‘Sixteen String Jack’ was born near Bath in Somerset in 1750 and christened John Rann. He was bright and quick-witted and at the age of twelve took service with a lady of sufficient means to move in the fashionable society of the time. He did well, gaining one promotion after another and became a coachman in London where, unfortunately, there were too many temptations. The capital was alive with toothsome young doxies and also contained many shops with elegant and expensive clothes. Jack developed a taste for both and took great pleasure in swaggering around at public events dressed like a fashionable grandee and making the acquaintance of the young ladies who flocked to such occasions to eye up the young bloods. The problem was that a humble coachman’s pay could not finance a lifestyle of the sort to which Jack aspired. There seemed no alternative to a life of rigorous self-denial or crime – he chose the latter. He tried his hand at pickpocketing but decided that it was risky and lacked style. Jack wanted to cut a dash and so decided to turn his hand to the highwayman’s trade. He proved to be a natural.
‘Sixteen String Jack’ soon became notorious for the audacity of his robberies and the gentlemanly courtesy with which he demanded that his victims part with their valuables. He was also noted for his sartorial elegance and gained his strange nickname because he frequently appeared in public in breeches of silk that had sixteen strings attached to the knees. He was arrested many times and charged with highway robbery but was acquitted because witnesses could not confirm his identity. Jack just could not keep out of the limelight, nor did he wish to. Once he pushed his way to the front of a crowd eagerly awaiting a hanging at Tyburn dressed in such an outrageously extroverted fashion that he almost stole the show from the condemned prisoner. He told people in the crowd that one day he would be the main participant in the proceedings at Tyburn, not merely a spectator.
On one occasion Jack was caught and charged with housebreaking. Although he considered burglary to be a menial crime way beneath him, he was caught red-handed, and to add to the ignominy he was actually arrested by one of the scorned ‘Charleys’ or decrepit old night-watchmen who were the butt of so much ribald humour at the time. Jack was hauled up before John Fielding, the ‘Blind Beak’, and related the sad story of how he had actually been making a call on a young lady, Doll Frampton. The tryst had been arranged for earlier that evening but Jack had been unavoidably delayed and Doll had given him up and retired to bed. Jack explained that he dared not knock on the door in case he awoke the other residents and so, not wishing to let Dolly down completely, he decided to break in but was caught in the act. Dolly made something of a sensation when she appeared in court to testify on Jack’s behalf dressed in a low-cut bodice. Jack was an engaging fellow and the ‘Blind Beak’ must have been feeling unusually charitable that day because he sent him away with a warning as to his future conduct. Jack left the court, his face wreathed in smiles, but then had to go home to face the justifiable wrath of Eleanor, his long-standing mistress.
By all accounts Jack was a cheerful, well-liked man and a favourite of the ladies. This was particularly evident when his luck had finally run out and he was in the condemned cell at Newgate. There he received many visitors, predominantly female ones, and even hosted a farewell dinner just before the date set for his execution. This gregarious and extrovert character made his final journey to Tyburn in November 1774, and used the occasion of his appearance on the scaffold to exchange banter with the hangman and to quip with a highly appreciative crowd. He had never dressed more extravagantly, wearing a suit of pea-green clothes ordered specially for the occasion with a large nosegay as an accessory.
Like Jack Rann, Jerry Abershaw was another not overawed by the majesty of the law. Abershaw was born in 1773 and was only seventeen years of age when he became a member of a gang of highwaymen who operated mainly on Putney Heath and Wimbledon Common and whose headquarters were at the nearby Bald Faced Stag. Jerry seems to have been more reticent than many of his kind and very little is known about him, except that he had a career on the road that lasted five years, during which time he defied every measure taken by the Bow Street Runners to capture him. One of his partners-incrime was Richard Ferguson whose horsemanship skills were such that he won the nickname ‘Galloping Dick’. Ferguson was born in Hertfordshire and was about the same age as Abershaw. Their working relations began in unusual circumstances.
‘Galloping Dick’ gained employment as a postilion and made a very good impression until he was caught in flagante delicto with one of the female servants and was promptly dismissed. Shortly afterwards his father died, leaving him a small inheritance which allowed him to set up as a man-about-town. He took himself to the theatre in Drury Lane and found himself sitting next to a very attractive young woman. She was a prostitute of a superior sort but Dick fell madly in love with her and showered her with all manner of presents which she was only too happy to accept. His income could not match the expenses he was accruing in courting the lovely Nancy and he was forced to get work as a postilion once more.
