Were highwaymen as dashing and gentlemanly as the stories would have us believe? How did these bandits pick the best locations to rob from the rich? And how much of the legend surrounding Dick Turpin is true? Lauren Good speaks to historian Bob Shoemaker about highwaymen…
When did highwaymen emerge?
Highwaymen have always existed as long as there have been roads and people travelling on them with valuables worth stealing, but they acquired a distinctive reputation in the Middle Ages. A sort of ‘cult of the robber’ emerged, in which these individuals were seen as courageous, daring and manly.
Highwaymen: everything you wanted to know
Bob Shoemaker answers listener questions on the criminal capers of highwaymen
Listen to the full interview on the podcast
How did highwaymen acquire this reputation?
Initially, highwaymen were written about mostly in fiction. In the Middle Ages, manuscript documents would often celebrate their activities, and with the spread of print in the 16th century, they were written about even more widely in various forms of printed literature.
What is particularly interesting is that highwaymen began to participate in their own self-promotion. They realised that their reputations would be enhanced – and their chances of avoiding punishment, too – if there were good stories about them being told. Often highwaymen would work with people who wanted to write their biographies, or they would sit – in the 18th century – to have their portraits.
How were highwaymen depicted in literature?
The ideal highwayman, certainly in the 18th century, was a gentleman or someone who behaved and dressed like one. He was polite and chivalrous. He robbed without any actual violence (although he may have threatened it). He would stop a coach, hold a pistol to it with one hand, offering his other hand to help any ladies to step out of the coach onto the ground, where they could surrender their valuables.
He was also apologetic, saying things like: “I’m very sorry to have to do this, but it’s a necessity.” The ideal highwayman always left a bit of money with the people he was robbing, so they could continue their journey without difficulty.
The whole aim was to present himself as above the common criminal. The idea was that he had come from a respectable background, but had fallen on hard times. A gentleman wouldn’t work for a living – but they might rob for a living.
What was the actual danger to victims of highwaymen, other than losing property?
There was always a chance of injury or even death during an encounter with a highwayman. The ritual of the highway robbery involves everyone playing their part. If a traveller put up any resistance – or if the highwayman detected any resistance – he could become violent.
This was especially the case if the highwayman thought the traveller had hidden their valuables from him. He might threaten or torture the victim to acquire them.
In cases where the highwayman thought he was in danger of being captured or arrested, he might resort to murder to save his skin. It’s difficult to put a number on how many murders actually happened – not many, but they did occur.
Most travellers would have escaped an encounter with a highwayman physically unscathed, but there were certainly dangers inherent in the whole ritual.
By what means did people protect themselves from highwaymen?
The best way to protect yourself was to think carefully about your journey and to plan it well. Travel during daylight hours on well-travelled roads, preferably in a group for added protection.
What legislation or policing measures were passed in response to highwaymen?
In the Middle Ages, being a highwayman was made a capital offence punishable by death – and this continued to be the case all the way into the 19th century.
However, this legislation didn’t actually result in many prosecutions. So, from the late 17th century, the Crown started offering a £40 reward for the reporting and conviction of highwaymen. Forty pounds at that time was a lot of money, equivalent to thousands today.
In 1720, an additional £100 was added to the reward. This caused its own problems because lots of people were then falsely prosecuted as a means of acquiring the money.
Efforts to improve policing to prevent highway robbery didn’t come in until the 1750s, when mounted patrols were introduced on the roads around London. This is one of the earliest examples of innovations in policing in this country to prevent crime. It demonstrates how seriously highway robbery was taken.
How many of these cases were taken to court?
At its peak, there were dozens of highway robbery cases every year in the London area. You can search for them very easily on the Old Bailey Proceedings online.
What kind of background did highwaymen actually come from?
The ‘gentlemen highwaymen’ were often exaggerating their status. The typical highway robber was more likely to be a skilled craftsman or tradesman. Then there were other people whose backgrounds placed them on the margins of gentility – people who would like to be a gentlemen and could try to play that part.
There was nonetheless a minimum level of wealth and status required to be a highwayman, because you needed access to a horse and the knowledge of how to use a pistol. It wasn’t really a crime for the poor.
What are the origins of Rotten Row in Hyde Park?
Rotten Row is a corruption of the French term Route du Roi, which translates as king’s road. It was a street that was built in 1690 between Kensington Palace and St James’s Palace to facilitate the travel of royalty and aristocracy into and out of the West End through Hyde Park. It was the first street in London to be lit (with lanterns) – and it was lit because of the threat of highway robbery.
Is the legend of Dick Turpin true?
Dick Turpin was a real highway robber – this is true. He was also a pretty nasty piece of work; violent, a horse thief and a murderer.
Turpin was executed in 1739. It was almost a century later that the positive reputation of Turpin as daring and romantic emerged. This was due to the publication, in 1834, of William Harrison Ainsworth’s Rookwood, which was a novel about Turpin’s life. Rookwood invented many of the myths about Turpin, particularly the famous tale that he rode 200 miles from London to York on his horse Black Bess.
What other famous highwaymen from history are there?
There are three famous ones from the 17th century: James Hind, Claude Duval and James Whitney. In the 18th century there was John Rann and my personal favourite highwayman, James MacLaine.
MacLaine was an effective self-promoter. The son of an Irish Presbyterian minister, he got into trouble in Ireland and so came to England, setting himself up as a gentleman. MacLaine certainly did mingle with the elites, but he had to go out on the road to support his lifestyle. He wasn’t particularly successful at it either. After maybe a year or less, he was caught, tried and eventually executed. But in the meantime, he successfully promoted his image as a gentleman highwayman. He even held up and robbed the aristocrat Horace Walpole, who later refused to prosecute MacLaine because he had such a positive reputation.
Were there any highwaywomen?
There were some women who robbed on the highways – but none of them were noted as highwaymen or highwaywomen. They didn’t achieve the same kind of notorious celebrity that highway men did. There is a clear reason for this: the perceived virtues of a highwayman were male virtues.
- Read more | Were there any real highwaywomen?
How did the age of the highwayman actually come to an end?
It came to an end for several reasons. The first is the decline of the myth; highwaymen ceased to become interesting to people, because values were changing.
There developed a much greater intolerance of violence, even the implicit violence of a highway robber. People probably don’t realise that 18th century attitudes towards crime were often quite mixed. People could condemn criminals, but they also could understand – better than we sometimes do today – why crimes happen.
However, from the late 18th century, crime was much less tolerated. It was seen as something committed by a separate class of people: the lowest of the low. A criminal class.
All of this undermined the possibility of a positive reputation for a highwayman. Robberies also fell because of practical reasons: roads became better and policing became more effective. Finally, and most importantly, new forms of banking and credit emerged that meant you could convey cash between two points more safely and there was no need to travel with large amounts that could be stolen.
The last mounted highway robbery in England reportedly happened in 1831. Of course, robbery continues to this day, but the methods have changed and obviously the reputation of those who steal or loot has changed.
Robert Shoemaker is Professor of British history at the University of Sheffield. He is an expert on London history, gender, and crime and criminal justice in the 18th and 19th centuries. He was speaking to HistoryExtra’s Lauren Good on the HistoryExtra podcast. Listen to the full episode here