Knights of the Road: The Highwayman's Story Britain's Outlaws: Highwaymen, Pirates and Rogues

For a period in the 17th and 18th centuries, crime was endemic.

On the open roads, robbers robbed with impunity.

On the high seas, pirates roamed.

Felons robbed, burgled and cheated.

Across the country, there was no established police force

and although the ultimate penalty was death,

who was there to enforce it?

In this series, I want to explore the world of the British outlaw,

the original antihero

in an age of swashbuckle,

daring and style.

And no outlaw was more glamorous, romantic and glorified

than the highwayman - the masked horseback robber

who stole hard cash and admirers' hearts

in pursuit of a merry life

and a short one.

Most people think of the highwayman as an underworld figure -

perhaps an 18th century rogue, like Dick Turpin.

GUNFIRE

But their origins lie much earlier,

with the fall from grace of the King's men

and the rise of gentleman robbers in the English Civil War,

the brutal conflict that erupted in the 1640s.

As the country tore itself apart,

a maelstrom of violence, disorder and distrust

created the perfect conditions for outlaws to thrive.

The Royalists had lost.

King Charles was executed.

Great houses were devastated in battle.

Suddenly, thousands of experienced military men

were unemployed and angry.

Some decided their best chance of survival was to take to the roads -

as what we would now call highwaymen.

Under Cromwell's rule,

reports began to emerge of lawlessness on the roads

on a scale never before seen.

Fantastical stories appeared of outlaws -

men whose political beliefs had failed them

and who now sought glory in a life of crime.

These were military trained sharpshooters,

who found themselves on the losing side.

There had been highway robbery

for as long as there had been roads, but this...

Well, this was something different.

It became a menace that marked the age

and lent a new air of romance to crime.

For these outlaws were motivated by principles as much as money -

former soldiers who clung to a broken sense of honour,

mixed with thievery.

Men like Captain James Hind.

In 1651, Hind was dragged out from a London barber shop

and arrested by heavily-armed soldiers.

A wanted man, he had been living under an alias for months,

until his hiding place was betrayed.

He was taken to Newgate Prison and clapped in irons.

Hind was a passionate Royalist

and he'd already fought - and lost - in the name of the crown.

But he was already well-known for a very different reason,

because Hind was the most notorious outlaw-highwayman in Britain

and his fame was about to explode.

Described as "the unparalleled thief",

the stories about him were almost unbelievable.

Hind was born in Oxfordshire, in 1616.

He wasn't a nobleman,

but his family were respected and comfortably well-off.

For the young James, education held little appeal,

so eventually, his father apprenticed him to a butcher,

hoping he would take to an honest trade.

After falling foul of his master's violent temper once too often,

the teenager decided to run away

and he headed to London, to seek his fortune.

Now, in the eyes of some,

the capital was a place that corrupted with vice and sin,

but for a man like Hind,

it simply offered the best entertainment around.

It wasn't long before the young Hind fell into bad company.

He was arrested whilst drunk in the arms of a prostitute

and thrown into a jail called the Poultry Compter.

In this grim and filthy dungeon, one inmate stood out from all the rest -

Thomas Allen, an experienced highwayman and gang leader.

After their release, the two decided to join forces.

But first, the inexperienced Hind

needed to prove himself a worthy partner.

As the gang hid, he was sent out on his first robbery.

They chose an ambush site at Shooter's Hill,

on the outskirts of London,

and waited until a gentleman and his servant came by, travelling alone.

If Hind was nervous, he didn't show it.

With pistols drawn, he demanded money

and the gentleman - in fear of his life - handed over £10.

A healthy sum, for a first attempt.

But then, something unusual happened.

It was said that Hind took pity on the man he had just robbed.

He put his hand back in the purse, took out 20 shillings

and gave it back to the man, saying it was for his travel expenses.

It was an act that marked him out as something different.

Handing back money was a calculated display of gallantry

and it piqued Allen's interest.

Hind quickly became his second-in-command.

His reputation was set as a principled and gentlemanly robber.

Hind had star quality.

But the politics of civil war were never far away.

Hind and Allen's gang had sworn oaths as Royalists

and began to single out Parliamentarians.

The list of Hind's supposed victims

reads like a who's who of the Roundhead regime.

One day, as he travelled through Dorset,

Hind spotted a chance to ambush John Bradshaw,

the judge who had actually condemned King Charles to death.

Knowing that his name now struck fear into the hearts of men,

Hind put his pistol to Bradshaw's head

and demanded his money with particular venom.

"I fear neither you, nor any king-killing son-of-a-whore alive.

"I have now as much power over you as you lately had over the King."

Judge Bradshaw placed a trembling hand into his pocket

and drew out a mere 40 shillings in silver.

The highwayman was distinctly unimpressed

and swore that he'd shoot him through the heart there and then,

if he didn't find coin of another species.

With his life hanging in the balance,

the judge handed over a purse full of gold instead.

After a lecture on the immorality of Parliament's cause,

Hind shot all six of the coach horses dead.

Stories like these - whether real or imagined -

were used by writers to question

the legitimacy of Parliament's authority.

