Highwaymen: The Road to Infamy

To use the highway in 17th-century England was to risk armed robbery: highwaymen were endemic. As the century wore on, the public grew particularly concerned with the alarming number of dastardly robbers who would stop travellers on England’s roads and demand that they ‘stand and deliver’ – the phrase was indeed the standard form of request – their goods. Such incidents were well documented – and sensationalised – by the media. The 18th-century exploits of Jack Sheppard and Dick Turpin have gained lasting notoriety, but the lives and deaths of highwaymen were a publishing staple from the beginning of the 17th century. In such stories, highwaymen were often presented as semi-heroic: gallant men who abhorred violence and stole from the rich to give to the poor. Highwaymen such as James Hind (who may, or may not, have helped Charles II escape capture by the Roundheads following the Battle of Worcester in 1651) repeatedly insisted that they disapproved of the ‘shedding of bloud unjustly’ and that they never did ‘wrong any poorman of the worth of a penny’ (as told in True and Perfect Relation of the Taking of Captain James Hind, 1651). Others were cast as prodigal sons whose failings were understandable and, to an extent, excusable because they were not deemed to be serious. Pamphlets such as The Knight Errant: Being a Witty, Notable and True Relation of the Strange Adventures of Sir William Hart Now Prisoner in the Tower (1652) and The Witty Rogue Arraigned, Condemned, and Executed. Or, The History of That Incomparable Thief Richard Hainam (1656) presented ‘severall exploits, cheats, and most witty tricks’ of highway robbers. Wit, clearly, was among the rogues’ inherent qualities. 

But in the late 17th century a new hero began to appear in print: the person who resists and arrests the highwayman. Public participation was considered one of the pillars of England’s criminal justice system; actively assisting in the arrest of a criminal was the duty of all bystanders. Given the small numbers of agents of law enforcement at the time, it was also very much necessary: the English prided themselves on a system that was safeguarded by all members of the commonwealth. While some highwaymen, such as Sheppard and James MacLaine, kept their status as heroes or gentlemen, crime narratives increasingly adopted the perspective of the victim and lionised resistance to highwaymen.

Justice overtakes roguery

With the lapse of the Licensing Act in 1695, newspapers began to proliferate. The end of the Act meant that newspapers and other printed materials (such as crime pamphlets) no longer needed to be cleared by a licenser before publication. Reportage of highway robbers increased in turn, but with an emphasis on the manner of their arrest, rather than sensational details of their crimes. In a typical example, recorded in The Protestant Mercury in December 1697, a highwayman is recognised by a butcher, who decides to give chase. Seeing the pursuit, a young gentleman’s servant asks his master to allow him to assist the hunt. The hero of the piece is the servant, who tirelessly pursues the highwayman. Even after the latter fires a blunderbuss at the young man and ‘three of which Bullets went thro’ the Sleeve of his Coat, without any harm’, this in ‘no way Daunting him, he pursued his Chase’. At last, the thief falls into a river where, after giving him a sound whipping, the young servant forces him to surrender. The report ends with the just rewards of virtue: the servant receives a reward of £40. In a similar fashion, The Weekly Packet of 4 February 1716 published a report of how some young men had pursued two highwaymen who had just robbed two gentlemen. Despite the best attempts of the highwaymen to make their escape, ‘Justice overtook Roguery’ and the young men valiantly arrested the robber, having them committed to prison.

Victims, too, were increasingly portrayed as heroic in their resistance. In January 1700 The Protestant Mercury reported that, when two highwaymen attempted to rob a wagon from Hounslow Heath, ‘many passengers well armed … gave them such a warm Reception, as forced them to Ride away, they being Wounded in several places’. Some months later, the same paper presented the story of a London citizen resolute in the face of death: after being assaulted by two footpads who ‘clapt a Pistol to his Breast, which he did not much regard’, he ‘drew forth a Pistol well Charged with Peas, which he let Fly between them with so good effect, that they both Scour’d off, leaving him to go Home without any farther Molestation’. Similar stories appear in various newspapers, including a ‘well arm’d man’, reported in The Weekly Packet of September 1716, firing at a highwayman who attempted to assault a stagecoach on Turnham Green. A story published in The Post Man and the Historical Account on 14 June 1701 describes a highway robber’s unfortunate attempt to rob a minister. The would-be victim feigns compliance, only to get closer to the robber so that he could pull ‘him from his Horse with that violence, that with the fall he broke his Neck’. In these stories the resistance of victims and the bold pursuit of bystanders was exalted – even when it led to the death of the criminal.

Vigilance, it was stressed, was necessary on the part of readers, who were warned to be on the lookout for suspicious individuals or items unlawfully obtained. Notices of the arrest of highwaymen often presented detailed descriptions of the criminals, requesting that anyone who had been robbed by them come forward and help identify the thieves. In April 1704 The London Post provided a description of some arrested highwaymen:

Benjamin Carr, a short fair Man, his Nose somewhat Crooked and large; John Webb, a tall Man, flat Noz’d, sometime wore his Black-Hair, but now wears a brown Perruke, much Powder’d; William Fox, a middle siz’d down look’d Fellow.

Identifying a wanted highwayman would not only allow the victims to reclaim any stolen goods still in the thieves’ possession, but would also make them eligible for a portion of the £40 reward given for their apprehension.

