Gentlemen Rogues & Wicked Ladies: A Guide to British Highwaymen and Highwaywomen

Gentlemen Rogues & Wicked Ladies: A Guide to British Highwaymen and Highwaywomen

by Fiona McDonald


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Product Details

ISBN-13: 9780752463766
Publisher: The History Press
Publication date: 12/01/2012
Pages: 224
Product dimensions: 5.00(w) x 8.00(h) x 1.00(d)

About the Author

Fiona McDonald is a writer and illustrator. She illustrated The Little Book of Genius.

Read an Excerpt

Gentlemen Rogues & Wicked Ladies

A Guide to British Highwaymen & Highwaywomen

By Fiona McDonald

The History Press

Copyright © 2012 Fiona McDonald
All rights reserved.
ISBN: 978-0-7524-7899-9


Part 1

A History Of Highwaymen and Highwaywomen

What is a Highwayman?

He'd a French cocked hat on his forehead, and a bunch of lace at his chin;
He'd a coat of the claret velvet, and breeches of fine doe-skin.
They fitted with never a wrinkle; his boots were up to his thigh!
And he rode with a jewelled twinkle
His rapier hilt a-twinkle
His pistol butts a-twinkle, under the jewelled sky.

When we speak of a highwayman, or highwaywoman, we conjure up a specific figure that looks like the man out of Alfred Noyes's famous poem. This, though, is only one type of highway robber, one that came from the mid to late eighteenth century. It is the clothes, in this instance, that maketh the highwayman or highwaywoman (the wicked lady of legend and film was also dressed in this style).

Robin Hood was a highwayman. He was not called such; but he was an outlaw, if not your average robber. He had an axe to grind with the wicked politicians of the day. That isn't to say that some of his victims wouldn't have been highly traumatised by the ordeal or that they all deserved what they got. Robin Hood, ultimately, fits into the highway robbery bracket because he performed a specific type of theft. The word 'rob' originally comes from a word of German origin, raub, meaning 'theft'. It came into English from the Latin, deraubare. To rob is, therefore, to thieve. Highway robbery is the theft of one person's belongings by another with the intent of depriving the owner of them permanently.

The common law definition concerning robbery used to be:

Robbery is the felonious and violent taking of money or goods from the person of another, putting him in fear, be the value thereof above or under one shilling.

Highway robbery was theft, with the intention of using fear on the victim, committed on the street, road or field; it didn't literally have to take place on a main road. We can include Robin Hood to the brother and sisterhood of highway robbery because that was where Robin committed his thefts: outside, in the open air of a public place.

The term 'highwayman' is thought to have come into common use in the early part of the seventeenth century. Men and women who have committed highway robbery have, for the most part, been very ordinary looking people: no romantic black coat, three-cornered hat or ruffles of lace. Very often, the robbery was not premeditated but an act of desperation made on a whim or because an opportunity arose. There were, however, organised highway robbers; some working in gangs, some in pairs and others always alone. Within the gangs, the main perpetrators of the actual robberies were men and the women would fence the goods to pawnbrokers or other outlets.

A few women did go out deliberately on the open road to point their pistols at coaches and demand the passengers to 'Stand and deliver!'. However, the stories of most women who were indicted for highway robbery were often quite banal: petty theft taken one step further.

Highway robbery had its heyday from the time of the English Civil War to the middle of the eighteenth century. After that, it began to wane. The last recorded highway robbery in England took place in 1831. The crime of mounted robbery continued much later in countries like Australia and America.

Highwaymen in Other Countries

Robbery committed in the open air, usually targeting travellers, was a world-wide phenomenon. In Australia, there were bushrangers and, in general, they have received a similar, romantic gloss to the English highwaymen. Their crimes are seen as deeds, their escapes as daring adventures and their rugged lifestyles as manly and heroic.

Famous names abound in the world of bushrangers (who hasn't heard of Ned Kelly, the Australian equivalent of Dick Turpin and Claude Duval?) and Australians are well aware of Ben Hall, Frank Gardiner and Captain Thunderbolt (whose hideout is a twenty-minute drive from my home town).

The Australian bushrangers worked in much the same manner as the highwaymen. They ambushed coaches and threatened to kill all the travellers, including the coachman and any guards, if valuables weren't handed over without resistance. They worked the highways of Australia from the beginnings of its colonisation in 1788 until the execution of Ned Kelly in 1880. One of the very first convicts sent to Australia on the First Fleet was a woman from England convicted of highway robbery. Her story is told later in this book.

The American West was another vast area that was in the process of being developed into towns and cities, and it faced similar problems to Australia. As people populated places across the continent, and supplies and travel could take days and weeks through wild lands, there were lots of opportunities for outlaws to waylay them and steal everything they had. In America these rascals were known as road agents. In South North America and Spain they were called bandits. France had brigands, Italy had brigantes and in Hungary they were betyars. In the Balkans and eastern Europe highwaymen were called hajduk.