But there's more,

because while these robberies of the great and the good

burnished his reputation,

he also became known as something of a Robin Hood figure -

a highwayman with a conscience.

After running short of money,

Hind held up a farmer who was on his way to market

to buy his wife and ten children a cow.

The farmer begged him not to take his meagre 40 shillings

as it was all he had, and had taken him two years to scrimp together.

Hind was desperate and took it anyway,

but the farmer was repaid double and extra a week later when,

true to his word, the highwayman returned to pay him back.

It was all good PR,

but simple farmers weren't enough to make a legend.

Hind craved infamy.

In several accounts of his life, there's a story of an attack

that proved to be the Hind gang's undoing -

on Oliver Cromwell himself.

They launched their assault as Cromwell's coach left Huntingdon.

It's unclear if it was meant to be a simple robbery or an assassination,

but he was heavily guarded and the attack went horribly wrong.

Thomas Allen and several of his men were captured and executed

and Hind barely managed to escape with his life.

He went on the run, riding his horse until it dropped and eventually

returning to the anonymity of his old haunts in London.

In the end, Hind was betrayed by one of his fellow Royalists.

A former soldier recognised him

and reported him to the Speaker of the House of Commons.

Hind, by now, had some very powerful enemies.

He was already well-known,

but now, something extraordinary happened -

he became a celebrity, the length and breadth of the country.

During the Civil War,

there was a boom in the production of printed material.

Hind's exploits were published in a rich tapestry of pamphlets,

ballad songs, chapbooks, poems and broadsheets,

published at a prodigious rate

and all claiming to relate his true words and story.

Hind is the first figure, to my knowledge,

who becomes a celebrated criminal.

The political changes and the war

were accompanied by a massive upsurge in print.

So, what we're looking at with Hind is two things -

it's the historical circumstances

that make a highwayman like Hind possible

and it's also the emergence of print culture

to a greater degree than before.

These printed works were something like early tabloids.

Their authors were untroubled with journalistic accuracy

and the readers didn't really care, either.

These weren't just morality tales,

nor were they bland, official accounts.

These stories were colourful, they were exciting,

they were designed to entertain.

In the press, Hind embodied the idea of the jovial Cavalier

resisting against the dour Puritans.

While the regime was busy banning Christmas,

he's out there, enjoying himself.

It's not through prayer and hard work -

he's drinking, carousing and having adventures.

Now, in the imagination, the highwayman is gallant,

he's principled and he's damn good fun.

From his jail cell, Hind actually denied many of the stories

attributed to him in the pulp press.

When asked about some of the pamphlets written about him,

he answered that they were fictions,

before adding, "But some merry pranks and revels I have played.

"That, I deny not."

But none of that mattered.

The regime simply could not let Hind become a rallying point

for Royalist sympathisers.

They wanted him dead.

The authorities were having none of it.

Hind wasn't just any Royalist soldier,

he'd fought alongside the future Charles II, right to the end.

He was taken to Worcester, the scene of Charles II's last battle,

where he was tried and convicted for treason.

Hind would suffer a traitor's death.

He was hung, drawn and quartered,

his head displayed on a spike above the bridge over the Severn.

Despite Hind's gruesome end, the horse had already bolted.

Highwaymen were a menace on the roads,

but their stories were bestsellers.

Technology was on the highwaymen's side.

The printing press made them famous

and the Civil War flooded the country

with a revolutionary invention that allowed them to flourish.

The flintlock pistol.

This weapon made the highwaymen's signature surprise attack much easier.

What were the advantages of this type of weapon, for the highwayman?

The flintlock gave the highwayman the chance to have his weapon

all primed and ready to go and then, in his coat.

The best way to really understand the advantages of the flintlock

is to look what had to be used before.

This is a matchlock and this is the match - hence the matchlock -

and for this to be ready to fire, that has to be glowing red.

There's no way you could load this

and then go about your business, with it ready to use.

It's as powerful as anything that came later,

but if you like, it's fire by appointment.

How does the flintlock work?

Well, three key components in a flintlock -

the cock, which is this piece here, which holds the flint.

The frizzen, which is what the spark comes from, and the pan.

So, to make this work, you would go back to half cock,

which is where we are there.

You would pour powder in the pan and then close the frizzen.

And then, the final thing to make it go -

you'd go back to full cock and when you pull the trigger,

that piece of flint flies forward, drags down the frizzen,

scraping off little bits of metal as red hot sparks

and then a few sparks and flames from the pan

goes into the barrel and sets off the main charge.

What sort of range did they fire over?

The pistols particularly would have been effective over a short range.

They were designed to hit a man-sized target at a range...

perhaps not that much greater than an arm's length, plus a sword.

GUNSHOT

-Wahey!

-Right on the chin. Well done.

He'd be staggering around now, wouldn't he?

After the Civil War, amidst a flood of weapons

and desperate men roaming the nation,

highway robbery became an epidemic.

Each infamous figure took the myth to a new level

and the state wasn't ready.

The age of the highwayman had arrived.

On the lonely 17th century roads,

you never knew who was lurking in the shadows.

Just outside of the cities, towns and villages,

England was like the Wild West.

Vast swathes of countryside stretched across the landscape.

