James Maclean (1724-1750) was born in Scotland and descended of a good family, before taking to a life on the road. He is arguably one of, if not the last classic highwayman after James Hind (1616-1652), Jack Sheppard (1702-1724), and Dick Turpin (1705-1739). Maclean it seems was given the best opportunities in life, but his father died when he was very young, and consequently the young Maclean found himself with a ton of money and very little instruction in spending it wisely, and soon he ran out of money. The Ordinary of Newgate’s Account records that:
Mr. Maclean’s Patrimony gone before he was much turned of 20, his Mother’s Friends who were the only Relations he had in Ireland, quarrelled with him for his Extravagance, and refused him either Advice, Shelter or Subsistence, his Brother was then in Holland, and he was too far removed, and too little acquainted with any of his Family in Scotland, to acquaint them with his Wants, or receive any Assistance from them.
Previously a moneyed man of leisure, James was now forced to seek employment, and became a servant in the household of a gentleman, Mr. Howard. In the typical moralistic style common to eighteenth-century criminal biographies, it seems his ‘ruling passions’ grew greater within him every day, and eventually he left Mr. Howard’s service without a character reference.
He did find further employment as a butler in another household, but as The Ordinary of Newgate’s Account records:
At last [he] was guilty of some little Pilfering and Embezzlement in his Trust, and was dismissed the Service without a Character, which deprived him of all Hopes of Service in the Country. 
Eventually he set out for London, having borrowed a quite substantial sum of money from a friend. In London he acquired some basic lodgings, and soon squandered all of his money on fine dress and good living. In London he married, and together he and his wife set up a grocer’s shop which thrived for a time. Unfortunately, his wife died which left him with a decent business and a modest amount of money. He wound up the business and soon squandered the money like he did his last inheritance, however, for:
He was too much addicted to Idleness and Pleasure, to confine himself to the Occupation of a Grocer […] and he had in Folly and Extravagance exhausted all he had left of his late Wife’s Portion.
It was just as he hit rock bottom with regard to his finances that he became acquainted with an apothecary called William Plunkett, who convinced him to take to a career of robbing people on the highway. It was his policy to always be courteous and polite to a person when he was robbing them, as The Ordinary’s Account records:
He reign’d long and successfully, and was never but once afraid of a Discovery; at that Time he went over to Holland till the Storm was blown over, and pretended a friendly Visit to his Brother, to whom he gave some sham Account of the Manner of his Living, and was by him introduced to some very polite Assemblies of Dancing, &c. where it is said some Purses and Gold Watches were missed; and since Maclean’s Commitment, the Suspicion seems to be fixed upon him, though at that Time no such Thing occurred. After he had staid some Time in Holland, he again return’d to his Trade.
And Maclean grew rich, and even became a bit of a heartthrob among the fashionable ladies of London:
With these Collections from the Publick, he lived in Splendor, but to avoid impertinent Questions, often shifted his Lodgings; though he appeared in the greatest Splendor in all publick Places, and kept Company not only with the most noted Ladies of the Town, but some Women of Fortune and Reputation were unguarded enough to admit him into their Company, without any other Recommendation than his appearing at all public Places with great Impudence, and a Variety of rich Cloaths. He had the good Fortune, even to make some Progress in the Affections of a Lady who really deserved a better Fate.
He became known as ‘The Gentleman Highwayman’, and rarely ever actually fired his pistol. The only time he did fire his pistol was when he robbed the author Horace Walpole in Hyde Park. After this event Maclean even wrote a letter to Walpole apologising for the fact that his pistol had misfired.
Eventually, however, the authorities caught up with him, and he found guilty and sentenced to hang at Tyburn on 3 October 1750. The Ordinary of Newgate’s Account records his last few days on earth:
Mr. Maclean attended constantly at Chapel, and shewed a very pious and resigned Deportment, he was assisted, being a Protestant Dissenter, in the the more particular Duty of Religion, by a Gentleman of that Persuasion. In the whole of his Department in Newgate, he shewed a very decent Behaviour, a Resignation to the Will of God, a quick Sense of the Wickedness of his past Life, and fortified by the Merit of out blessed Redeemer, looked upon Death as deprived of its Terror, yet could not divest himself of that Horror natural to a Man at the Thoughts of a last and final Dissolution. In short, he was not arrogant enough to brave Death, nor so much wedded to Life, as to dread it like a Coward.
Throughout his life Maclean was not ‘bad’ or ‘evil’ as such. He is represented in the Accounts simply as a man who fell in with the wrong crowd, and allowed himself to fall into a life of sin and vice. It was a love of good living which got him into trouble. For example, when the scheme of robbery is first put to him by Plunkett, Maclean initially is apprehensive of such a scheme:
This Discourse was soon understood by the unhappy Maclean, who tho’ at first shock’d with the bare Mention of it, yet the Necessity of his Pride and Indolence suggested so strong, that he yielded to the Temptation.
We are told that on his first robbery:
He felt every Symptom of Fear and Cowardice, aggravated by the Stings of Conscience, which Vice could not harden. However, the Success of this first Enterprize, was (on a Grazier’s coming from Smithfield Market, from whom, on Hounslow Heath, they took above sixty Pounds) encourag’d him to stifle the Checks of Conscience, and to persevere in a Way, which though to him it appear’d wicked, yet was found so lucrative.
