It was to be expected that highwaymen would largely be supporters of the King in the Civil War of the 1640s. Many of them were fast-living freebooters and mavericks who supported the King because he represented the long-established land-owning class from which many of them came. They strongly resented the yeomen farmers, merchants, jobbers, intellectuals and other bourgeois parvenus who seemed intent on destroying a system that had lasted for 500 years or more. The Parliamentary ranks contained many puritanical killjoys who disapproved of the sexual and bibulous pleasures in which many highwaymen and others indulged. They closed down alehouses and attacked many other traditional aspects of popular culture.
There were other highwaymen who had more cynical and materialistic reasons for hoping that the supporters of the King would prevail. Not for them the risks entailed by actually enlisting in the Royalist forces; after all business was business. These gentlemen feared that the dead hand of Puritanism would descend on society as a whole and especially the rich. Those who travelled by coach or carriage were usually well off. To cope with the various discomforts and frequent inconveniences that accompanied road travel in the seventeenth century, many travellers not only imbibed fully at the various halts for refreshment along the way but carried further alcoholic sustenance with them for the between-times. A carriage full of intoxicated travellers was easy game, but Parliament’s forces, strongly influenced by the Puritans, sought to discourage the sale of alcoholic liquors. What better reason could there be for giving moral support to the Royalist forces?
Some of the more idealistic highwaymen did indeed take the King’s Shilling. Many paid with their lives, cut down at the battles of Marston Moor, Naseby, Edgehill and the rest. Those who survived and were known Royalist supporters were wanted men, dispossessed and with a price on their heads. Their horses and the military skills they had picked up were often their only stock-in-trade. Where else could they go but on to the highways as robbers? During the Civil War, and even more so during the Commonwealth which followed, the roads became infested with highwaymen and footpads, individually or in gangs. Most were ex-soldiers. They became such a nuisance that large rewards were offered for the apprehension of known highway robbers. This led to many being caught and executed.
Typical of the gentleman highwaymen who paid dearly for their Royalist sympathies was Captain Phillip Stafford who suffered the sequestration of his property by the Parliamentarians and was left penniless. With an understandable sense of grievance he set out to get his own back. He did not discriminate between supporters of either side in the Civil War and held up and plundered all travellers at random, accumulating enough money to retire to the north of England where he eventually became a minister. However, such an existence was too humdrum and he went back on the road, not forgetting to take the church plate with him as he left. He was sentenced to death for robbing a farmer of £33 near Reading. He was something of a trailblazer and popular with the watching crowds because he went to the scaffold with an insouciant hauteur that made him into a role model for successive generations of Cavalier highwaymen. He sported a nosegay and wore a new and expensive outfit bought specially for the occasion. Some of the highwaymen of this period were exuberantly Royalist and Cavalier in loyalty, appearance and in gesture. Captain Reynolds, for example, is supposed to have cried, ‘God bless King Charles! Vive le Roi!’ while he stood on the scaffold awaiting execution.
Captain Zachary Howard was such a zealot for the Royalist cause that on being deprived of his estates and forced to take to the road he robbed only those who were clearly supporters of the Parliamentary side in the war. He was evidently not concerned simply with pecuniary gain because he carried on a personal vendetta against all supporters of the hated new regime. He picked his victims with great care. An early one was the Earl of Essex, a former commander-in-chief of the Parliamentary forces. Despite the fact that the Earl had at least six retainers with him, Howard managed to lighten his purse by no less than £1,200.
As well as steely nerve, Howard must have had an effective intelligence system because he heard that General Fairfax was sending a consignment of silver plate to his wife. He waylaid the courier and made off with the plate and a letter addressed to Lady Fairfax. He stowed the plate away safely and then rode with the letter to the Fairfax family home, purporting to be the courier himself. Asked why he had not brought the plate with him, he explained that the area was notorious for highwaymen and therefore he had left it in the safekeeping of a nearby innkeeper of unimpeachable probity. If Lady Fairfax agreed, he would deliver the plate in a couple of day’s time. Lady Fairfax was impressed by the stranger’s apparent sincerity and told him that he was welcome to stay the night in the servants’ quarters. When all were settled down for the night, Howard tied the servants to their beds and gagged them. He then proceeded into the family quarters where it is alleged he coolly raped Lady Fairfax and her daughter, rifled through their possessions, pocketed the choice items and then let himself out by the front door. General Fairfax was obviously outraged and he offered a reward of £500 for the capture of Howard. This seems a rather miserly sum given the ordeal that Fairfax’s womenfolk had undergone. Howard wisely retreated to Ireland until he felt it was safe to return to the mainland.
