)

This French highwayman has the macabre distinction of being the first person to be executed by the guillotine. Little is known about his early life barring the fact that he was part of a gang of criminals who terrorized lonely travelers in France. While some highwaymen often have false romanticism attached to their names and deeds, Pelletier is not one of them! He was notorious for performing brutal robberies and didn’t hesitate to murder victims who wouldn’t immediately hand over their possessions.

As is the case with the vast majority of highwaymen, Pelletier’s career didn’t last long and came to a brutal end. His downfall started when he stole a wallet from a passerby, and the victim apparently died during the assault. Cries for help alerted nearby police who quickly apprehended Pelletier. Where this case differs from others on this list is not only the method of execution but the length of time it took for the death sentence to be carried out. In most cases, highwaymen died within days of their sentence, but it took almost four months for Pelletier to die and almost six months from the day of his arrest.

He was arrested on October 14, 1791, but the death sentence was not passed until December 31. As it transpired, France was undergoing major upheaval due to the Revolution. In 1789, Dr. Joseph-Ignace Guillotin lobbied for equality in the field of capital punishment. He said it was wrong for convicted criminals to be punished by barbaric methods such as hanging, breaking on the wheel and burning at the stake. In contrast, aristocrats were executed in swift and painless fashion via decapitation.

The National Assembly decreed that decapitation should be the only method of execution in France in 1791. The problem was, the country didn’t have enough skilled executioners to carry out all the necessary beheadings. Guillotin solved this problem with the unveiling of his decapitation device that became known as the guillotine. After conducting numerous tests on animals, the device was ready for use on a human being.

Meanwhile, Pelletier’s execution was delayed because the means of his death had yet to be finalized. Eventually, the device was ready, and on April 25, 1792, Pelletier was swiftly and cleaned dispatched by the guillotine. Not everyone was pleased with the outcome. A huge crowd had gathered to witness the execution and was angered by the fast and clinical nature of the new death machine. Some pined for the return of the gallows.

Your Money or Your Life: 5 Famous Highwaymen Who Lived Fast and Died Young
Jack Sheppard. WordPress

5 – Jack Sheppard (1702 – 1724)

During his extremely short life and career, Sheppard gained a reputation not only as a highwayman but also as an extraordinary escape artist. Like the vast majority of thieves during the era, Sheppard was born into extreme poverty. He was surrounded by death from an early age as his father and sister died while he was still only a boy. Because of their desperate circumstances, Sheppard’s mother sent him to a workhouse when he was just six years of age.

He became an apprentice to a cane-chair maker until his new master died. Sheppard ended up working for another cane-chair manufacturer who treated him extremely poorly. After a few hard years, he worked as a shop boy for a wool draper called William Kneebone. Sheppard’s mother had been in Kneebone’s employee for years, and this man taught his new apprentice how to read and write.

Sheppard’s criminal career was brief and memorable. He worked as a carpenter until 1722, and the diminutive young man (he was around 5ft 4 inches tall) showed great potential and had just one year left in his apprenticeship. His life changed when he started to frequent the infamous Black Lion Tavern which was the haunt of many criminals in London. It was there that he met and fell for a prostitute named Elizabeth Lyon.

Soon, he threw himself into the world of drinking, whoring, and crime and started to shoplift to supplement his income. His carpentry suffered, and he quit his master’s employ in August 1723. By now, he had graduated to grander crimes including burglary. Initially, at least, Sheppard was able to avoid detection, and as he still worked as a journeyman carpenter, he was able to steal goods from the homes he worked in. He also became acquainted with notorious gang leader Jonathan Wild.

Over the next year, Sheppard became famous for his ability to escape detention. On four occasions, he escaped from prison. The second escape on August 30, 1724, was the first time he escaped while under a death sentence. His most famous escape act occurred on October 15, 1724, when he slipped off his handcuffs, picked his chain with a nail, scaled the roof of Newgate Prison and used his bedsheet to slide onto another roof before finally escaping through the front door. However, his fondness for alcohol caught up with him and two weeks after his Newgate escape; he was caught because he was too drunk to resist arrest.

The day of his execution, November 16, 1724, was a dramatic occasion as an estimated 200,000 people made their way to Tyburn to see the folk hero die. As it turned out, the crowd’s affection for Sheppard foiled his last daring escape plan. The route to his execution was lined with weeping women in white who threw flowers at the condemned man. The Houdini of his day had no intention of surrendering meekly and hatched a daring plan with his publisher Appleby and the famed writer Daniel Defoe.

After a hanging, the body was traditionally left dangling for 15 minutes, and in rare cases, the person could survive. The idea was to retrieve the body and try to revive him. Sadly for Sheppard, his adoring crowd had no way of knowing this so when the trap door opened, they rushed forward and pulled on his legs to ensure their hero died swiftly.