One evening as ‘Galloping Dick’ drove a gentleman along the Great North Road he was stopped by two highwaymen, one of whom he recognised as another of Nancy’s paramours. Abershaw realised that he had been recognised and went to an inn that Dick frequented and bribed him to keep silent. Abershaw alluded disparagingly to Dick’s employment as a mere postilion, working in a servile capacity for a pittance and persuaded him to join his band. At first Dick acted as an informant identifying likely victims for robbery and only later as a fully fledged highwayman. This was shortly before Abershaw himself was caught, tried and condemned to death. Abershaw enraged the judge by mimicking him when he put the black cap on to pronounce the death sentence. He also displayed his complete contempt for authority by decorating the walls of his cell in Newgate with representations of his adventures, painted with a substance said to consist of the juice of black cherries. He was hanged on 3 August 1795 on Kennington Common and gave the crowd good value because of his nonchalance and the scorn he poured on the law and its representatives in the speech he made from the scaffold. His body was gibbeted at Putney and attracted large crowds. ‘Galloping Dick’ was caught and likewise hanged five years later.
William Parsons was born in 1717, the youngest son of a baronet and the nephew of the Duke of Northumberland. He could not plead poverty as a reason for taking to the road as a highwayman, and his father had always treated him well and ensured that he received a good education. Parsons is the only Old Etonian to feature in these pages as a highway robber. He was a habitual gambler and to pay the debts that were continually piling up he stole quite shamelessly from family and friends, including relieving his illustrious aunt of a gold-mounted miniature. The theft and his part in it were quickly discovered and his contrite father packed him off into the Royal Navy as a midshipman, but this new venture did not last long.
Parsons was discovered cheating at cards and this was viewed with almost the same degree of seriousness as cowardice in action or corresponding with the enemy. He was forced to leave the Navy and his father then sent him to do an administrative job in West Africa, but he still had debts to pay for which he forged a letter from his aunt purporting to guarantee him for up to £70. When the lady discovered the deception she altered her will, under which Parsons would have been the sole beneficiary. She died some time later leaving £25,000. Penniless, he returned to England and married a girl with a dowry of £4,000, but this was soon spent and he enlisted in the Army as an ensign. He could not keep out of trouble and after being found guilty of forgery was transported to Virginia. There he was noticed by the benevolent and gullible Lord Fairfax who regretted that one of Parsons’ pedigree should have come down so much in the world. He did Parsons several kind services and the latter rewarded him by stealing one of his finest horses, mounted on which he went on the road as a highwayman.
Parsons met with considerable success in his newfound career and presumably acquired enough money to get the return fare home because he is next heard of in England. His aunt had just died and left her large fortune to his sister, but Parsons was determined to get his hands on it. He plotted with an accomplice, a disreputable ex-footman, who would try to woo her into marriage and, failing that, terrify her into becoming his wife but this scheme was soon discovered and had to be abandoned. The egregious Parsons returned to robbery to finance his gambling habit but was caught on Hounslow Heath and hanged at the age of thirty-four despite the efforts of his influential relations to secure him a reprieve. Nothing can be said in his favour.
A striking number of the sons of clergymen also ended up on the scaffold, often as a result of committing robbery on the highways. This may be because their fathers had social status but often lacked the income necessary to ape the lives of the rich landowners that were their patrons and with whom they mixed. The sons, therefore, got a taste of the lifestyle of the very rich and, liking what they saw, decided that they wanted some of it. The income required could not possibly be gained through honest toil and so it was natural to drift into gambling and highway robbery. One example of this is James Maclaine, whose conduct earned him the nickname ‘Gentleman Highwayman’ during his lifetime.