In our own time, we still suffer highway robbery. In some countries little has changed in the way thieves ambush travellers, often tourists, and threaten them with guns and knives. In modern, first-world cities carjacking has become a common crime in which the vehicle itself is taken, often with the victim in the driver's seat driving to the directions of the thief.

The Law, Prisons and Sentences

In the early days of apprehending criminals there were no policemen. There were soldiers, guards and ordinary citizens who could grab hold of an offender and drag them to a place of confinement. To be accused of stealing goods worth more than 1s meant an arrest, a hearing, a trial and then, if found guilty by a jury, sentencing, which could result in hanging.

In Tudor times, a system of watchmen and constables was established. Members of the community volunteered or were selected to work on a roster with no pay to keep the streets of their villages and towns safe from criminals. Similarly, during the eighteenth century, a class of men (possibly including women) was established known as thief-takers. They were civilians who were hired by victims of crime to hunt down and capture those that they suspected had wronged them. This system, like any other, led to a great deal of corruption. Jonathon Wild, in the 1720s, was known as the Thief-Taker General and in this position he was able to continue and expand his own criminal empire. One of the scams he worked was to have his gang members steal goods and then return them to the owner to get the reward or fee. No one was safe from Wild. He would turn in his own employees to aid his disguise as an upstanding citizen. In 1725, Wild himself was taken, tried and hanged.

It wasn't until 1829 that the beginnings of a professional police force emerged at the instigation of Sir Robert Peel. They functioned largely as a preventative force and were known as the London Metropolitan Police.


Where were these accused felons taken after their arrest? In the time of Robin Hood, they would be put in the dungeon of the local castle or fortress. Later, they were put in prison. In London there were a number of prisons of different quality and security to suit different crimes. There were debtors' prisons, which were generally low security for housing men, women and complete families who were in debt. The debtor had to stay in prison, though the family was free to come and go, until they paid their debts and a prison fine as well. This was a bit difficult to do if you were locked up in gaol, so debts had to be paid by friends and relatives. It was this kind of prison – Marshalsea – that was the birthplace of Dickens's Little Dorrit, and it was where she remained until she was an adult.

Other prisons include Poultry Compter in Cheapside, named after the livestock sold in the area, and Bridewell Palace, originally one of Henry VIII's houses. In 1553, Edward VI gave the building to the City of London to be used as a poorhouse. In 1556, it also became a prison, hospital and workhouse. Bridewell did not house hardened criminals, but acted more as a place to home the impoverished. A good many debtors ended up in Bridewell. The name was used by similar prisons across England, Scotland and Ireland. The building was destroyed in the Great Fire of London only to be rebuilt in 1666–67. By 1863, it was completely pulled down.

And then there was Newgate. This prison was for true criminals who were a danger to the public and needed to be secured so that they couldn't escape. Many of Newgate's inmates left only to face the gallows.

The system in gaol was quite different to how it is in today's prisons. The prisoner was fed the bare minimum unless they had private funds to pay for a better quality and quantity of food. The gaolers were open to corruption and for a few coins would do all sorts of favours for the prisoners (except, of course, releasing them).

Inmates awaiting trial, sentencing or execution could entertain visitors if they wanted. Notorious criminals, often highwaymen, attracted large audiences to hear stories of their adventures. The guards charged admittance for the privilege of hearing the tales from the criminal's own lips and made a nice little sum on the side.


England had an overcrowding problem in prisons that lasted for decades. One solution was to sentence criminals to transportation. This meant sending them overseas to a British colony to work for seven years. Before the discovery of Australia, transportation involved going to the plantations in Virginia in America. Several of the highway robbers featured in this book, both men and women, suffered this fate. Once Australia was on the map, convicts were sent there instead. One of those convicted of highway robbery, amongst other things, was Mary Bryant, who became one of the first prisoners to be sent to the brand-new colony.

Transportation was the soft option. Sometimes, perhaps if it was a first offence, convicted criminals would have their death sentences lessened to one of transportation for seven years. The idea was to give the person a second chance. If the colonies didn't kill them off they would be only too grateful to be able to leave those far-flung places and return home, punished enough never to offend again.

If a prisoner returned before their seven years were up and they were caught, the sentence was automatically one of death. It didn't always happen quite like that, though. There were petitions made on behalf of prisoners, juries could take pity on the accused, pardons could be granted and even escapes made.


Execution was the ultimate punishment; there was no coming back from being hanged by the neck until you were dead (except for a couple of interesting cases). Death, however, didn't always follow the sentence; a prisoner could receive a pardon before the execution took place or they could escape.

The method of hanging at Tyburn, the short drop method, ensured that you choked to death. It could be a slow process and bodies were left to hang for several hours after execution to make sure that they were well and truly dead. The most notorious set of gallows in London, if not the whole of England, was at Tyburn.