There was no police force and out here,

law and order of any description had very little reach.

People and possessions could simply vanish.

Highwaymen swarmed around wealth.

Their main hunting grounds were the arterial King's roads

that headed out from the major cities - especially London -

carrying the richest members of society.

A few miles from the capital and you were a sitting duck.

Highwaymen lay in wait around areas like Hounslow Heath, Shooter's Hill

and the Great North Road, which all became notorious robbery hot spots.

Travel was expensive.

Coach passengers by definition were wealthy,

and so, they were frequently targeted.

But highwaymen saw everyone on the road as fair game.

To make matters worse, the roads of the period were terrible -

deep-rutted in summer and impassable quagmires in winter.

They were little more than trackways, badly-maintained

and cursed by those who travelled on them.

The rough, countryside terrain

worked to the highwaymen's advantage.

Coaches plodded along at around 5mph on a good road,

slower on a poor one.

Hills were particularly dangerous,

because coaches were forced to slow down,

which made them an ideal location for ambush.

Heathland and forests provided plenty of cover for robbers to hide

and urban centres were an ideal location to lie low.

After the death of Cromwell, the English Republic fell apart

and in 1660, Charles II was brought to England to take the throne.

CHEERING

The time of disgruntled Royalist highwaymen

running riot around the countryside came to an end.

They had been valiant losers in the new order,

but the monarchy was back.

Jubilant Royalists returned home triumphant with the new king.

They were extravagant and hedonistic and they brought someone with them -

Claude Duval, the man who gave highwaymen sex appeal.

He was from Normandy and worked as a footman

to an exiled English aristocrat.

Footmen were expected to be good shots and keen horsemen,

with a reputation for hauteur and insolence.

Being a footman was a great training for being a highwayman,

because you were essentially an armed guard

to protect the noble family that you worked for.

You were chosen for your height and good looks,

so the kind of glamour was written into it.

Very fast runners, sure shots, because they were trained to fire.

I mean, it was almost like training someone to be a highwayman.

Restoration aristocrats were a bunch of dissolute hedonists.

Their French-style fashion was elaborately decadent

and debauchery was positively encouraged.

All of which rubbed off on their entourage.

Duval would have been described as a popinjay

for his fashionable French clothes

and he soon gained a reputation for fine living.

He was an insatiable drinker, womaniser and gambler,

but this was a lifestyle that he simply couldn't afford.

Now, for a man with an ego like Duval's,

getting a proper job was simply out of the question,

so instead, he turned highwayman.

Unlike Hind, Duval wasn't interested in politics.

He robbed simply to keep the party going.

He became a thief with style to match his daring

and with Duval, panache was added to the highwayman legend.

Soon enough, Duval found his way to the top of the nation's wanted list,

with a reward of £20 offered for his capture.

He robbed travellers and royal officials -

anyone with money that came his way.

This was a highwayman with no pretence to any social mission.

He doesn't seem to have had any scruples about robbing from the poor.

Robin Hood, he was not.

On one occasion, Duval and an accomplice

came across two gentlemen and their servants.

Engaging them in conversation,

they then robbed every penny from the servants,

without even bothering to search their wealthy employers.

But there was a particular theme in the tales of Duval's career

that really made his name -

and that was his pursuit of women.

He gained a reputation for gallantry, particularly

for returning keepsakes or trinkets to women, after he'd robbed them.

He was as keen on stealing their heart as their money.

This persona is perfectly captured

in an 1860 painting by William Frith of an encounter on Hounslow Heath.

With Duval, it was your money or your wife.

Duval's gang held up a coach carrying a gentleman and his wife

with the enormous sum of £400 on board.

As the gang approached,

the lady played a tune on her flageolet,

to show she wasn't scared.

Duval was intrigued.

After complimenting the man on his wife's musical skills,

he asked if she danced as well as she played

and if the gent would allow her to dance with him.

Surrounded by pistols,

it's perhaps unsurprising that the husband promptly agreed.

Leaping down from his horse,

Duval and the lady danced the courante together,

while his cronies played music to accompany them.

Of course, Duval is as skilled with his feet as he is with his blade,

and when the dance is over,

he hands his dancing partner back into the coach.

Duval then takes £100 from her husband as payment for the music,

but excuses him from the remaining £300 for being a good sport.

The incident really sums up what Duval's all about.

There's swashbuckle and ladies going weak at the knees when Duval's around,

but that's exactly what he brought to the idea of the highwayman -

romance, a bit of dash and sexual frisson.

In the end, it was Duval's hedonistic lifestyle

that brought him down.

To celebrate a successful robbery, he stopped off at the pub.

The Frenchman had a reputation for being handy with sword and pistol,

but by the time a bailiff arrived to arrest him, he was legless.

Too drunk to resist,

he was thrown into Newgate Gaol to await his fate.

At his trial, well-placed ladies of the court

tried to intervene for a reprieve, but it was to no avail.

Claude Duval was found guilty and sentenced to hang.

Duval rode to the gallows in 1670 watched by thousands of women,

from duchesses to prostitutes.

He was 27.

For the poor, he was an iconic figure -

a rock star criminal, a glamorous gangster.

