James MacLaine – The Gentleman Highwayman

James MacLaine

James MacLaine, Public Domain

James MacLaine was a notorious highwayman who was so polite and courteous, he became known as the “Gentleman Highwayman.” Physically MacLaine was described as “middle size, well-limbed, and [possessing] a sandy complexion, [and] a broad open countenance pitted with the small-pox.” He was born in 1724, the second son of an Irishman, who was a dissenting Presbyterian minister and was said to have been “educated in virtuous and religious principles, but unhappily counter-acted them [by taking up a life of crime].” Besides acquiring religious instruction from his father, MacLaine also acquired a good education “grounded in Latin, writing and accompts [sic].” MacLaine would have pursued a mercantile career but he had an aversion to hard work. At the age of eighteen he became an orphan. His mother had died several years earlier and then his father died prematurely.

MacLaine’s older brother was serving as a minister at the Hague at the time of his father’s death. James, known as Jemmy, Jemmie, M’Clean, Maclean, MacLean, or Maclane, “immediately took possession of all their little inheritance and applied it to his own purposes. His contempt for learning he displayed by selling his father’s books, and his vanity by the purchase of a gay coat and a gelding.” He also turned on the charm with the women. As he was considered good-looking, he quickly wooed the daughter’s of neighboring farmers. When he had frittered away most of his inheritance and enjoyed the sexual delights of his neighbor’s daughters, he decided to acquire a fortune not through hard work but by marrying a rich woman.

Eventually MacLaine did marry. But he did not marry for love rather he was enticed by the five hundred pounds the woman possessed. She was “a Miss MacGlegno, the daughter of a respectable innkeeper and horse-dealer.” MacLaine then became a commonplace grocer on Welbeck street in Cavendish Square where he “earned the reputation of being both industrious and obliging.” Unfortunately, his wife died three years later. During her illness she was attended by an Irish apothecary named William Plunkett. Plunkett “took upon himself the task of lightening the affliction of the widower” by promising MacLaine he could find him a woman worth at least £10,000.

With such a fortune possible, it did not take long for MacLaine to consign the care of his child to his mother-in-law and to emerge “in all the glory of laced clothes, hat, and feather.” He also took the title of a peer and with Plunkett as his servant “set out upon his quest [to find a rich wife].” He arrived in Wells all set to marry but found himself involved in an altercation at a public house: He was recognized “and ignominiously kicked out.”

He returned to London and gathered enough money to go to Jamaica. Unfortunately, before his ship set sail he gambled away the sixty guineas needed for his trip. In financial straits once again, Plunkett now tempted MacLaine to take up a life of crime by telling him he “had a right to live and not want the conveniences of life while dull, plodding, busy knaves carried cash in their pockets — upon such they must draw to supply their wants.”

For a time the two confederates confined their thefts “to the environs of London,” but as quickly as they acquired money, they spent it. Eventually, MacLaine went to the Hague to visit his brother and during his visit there he became extremely popular, although after his departure his guests “were able to date the disappearance of their property from their acceptance of his hospitality.”

Plunkett in the meantime was dealing with his own problems.

“He had the misfortune to fall from his horse and dislocate his shoulder … he was unable to dispose of the watches he carried … he ran into debt, and, altogether … he was ‘fretting his guts to fiddlestrings.'”

So, when Maclaine returned Plunkett insisted that all their problems could be solved if MacLaine married a rich woman, but again, despite their attempts, no marriage occurred.

Horace Walpole, Courtesy of Wikipedia

Horace Walpole, Courtesy of Wikipedia

In 1749, after Maclaine’s return to London, he achieved his most infamous exploit when he robbed the famous Whig politician, man of letters, and antiquarian, Horace Walpole, in Hyde Park. This was the first and only time he fired a shot. “His pistol … went off by accident, the ball passed through the top of the coach, and Walpole’s face was scorched by the explosion.” MacLaine, now known as the Gentleman Highwayman, was appalled and wrote a letter to his victim “apologising for having been compelled by disappointment in a matrimonial scheme to resort to this method of raising supplies.” MacLaine also offered to return “any trifles” Walpole might value and arranged a meeting at Tyburn at midnight. Plunkett attended on behalf of MacLaine “but Walpole, satisfied … with one escape, failed to put in his appearance.”

