Highwayman

A highwayman was a robber, typically mounted on horseback, who held up travelers and coaches on public roads, especially during the 17th and 18th centuries. These figures often operated in areas outside of towns and cities where law enforcement presence was limited. They relied on surprise, intimidation, and often violence, to seize valuables from their victims. Highwaymen were romanticized in literature and folklore, sometimes depicted as dashing figures who robbed from the rich and, though inaccurately, sometimes giving to the poor, despite usually being driven by simple greed. Many historical accounts document their daring exploits, frequent captures and executions, and often short lifespans.

Highwayman meaning with examples

• The flickering lantern light illuminated the lone traveler as the highwayman emerged from the shadows. His pistol glinted, and he demanded the coachman halt. Terrified passengers surrendered their purses and jewelry as the highwayman efficiently pilfered their possessions before vanishing into the night. The incident caused widespread alarm, leading to increased security patrols and the eventual decline of highway robbery.
• Legend had it that Black Bart, a notorious highwayman, was known for his elaborate disguises and witty letters left at the scenes of his crimes. Unlike some of his brutal counterparts, he often spared the lives of his victims and even displayed a perverse sense of humor. Bart's romanticized image captured public imagination, although his victims, with lighter pockets and shattered lives, likely did not find it so funny.
• The historical records show a significant spike in highwayman activity following the political turmoil and economic hardship of the English Civil War. Disbanded soldiers and desperate individuals turned to robbery for survival, preying upon the wealthy and the vulnerable alike. Law enforcement faced a constant struggle to apprehend these elusive criminals who knew the countryside so well.
• Popular novels of the era often featured the highwayman as a key character, sometimes as the villain and other times as a daring antihero. The character's appeal stemmed from a combination of fear, admiration for a perceived defiance of authority, and a touch of romantic allure despite their fundamentally criminal behavior.