Through Duval, they could escape the status of their birth,

even if in fantasy.

For the nobility,

he added a touch of danger and excitement to their world.

It would have been a thrill to have been robbed by him.

Writers recounting Duval's adventures often did so

to express concern about the Restoration elite -

that they were dissolute and robbing the public to pay for their excess.

Some thought they were less interested in ruling

than womanising and gambling.

There was also the feeling that courtly manners

were becoming feminised and even worse, French.

All of which was a nasty foreign corruption of good old English morality.

One of the interesting things about Claude Duval

is that he kind of reflects the society that produced him.

He likes women and gambling and dancing,

and presumably, all the other vices of the court of Charles II.

And so, he's a focus for criticism of Charles II's court.

Frith's painting of Duval captures the moment of a hold-up

in a way that instantly mythologises it.

Duval is at the centre, being all gallant,

whilst his less respectable sidekicks do the rest.

He's got the clothes, the style and a mask.

Highwaymen were noted for dressing like the wealthy gentlemen of the day.

This was partly out of vanity,

but partly to blend in with the well-to-do passengers.

Crime was considered the province of the poor,

so dressing this way was intended to allay suspicion.

Every highwayman had a different approach to disguise.

Some accounts mention that some highwaymen

pulled their periwigs down to cover their eyes, or more bizarrely,

tucked their tails into their mouths.

Others wore their hats pulled down low, wore false beards

or simply did nothing at all - a risky and cocky approach.

The famous tricorn hat arrived around 1700,

but what about that iconic black mask?

Well, we know that some highwaymen did wear a mask,

but by far the most common disguise was a simple scarf.

As important as choosing their disguise

was selecting the right victims.

The best operators carefully gathered intelligence

on prime targets.

In 1674, an obscure highwayman named Francis Jackson

recorded his adventures in a confessional pamphlet.

If Jackson hoped it would give him a reprieve, he was wrong -

and he was hanged.

But its value to us today is that he's left us

a kind of highwayman's manual -

a how-to guide for robbery on the road.

In his book, Jackson explains how highwaymen had a spy network

working throughout the coaching inns and taverns

that dotted the landscape.

Everyone was involved, from the landlords to the stable hands,

each getting a cut of the profits for a good tip-off.

He also explained how highwaymen employed deception

and confidence tricks,

building false familiarity with potential victims,

ingratiating themselves into fellow travellers' company

before attacking.

And Jackson also had advice for those who got caught.

"To procure mercy from the bench,

"there must be a plausible account given

"how you fell into this course of life.

"Fetching a deep sigh, saying that you were well-born,

"but by reason of your family falling into decay,

"you were exposed to great want.

"And rather than shamefully beg, for you knew not how to labour,

"you were constrained to take this course for a subsistence.

"That it is your first fault, which you are heartily sorry for

"and will never attempt the like again."

Most interestingly of all, I think, he also has advice for travellers.

Never say goodbye and never reveal your destination,

in case a highwayman is listening.

Also, never travel on a Sunday,

because the roads are deserted and the authorities won't help.

Then there was the robbery itself,

the riskiest part of the venture for all concerned.

To minimise the risks, highwaymen often worked in gangs

and they developed strategies to make robberies go smoothly.

Sometimes, they simply chatted to the driver before pulling a gun,

but if that wasn't an option, there was the direct approach - an ambush.

One of the gang would approach directly from the front,

with pistol drawn to hold up the driver.

Attacking head-on shielded him from the passengers inside -

who might be armed -

and it allowed him to make sure the driver surrendered.

A second highwayman would head for the passengers.

He might approach from directly behind the coach,

minimising the chance of getting shot.

From the rear or side window,

he would then threaten or charm the passengers.

Guttural threats of violence alternating with witty provocations,

both intended to coerce victims

into handing over their goods without resistance.

Then, the gang made their escape.

To prevent pursuit, or out of spite,

they would sometimes cut the bridles or kill the horses.

Finally, they would flee into a busy city or head to a friendly inn

and establish an alibi.

Escape and evading the law were vital skills in highway robbery.

In highwayman legend, the greatest of all escape tales

belonged to the robbers of the Great North Road -

and they don't come any more sensational

than those of John Nevison.

Years before Dick Turpin,

he became famous for his ingenious and daring escapes.

This is the Peak District in Derbyshire,

John Nevison's stamping ground.

It's the ideal environment for highwaymen.

In reality, Nevison was a bit of a thug.

He operated protection rackets

on the routes to the markets down south.

He took money, not from wealthy aristocrats,

but from drovers, from butchers, from shopkeepers.

He was also a horse thief and a murderer,

killing a parish constable sent to arrest him.

Nevison was a hard man.

He was also a survivor.

Like many highwaymen stories,

it's unclear what's true and what is just a good yarn,

but Nevison's legend was full of incredible escape routines.

In 1674, he broke out of Wakefield Gaol

before charges could be brought.

A few years later, he was sentenced to transportation

and hopped ship before it left the docks.

But he wasn't done yet.

According to the Newgate Calendar,

in 1681, the law caught up with him again

and he was sent to Leicester Gaol -

but this time, escape seemed impossible.