Before a criminal got as far as begin either transported or hanged at Tyburn, they were taken to the Old Bailey, the Central Criminal Court of England. Conveniently, the court was housed next door to Newgate prison. The original building was destroyed in the Great Fire of London, but was rebuilt some years afterwards as an open-air court in an attempt to stop the spread of disease. In 1734 it was enclosed, but in 1750 sixty people died of Typhus, including the Lord Mayor of London. The cause was the unsanitary condition of the Old Bailey. The court was rebuilt yet again in 1750 and further developed in 1824.

Once arrested, the criminal would stand trial before the judge and a jury. The jury would decide whether the accused was innocent or guilty and the judge would determine the sentence. If the guilty party was sentenced to death then they would go back and wait in Newgate for the next hanging date at Tyburn.


Tyburn was a name that struck terror into the hearts of all serious criminals for centuries. It was the last place that a condemned man would breathe air before a heavy rope, tied in its artful knot, was placed around their neck. Tyburn was a village that took its name from the stream bearing the same name, a tributary of the Thames. It was an important place for several reasons. It was from Tyburn Springs that Sir Gilbert de Sanford, who owned the village, agreed to let London pipe water for its citizens. The water ran along an intricate system of lead pipes that ran through the city to Cheapside and into a public conduit for free public consumption.

Tyburn witnessed its first public execution as early as 1196 when William Fitz Osbert was stripped naked, dragged behind a horse to Tyburn and hanged for his part in giving the poverty stricken people of the city a public voice. He was seen as a troublemaker and rebel: a threat to the throne and the comfort of every well-off person in London.

In the time of Henry VIII, Tyburn was used again for hanging the leaders of a possible rebellion. The death of Nicholas Tempest, the king's bowbearer, is an example of this. He was executed for being an instrumental part in the Pilgrimage of Grace. Thirty-four years later, Tyburn became an official place of execution by hanging. In 1571, the 'Tyburn Tree', as they called the triple gallows, was erected for the purpose of mass executions. It was set right in the middle of the road in an unmistakable attempt to put fear into all who might be tempted to turn to crime.

Elizabeth I had Dr John Story hanged from the Tree. He was a Catholic who would not acknowledge her as the true monarch of England; he was also the tree's first customer.

Later, when Charles II had ascended the throne, certain enemies of the Crown, Oliver Cromwell included, were disinterred and hanged from the gallows as a symbol of the King of England's authority and sacredness: the men who beheaded Charles I were treated like common murderers.

As the executions became more frequent they attracted a growing crowd of spectators. Stands for the audience, also known as Mother Proctor's Pews, were erected for the comfort of the public (at a cost, of course) and refreshments were sold. The stands were easily overcrowded and one of them later collapsed, killing many of the people on it. It was nevertheless an early and extremely popular form of tourist attraction. In fact, on execution days (along with festive days), apprentices were allowed the time to go and witness them.

The days set for Tyburn executions had to correspond to the days that the local assizes were held. This meant that there could only be up to eight days a year on which hangings could be performed. When they did take place, it was a real spectacle with the trip from Newgate prison to the Tyburn Tree taking up to three hours, despite being only 2 miles away. Revellers would watch as the convoy (which could consist of several open carts and a mourning coach) would arrive accompanied by an armed guard. Criminals who had no money went in the open carts, dressed in simple linen shifts or clothes, perched on top of their own coffins for all to see, but some of the richer ones were able to go in the mourning coach dressed in black silk or satin. The convoy would make comfort stops along the route to let the condemned prisoners have refreshments before their last ordeal.

The last criminal to be hanged on Tyburn Tree was, fittingly, a highwayman called John Austin in 1783.

Costumes and Weapons


The timeline for highway robbery spans centuries: too many to show the range of clothes that the robbers would have worn. Instead, we'll concentrate on those couple of hundred years in which the highway robber was most prevalent.

The seventeenth century saw the rise of the highwayman and highwaywoman as England's bloody Civil War dominated the middle decades. Two very different factions arose with two completely different sets of political and cultural beliefs. The old system, that of monarchy, was disposed of and the Parliamentarians took the place of the king. The leader of this group was Oliver Cromwell. His soldiers came to be known as Roundheads on account of the distinctive bowl-shaped helmets they wore.

The Cavaliers, as the opposing Royalist soldiers were called, wore lavish outfits with lace trims and plumed hats to reflect the aristocratic state that they had enjoyed and hoped to enjoy again once the war had been won.


Excerpted from Gentlemen Rogues & Wicked Ladies by Fiona McDonald. Copyright © 2012 Fiona McDonald. Excerpted by permission of The History Press.
All rights reserved. No part of this excerpt may be reproduced or reprinted without permission in writing from the publisher.
Excerpts are provided by Dial-A-Book Inc. solely for the personal use of visitors to this web site.

Table of Contents


Author's Note,
Part 1 A History of Highwaymen and Highwaywomen,
What is a Highwayman?,
The Law, Prisons and Sentences,
Costumes and Weapons,
Part 2 Lives of Highwaymen and Highwaywomen,
Part 3 Fictional Highwaymen and Highwaywomen,

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