Maclaine’s father was a Presbyterian minister of Scottish origins with a living in County Monaghan in Ireland. James was well educated and had been destined to enter business as a clerk. However, his father died when he was aged eighteen leaving him a sizeable inheritance. This was quickly spent and Maclaine to his chagrin had to take a job as a butler. The wages for such a job could not possibly support the lifestyle that Maclaine hankered after and so he started stealing and selling items of his employer’s property. The thefts were discovered and he was discharged with a bad character. However, he moved to London where he managed to obtain further domestic employment while developing a taste for expensive women. He had charm, looks and style and soon met a woman who attracted him because of the £500 dowry she would bring the man who married her. With the £500 the couple, once married, set up a grocery business but trade was poor and when his wife died Maclaine decided to try his luck as an eligible widower in the fashionable towns of Bath and Tunbridge Wells where conquests and generous dowries might be found. He posed as a gentleman of breeding and substance and engaged a bankrupt apothecary named Plunkett to act as his ‘footman’ but in reality to be his partner-in-crime. Maclaine was disappointed to find that few women were falling over themselves to share his bed let alone place dowries at his disposal in exchange for matrimony. Establishing these hard facts of life proved very expensive and when Plunkett suggested that they should become highwaymen it seemed an excellent idea.
Maclaine and Plunkett did quite well from highway robbery but the credit must actually go to Plunkett, as the very idea of stopping strangers on the highway and demanding their valuables distressed Maclaine. He was a congenital coward who hated the idea of waving pistols around or any other physical unpleasantness. Therefore, he always allowed Plunkett to take the lead whenever personal courage was required while he continued avidly to pursue ladies. On two or three occasions he almost secured unions supported by a substantial dowry, but each time the lady concerned called the nuptials off at the last moment. Maclaine nearly married the sister of the Duke of Newcastle, the Prime Minister. The wooing of such ladies was an extremely expensive business and Maclaine had to take suitably prestigious accommodation in London’s West End. To look the part, he started wearing a crimson damask frock coat, a silk waistcoat with lace trimmings and black velvet breeches, white silk stockings and yellow morocco slippers.
Plunkett with Maclaine cowering timorously nearby had many rewarding successes on the road, the best-known of which was their hold-up of Horace Walpole (1717–97), the well-known author who recorded the experience in his writings. It happened in Hyde Park one moonlit night in 1749 and Walpole does not disclose how much he was actually forced to hand over. He does mention, however, that he was shot at by Maclaine and that Maclaine’s pistol, ‘going off accidentally, razed the skin under my eye, left some marks of shot on my face, and stunned me. The ball went through the top of the chariot, and, if I had sat an inch nearer to the left side, must have gone through my head.’ Apparently, the following morning he received a very polite, cultured letter from Maclaine offering his apologies for any inconvenience caused. Walpole’s comment was that his brief relationship with the highwayman was carried out ‘with the greatest good breeding on both sides’.
Money, or rather the lack of it, continued to be the bane of life for this rather ill-assorted duo and it probably spurred them on to commit two robberies in one night. The first was to hold up the Salisbury stagecoach at Turnham Green, just west of London, where they carried away a case containing clothes belonging to a Mr Higden. Later, at Hounslow Heath they held up a carriage containing the Earl of Eglinton, who they relieved of a range of valuables, some clothes and a blunderbuss. A pawnbroker was contacted who recognised some of the items as being listed in a broadsheet describing the robberies and informed the authorities. Plunkett disappeared, but Maclaine was arrested. He confessed when charged but on appearing in court put the blame for his transgressions entirely on to the absent Plunkett’s shoulders and denied ever being involved in robbery. Nine character witnesses spoke on his behalf but for all that he was extremely unconvincing and was quickly found guilty. Even the well-intentioned statement by Lady Petersham that she regularly received him in her house yet had never known him to take anything that was not his was greeted with a flurry of knowing nudges in court, rather than providing a useful declaration in support of his character. Huge numbers flocked to visit him in the condemned cell but the massive crowds who turned out to watch his execution in 1750 were greatly disappointed. He was so scared that he totally failed to provide any entertainment.
Isaac Darkin was another highwayman very much in the ‘gentleman-dandy-paramour’ category. He was born in 1740, the son of a prosperous businessman and had a good education. Darkin was a successful scholar until his father died, when the family income plummeted and he was forced to find employment. This very sudden change in his circumstances had a traumatic effect upon the youth who was used to mixing with the sons of very wealthy parents and liked their gracious lifestyle. Darkin did not wish to pursue a life of ill-paid drudgery and therefore decided that becoming a highwayman offered a quick and easy route to riches. Darkin went on to make a name for himself during a short but extremely eventful career.