His escapades were well-known

and it was reported that he was so elaborately shackled

that he could scarcely move.

To get out of this one, he'd need a plan with a new level of cunning

and a little bit of help from his friends.

The first step was to get out of the closely-guarded cell.

He did this by feigning a deadly sickness

and calling for his friends to pay their last respects -

one of whom was a physician.

On his arrival, his friend declared that Nevison had the plague

and he would infect the whole prison - wardens included -

if he was not isolated.

Nevison was moved and unshackled and the guards kept their distance.

Then he brought in an artist,

who set about painting the fatal symptoms of plague

all over his body.

His physician friend then gave him a sleeping draught

and they claimed he was dead.

After a cursory examination from his jailors,

who were too scared to get close,

his friends were allowed to come and claim his body

and take it away in a coffin.

He was soon up on his feet, however -

only this time, as a highwayman robbing as his own ghost,

which made him even more terrifying to his victims.

But there was another highwayman on the North Road

with an escape story that became even more famous,

known as Swift Nix.

A shadowy figure, nicknamed for being as fast as the devil himself.

The story goes that he relieved a debt collector of £500

near Rochester one morning, but he was worried that

the victim would be able to identify him in court.

Now, a lesser man might have killed the collector,

but Swift Nix decided on a more elaborate alibi.

He decided to ride the 230 miles to York in one day -

a feat then considered impossible.

After hatching his plan, he sped off,

tearing through Chelmsford and Cambridge

before haring up the Great North Road.

Riding several horses into the ground,

he arrived in York around 7.30 -

and, changing into his finest clothes,

he finally arrived, breathless, at his destination...

..a bowling green.

Swift Nix stepped onto the green

and exchanged pleasantries with the mayor,

who would later swear that he'd been his guest that evening

and couldn't possibly have been in Kent that very morning.

This story was later attributed to Dick Turpin riding Black Bess,

but the original was Swift Nix.

But all of these stories - whether true or not -

tell us what people wanted to see in their highwaymen.

They needed to be charming, generous and clever.

Who'd have thought that a game of bowls

was a way of staying out of gaol?

There was little to actually stop highwaymen plying their trade.

The state was small

and its ability to control the population was limited,

which meant it reacted to crimes, but did not try to prevent them.

Fear of brutal punishment was supposed to keep criminals in check.

Law enforcement was a localised affair.

Constables were unpaid amateurs whose job it was to keep the peace

and occasionally arrest villains, if they didn't look too dangerous.

In London, watchmen were tasked with keeping some sense of peace

in the disorderly city.

Watchmen were hired by the parish to walk round at night.

Like the constables, they're seen as pretty ineffectual.

Quite often paid off, quite often old men.

You know, it's a job you give to someone who's retiring.

In most cases, they're seen as laughably inefficient.

Perhaps the main hindrance to a highwayman early on

seems to have been the "hue and cry"...

..a posse of regular citizens

gathered by their victims to hunt them down.

Eventually, though, it was a change in the law

that posed the biggest threat to highwaymen

as the 18th century dawned.

By this time, it was acknowledged

that things had got completely out of control,

but the aristocracy who ran the state

had no interest in founding a police force.

It had more than a little whiff of French tyranny and expense about it.

Justice was about making the legal penalties stronger,

rather than prevention.

They wanted to use the law to bring down the knights of the road.

The Highwayman's Act came into force in 1693,

and you've got relatively wealthy people being robbed

in inaccessible places, by men on horseback.

So, their getaway was pretty easy

and the detection was pretty unlikely,

so they offered rewards to people who apprehended highwaymen.

The other section, of course,

was to try and turn criminals against criminals, get grasses.

So, if you are convicted of a robbery

and therefore, you are facing the death penalty yourself,

if you are prepared to turn Queen's Evidence

and shop at least two of your confederates,

you would receive a pardon for the robberies that you had committed.

Any private citizen could bring in a highwayman - if they dared -

but taking them to court wasn't simple.

It was their victims who had to pay for a prosecution

and provide evidence.

For many, it simply wasn't worth it.

These were not men to cross lightly.

When one highwayman couldn't get a ring off his victim's hand,

he cut off her finger.

When another swallowed her jewellery to keep it safe,

the robber cut her open.

And when their identity was threatened,

they could be particularly ruthless.

On one occasion, a local woman witnessed a robbery

and called out that she recognised the robbers

and that she would report them.

They turned around and cut out her tongue.

But there were also some instructive accounts of victims fighting back

against their attackers,

including an incident with two highwaymen

at the Surrey village of Ripley.

Their victims alerted the local population,

who chased their attackers across a village green

into the middle of a game of cricket.

Now, one of the attackers managed to escape,

but the other was beaten into submission

with cricket bat and stumps.

Whatever the truth about their methods,

as the 1700s progressed, highwaymen's stories became

an increasingly popular form of entertainment.

As their fame grew, so did the sense of romance

around the idea of who they were and what they stood for.

In 1714, Captain Alexander Smith's book,

The Complete History Of The Lives And Robberies Of The Most Notorious Highwaymen,

caused a sensation.

It set the bar for colourful

and slightly dubious accounts of the big names in highway robbery.