On Howard’s return he really put his head in the lion’s mouth. He booked into an inn at Chester where Oliver Cromwell, the Lord Protector, was staying. He insinuated himself into Cromwell’s company and got on so well with him that the Lord Protector invited him to his bedroom for prayers. Scarcely able to believe his luck, Howard knelt down devoutly next to the most powerful man in the country. He then whipped out a pistol, gagged and bound Cromwell, seized a few valuables and made good his escape, but not, allegedly, without emptying the contents of a chamber pot over the Protector’s head! On another occasion he stopped the Earl of Portsmouth near London when he was accompanied by just one manservant. He relieved the Earl of his valuables but could not resist inflicting further humiliation. He forced him to mount his horse behind his servant but facing backwards and he then tied the two together, back to back. What pleasure he must have derived from seeing the horse trot off with its master’s face glowering at him from its unaccustomed and undignified position.
Howard was eventually captured at Blackheath near London after unwisely taking on no fewer than six Parliamentary officers single-handed. After a fierce struggle, he was arrested and incarcerated in Maidstone Gaol. While awaiting execution, Howard was visited by none other than Oliver Cromwell himself. Unfortunately, no record exists of what must have been a priceless conversation. Howard was executed in 1652. He seems to have been motivated by an almost pathological hatred of the Parliamentary leaders. Brutal he may have been yet he was clearly a man of outstanding personal courage. There is no way of establishing how far these tales are actually true. It is unlikely that they are total fabrications but they have certainly been embellished and exaggerated in the retelling. Those who chronicled the exploits of men like Zachary Howard often had an axe to grind. They wanted to write a rattling good story that would sell and put those they disliked, such as the dour, humourless Cromwell, in an unfavourable light.
Another fanatical supporter of the Crown, though of more humble origins, was John Cottington, nicknamed ‘Mulled Sack’. Born in about 1612, he was the youngest son of a London haberdasher who drank himself to death and left absolutely nothing for his nineteen children. At the age of eight, Cottington became a chimney sweep’s apprentice but he quickly decided that slithering about in sooty flues was not the career for him and he took to the streets as a pickpocket. He proved to be an exceptionally skilled and successful one. Even as a youth he displayed a taste for alcohol, and his favourite drink was mulled sack, hence his nickname.
Cottington decided only to pick the pockets of those associated with the Parliamentary side, and among his victims was the selfsame Lady Fairfax whose virtue had been assailed by Zachary Howard a few years earlier. Split-second planning and timing were needed in order to rob her. Having learnt that Lady Fairfax was due to attend worship at St Martin’s in Ludgate, Cottington paraded up and down outside the church dressed in his best. Lady Fairfax’s coach drew to a halt and then started to tip over just as she was alighting. A group of gallant gentlemen then rushed forward, Cottington at their head. He rescued her from physical danger and indignity and received in return the sweet thanks and winning smile of the shaken but safe Lady Fairfax. He also acquired a valuable gold watch, which he surreptitiously removed from her watch chain. Ever the gallant, he accompanied her to the church door and bid her adieu with a flourish of his hat. His accomplices of course had tampered with the coach’s axle-pin so that it was timed to work itself out and topple the coach just when it arrived at the church.
Cottington next decided to try his hand properly at the highwayman’s trade. Hounslow Heath was his favourite stamping ground and he worked the area with a partner called Tom Cheney. One day they spotted a colonel of the New Model Army by the name of Hewson, riding along a few hundred yards ahead of his troops. Without any ado, they called on him to halt and robbed him of his purse. They then turned and galloped away, hotly pursued by Hewson’s men. Cheney gave his adversaries a run for their money but was eventually captured and later executed. Cottington escaped. Even more audacious was his hold-up of an Army payroll wagon on Shotover Hill outside Oxford. Some accounts state that he did this single-handed despite the fact that the wagon had a sizeable armed escort. He seized no less than £4,000 on this occasion and before leaving the scene treated the bemused soldiers to a brief homily on the greed of the Commonwealth government. On another occasion he was arrested and charged with robbery but by this time was rich enough to buy the jury off. Later accounts of Cottington’s activities became somewhat confused but he was eventually hanged after being convicted of murdering his lover’s husband as well as of highway robbery. The year was 1659. He had enjoyed a long run.