Darkin first stood trial for his life in 1758 and was sentenced to execution, which was later commuted to fourteen years transportation. He was herded together with dozens of other felons awaiting a ship and found out they were plotting a mass escape during which they would kill their hated jailer. Darkin always seems to have abjured violence but he was an opportunist and he therefore bravely but perfidiously informed on his fellow prisoners. He was given a free pardon on condition that he enlisted as a soldier in an infantry regiment based in Antigua. This was scarcely better than transportation! His career as a soldier was not a success, and lasted only seven weeks. During this time he was disciplined at least three times but it ended when he managed to bribe the captain of a merchant ship to take him back to England.
Darkin took to the road again and ranged widely across southern and central England combining robbery with philandering. He always dressed impeccably, was polite, witty, thoroughly good company and strikingly handsome so it is quite possible that he broke more hearts than he ever lifted purses. He got into innumerable scrapes and appeared in court many times on capital charges but walked free owing to discrepancies in the evidence or on other technicalities. Predictably, in 1761 Darkin’s luck ran out, by which time he was firmly cast in the role of popular hero. As he lay in the condemned cell he was visited by large numbers of tearful women pledging to him their undying affection. A vast crowd turned out to witness his execution, for which he dressed immaculately and faced with great courage but no bombast. Darkin was ten days short of his twenty-first birthday.
William Page was a country boy sent to London by his father to learn the haberdashery trade. Like so many before him, he was in turn spellbound and then seduced by the vitality of the capital, its cosmopolitanism and its sharp contrasts between the rich few and the teeming impoverished masses. London gave him a taste for the good life and also made him aware of the many prospects for criminal activity that it harboured. He was a vain young man, determined to cut a dash in all the latest fashions, but when he found that his wages were insufficient to allow him to do this he started to take money from his employer’s till. Page was caught out and dismissed, which resulted in his father disowning him and him gaining employment as a liveried servant, a role that he felt was far beneath his dignity.
While on a journey with his employer Page experienced a highway robbery at first hand. It is not known who the highwayman was but he made the act seem so simple and acquired in a couple of minutes what it would have taken Page as a servant two or three years to earn. Page was profoundly impressed, and it did not take him long to make up his mind – he would also become a highwayman. He managed to beg the money for some pistols and the hire of a horse, set off to rob and was rewarded with a total of £4, which happened to be exactly what it had cost him to accumulate the equipment he needed for the venture in the first place. He quickly achieved greater success, took fashionable lodgings and dressed himself in the latest modish finery, joining a select gambling circle and entering polite society.
Page decided to operate rather differently from most highwaymen. First, he taught himself cartography and drew up his own highly detailed maps of London and its surrounding districts. Secondly, he went to work in a phaeton hauled by two horses. At a suitable secluded spot, he would park the phaeton, detach one of the horses, put on his mask and other working togs and then ride to the place he had chosen for the robbery. One day, when he returned from robbing some travellers near Putney, he found to his consternation that the phaeton had disappeared along with his other horse. He rode on and soon found that they had been purloined by a party of haymakers who were engaged in a heated discussion with the very same group of travellers he had just robbed. These indignant travellers were loudly accusing the haymakers of being accomplices of the highwayman. Page reacted quickly to this rather complicated scenario. He threw his highwayman’s clothes away and then, clad only in his underwear, he walked up to the group of arguing people declaring that the phaeton was his and accusing the haymakers of having robbed him and taken his outer clothes as well. Everyone involved was brought up before a magistrate who was convinced that the haymakers had indeed stolen the phaeton. Page decided not to press for the prosecution of the haymakers and chastened by the whole affair he sold his phaeton.
Page later held up the notorious rake Lord Ferrers who was called upon to act as chief witness for the prosecution when Page was brought to court charged with highway robbery. Page had astutely researched the many and various shady events of his lordship’s past. He unearthed the priceless fact that Ferrers had earlier been excommunicated by a consistory court. In defending himself in court, Page argued that any evidence Ferrers gave would therefore be inadmissible. Choking down his rage, the judge had no option but to let him go free. Page then went into partnership with an old schoolfriend by the name of Darwell and enjoyed several years of such successful robbery that he was able to dress like an aristocrat and drink like a lord. His career ended abruptly in 1758 when a patrol found Page and Darwell in the act of robbery. Darwell was caught and showed the extent of his friendship by turning King’s evidence. Page escaped briefly but was soon arrested, tried, sentenced and executed.