But whilst the public might find them romantic,

the elite weren't so keen.

They represented a threat to the social order.

Not only were they attacking property with impunity,

without any regard to the rank of their victims,

but the robberies were giving them wealth and pretensions of status.

To satirists, there was a delicious irony

to the howls of outrage about highwaymen.

For them, politicians in the Georgian government

were even worse thieves.

In 1728, John Gay penned The Beggar's Opera,

using a highwayman called Macheath

as a central character in his staged satire.

Macheath was the theatrical incarnation of the gentleman robber,

but he wasn't the villain of the piece.

He was moral, he was noble

and it was set against the rapaciousness of the elite.

His character was used to dissect the hypocrisy of the ruling classes,

who were losing more at the gambling tables than they were on the roads.

Then, there was the corruption.

In John Gay's eyes,

highwaymen were more honest thieves than the government.

The ruling class were committing robberies of their own,

but they were getting away with it.

Prime Minister Robert Walpole spirited away thousands of pounds.

And when the Chancellor - the Earl of Macclesfield -

took £100,000 in bribes, all he got was a fine.

The highwayman epidemic was a sign of the times.

Britain was becoming a modern state.

Commerce and capitalism were accelerating rapidly,

leaving the old order behind.

Highwaymen had been said to symbolise this process,

as upwardly mobile, ruthless and heavily profit-oriented.

Highwaymen stole because they wanted the money to support their lifestyle

and didn't want to work for it, but there was still a sense

that there were good and bad thieves in England.

Criminality had its own hierarchy

and right at the top were highwaymen.

Many even considered themselves gentlemen.

MUSIC: The Seeker by The Who

None more so than James Maclaine.

He was the son of a wealthy Scottish clergyman with connections.

Not quite a gentleman, but not far off.

He was raised to become a merchant, but early on,

it was clear that he had a better eye for fine clothes than business.

Maclaine was also a hopeless gambler

and frittered away a considerable inheritance.

Eternally on the scrounge,

he then moved to London to find himself a rich wife.

He quickly married a tradesman's daughter

and used her £500 dowry to set up a grocer's shop.

For a while, it looked like he'd turned his life around.

When his wife died, it quickly became clear

that she had been the one running the business.

Maclaine was clueless,

so he sold up and packed his kids off to their grandparents.

With his remaining funds, he then bought expensive clothes

and began to mingle in high society

in an attempt to bag himself a wealthy wife.

But he had no luck and soon, the money ran out.

Maclaine had become desperate, when he met a man named William Plunkett.

Now, he was an apothecary and a fellow bankrupt

and he suggested that they start up a new business together,

setting up shop as highwaymen.

MUSIC: Rumble by Link Wray

Plunkett recognised that Maclaine's gentlemanly pretensions

might actually come in handy.

Expressing sympathy for his plight,

Plunkett urged Maclaine to join him on the roads.

"I thought, Maclaine, that thou hadst spirit and resolution,

"with some knowledge of the world.

"A brave man cannot want.

"He has a right to live and need not want the conveniences of life

"while the dull, plodding busy knaves carry cash in their pockets.

"We must draw upon them to supply our wants -

"there needs only impudence

"and getting the better of a few silly scruples.

"There's scarce courage necessary."

Their ruse was simple, but effective.

While Maclaine mingled with the great and the good,

Plunkett posed as his footman,

which gave him access below stairs,

where he could get information from the staff.

And so, with Maclaine listening upstairs

and Plunkett downstairs, loose lips would provide juicy targets.

Maclaine, though, was a bit of a coward.

During a hold-up, Plunkett sent him to stop the driver of a coach

while he searched the passengers, but Maclaine's courage failed him.

Trembling with fear, he tried several times,

but just couldn't do it,

and Plunkett had to step in.

But eventually, Maclaine got the hang of it,

until one incident made them the talk of the town.

In Hyde Park, they held up the coach of Horace Walpole,

the Prime Minister's son and gothic novelist,

who soon found himself in a horror story of his own.

The ever-nervous Maclaine was collecting the passengers' valuables

when his gun went off by accident, nearly blowing off Walpole's head

and severely scorching the shocked man's cheek.

After profuse apologies,

Maclaine gathered the goods and they scarpered.

True to his gentlemanly credentials,

the mortified Maclaine wrote to Walpole the next day to apologise,

and to try and sell him his own belongings back.

Maclaine became known as the "Gentleman Highwayman,"

and by reputation, he was courteous to a fault.

Finally, he got to live as he'd always seen himself -

a high-flyer, mixing with the very best people in society.

And then, inevitably, it all went wrong.

The blundering duo robbed the Salisbury stagecoach,

relieving Lord Eglinton of his purse and blunderbuss

and a wealthy passenger named Josiah Higden of his clothes

and expensive fabrics.

Maclaine then tried to sell some of the stolen goods.

Firstly, he went to a lacemaker

with some of Josiah Higden's golden lace -

but unluckily for him,

it was exactly the same lacemaker who had just sold it to Higden.

After narrowly escaping that encounter, Maclaine was arrested.

Higden recognised his stolen property in the local shop

where Maclaine had eventually sold it,

and unbelievably, had left his name and address.

