as in brigand
a man especially in the past who stopped travelers on roads and robbed them
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Recent Examples of highwayman
Shortly before midnight on May 23, 1798, highwaymen just north of Dublin intercepted and set on fire a mail coach headed to Belfast.
—
Joseph Patrick Kelly, The Conversation, 20 May 2025
The sybaritic highwayman Macheath maneuvers between a cutthroat capitalist milieu (Mr. and Mrs. Peachum) and a corrupt police force (led by Tiger Brown) while seducing daughters from both worlds (Polly Peachum and Lucy Brown).
—Alex Ross, New Yorker, 14 Apr. 2025
In the irreverent retelling of the 18th-century highwayman’s life, Turpin is the most famous but least likely of robbers, whose success is defined mostly by his charm, showmanship, and great hair.
—Jake Kanter, Deadline, 16 Jan. 2025
Written by Fielding, Richard Naylor and Jon Brittain, the series followed the contemptuous life of the 18th-century highwayman, known in York, England, as a thief, poacher and killer but whose exploits have been widely romanticized in modern culture.
—Lily Ford, The Hollywood Reporter, 16 Jan. 2025
Dick Turpin was an English robber and highwayman whose criminal activities gained him notoriety in the early eighteenth century.
—Ben Morse, CNN, 14 Jan. 2025
The group gets further assistance from a charming aristocratic dandy/secret highwayman named Charles Devereaux (Frank Dillane).
—Ars Technica, 24 Dec. 2024
He is captured by Bedouin highwaymen, who plan to rob him.
—Steve Hindy, Foreign Affairs, 27 Aug. 2015
Joseph Patrick Kelly, The Conversation, 20 May 2025
The sybaritic highwayman Macheath maneuvers between a cutthroat capitalist milieu (Mr. and Mrs. Peachum) and a corrupt police force (led by Tiger Brown) while seducing daughters from both worlds (Polly Peachum and Lucy Brown).
—Alex Ross, New Yorker, 14 Apr. 2025
In the irreverent retelling of the 18th-century highwayman’s life, Turpin is the most famous but least likely of robbers, whose success is defined mostly by his charm, showmanship, and great hair.
—Jake Kanter, Deadline, 16 Jan. 2025
Written by Fielding, Richard Naylor and Jon Brittain, the series followed the contemptuous life of the 18th-century highwayman, known in York, England, as a thief, poacher and killer but whose exploits have been widely romanticized in modern culture.
—Lily Ford, The Hollywood Reporter, 16 Jan. 2025
Dick Turpin was an English robber and highwayman whose criminal activities gained him notoriety in the early eighteenth century.
—Ben Morse, CNN, 14 Jan. 2025
The group gets further assistance from a charming aristocratic dandy/secret highwayman named Charles Devereaux (Frank Dillane).
—Ars Technica, 24 Dec. 2024
He is captured by Bedouin highwaymen, who plan to rob him.
—Steve Hindy, Foreign Affairs, 27 Aug. 2015
Recent Examples of Synonyms for highwayman
Noun
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Then rumors started spreading about armed brigands that would come to town to steal what little harvest folks had left, so towns raised militias to fight back.—
Popular Science Team,
Popular Science,
24 Sep. 2025
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Captured by brigands, the immigrants are herded into a remote Libyan prison camp where they are tormented and tortured.—
Peter Rainer,
The Christian Science Monitor,
22 Feb. 2024
Noun
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There can be no doubt that in tax terms, America’s wealthiest families make out like bandits.—
Business Columnist,
Los Angeles Times,
8 Jan. 2026
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The robbery lasted less than seven minutes, as the bandits used a truck with an extendable ladder to cut through a window on a second-floor balcony, according to police.—
Mason Leath,
ABC News,
27 Dec. 2025
Noun
-
These oil fields basically are pirate operations.—
ABC News,
ABC News,
4 Jan. 2026
-
Notorious pirate Jean Lafitte frequented neighboring Grand Terre Island in the early 1800s.—
Kristy Christiansen,
Southern Living,
31 Dec. 2025
Noun
-
Though detectives conclude that assassin cult members Ash (Jon Pointing) and Dee Dee (Maeve Courtier-Lilley) were the ones who killed Aaron, Paige revealed that the real killer was Ingrid.—
Emily Blackwood,
PEOPLE,
5 Jan. 2026
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Maduro is being held in the same federal jail in Brooklyn as accused assassin Luigi Mangione.—
Michael Ruiz , Maria Paronich , Brendan McDonald,
FOXNews.com,
5 Jan. 2026
Noun
-
The first thing to do is to reduce the damage to the United States, the inflow of guns and criminals and immigrants and drugs into the United States, the destabilizing of a key part of the Western Hemisphere.—
CBS News,
CBS News,
11 Jan. 2026
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Also, place freezes with ChexSystems and the National Consumer Telecom and Utilities Exchange to stop criminals from opening bank accounts, phone lines, or utility services in his name.—
Kurt Knutsson,
FOXNews.com,
11 Jan. 2026
Noun
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For his battle-worn, brooding rendition of the heroic outlaw in the A24 film, the Les Misérables actor shows off a long gray beard paired with silver locks—a far cry from other Robin Hoods portrayed by actors like Kevin Costner, Sean Connery, and Russell Crowe.—
Lara Walsh,
InStyle,
6 Jan. 2026
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At 97% fresh on Rotten Tomatoes, the pic stars Bill Skarsgård, Dacre Montgomery, Cary Elwes, Myha’la, Coleman Domingo and Al Pacino in a story inspired by the 1977 hostage standoff that turned aspiring entrepreneur Tony Kiritsis into an eccentric outlaw folk hero.—
Anthony D'Alessandro,
Deadline,
6 Jan. 2026
Noun
-
These are desperadoes in the White House.—
Anne Thompson,
IndieWire,
26 Nov. 2025
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And sometimes the best care is not bringing in a bunch of — as Kareem Abdul-Jabbar put it — a throbbing scum of fame-hungry desperados.—
Andy Greene,
Rolling Stone,
31 July 2025
Noun
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Boardman imposed a sentence of 97 months, citing Roske’s mental health and concerns about incarceration conditions and his status as a first-time criminal offender.—
Kaelan Deese,
The Washington Examiner,
8 Jan. 2026
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Since 2013, the law has allowed juvenile offenders serving life without parole to petition to have their sentence recalled and to be resentenced.—
Teri Figueroa,
San Diego Union-Tribune,
7 Jan. 2026
Cite this Entry
“Highwayman.” Merriam-Webster.com Thesaurus, Merriam-Webster, https://www.merriam-webster.com/thesaurus/highwayman. Accessed 19 Jan. 2026.
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