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The Highwaymen

English for Fun <<< Legends, Myths... <<< The Highwaymen

Lies, Exaggeration and Truth

The legend of the highwayman is that of a gentleman. High or low born, the legendary highwayman dressed well (with a kerchief over his face), was well-mannered, and used threats rather than violence. "Stand and Deliver" and "Your money or your life," were his greetings.

This legend is one of long standing. In 1737 the Abbe le Blanc wrote of Englishmen's attitudes toward highwaymen: "Tales of their cunning and generosity were in the mouths of everybody, and a noted thief was a kind of hero."(Newark, 21) Thomas de Quincey (1785-184) wrote that being a highwayman required "a bountiful endowment of qualifications; strength, health, agility, and excellent horsemanship" and that "the very noblest specimen of man, considered as an animal, were the mounted robbers who cultivated their profession on the great roads." (Newark, 22) Henry Fielding was so concerned about the romanticism attached to the highwayman, that he asked Garrick to suppress his production of The Beggar's Opera, which made a hero out of a highwayman. (Newark, 25)

Although there were well-born and well-mannered highwaymen, they were far outnumbered by those who practiced their trade with brutality. Violence and rape were common. When Tom Wilmot had difficulty removing a woman's ring, he cut off her finger.(Newark, 27)

Origins of the Legend

The gentleman highwayman has its origins in the English Civil Wars. When Charles I was defeated, many Royalist officers were ruined, their estates confiscated, and they were left without resources. These cavaliers set the pattern for the gentleman robber. Condemned to the gallows, former Cavalier Captain Phillip Stafford wore his finest clothes, and had a final drink at a tavern, promising to pay for it on his way back. Captain James Hind was the epitome of the gentleman robber. Hind was not a gentleman by birth, but the son of a saddlemaker who had a distinguished career in the civil war. He was also known to help the poor. Hind fought with Charles II. In 1651 he was arrested and hanged, drawn and quartered for treason rather than robbery. (Lives, 61) Captain Zachary Howard, a former Cavalier, reportedly held up Cromwell himself. However, he was no gentleman. Learning Lord General Thomas Fairfax was sending supplies to his home, Howard attacked General Fairfax's house, raping Lady Fairfax and her daughter while Fairfax was away.

Highwaymen's Demise

The demise of the highwayman began with the establishment of the Horse Patrol around London in 1805, and was furthered by the founding of the Metropolitan Police in 1829. Although highwaymen persisted in isolated areas, the growth of a paid police force meant their heyday was over. The last major gang was the "the Hanham and Cock-road Gang," a group of five men who robbed and brutalized residents around Brislington and Kensham. They were apprehended by a police sergeant in 1850. (Newark, 34)


Finger, Charles J. Highwaymen (a book of gallant rogues with illustrations from woodblocks by Paul Honore) Robert McBride & Co: New York, 1923.

Newark, Peter. The Crimson Book of Highwaymen, Jupiter Books: London, 1979.

Lives and Exploits of The Most Noted Highwaymen, Robbers and Murderers, of All Nations (drawn from the most authentic sources and brought down to the Present Time). D. W. Evans & Co: New York, 1860.

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