He'd been caught red-handed.

Plunkett fled, never to be seen again.

Maclaine was sent to jail, where he became a celebrity inmate.

3,000 people paid his jailers to visit him,

including several of the aristocratic circle

he had been so desperate to court.

Being unable to tell a common criminal apart from a gentleman

posed a threat to the social order

and Maclaine's story was used as a dire warning.

But status was important to criminals.

Whilst in jail, Maclaine apparently wrote a treatise -

published after his death -

that attempted to distinguish the types of crime he committed

from those of other mere criminals.

Highway robbers were considered "gentlemen of the road".

In order to be a highwayman, you had to have the accoutrements.

He had to have a horse, he had to be able to feed the horse, he had to have a saddle.

Well, I suppose you could nick those, but more often than not,

you inherited those, because you came from that sort of class.

And you had to be able to ride -

and not everyone could ride a horse, but the gentry could -

well, the well-off or the better off could.

Highwaymen were, no doubt, at the top of the criminal hierarchy.

They got to ride at the front of the cart to execution at Tyburn.

A highwayman, Maclaine insisted, would only ever rob the rich,

whereas the lowly footpad had little nobility in his work.

Standing at Tyburn Tree,

Maclaine faced his end as he had carried out his career.

His last words as he saw the gallows?

"Oh, Jesus."

All of the colourful tales of the highwayman age

were later taken and distilled into the story of one man -

Dick Turpin.

Popular culture down the centuries would embellish and exalt his legend

through entertaining yarns,

but lurking behind the glamorous Turpin of myth

was a real man, with a far darker story.

Turpin's real life was probably more typical of the average highwayman.

He was a braggart, a bully and a coward.

Violence was his modus operandi, not gallantry.

Like the Royalist robber James Hind,

he trained as a butcher, with a shop in Essex.

Butchery was a respectable profession,

but feeling the pinch in changing times.

Turpin's downward spiral began

when he started selling meat for a dodgy gang of poachers.

When the law got involved, he left his business

and joined his suppliers, the Gregory Gang.

Soon, however, even poaching became too risky, so ironically,

they turned to something that they thought would be safer -

armed robbery.

There was no glamour or panache to these outlaws.

The gang was ruthless,

with a reputation for violence, torture and rape.

Far from the cheeky and respected thieves of popular fiction,

they were housebreakers who preyed on the defenceless.

And they were perfectly prepared to carry out their threats -

beating, burning and slashing their victims.

The gang turned to house robbery

and in early 1735, this gang attacks an isolated farmhouse in Edgware,

which was a village on the outskirts of London,

which involves torturing a 70-year-old man

who's the householder,

to get him to reveal where valuables in the house are hidden.

This involves sitting on the fire bare-buttocked, whipping him.

While this is going on, one of the leaders of the gang is upstairs,

raping a maid at pistol point.

These are not folk heroes.

The gang was eventually brought down by a Justice of the Peace

and Turpin fled.

But one of their members had been captured and confessed everything -

and he even gave a description of Turpin, now a wanted man.

"Richard Turpin - a butcher by trade -

"is a tall, fresh-coloured man,

"very marked with the smallpox.

"About 26 years of age, about five feet nine inches high,

"wears a blue-grey coat and a light, natural wig."

After a time on the run, Turpin ended up in Epping Forest.

A busy route from London, it provided the perfect location

for his transformation into a highwayman.

And an ideal hiding place for a man with a price on his head.

For a short time, Turpin and his small gang of associates

were prolific thieves, but inevitably, they got greedy.

Turpin spotted a horse that he thought

looked much finer than his own

and forced the owner to hand it over at gunpoint.

It was to be his downfall.

The horse was an expensive racehorse named Whitestockings,

for the white marks on its lower legs.

And it wasn't long before the horse - and Turpin - were tracked down.

They were found at a pub in Whitechapel.

A local constable was summoned and a posse raised to set an ambush.

In the ensuing melee, one of his gang was shot and mortally wounded.

Accounts differ as to who pulled the trigger, and why.

Some reports say that Turpin fired in order to silence his colleague.

Others say he was trying to free him.

Either way, his luck was running out.

As the noose tightened, Turpin's notoriety came back to haunt him.

Eager to claim the large reward on his head,

a forest keeper's servant, Thomas Morris,

set out to capture him.

But Turpin wasn't going to go quietly and he shot Morris dead.

GUNSHOT

The reward was raised to £200.

Turpin resurfaced in Yorkshire and changed his name to John Palmer.

He then became a horse dealer -

the 18th century equivalent of a second-hand car salesman -

and of course, all of Palmer's horses were stolen.

For a few years, he blended in,

gaining a measure of respectability and friendship in the local area.

But then, after a hunting trip with some locals,

the man everyone knew as John Palmer

made a bizarre and fatal mistake.

To the utter bewilderment of the hunting party,

he took out his pistol

and blew the head off one of his landlord's chickens.

Then, when a neighbour complained,

Palmer threatened to do the same to him.

A constable was summoned and John Palmer was sent to the local gaol.

The authorities began to suspect

that there was more to this strange "John Palmer" chap.

No-one knew anything about him

before he arrived a few years earlier, or how he earned a living.