In 1766 a macabre event was enacted at Nottingham concerning James Bromage and William Wainer, two highwaymen who had been sentenced to death. They were brought from the Shire Hall to St Mary’s Church in High Pavement to hear the execution sermon and after that were required to go into the churchyard to view their graves and to lie in them for a moment to ensure that they would fit. They were then marched off to be executed and a few hours later their bodies were buried in the graves they had only just tried out for size.
There were a number of highwaymen who worked together, but few brothers who joined forces. George and Joseph Weston were an interesting exception to this. Again they were young men from the provinces who moved to London and then erred in their ways to pay for the raffish delights offered by the capital. George swindled his employer and then with his brother frittered the money away on fast living. The fraud was discovered and the Weston brothers had to leave London immediately, and after various adventures arrived in Manchester. George, who was certainly versatile, became a teacher. Not only did he teach but he apparently became a staunch pillar of the community and was appointed High Constable. This post involved too many temptations and he was dismissed for blackmailing innkeepers. The brothers left Manchester and tried their hand at horse-stealing, confidence trickery, forgery and smuggling before deciding to become highwaymen.
Not bothering to work their way up the ladder by risking their necks for a few guineas or the occasional gold watch, the Weston brothers decided to hold up a coach containing the Royal Mail. These coaches were well guarded but the potential rewards for the bold robber were high. The date was January 1781 and without being recognised they escaped with thirty-five mailbags full of bills and banknotes with an estimated value of £15,000, an enormous sum by the standards of the time. The problem for the Westons, of which they were quite aware, was that descriptions of these bills would soon be circulated and therefore they had to be cashed very quickly. George, who was definitely the thinker of the duo, hit on the ingenious ploy of dressing himself as a naval officer with Joseph accompanying him in servant’s livery. They then set off at high speed in a hired post-chaise on a roundabout tour of the country, negotiating the bills and banknotes in small numbers in the towns through which they passed. They were first identified after changing a bill in Nottingham and the Post Office authorities hired a team of Bow Street Runners to apprehend them. The Weston brothers led the Runners on a tortuous trail up and down England, always seemingly one jump ahead. They passed through London where their identity was revealed but the Runners were baffled because the trail seemed to go cold.
The brothers had set themselves up in the Sussex seaside town of Winchelsea as men of some financial substance and they were soon moving in fashionable local society. Again George was the more prominent of the two and exuded such an aura of respectability that he was elected a churchwarden, an honour for which he stands out uniquely among highwaymen. However, his tastes remained expensive and although still living undetected under the pseudonym ‘William Johnson’, he accumulated massive debts that meant that one of his creditors eventually called on the authorities to assist. Two Sheriff’s Officers were sent to arrest him and the brothers met them by chance while they were riding outside the town. They were extremely alarmed by this unexpected intrusion into their blissful semi-retirement and so George knocked one of them down with his riding whip and threatened them both with his pistols. The Westons then fled to their sumptuous town house, convinced that the net was closing in. Scooping up a few valuables and necessities, they rode off hotfoot in the direction of London, the place they thought offered the best hiding place. The authorities were now well aware that they were dealing with the notorious Weston brothers. They were traced to London and the persistent Runners eventually caught them in the Soho district.
The Weston brothers appeared in court charged with the robbery of the Royal Mail but the main prosecution witness died at this crucial moment and the case had to be adjourned. George and Joseph remained in Newgate and were visited by their ladyfriends, who brought them a few comforts such as food and drink and, even better, a file and a brace of pistols. They got out of their fetters, overpowered a warder and ran for it, but both were captured within the hour and soon found themselves in a reconvened court. This could not find them guilty of the Royal Mail robbery for lack of evidence but found George guilty of forging endorsements on the stolen bills, which was a capital offence. A similar sentence was passed on Joseph for firing at and injuring a market porter who had tried to stop him when he was escaping from Newgate. The brothers were hanged together at Tyburn on 3 September 1782. Like Dick Turpin who was immortalised by Harrison Ainsworth in his novel Rookwood, the Weston brothers also became characters in fiction, appearing in Thackeray’s novel Denis Duval. While Rookwood makes a hero out of Turpin, Thackeray extends no adulation to the Weston brothers. They are portrayed as a pair of singularly graceless villains whose misdeeds only failed to conclude on the scaffold because Thackeray did not complete this particular novel.