On occasion victims could meet their attackers again by chance. Most highwaymen lurked around London and often returned to the city to spend their ill-gotten gains. In various articles we see how a victim ‘happen’d to spy two Highwaymen who had robb’d him’ (The Weekly Packet, 18 February 1716), or how another in St Paul’s Churchyard ‘met a Highway-man who robb’d him on the Road’ (The Weekly Packet, 12 January 1716). The pamphlet A full and true account of the apprehending, taking and examination of one Mr. Harris, and carried befoe [sic] Justice Tully, sworn against by Mr. Stagg, to be that notorious highwayman that used to robb on the black mare on Hounslow-heath (1704) outlines one such example of this happening. A lawyer travelling by stagecoach to London sees a group, including a suspicious-looking man, overtake his party and ‘had time to make Observations of the Man on the Black Mare, and Observ’d that he had a Cut on his Face, besides several other markes’. When the highwaymen finally stop the stagecoach, they are wearing masks to hide their identity, but it is too late. When they later meet again in Hyde Park the lawyer is able to recognise the robber and arrest him with the help of a constable. He is even brought to testify against the criminal and, ‘very well remembring the Scar on his Face’, he ‘positively Swore before Justice Tully that he was the Man that Rob’d him on Hounslow-heath’. The robber was duly sent to the Gatehouse prison in Westminster.

No questions asked

Despite their heroism, defiant victims were clearly treading a fine line between risk and reward: a highway robber denied the requested money could, of course, make good on his promise to otherwise take his victim’s life. Such was the case when a baker tried to outrun two highwaymen, but, ‘seeing they could not reach him, they shot him through the Back, of which he instantly Died’, as reported by The Protestant Mercury on 20 October 1699. Similarly, when a gentleman fired his pistols at a robber in order to protect his property, the highwayman responded by shooting his servant dead and robbing the gentleman anyway (The Post-Man and the Historical Account, 24 August 1700). Fearing for their lives, victims often opted for negotiation rather than confrontation. A gentleman who was robbed of 30 guineas and a gold watch persuaded the highwaymen to return his watch ‘upon Promise, that if they should be taken, he would not prosecute them’ (The Weekly Packet, 7 January 1716). Many advertisements, such as one listed in The Post Boy in November 1712, offered a reward for the return of stolen goods ‘no Questions askt’. Such advertisements put forward a safer alternative to criminals: would they rather keep the goods and risk their lives if caught, or return them and receive a reward?

But the promise of reward could also appeal to members of the public, fortifying them with the required courage to partake in apprehending highwaymen. From 1692 onwards, a reward of £40 was given by the state to those who assisted in any capacity with their arrest and prosecution. Some notices of stolen goods promised an extra reward for anyone who would ‘discover the Persons who stole ’em, so as they may be brought to Punishment’ (Post Boy, 5 January 1714). In 1693 the pamphlet The life of Captain James Whitney narrated how a landlord, realising that the infamous highway robber often visited a tenant of his, decided to ‘bid fair for the 40 l. set upon his Head’ and called a constable in order to assist him in capturing Whitney.

Those who arrested highway robbers were commended not only for their bravery, but also their guile. A 1694 pamphlet narrates how a country gentleman’s servant, whose master had been robbed by highwaymen, happened to see the villains again on the road to London and, ‘Remembring their Faces’, he ‘began and continued a familiar Conversation with them upon the Road, till they came to London, the fittest Place for the Apprehending of unlawful Livers, whose Resolutions are generally desperate’. He then followed them to Temple Bar, where ‘after great Resistance’ he apprehended them with the help of a constable.

An even more outrageous tale of cunning was presented in A full and true ACCOUNT Of a Notorious and Bold ROBBERY, COMITTED On Hounslow-Heath on Friday last, 1700. By Jonathan Lan, and Guy Cook, Two Highway-Men (1700). Contrary to what the title suggests, the pamphlet focuses almost exclusively on the arrest of the highwaymen by an unnamed country farmer who, seeing Lan and Cook robbing a nobleman, decides to follow them. Realising this, the highwaymen threaten to kill him:

But the Country Man being a subtil Blade, Counterfeited himself Drunk, and Acted his Part so natural, by making strange Faces, Antick Gestures, &c. that they really believe’d him to be no less than what he pretended, and thereupon calling him Drunken Sot, they left him and went forward, but he still follow’d them.

Avoiding suspicion through this pretence, the farmer was able to follow the robbers until they reached a ferry, where he found assistance and saw them arrested.

Vigilante justice

Encouraging the public to resist and arrest highwaymen could, however, be a double-edged sword. In August 1698 The Protestant Mercury subverted the trope of brave and upstanding bystanders in a story of some men who, after apprehending a highwayman who had robbed and killed his victim, hanged him themselves, assuming that they had the right to mete out punishment. They were imprisoned for their actions, but were acquitted when their neighbours testified on their behalf. The story itself was unusual, but what made it most surprising is that the newspaper’s editor introduced it as a ‘comical story’. Though standards of humour were naturally different in the 17th century, comments of this kind were rare in newspaper reports, more usually found in a crime pamphlet. Though the men had subverted the justice system, the story and the editor’s comment, seemingly condoning the hanging of the highwayman without a fair trial, reveals how far the once heroic highwayman’s stock had fallen by the late 17th century. The implication is that what we would today call vigilantism was accepted as appropriate – or at least easily excusable – behaviour.

It is unclear why this shift in perception – or growth in acts of bravery – took place; it could be related to the increase in policing in London. Nonetheless, the 18th century saw a significant change in understandings of crime, with victims and vigilantes becoming the new heroes of narratives which had no scruples celebrating their actions. The image of the gallant or witty highwayman coexisted uncomfortably with stories which lionised those who thwarted their plans. It was only in the 19th century that this struggle reached its end, as crime stories were increasingly told from the point of view of a new figure: the detective. But by that point highway robbers had been consigned to the past, their legend enduring only in literature.

Lena Liapi is an Honorary Research Fellow at Keele University. She is the author of Roguery in Print: Crime and Culture in Early Modern London (Boydell & Brewer, 2019).