From his accent, he clearly wasn't local.

Enquiries were made in Lincolnshire, where "John Palmer" had lived before

and sure enough, they recognised the man.

He'd been arrested for the theft of livestock and horses

and had since escaped.

Realising they had a bigger case on their hands,

they brought him here, to York Gaol.

But they still didn't know his true identity.

In 1739, the man known as John Palmer

wrote a letter to his brother-in-law,

Pompr Rivernall back in Essex, asking for his help.

But when Rivernall looked at the letter,

he claimed not to know anyone from York

and refused to pay the postal charge.

By a bewildering coincidence,

the letter was seen by a man called James Smith,

the very man who had taught Richard Turpin how to write.

Recognising the handwriting, he went straight to the authorities.

John Palmer had been rumbled.

At York Assizes in 1739,

Richard Turpin was put on trial for horse theft.

Despite repeated denials,

at the trial, John Palmer was identified as Dick Turpin

and he was found guilty.

When asked by the judge why he had failed to bring

any character witnesses to his defence,

Turpin said that he had been told

that his trial would be moved to Essex

and that he was unable to bring anyone here,

where he was a stranger.

It seemed he never even expected it to get this far.

In the end, Turpin was condemned as a simple horse thief

and he was hanged here, at York racecourse.

And in an irony that can't have escaped him,

the hangman was a fellow highwayman,

who'd been spared the noose for carrying out the day's executions.

Perhaps the only act that Turpin carried out

that was anything close to the legend

was when he was standing on the cart with the noose around his neck

and he stamped his shaking leg, until it was still.

And then, he jumped off into oblivion -

before he could be pushed.

During his life, Turpin was reviled by Walpole's weak administration.

He was ammunition for their opponents,

who suggested that they were not being tough enough on law and order.

But the public would remember men like Turpin differently.

As memories of the real man faded,

the myth took over.

A few decades after his death,

Turpin reappeared in song as a much-rehabilitated character.

# Said Turpin

# He'd never find me out I've hid my money in my boot

# The lawyer says

# There's none can find I hid my gold in my cape behind

# O rare Turpin hero O rare Turpin O

# As they were riding past the mill

# Turpin commands him to stand still

# He says

# Your cloak I must cut off My mare she needs a saddle cloth

# O rare Turpin hero O rare Turpin O. #

It's such a fantastic song,

but it's one of so many about highwaymen.

Why was it so popular?

Well, people just love to have their own rogue, their own supervillain,

especially their own local one - and someone to stand up to authority.

When you look at it as a historian,

it's very clear that the myth and the reality are not the same.

And in real life, these people were very unpleasant.

They were violent, armed robbers.

Often, when these ballads were originally sold,

they were telling the news.

They told the truth, so they would say what actually happened

to these characters - usually hung -

but as soon as these songs got into the mouths of the people,

the stories were very different and usually, they'd get away scot-free.

The songs took these legends around the country

and if you had a fantastic story,

-coupled with a really catchy tune...

-Yes!

..then that's just going to spread like wildfire.

In the early 1800s, captivated by the old tales of highwaymen

was a young writer called William Harrison Ainsworth.

It was largely through his writing that Dick Turpin and all highwaymen

came to be the heavily-romanticised mythical rogues we know today.

Through Ainsworth's 1834 novel Rookwood,

Turpin became associated with Black Bess

and the famous escape ride to York.

He was remodelled with the virtues of an 1830s gentleman fit for a new age -

an icon of Englishness and manly, imperial pride.

With Ainsworth, highwaymen were transformed

from the exciting but ultimately doomed criminal

to the fantasy hero of Boys' Own adventures.

But the fictional highwayman could only become a proper hero

because the real thing was no longer around to spoil the illusion.

By the 1800s, mounted robbers had long since ceased

to be a threat to society.

The age of the highwayman was over.

The world around them had changed.

The enclosure of fields and open countryside

had limited their movement.

Faster coaches travelled on smoother roads,

which were, in turn, policed by mounted patrols.

Railways were perhaps the final nail in their coffin,

as the wealthy simply ceased to travel by road.

Writers seized upon the idea of highwaymen

as lovable and misunderstood rogues

who did as they liked and did it with style -

and they developed these ideas

just as the highwaymen were fading into the past.

They became the star attraction of Penny Dreadfuls,

cheap theatre shows and children's toys.

And one day, Ainsworth's story would find its ultimate expression

on Hollywood's silver screens.

As the prospect of violence disappeared,

so did the darker, unsavoury aspects of the highwayman's story.

As Victorian heroes, highwaymen became fancy dress outlaws,

with straightened-out morals and a firm sense of social justice.

They also brought a hint of danger, rebellion and free spirit

to a very strait-laced age.

But they were outlaws who would accompany us on adventures

rather than steal our wallets - and it was a potent mix.

The real thing may have gone,

but in our imagination, they were here to stay.

GUNFIRE

Next time, from the highways to the high seas -

the British outlaw turns to piracy.

Their plunderings threaten a fledgling maritime empire

and the bloody exploits of swashbucklers like Captain Kidd and Blackbeard

make them into the most hunted renegades in history.