One rather unusual highwayman was James or Robert Snooks who ambushed a postboy in Hertfordshire in 1801. He was rewarded with the sum of £1,500 which meant that the authorities soon put the uncommonly high price of £200 on his head, in addition to what by then was the usual payment of £100 under the law. Snooks decided to lie low back in his home town of Hungerford in Berkshire but like so many of his kind, he could not resist bragging and was betrayed by an old school companion. He was hanged at the scene of his crime, Boxmoor Common, in 1802. He went to his death with courage but treated the crowd to a homily on the absolute necessity of strictly observing the Sabbath and always taking heed, as a child, of parental advice. He warned his listeners that failure to do so was the cause of much crime in later life. This was not the kind of speech the spectators had turned out in large numbers to hear and they showed their disapproval by stamping and hissing.
By the late eighteenth century, highwaymen were in decline due to a number of inter-related factors, some of which have already been mentioned. They included the use of rewards as incentives for thief-takers and for ordinary citizens to turn informer. Improved road surfaces, especially on the turnpikes, increased the speed at which travellers and their horses and conveyances could travel. This made them more difficult to stop and also assisted mounted pursuers. Turnpikes were hedged and fenced which greatly restricted the highwayman’s freedom of movement. The process of enclosure, an integral part of the drive to increase the output and productivity of agricultural land, also involved laying hedges and fences. These further impeded the ability of a highwayman to evade his pursuers. At the same time the licensing magistrates became more zealous in their efforts to close down inns known to harbour highwaymen and other robbers on the road. The spread of the banking system across the whole country meant that there was much less need for travellers on business and others to carry large amounts of coinage and bank notes, cheques and billsof-exchange were obviously more difficult for robbers to negotiate. In 1805 the Bow Street Runners set up horse patrols and these could be found along the main roads into London which had long been notorious as the happy hunting grounds of the ‘gentlemen of the road’.
It is not surprising that highwaymen continued to thrive for somewhat longer in the provinces. In 1807 the roads of West Sussex around Arundel and Chichester saw considerable activity by a highwayman named Allen, whose victims were mostly farmers returning with wallets bulging after a good day at market. He was eventually shot dead. Not far away the only known father and son highwayman partnership operated, although John Beatson was only the father by legal adoption of his partner-incrime William Whalley.
It has been emphasised throughout that highway robbery was a young man’s game but Beatson made history by riding out as a highwayman for the first time at the ripe old age of seventy. In July 1801 the pair held up the Royal Mail coach at East Grinstead in Sussex and carried off a substantial quantity of bank notes which they needed to negotiate speedily before the details of these notes were circulated around the country. They successfully cashed many of these in the London area, converting them to gold and then bought a horse and gig with a view of going to Ireland. They got as far as Knutsford in Cheshire where they stupidly drew unwelcome attention to themselves by mistreating their horse. As ill luck would have it, this happened just before the coach from London arrived in the town with all the latest news including details of the East Grinstead robbery and of the robbers involved. The description fitted the horse-abusers. A Post Office Surveyor set off after them in the Liverpool direction and they were soon traced and arrested, and found to be in possession of a large number of bank notes. They were taken for trial at Horsham in Sussex and caused a minor sensation by escaping from custody and taking refuge in the town’s main sewer from which they apparently were only too glad to be rescued. They were hanged on 7 April 1802.
By the early nineteenth century highwaymen had become an anachronism. However, this did not stop George Cutterman from holding up and robbing travellers in the North Riding of Yorkshire in about 1815. He certainly deserves more than a mere footnote in the history books because after he had been caught and taken to York to stand trial he persuaded his somewhat lax guards to remove his handcuffs. Minutes later he leapt out of the coach and sprinted out of sight and into oblivion. He was never heard of again. As late as 1850 the ‘Hanham and Cock Road Gang’ carried out numerous violent robberies in the country areas surrounding Bristol. They ignored the gallant highwayman tradition and what they lacked in social finesse they made up for with extreme brutality. They made a point of preventing their victims from calling for help by stuffing their mouths full of dirt or throttling them. These vicious thugs had little in common with such urbane highwaymen as Jack Rann, James Maclaine or Isaac Darkin.