In seventeenth-century criminal cant, a ‘prig’ was a thief, and James Hind was immortalised even during his lifetime by being made the hero of a play entitled The Prince of Prigs, the author of which used the pseudonym ‘J.S.’. Hind was the archetype of the highwayman-hero with a reputation for gallantry towards the fair sex and of courtesy towards all those he robbed, irrespective of their sex. Born in 1616 at Chipping Norton in Oxfordshire, the son of the local saddler, he went to work as a trainee butcher. Possessing a mercurial temperament, however, he realised that he was never going to be content selling joints of meat. Disappointing his parents and displaying that blissful certainty and confidence reserved only for youth, he set off to find his fortune in London where he quickly made the acquaintance of various members of the underworld.
Hind became friendly with Thomas Allen who was the leader of a successful gang of highwaymen. Hind wanted to join them but they needed to assure themselves that he had the necessary courage and skill. They told him to go to Shooter’s Hill and hold up the first traveller who appeared while they secreted themselves in a nearby thicket to watch how he handled the situation. Hind had no problem relieving a rather docile traveller of the sum of £15 but then to the amazement both of spectators and victim, he gave the traveller a coin back because, he said, the man was destitute. Some of the gang deplored this as cheap gamesmanship and because it might establish an undesirable precedent, but Allen was impressed by Hind’s sang-froid and accepted him as a member.
Like many highwaymen, Hind eagerly joined the Royalist side when the Civil War broke out. He enlisted in the ranks but his leadership qualities were recognised and he was commissioned. When his beloved King was executed in 1649, Hind decided to wage his own unofficial war on the regicides. In company with Allen and some of the old gang, he planned one of the boldest exploits in the whole history of highwaymen. They resolved to ambush Cromwell’s party just outside Huntingdon but he proved to be better guarded than they had expected and a bloody skirmish took place in which Allen was captured and hanged shortly afterwards. Hind just managed to escape, literally riding his horse to death. Before long he was back and among a new crop of victims was a senior Church of England clergyman who, on being accosted, harangued Hind with dire verbal warnings about what the Almighty would do to those who infringed the Eighth Commandment. This prattling prelate was dumbfounded when Hind rapidly responded with a series of apt biblical quotes about the ungodliness of Mammon and how the virtues of humility and charity expounded by Jesus contrasted with the practices of the hierarchy of the Church. The cleric, in spite of his initial bluster and bombast, was quickly reduced to silence.
Hind continued to specialise in robbing leading Parliamentarians so the authorities viewed him as a major threat, while the public viewed him as their darling. His philosophy was the simple one that you might as well go for the big prizes rather than bother with paltry amounts because the law viewed robbery at either end of the scale in precisely the same light. Hind was even prepared to emulate Robin Hood and he is said to have been generous with poor people who he felt were in real need. His fame grew and his actions were those that help to create legends. On one occasion he found a publican in Warwick being turned out of his alehouse by a bullying moneylender to whom the man owed a large sum. Presumably he knew the publican because Hind paid the money owed and sent the moneylender on his way. A few minutes later, disguised, he took the money back at pistol-point. Whether or not there is any truth in this episode, it has two favoured themes: the highwayman helping someone in need and getting the better of a person loathed by the populace.
On another occasion Hind was seeking regicides to rob but with little success as there were few about. Money was running short and so he stopped the first coach that appeared. To his considerable surprise, the coach turned out to be occupied by a group of well-dressed young ladies. Hind was noted for his courteousness to women. Unashamedly playing to the audience, he spun a long yarn to the effect that he was passionately in love with the world’s most wonderful woman but was unable to advance his courtship because of a temporary, embarrassing lack of funds. With Hind holding forth so eloquently his listeners vied with each other to express their deepest sympathy and assure him of their best wishes for a hasty resolution to his financial problems. None of the women could actually spare any cash to help him. The only one who had any money at all was taking her dowry of £3,000 in gold coin to her future husband. Hind silently digested this rather indiscreet revelation. What a shame, agreed the girls, that this money was already earmarked. Hind thought it unfortunate too. A master of melodramatic timing, he now revealed his identity. He had already charmed the women so this declaration was met with a chorus of giggles and knowing nudges.