It is poverty, caused by his own recklessness in youth, which has reduced him to crime, which of course ties into the eighteenth-century conceptualisation of the criminal-as-sinner; everyone was the same – and anyone, at any moment, could, as a consequence of original sin and their inherent human depravity, fall into a life of vice and crime.  It is a belief that first appears in print in 1655 (though it stretches farther back than that) in A Funeral Elegie upon George Sonds, Esq, in which Sonds’ life is presented as a catalogue of ever increasing human depravity. His sins begin small in scale, but inevitably these small sins lead to larger ones, until eventually he is executed by the authorities for some criminal act.  Crime was therefore a consequence of sin – an addiction almost. Indeed, it was said earlier that Maclean was ‘addicted to idleness’. Small scale sins were almost like ‘gateway’ sins, which led the offender onto harder offences, in much the same way that it is believed today that ‘soft’ drugs lead onto harder drugs.  As the author of The London Merchant (1731) exclaimed:
One vice naturally begets another.
This doctrine of the criminal-as-sinner can be found being repeated in various more famous works such as Richard Head’s The English Rogue Described in the Life of Meriton Latroon (1665). In Head’s work, the first instance of sin, or cruelty, is when he was around five years of age, for he took one of his father’s turkeys, and:
[Used] what little strength I had, to beat his brains out with my cat-stick; which being done, I deplumed his tayl, sticking those feather’s in a bonnet, as the insulting trophies of my first and latest conquest.
In Alexander Smith’s A Complete History of the Lives of the Most Notorious Highwaymen (3 Vols., 1719), someone who we today might consider the greatest and most heroic thieves, Robin Hood, is not even immune from the consequences of sin. Smith records how:
Robin Hood had continued in his licentious course of life for 20 years.
Thus people in the eighteenth century had a very different notion of the causes of crime when compared to our own class-based, sociological explanation we hold today.
Maclean’s case is significant because he was really the last ‘heroic’ highwayman of the eighteenth century. After Maclean, the reputation of highwaymen begins to decline. When the highwayman, Jack Rann (executed in 1774), had his story told in the press shortly before he died, he came across as a pathetic figure; laughable, and almost contemptible. There are several reasons why this happened. Firstly, the literary marketplace was saturated with biographies of highwaymen. There were so many of them featured in the press after 1750 that they scarcely held the public’s interest, much less generate any admiration for them. This decline in popularity was also partly a result of the growth of newspapers. Whereas earlier criminal biographies went into lengthy details of the offender’s life, newspapers only devoted a few lines to crime reports; focusing solely upon the offence committed, this gave the reading public the impression that a lot of crime committed by highwaymen was savage. Prior to 1750 the public had always opposed any form of policing in the country, but in that year the Bow Street Runners – London’s first law enforcement agency – was established, which suggests that the public was becoming aware of the fact that crime was becoming a problem. Thus Maclean really is the ‘watershed’ highwaymen.
Maclean is probably the least well-known of all the classic highwaymen. He never featured in any of the Newgate novels of the 1830s, where Jack Sheppard and Dick Turpin enjoyed a resurgence of popularity, and featured in subsequent penny dreadful novels. Maclean was the subject of a long-running narrative in the penny dreadful version of The New Newgate Calendar (1863-65) (See my Conference Paper here) but he only really has come to public notice again through the movie Plunkett and Maclean (1999). The movie is an enjoyable, though heavily fictionalised account, of the two robbers, which I do recommend.
 Anon. THE ORDINARY of NEWGATE’S ACCOUNT of the Behaviour, Confession, and Dying Words, of the TWELVE MALEFACTORS Who were executed at TYBURN On Wednesday the 3d of OCTOBER, 1750. BEING THE Third EXECUTION in the MAYORALTY OF THE Right Hon’ble John Blachford, Esq ; LORD-MAYOR of the CITY of LONDON. NUMBER VI. for the said YEAR (LONDON: Printed for, and sold by T. PARKER, in Jewin-street, and C. CORBETT, over-against St. Dunstan’s Church, in Fleet-street, the only authorised Printers of the Dying Speeches, 1750), 84.
 Anon. THE ORDINARY of NEWGATE’S ACCOUNT, 85.
 Anon. THE ORDINARY of NEWGATE’S ACCOUNT, 86.
 Anon. THE ORDINARY of NEWGATE’S ACCOUNT, 91.
 Anon. THE ORDINARY of NEWGATE’S ACCOUNT, 87.
 Anon. THE ORDINARY of NEWGATE’S ACCOUNT, 88.
 Lincoln B. Faller, Turned to Account: The Forms and Functions of Criminal Biography in Late Seventeenth- and Early Eighteenth-Century England (Cambridge: Cambridge University Press, 2009), p.54.
 William Annand, A funeral elegie, upon the death of George Sonds, Esq; &c. Who was killed by his brother, Mr. Freeman Sonds, August the 7th. anno Dom. 1655. By William Annand Junior, of Throwligh. Whereunto is annexed a prayer, compiled by his sorrowfull father Sir George Sonds, and used in his family during the life of the said Freeman (London: John Crowch, 1655), see Faller, Turned to Account, p.94.
 Andrea McKenzie, Tyburn’s Martyrs: Execution in England, 1675-1775 (London: Hambledon Continuum, 2007), p.59.
 George Lillio, The London Merchant; or, the History of George Barnwell  cited in McKenzie, Tyburn’s Martrys, p.61.
 Richard Head, The English Rogue Described in the Life of Meriton Latroon, A Witty Extravagant. Being a Compleat History of the Most Eminent Cheats of Both Sexes (London: Printed for Henry Marsh, at the Princes Arms, Chancery Lane, 1665), p.16.
 Alexander Smith, A Complete History of the Lives and Robberies of the Most Notorious Highwaymen, Foot-pads, Shoplifts, and Cheats, of Both Sexes. Wherein their most Secret and Barbarous Murders, Unparalleled Robberies, Notorious Thefts, and Unheard-of Cheats are set in a true light and exposed to Public View for the Common Benefit of Mankind Ed. Arthur Heyward (3 Vols. London: J. Morphew, 1719 repr. London: George Routledge & Sons, 1933), 408-412.