The Connotations of 30 Synonyms for “Cheat” and “Fool”

Numerous terms, many of them derived from colorful underworld slang, exist to refer to the action of cheating or fooling someone. This post describes the connotation inherent in some of these words and phrases.

1–2. The implication of the nonsense words bamboozle and hornswoggle is that the perpetrator sets out to confuse the mark, or victim.

3. Beguile suggests that the mark is lulled into a false sense of security.

4. Bluff implies that the perpetrator is boasting or making false claims, as someone would to gain an advantage in a card game.

5. Buffalo alludes to the stolid strength of an animal, appropriate to refer to the perpetrator’s efforts to overcome the mark’s caution or reluctance by sheer determination.

6–7. Bleed suggests slowly draining the mark of his or her wealth; squeeze has the same implication.

8. Burn implies that the mark has been damaged by the perpetrator, as if exposed to flame.

9. Chisel suggests that the perpetrator is whittling away at the mark’s defenses to achieve the desired outcome.

10. Con, a truncation of confidence, alludes to the perpetrator’s efforts to gain the mark’s trust so that the person is vulnerable to the persuasion necessary to cheat him or her.

11. Cozen suggests coaxing or trickery.

12. Euchre refers to the act of preventing someone from winning in the game of that name and, by extension, means “cheat” or, because the game rounds are called tricks, “trick.”

13–14. Fleece and skin allude to the idea of being deprived of one’s protection.

15. The origins of gaff are obscure, but the word was once slang for a music hall or theater, so the implication may allude to the deceitful promise of an entertainment that was falsely advertised as being worth the admission price.

16–17. Game—and gammon, perhaps derived in Middle English from game—connote both the playful and strategic aspects of cheating, as if the perpetrator is not only toying with the mark but has also carefully planned the ruse.

18. Gyp derives from the widespread association of the nomadic Romani people, long called gypsies (from the mistaken belief that they originated in Egypt, though the ethnic origins of the Romani are in India), with deceitfulness and thievery. (The terms are now widely considered offensive.)

19. Hoodwink originally meant “blindfold,” so the connotation is of the perpetrator blinding the mark about the truth.

20. Hoax implies an elaborate scheme to persuade the mark that something false is true.

21. Hustle conjures an image of someone being pushed and prodded along toward an outcome advantageous to the perpetrator and detrimental to the mark.

22. Juggle suggests manipulating the mark by constantly keeping him or her off balance as if the mark were being thrown about without a chance to ground himself or herself.

23. Mulct originally meant “fine,” but its meaning was extended to “defraud.”

24. Shortchange refers to the literal act of giving someone less money than he or she is owed.

25. Snooker may come from the name of the variation of the game of pool, perhaps from the notion that the mark is tricked into betting that he or she can defeat the perpetrator.

26. Snow compares the perpetrator’s effort to the blinding quality of a snowstorm, preventing the mark from seeing the trick.

27–28. Stick and sting, like burn, allude to the pain that the deception causes the mark.

29. “String along” implies that the mark is being led to perform an action that will be to his or her detriment. The perpetrator figurative pulls the mark along, but not so heavy-handedly that the mark is dragged; the suggestion is that the leading occurs subtly, little by little, encouraging the mark to do what the perpetrator wants of his or her own volition, with a minimum of provocation.

30. Swindle, which comes from a German word meaning “dizzy,” connotes disorientation of the mark.

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