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
-
As did most of the 4,500 caught in the region as feds traveled willy-nilly originally from their base at Naval Station Great Lakes in North Chicago, like roving bands of masked brigands seeking human loot.—
Charles Selle,
Chicago Tribune,
7 Jan. 2026
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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
Noun
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The story revolves around Davis, the sort of gentleman bandit who thoughtfully returns his victims’ cell phones before making his departure and who, in the grand tradition of cinematic thieves, is looking to get out of the business after that last big score.—
Frank Scheck,
HollywoodReporter,
11 Feb. 2026
-
Fleeing into the desert with her father, she is hunted by a merciless army and forced to trust a legendary bandit (Mackie) with secrets of his own.—
Matt Grobar,
Deadline,
11 Feb. 2026
Noun
-
Fans are not just remembering this historic home run, but rather a humble pirate who spent his entire career here in Pittsburgh.—
Jessica Riley,
CBS News,
22 Feb. 2026
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As such, the Italian fighter pilot now spends most of his time as a bounty hunter hired to attack air pirates.—
Danny Horn,
Entertainment Weekly,
22 Feb. 2026
Noun
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Statham stars as a retired assassin living off the coast of Scotland who has to get back to work while trying to stop the agency that used to pay him and protecting a young girl named Jessie (Bodhi Rae Breathnach).—
Brian Tallerico,
Vulture,
28 Feb. 2026
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Watching General Pinochet’s man on the spot, the American assassin Michael Vernon Townley, murder some of Chile’s finest leaders shows that the allure of espionage was largely a fiction, a cinematic fabrication.—
Alfred McCoy,
Literary Hub,
26 Feb. 2026
Noun
-
Whenever there is American resolve, global criminals weaken.—
Rebecca Schneid,
Time,
28 Feb. 2026
-
And whenever America is determined, global criminals weaken.—
CBS News,
CBS News,
28 Feb. 2026
Noun
-
And America's armed forces overwhelmed all defenses and utterly defeated an enemy -- good fighters -- to end the reign of outlaw dictator Nicolas Maduro and bring him to face American justice.—
February 25,
NPR,
25 Feb. 2026
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Season two of Robin Hood expands the world beyond Sherwood and Nottingham into the treacherous courts of England, France, and Rome, transforming the outlaw rebellion into a high stakes battle for the soul of a kingdom.—
Max Goldbart,
Deadline,
24 Feb. 2026
Noun
-
Liu returned to skating in late 2024 after two and a half years, with the clearheaded intention to be a performance artist, not a medal-seeking desperado.—
Sally Jenkins,
The Atlantic,
22 Feb. 2026
-
These are desperadoes in the White House.—
Anne Thompson,
IndieWire,
26 Nov. 2025
Noun
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According to multiple people briefed on the discussions, the committee could propose to remove the carryover suspension part of the punishment for first-time offenders on second-half targeting penalties, leaving in place a 15-yard penalty and ejection.—
Chris Vannini,
New York Times,
22 Feb. 2026
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What emerged, Jackson told the court Thursday, was the portrait of a transient and calculating offender who operated across multiple states and evaded law enforcement for years.—
Austin Sanders,
Austin American Statesman,
21 Feb. 2026
Cite this Entry
“Highwayman.” Merriam-Webster.com Thesaurus, Merriam-Webster, https://www.merriam-webster.com/thesaurus/highwayman. Accessed 1 Mar. 2026.
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