Another interesting story about MacLaine involves Button’s Coffee House and William Donaldson, Esq., who was a scholar and writer. Apparently, MacLaine took a shine to the landlord’s daughter at Button’s. Donaldson observed this and warned her father. The father in turn warned his daughter “and imprudently told her by whose advice he put her on her guard; she as imprudently told Maclaine.”

Of course, this did not sit well with MacLaine. The next time MacLaine saw Donaldson at Button’s, he insisted they speak in private.

“Mr. Donaldson being unarmed, and naturally afraid of being alone with such a man, said in answer…[there was nothing that] could pass between that he did not wish the whole world to know.”

Maclaine warned him “we shall meet again.”

They almost did a few days later when Donaldson was walking to Richmond. He spied MacLaine on horseback just as MacLaine spied him. MacLaine spurred his horse towards Donaldson but a carriage appeared in view and this forced Maclaine to change his course. It also allowed Donaldson time to rush off to safety in Richmond.

In late June of 1750, shortly after Donaldson’s escape, Plunkett and MacLaine robbed the Salisbury coach. It had six passengers aboard and a man named Lord Eglinton. Among the passengers was also a Mr. Josiah Higden who immediately advertised his losses. In the meantime, MacLaine attempted to unload his booty with a shop owner named Mr. Loader of Monmouth Street. He purchased certain items from Maclaine but later noticed the gold lace was similar to some he had sold to Higden. “His suspicions moved him to send for that gentleman; he came, and there followed a warrant for … Maclaine.” When MacLaine was apprehended, his lodgings were searched and property belonging to Lord Eglinton and the Salisbury coach passengers were also discovered.

London was a buzz with MacLaine’s nefarious exploits. Moreover, the belongings pilfered by MacLaine were arranged upon tables, and the proceeding against MacLaine was watched by numerous ladies with “breathless interest.” MacLaine “whined and wept, offered to betray … Plunkett to save his own life and when his offer was refused [he] made a full confession.”

His trial was set at Old Bailey. At trial, numerous ladies accompanied him and listened with tears streaming down their face. The women also offered “their sympathy in the shape of a purse of gold, and up to the time of his trial he was daily visited by a crowd of persons of fashion who contributed liberally to his support.” In fact, it is estimated that while he was imprisoned at Newgate, he had some 3,000 visitors.

MacLaine’s trial was short. The verdict inevitable: He was found guilty. Following his conviction, he was provided with an opportunity to appeal for mercy and a friend wrote his appeal, but he could not deliver it, and “though the Gentleman Highway could say so little for himself, petitions in his favour were started on all sides.” The petitions proved fruitless.

Early on the morning of the fatal day, Wednesday, 3 October, MacLaine traveled in a cart with two other convicted criminals — William Smith, the son of an Irish clergyman convicted of forgery, and a man named Sanders, who had stolen a watch. All three faced the hangman, a Mr. John Thrift. Thrift did his duty, and MacLaine’s body was buried at Uxbridge.

After his death, MacLaine was immortalized in a song sung by those at Tyburn:

“Ye Smarts, and ye Jemmies, ye Ramillie beaux,

With golden cocked-hats and with silver laced clothes,

Who by wit and invention your pockets maintain,

Come pity the fate of poor Jemmy Maclaine.

He robb’d folks genteelly, he robb’d with an air,

He robb’d them so well that he always took care

My lord was not hurt, and my lady not frighted,

And instead of being hanged he deserved to be knighted.


  • Court Magazine and Le Belle Assemblee, Vol. 1, 1832
  • Kimber, Edward, London Magazine, 1750
  • “London,” in Caledonian Mercury, 2 Aug 1750
  • Museum of Foreign Literature Science and Art, 1833
  • Percy, Reuben, etal., The Mirror of Literature, Amusement and Instruction, Vol. 20, 1832
  • Seccombe, Thomas, ed., Lives of Twelve Bad Men, 1894
  • Taylor, John, Records of My Life, 1832
  • Thornbury, George Walter, Old and New London, 1880
  • Timbs, John, Club Life of London with Anecdotes of the Clubs, Coffee-House and Taverns of the Metropolis During the 17th, 18th, and 19th Centuries, 1866

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