Hind went on to excel himself. Surely the young lady would not mind lending him £1,000 which would just about see him through this crisis on which the rest of his life’s happiness depended? Before long her friends were urging her to hand over the money on the strict agreement of course that it was a loan. How could anyone mistrust the charming and surely misrepresented Capt Hind? Soon, £1,000 richer, Hind trotted off on his horse, offering his felicitations to the young lady for a long and happy marriage and promising to repay the loan fully at the earliest possible opportunity. It was a brazen confidence trick on Hind’s part and had a sad outcome, although he neither knew nor cared. The young girl’s fiancé was livid about the trick that had been played by Hind and told the girl that unless her father replaced the missing money, the marriage was off. Perhaps she had a lucky escape from marriage to a man of such mercenary priorities but she did not see it that way and, brokenhearted, she remained unmarried for the rest of her life.
In due course, Hind was wanted not only because of his exploits on the highway but also because of his continued support for the Stuart cause even after the execution of Charles I. Nobody could be found to testify against him on charges of highway robbery but early in 1652 they charged him with the manslaughter of a friend he had killed in an argument. He was found guilty and sentenced to death. To the disgust of those who wanted Hind called to account, Cromwell issued an amnesty for virtually every offence except high treason. Those who wanted rid of Hind then arraigned him for treason on account of his blatant support of the deceased King and because he had also rallied to the support of Charles II when he made his abortive attempt to claim the throne of England in 1651. Hind did not conceal his contempt for his tormentors and indeed made it clear that he stood by the support that he had given to the Stuart monarchy. On 24 September 1652, he was hanged, drawn and quartered at Worcester as a traitor to his country. So died one of the most colourful of the early highwaymen. Legend says he was still smiling when his severed head was put up for display on the Severn Bridge.
Hind’s life was the very stuff of which legends are made. It contributed to the enduring image of the gentleman highway robber who displayed an impeccable range of the social graces. Once, when times were hard, Hind is said to have stopped a shabby looking countryman driving a cow to market. He admitted having 40s on him and told Hind that it had taken him two years to save the money. Hind relieved him of the money but promised to return to the same spot a week later when he would repay double the sum as long as the man told nobody. Hind was as good as his word.
James Hind may be the role model for the romantic and chivalrous highwayman of legend, but it is certain that for every one of his sort there were far more who were rude, violent and unpredictable. One, a graduate of Cambridge University, is said to have sneered at a female victim who was tearfully appealing to him to be allowed to keep her money: ‘You whining bitch, how you throw your snot and snivel about nothing at all!’ More serious was the action of Jacob Halsey who, on having deprived one young lady of her jewellery and money, proceeded to rape her. He purportedly uttered these words: ‘My pretty lamb, an insurrection of an unruly member obliges me to make use of you on an extraordinary occasion; therefore I must mount thy alluring body, to the end I may come into thee.’
The themes of politeness and gallantry that are ascribed to highwaymen fly in the face of reality. In practice, almost every traveller was potentially dangerous but they were far more likely to surrender their valuables quickly if they met a show of menacing ferocity. Time spent soft-soaping groups of riders or charming a bevy of flustered lady travellers might allow the bolder among them to produce a weapon or slip away in search of help. However, the idea of the courteous villain is deeply embedded in the aura of romance that surrounds highwaymen. In practice, travellers probably extracted little comfort from being robbed by a polite and personable highwayman rather than an ugly, uncouth, evil-smelling and probably trigger-happy brigand on horseback, the end result being the same. It is likely that highwaymen of the violent and charmless sort considerably outnumbered those who were suave, genteel and polite.
The disruptions of the even tenor of life created by the Civil War alongside the continuing growth of trade and commerce meant that these years were fruitful ones for highway robbers. Although some of those mentioned fit the role model for the dashing, gallant gentlemen robber of legend, this should not obscure the fact that many others were uncouth opportunists who made violence and murder part of their stock-in-trade. For every highwayman whose exploits were notable enough to be recorded, there must have been substantial numbers who were captured and ignominiously executed after only one or two forays on to the road. It was not the nature of the highwayman’s career for it to end in affluent retirement and in the spinning of yarns and reminiscences for the benefit of adoring grandchildren.